CN110292652B - Mercaptobenzeneboronic acid activated gold nanoparticles as well as preparation method and application thereof - Google Patents
Mercaptobenzeneboronic acid activated gold nanoparticles as well as preparation method and application thereof Download PDFInfo
- Publication number
- CN110292652B CN110292652B CN201810255084.1A CN201810255084A CN110292652B CN 110292652 B CN110292652 B CN 110292652B CN 201810255084 A CN201810255084 A CN 201810255084A CN 110292652 B CN110292652 B CN 110292652B
- Authority
- CN
- China
- Prior art keywords
- acid
- gold nanoparticles
- dressing
- electrospun
- mercaptophenylboronic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 239000002105 nanoparticle Substances 0.000 title claims abstract description 107
- 238000002360 preparation method Methods 0.000 title abstract description 22
- 239000010931 gold Substances 0.000 claims abstract description 79
- 229910052737 gold Inorganic materials 0.000 claims abstract description 78
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims abstract description 76
- 230000000844 anti-bacterial effect Effects 0.000 claims abstract description 49
- RADLTTWFPYPHIV-UHFFFAOYSA-N (2-sulfanylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1S RADLTTWFPYPHIV-UHFFFAOYSA-N 0.000 claims abstract description 37
- 239000012528 membrane Substances 0.000 claims abstract description 32
- 238000000034 method Methods 0.000 claims abstract description 30
- 238000010041 electrostatic spinning Methods 0.000 claims abstract description 29
- -1 mercaptophenylboronic acid activated gold Chemical class 0.000 claims abstract description 23
- 206010052428 Wound Diseases 0.000 claims abstract description 22
- 208000027418 Wounds and injury Diseases 0.000 claims abstract description 22
- 239000000463 material Substances 0.000 claims abstract description 12
- 239000000126 substance Substances 0.000 claims abstract description 11
- 238000009987 spinning Methods 0.000 claims description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- 239000000243 solution Substances 0.000 claims description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 21
- 239000004632 polycaprolactone Substances 0.000 claims description 20
- 229920001610 polycaprolactone Polymers 0.000 claims description 20
- 108010010803 Gelatin Proteins 0.000 claims description 19
- 229920000159 gelatin Polymers 0.000 claims description 19
- 239000008273 gelatin Substances 0.000 claims description 19
- 235000019322 gelatine Nutrition 0.000 claims description 19
- 235000011852 gelatine desserts Nutrition 0.000 claims description 19
- 229920000642 polymer Polymers 0.000 claims description 17
- 239000002243 precursor Substances 0.000 claims description 17
- 239000002245 particle Substances 0.000 claims description 15
- OBCKMTLUSKYKIW-UHFFFAOYSA-N (3-sulfanylphenyl)boronic acid Chemical compound OB(O)C1=CC=CC(S)=C1 OBCKMTLUSKYKIW-UHFFFAOYSA-N 0.000 claims description 13
- AUVSUPMVIZXUOG-UHFFFAOYSA-N (4-sulfanylphenyl)boronic acid Chemical compound OB(O)C1=CC=C(S)C=C1 AUVSUPMVIZXUOG-UHFFFAOYSA-N 0.000 claims description 11
- 238000011282 treatment Methods 0.000 claims description 11
- XYYVDQWGDNRQDA-UHFFFAOYSA-K trichlorogold;trihydrate;hydrochloride Chemical compound O.O.O.Cl.Cl[Au](Cl)Cl XYYVDQWGDNRQDA-UHFFFAOYSA-K 0.000 claims description 10
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 claims description 9
- 208000015181 infectious disease Diseases 0.000 claims description 8
- 229920005615 natural polymer Polymers 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 102000008186 Collagen Human genes 0.000 claims description 7
- 108010035532 Collagen Proteins 0.000 claims description 7
- 229920001436 collagen Polymers 0.000 claims description 7
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims description 7
- 229920000053 polysorbate 80 Polymers 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 238000001523 electrospinning Methods 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 206010053615 Thermal burn Diseases 0.000 claims description 5
- 229920001577 copolymer Polymers 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- 229920001661 Chitosan Polymers 0.000 claims description 4
- 239000002202 Polyethylene glycol Substances 0.000 claims description 4
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 4
- 239000005457 ice water Substances 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- 229920001223 polyethylene glycol Polymers 0.000 claims description 4
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 4
- 239000012279 sodium borohydride Substances 0.000 claims description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 3
- 206010011985 Decubitus ulcer Diseases 0.000 claims description 3
- 108010022355 Fibroins Proteins 0.000 claims description 3
- 229920002678 cellulose Polymers 0.000 claims description 3
- 239000001913 cellulose Substances 0.000 claims description 3
- 239000004626 polylactic acid Substances 0.000 claims description 3
- 230000001954 sterilising effect Effects 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- 239000011259 mixed solution Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 229920000747 poly(lactic acid) Polymers 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 238000001291 vacuum drying Methods 0.000 claims description 2
- 241000894006 Bacteria Species 0.000 abstract description 24
- 239000000835 fiber Substances 0.000 abstract description 24
- 230000008859 change Effects 0.000 abstract description 5
- 230000006378 damage Effects 0.000 abstract description 5
- 206010059866 Drug resistance Diseases 0.000 abstract description 4
- 238000005516 engineering process Methods 0.000 abstract description 4
- 239000003344 environmental pollutant Substances 0.000 abstract description 2
- 238000011031 large-scale manufacturing process Methods 0.000 abstract description 2
- 231100000719 pollutant Toxicity 0.000 abstract description 2
- 239000003242 anti bacterial agent Substances 0.000 description 15
- 238000012512 characterization method Methods 0.000 description 15
- 241000282414 Homo sapiens Species 0.000 description 11
- 150000002343 gold Chemical class 0.000 description 10
- 239000002121 nanofiber Substances 0.000 description 9
- 230000001580 bacterial effect Effects 0.000 description 8
- 239000002131 composite material Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 206010040872 skin infection Diseases 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 6
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 5
- 241000191967 Staphylococcus aureus Species 0.000 description 5
- 206010048038 Wound infection Diseases 0.000 description 5
- 230000009102 absorption Effects 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 230000015556 catabolic process Effects 0.000 description 5
- 238000006731 degradation reaction Methods 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 5
- 238000001308 synthesis method Methods 0.000 description 5
- 238000013461 design Methods 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 239000002086 nanomaterial Substances 0.000 description 4
- 208000035143 Bacterial infection Diseases 0.000 description 3
- 241000192125 Firmicutes Species 0.000 description 3
- 208000022362 bacterial infectious disease Diseases 0.000 description 3
- 125000005619 boric acid group Chemical group 0.000 description 3
- 210000002421 cell wall Anatomy 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 210000002950 fibroblast Anatomy 0.000 description 3
- 230000035876 healing Effects 0.000 description 3
- 239000000017 hydrogel Substances 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 238000004627 transmission electron microscopy Methods 0.000 description 3
- 210000003606 umbilical vein Anatomy 0.000 description 3
- 229920002749 Bacterial cellulose Polymers 0.000 description 2
- 238000002965 ELISA Methods 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- 206010018910 Haemolysis Diseases 0.000 description 2
- MSFSPUZXLOGKHJ-UHFFFAOYSA-N Muraminsaeure Natural products OC(=O)C(C)OC1C(N)C(O)OC(CO)C1O MSFSPUZXLOGKHJ-UHFFFAOYSA-N 0.000 description 2
- 229930182555 Penicillin Natural products 0.000 description 2
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
- 108010013639 Peptidoglycan Proteins 0.000 description 2
- 208000004210 Pressure Ulcer Diseases 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 241000191963 Staphylococcus epidermidis Species 0.000 description 2
- 230000003213 activating effect Effects 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- 239000005016 bacterial cellulose Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000000502 dialysis Methods 0.000 description 2
- 238000012377 drug delivery Methods 0.000 description 2
- 238000002296 dynamic light scattering Methods 0.000 description 2
- 210000002889 endothelial cell Anatomy 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 230000008588 hemolysis Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 210000004962 mammalian cell Anatomy 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 238000001000 micrograph Methods 0.000 description 2
- 239000013642 negative control Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 229940049954 penicillin Drugs 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- 239000013641 positive control Substances 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002791 soaking Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- 230000017423 tissue regeneration Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 230000029663 wound healing Effects 0.000 description 2
- 206010011409 Cross infection Diseases 0.000 description 1
- 108010037362 Extracellular Matrix Proteins Proteins 0.000 description 1
- 102000010834 Extracellular Matrix Proteins Human genes 0.000 description 1
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 1
- 206010029803 Nosocomial infection Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 206010072170 Skin wound Diseases 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 229940124350 antibacterial drug Drugs 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000003796 beauty Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000036760 body temperature Effects 0.000 description 1
- 210000000845 cartilage Anatomy 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229960001701 chloroform Drugs 0.000 description 1
- 238000003501 co-culture Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 210000003038 endothelium Anatomy 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 210000002744 extracellular matrix Anatomy 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 238000011866 long-term treatment Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 230000004660 morphological change Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003009 phosphonic acids Chemical group 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000004626 scanning electron microscopy Methods 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000006557 surface reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 150000003573 thiols Chemical group 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/18—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing inorganic materials
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/20—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing organic materials
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/22—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing macromolecular materials
- A61L15/26—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/22—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing macromolecular materials
- A61L15/32—Proteins, polypeptides; Degradation products or derivatives thereof, e.g. albumin, collagen, fibrin, gelatin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/22—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing macromolecular materials
- A61L15/32—Proteins, polypeptides; Degradation products or derivatives thereof, e.g. albumin, collagen, fibrin, gelatin
- A61L15/325—Collagen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/42—Use of materials characterised by their function or physical properties
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/42—Use of materials characterised by their function or physical properties
- A61L15/425—Porous materials, e.g. foams or sponges
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/42—Use of materials characterised by their function or physical properties
- A61L15/46—Deodorants or malodour counteractants, e.g. to inhibit the formation of ammonia or bacteria
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01D—MECHANICAL METHODS OR APPARATUS IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS
- D01D5/00—Formation of filaments, threads, or the like
- D01D5/0007—Electro-spinning
- D01D5/0015—Electro-spinning characterised by the initial state of the material
- D01D5/003—Electro-spinning characterised by the initial state of the material the material being a polymer solution or dispersion
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01D—MECHANICAL METHODS OR APPARATUS IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS
- D01D5/00—Formation of filaments, threads, or the like
- D01D5/0007—Electro-spinning
- D01D5/0061—Electro-spinning characterised by the electro-spinning apparatus
- D01D5/0069—Electro-spinning characterised by the electro-spinning apparatus characterised by the spinning section, e.g. capillary tube, protrusion or pin
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01D—MECHANICAL METHODS OR APPARATUS IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS
- D01D5/00—Formation of filaments, threads, or the like
- D01D5/0007—Electro-spinning
- D01D5/0061—Electro-spinning characterised by the electro-spinning apparatus
- D01D5/0076—Electro-spinning characterised by the electro-spinning apparatus characterised by the collecting device, e.g. drum, wheel, endless belt, plate or grid
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01D—MECHANICAL METHODS OR APPARATUS IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS
- D01D5/00—Formation of filaments, threads, or the like
- D01D5/0007—Electro-spinning
- D01D5/0061—Electro-spinning characterised by the electro-spinning apparatus
- D01D5/0092—Electro-spinning characterised by the electro-spinning apparatus characterised by the electrical field, e.g. combined with a magnetic fields, using biased or alternating fields
-
- D—TEXTILES; PAPER
- D04—BRAIDING; LACE-MAKING; KNITTING; TRIMMINGS; NON-WOVEN FABRICS
- D04H—MAKING TEXTILE FABRICS, e.g. FROM FIBRES OR FILAMENTARY MATERIAL; FABRICS MADE BY SUCH PROCESSES OR APPARATUS, e.g. FELTS, NON-WOVEN FABRICS; COTTON-WOOL; WADDING ; NON-WOVEN FABRICS FROM STAPLE FIBRES, FILAMENTS OR YARNS, BONDED WITH AT LEAST ONE WEB-LIKE MATERIAL DURING THEIR CONSOLIDATION
- D04H1/00—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres
- D04H1/70—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres characterised by the method of forming fleeces or layers, e.g. reorientation of fibres
- D04H1/72—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres characterised by the method of forming fleeces or layers, e.g. reorientation of fibres the fibres being randomly arranged
- D04H1/728—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres characterised by the method of forming fleeces or layers, e.g. reorientation of fibres the fibres being randomly arranged by electro-spinning
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/10—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing inorganic materials
- A61L2300/102—Metals or metal compounds, e.g. salts such as bicarbonates, carbonates, oxides, zeolites, silicates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
- A61L2300/404—Biocides, antimicrobial agents, antiseptic agents
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Materials Engineering (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Hematology (AREA)
- Textile Engineering (AREA)
- Mechanical Engineering (AREA)
- Dispersion Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Materials For Medical Uses (AREA)
Abstract
The invention provides a mercaptophenylboronic acid activated gold nanoparticle, and a preparation method and application thereof. The preparation method of the gold nanoparticles activated by the mercaptophenylboronic acid is simple, the drug resistance of bacteria can not be induced, and the antibacterial effect is obvious; has higher biological safety; the antibacterial fiber membrane prepared by the electrostatic spinning method has stable physical and chemical properties and high porosity, can isolate pollutants, is soft and breathable, has good wettability, can be perfectly attached to wounds with different shapes, is prepared by degradable materials, and reduces secondary damage caused by dressing change; the gold nanoparticles activated by the mercaptophenylboronic acid are stable and easy to store, and have high stability, large-scale production potential and wide clinical application prospect after being prepared into the dressing by the electrostatic spinning technology.
Description
Technical Field
The invention belongs to the field of biological materials, and particularly relates to a gold nanoparticle activated by mercaptophenylboronic acid, and a preparation method and application thereof.
Background
Bacterial infections, particularly wound infections, are a serious threat to human health and can even directly lead to death. Gram-positive bacteria are more likely to cause skin and cartilage tissue infections than gram-negative bacteria. In recent years, the number of patients who die as a result of bacterial infections has increased dramatically, a phenomenon that is closely related to the abuse of antibiotics. With the abuse of antibiotics, serious drug resistance is induced to the bacteria, thereby causing the super bacterial crisis. The search for effective new antibacterial agents is therefore very urgent, in particular for multi-drug resistant superbacteria. Since the nano material has the characteristics of large specific surface area, high degree of surface functionalization and unique physicochemical properties, many nano materials have been used for developing and preparing novel antibacterial drugs. The gold nanoparticles have many unique properties on the premise of combining the above excellent properties, such as: good biocompatibility, excellent antibacterial activity and rapid synthesis method. Many studies have shown that gold nanoparticles themselves have no antibacterial activity, but show effective antibacterial activity after being modified by functional groups such as thiol, amine and phosphonic acid compounds. The phenylboronic acid and the derivatives thereof can be used as intermediates for drug synthesis, and have remarkable effects in the field of drug delivery. The mercapto phenylboronic acid is combined with peptidoglycan on the surface of the bacteria through boric acid groups, so that the selectivity of the bacteria is improved; and a gold-sulfur bond is formed on the surface of the nano-particle by utilizing sulfydryl, so that ligand molecules are stably modified on the surface of the gold nano-particle. In view of the above considerations, activation of gold nanoparticles as ligands for antimicrobial agents by mercaptophenylboronic acid is a suitable option.
The skin is the largest organ of the human body and has the physiological functions of barrier protection, body temperature regulation, secretion and excretion, absorption and metabolism, immunity and the like. The moist environment of the wound surface facilitates the propagation of bacteria and at the same time accelerates cross-infection in the affected area. With the development of wound dressing research, an ideal functional medical wound dressing should have the function of preventing bacterial infection of the wound while satisfying the requirement of isolating the damaged skin from the external environment. As an effective preparation method of the micro-nano fiber, the electrostatic spinning technology has irreplaceable advantages in the fields of biomedicine, wound dressing, drug delivery and the like. Such as: large specific surface area, good flexibility and wide selectivity of polymer materials. Scholars at home and abroad use the nano material to prepare the antibacterial agent and explore the application field of the antibacterial agent in the aspect of skin infection. The prior art discloses a preparation method of a silver-loaded bacterial cellulose hydrogel antibacterial dressing and a product thereof, a bacterial cellulose hydrogel film is soaked in a silver metal precursor solution, and the antibacterial effect is realized through a plurality of steps of washing, dehydration, sterilization and the like, but the preparation process of the method is complex, the nano silver is unstable, and has strong toxicity to a human body, the use of the nano silver in the medical aspect is definitely forbidden by the US FDA, and the nano silver is also limited by the CFDA in China in the medical field. The prior art also discloses an antibacterial dressing containing nano-gold and a preparation method thereof, the ligand modified gold nanoparticles are used for preparing an effective antibacterial agent without drug resistance to bacteria, but the steps of padding, drying and the like are required when the antibacterial dressing is prepared, the preparation process is complicated, the nano-gold particle antibacterial agent needs to be attached to other dressings, can not be slowly released, and is not suitable for long-term treatment. The prior art discloses chitosan hydrogel for an antibacterial dressing and a preparation method thereof, raw material components comprise a water-soluble monomer, an antibacterial agent, a cross-linking agent, a condensing agent, an activating agent and an initiator, the components are complex, the influence among various components is not clear, and the air permeability of a wound cannot be realized, so that the exploration of a functional wound dressing with a simple preparation process has important significance.
Disclosure of Invention
Therefore, the invention aims to overcome the defects in the prior art and provide the mercaptophenylboronic acid activated gold nanoparticles, and the preparation method and application thereof.
Before setting forth the context of the present invention, the terms used herein are defined as follows:
the term "4 MBA" means: p-mercaptophenylboronic acid.
The term "3 MBA" means: m-mercaptophenylboronic acid.
The term "PCL" means: polycaprolactone.
The term "high molecular weight polymer" means: high molecular weight (usually up to 10) consisting of a multiplicity of identical, simple structural units which are repeatedly linked by covalent bonds 4 ～10 6 ) A compound is provided.
The term "natural polymer" refers to: the composition of natural animals and plants (including human beings) is a high molecular weight compound having a basic structure of a linear long chain formed by connecting repeating units.
In order to achieve the above object, a first aspect of the present invention provides a mercaptophenylboronic acid activated gold nanoparticle, wherein the mercaptophenylboronic acid is p-mercaptophenylboronic acid or m-mercaptophenylboronic acid;
preferably, the average particle size of the gold nanoparticles is 1-50 nm, preferably 1-10 nm, and most preferably 1-5 nm.
The second aspect of the present invention provides a method for preparing mercaptophenylboronic acid-activated gold nanoparticles according to the first aspect, which may include the steps of:
(1) dissolving mercaptophenylboronic acid, chloroauric acid trihydrate, triethylamine and tween 80 in a methanol solution, and mixing in an ice-water bath until the mercaptophenylboronic acid, the chloroauric acid trihydrate, the triethylamine and the tween 80 are completely dissolved;
(2) dissolving sodium borohydride in methanol, and dropwise adding the solution into the mixed solution obtained in the step (1) to react;
(3) and (3) dialyzing and filtering and sterilizing the product obtained in the step (2) to obtain the gold nanoparticles.
The preparation method according to the second aspect of the present invention, wherein in the step (1), the molar ratio of the mercaptophenylboronic acid to the chloroauric acid trihydrate is 1:0.1 to 10, preferably 1: 1.
A third aspect of the invention provides an electrospun dressing, the dressing comprising:
is prepared from linear long-chain natural high-molecular substance and has weight-average molecular weight of 10 4 ～10 6 The electrostatic spinning film made of the high molecular polymer; and
the mercaptophenylboronic acid of the first aspect activates the gold nanoparticles.
According to the electrospun dressing of the third aspect of the invention, the high molecular polymer is selected from one or more of the following: polyethylene glycol, polylactic acid, polyvinyl alcohol, polycaprolactone, polylactic acid-glycolic acid copolymer; preferably polycaprolactone or polylactic acid-glycolic acid copolymer;
the natural high molecular substance is selected from one or more of the following substances: fibroin, chitosan, cellulose, gelatin and collagen; preferably gelatin or collagen.
A fourth aspect of the present invention provides a method of preparing the electrospun dressing of the third aspect, which may comprise the steps of:
(1) adding a high molecular polymer, a natural high molecular and the mercaptophenylboronic acid activated gold nanoparticles as claimed in claim 1 into a solvent, stirring to dissolve and uniformly mix the high molecular polymer, the natural high molecular and the gold nanoparticles, and preparing an electrostatic spinning precursor solution;
(2) and (2) sucking the electrostatic spinning precursor solution prepared in the step (1) into an injector fixed on a propulsion pump for electrostatic spinning, and performing vacuum drying to obtain the electrostatic spinning dressing.
The production method according to the fourth aspect of the present invention, wherein, in the step (1), the solvent is selected from one or more of: hexafluoroisopropanol, trichloromethane, acetone, N-dimethylformamide, formic acid, acetic acid, tetrahydrofuran and trifluoroacetic acid, preferably hexafluoroisopropanol;
the mass fraction of the solute in the precursor liquid is 5-20 mass percent, preferably 10 mass percent.
The production method according to the fourth aspect of the present invention, wherein, in the electrospinning process in the step (2): the propelling speed of the propelling pump is 0.8-1.5 ml/h, and the flow of the spinning solution is kept stable; the spinning nozzle is a flat needle head with the diameter of 0.2-0.6 mm and is connected with a positive electrode of 10-20 kilovolts of a high-voltage direct-current power supply; the distance between the spinning nozzle and the collecting electrode is 6-10 cm;
preferably, the rate of advancement is 1.2 ml/hour; a 0.4 mm flat needle head of a spinning nozzle; a high voltage power supply of 14 kv; the collection spacing was 8 cm.
A fifth aspect of the invention provides the use of the mercaptophenylboronic acid-activated gold nanoparticles according to the first aspect of the invention or the mercaptophenylboronic acid-activated gold nanoparticles prepared according to the method of the second aspect for preparing an antibacterial material.
A sixth aspect of the invention provides the use of the mercaptophenylboronic acid activated gold nanoparticles of the first aspect of the invention or the electrospun dressing of the third aspect of the invention in the manufacture of a medical device or a medical consumable; preferably, the medical device or medical consumable is used for clinical wound treatment, cosmetology, treatment of burns, scalds, decubitus infections.
The invention aims to provide a one-step synthesis method of an antibacterial agent of gold nanoparticles activated by mercaptophenylboronic acid, and a preparation method and application of the gold nanoparticle electrostatic spinning dressing activated by the mercaptophenylboronic acid. The gold nanoparticles exhibit potent antibacterial activity and excellent biosafety. Electrospun dressings incorporating gold nanoparticles resistant to multidrug-resistant bacteria exhibit healing potential for bacterial wound infection in animal skin infection models.
In order to realize the application of the ideal functional medical wound dressing, the invention designs and provides a one-step synthesis method of an antibacterial agent of gold nanoparticles activated by mercaptophenylboronic acid, and a preparation method and application of the gold nanoparticles electrospun dressing activated by the mercaptophenylboronic acid. The gold nanoparticles exhibit potent antibacterial activity and excellent biosafety. In the using process of the dressing, along with the degradation of gelatin, gold nanoparticles are gradually released from the electrospun fiber membrane, the slow-release effect is realized, multidrug-resistant bacteria can be effectively resisted, the healing capacity of bacterial wound infection is shown in an animal skin infection model, the dressing can be used for clinical wound treatment, beautifying, treatment of various wounds such as burn, scald, bedsore infection and the like, and the dressing is an extremely excellent medical dressing.
In order to design an ideal antibacterial nano material to realize preparation of functional medical wound dressing, the invention designs and provides a molecular activated gold nanoparticle antibacterial agent which is low in cost, good in biological safety and good in curative effect aiming at multidrug resistant bacteria, and gold nanoparticles are loaded through electrostatic spinning to develop a novel functional antibacterial dressing for treating skin infection. In this work, the inventor develops a one-step synthesis method to prepare the mercaptophenylboronic acid (MBA ortho-2 MBA, meta-3 MBA and para-4 MBA) surface functionalized activated gold nanoparticles to synthesize the functional antibacterial nano antibacterial agent, and the antibacterial nano antibacterial agent has good antibacterial effects on sensitive strains of gram-positive bacteria and clinically isolated multidrug-resistant strains. The mercapto phenylboronic acid contains functional groups of a boric acid group and a mercapto group, and the boric acid group can be combined with peptidoglycan on the surface of bacteria, so that the selectivity and the targeting property of the bacteria are improved; the sulfydryl can be stably combined with the nano-particles through gold-sulfur bonds, and ligand molecules are stably connected to the gold nano-particles. Gold nanoparticles activated by mercaptophenylboronic acid (Au _ MBA NPs) increase the permeability of cell membranes by destroying the cell walls of bacteria, so that bacteria die, but the gold nanoparticles show extremely high biological safety to mammalian cells, and the injection safety dose exceeds 200 times of the minimum inhibitory concentration. Electrospun dressings incorporating gold nanoparticles resistant to multidrug-resistant bacteria exhibit healing potential for bacterial wound infection in animal skin infection models.
In order to achieve the purpose, the invention adopts the following technical scheme:
according to the invention, micromolecule activated gold nanoparticles are provided as an antibacterial agent, wherein the micromolecules have derivatives of phenylboronic acid with higher biological safety, such as mercapto as a substituent on a benzene ring. The substituent positions are meta and para.
According to the one-step synthesis method of the gold nanoparticle antibacterial agent activated by the mercaptophenylboronic acid, provided by the invention, the ratio of the chloroauric acid to the mercaptophenylboronic acid during synthesis of the gold nanoparticles is 1:5-5:1 (namely, the molar mass ratio). Preferably, the gold nanoparticles having an antibacterial effect have an average particle diameter of 50nm or less. More preferably 1-5 nm. The gold nanoparticles activated by the mercaptophenylboronic acid prepared by the method have excellent antibacterial property, can resist multidrug-resistant bacteria, has extremely high biological safety to mammalian cells, and has the injection safety dose more than 200 times of the minimum antibacterial concentration.
According to the antibacterial electrostatic spinning dressing containing the gold nanoparticles activated by the mercaptophenylboronic acid, provided by the invention, the electrospinning precursor liquid is high polymer PCL and PLGA; the natural polymer is selected from gelatin and collagen. Preferably, the mass fraction of the precursor liquid is 5 to 20 mass% (i.e., mass percentage). More preferably, the electrospinning precursor solution is a mixture of 10 mass% of PCL and gelatin.
The invention also provides a preparation method of the electrostatic spinning gold nanoparticle antibacterial dressing loaded with mercaptophenylboronic acid activated, wherein the propelling speed of a propelling pump is 0.8-1.5 ml/h, and the flow of a spinning solution is kept stable; the spinning nozzle is a flat needle head with the diameter of 0.2-0.6 mm and is connected with a high-voltage direct-current power supply 10-20 kV positive electrode; the distance between the spinning nozzle and the collecting electrode is 6-10 cm. Preferably, the rate of advancement is 1.2 ml/hour; a 0.4 mm flat needle head of a spinning nozzle; a high voltage power supply of 14 kv; the collection spacing was 8 cm.
The gold nanoparticles activated by the supported mercaptophenylboronic acid are further used for developing novel functional antibacterial dressings through electrostatic spinning. Electrospun materials include: 1. high polymers: polyethylene glycol (PEG), polylactic acid (PLA), polyvinyl alcohol (PVA), Polycaprolactone (PCL), polylactic-co-glycolic acid (PLGA), and the like; 2. natural polymers: fibroin, chitosan, cellulose, gelatin, collagen, etc. The high polymer with good biocompatibility and the natural polymer are used for electrostatic spinning, and the mechanical property of the high polymer is perfectly combined with the biological property of the natural polymer. The composite fiber membrane prepared by electrostatic spinning has a porous microstructure, and the structure similar to extracellular matrix is beneficial to adhesion and migration of cells, and can promote wound healing while realizing antibiosis as an antibacterial skin dressing. The schematic diagram of the design of the present invention is shown in fig. 1. Adding gold nanoparticles activated by mercaptophenylboronic acid into spinning precursor solution to prepare the antibacterial dressing loaded with the antibacterial particles. In the using process, along with the degradation of spinning, the antibacterial particles are gradually released from the electrospun fiber membrane, so that the slow release effect is realized. The feasibility of the antibacterial nanofiber membrane in treating skin infection wounds is further verified through a skin wound infection model.
The antibacterial dressing of the gold nanoparticles activated by the electrostatic spinning load mercaptophenylboronic acid prepared by the invention has good hydrophilicity, the biodegradable material is selected, and the composite nanofiber membrane shows that the quality loss is caused by slow linear hydrolysis of gelatin in the fiber in the first two weeks and simultaneously releases the loaded antibacterial gold nanoparticles; by testing the infrared absorption peaks before and after the electro-spinning composite nanofiber membrane loads the gold nanoparticles, no new absorption peak appears, which indicates that the doping of the gold nanoparticles has no obvious influence on the chemical composition of the polymer matrix, a tensile testing machine is used for testing the mechanical performance of the electro-spinning fiber membrane, and the breaking elongation of the fiber membrane exceeds 6%, so that the requirement of supporting attachment as a tissue regeneration material is met.
The electrostatic spinning gold nanoparticle-loaded antibacterial dressing activated by mercaptophenylboronic acid has excellent biocompatibility, can resist multidrug-resistant bacteria, avoids secondary damage caused by dressing change through slow degradation of natural components in the dressing, slowly releases the antibacterial gold nanoparticles during degradation, realizes long-acting treatment, can be used for clinical wound treatment and beauty treatment, and can be used for treating various wound infections such as burns, scalds and bedsore infection, and is an extremely excellent medical dressing.
The mercaptophenylboronic acid activated gold nanoparticles of the present invention may have the following beneficial effects, but are not limited to:
1. the preparation method of the gold nanoparticles activated by the mercaptophenylboronic acid is simple, the bacteria can not be induced to generate drug resistance, and the antibacterial effect on sensitive strains and multi-drug resistant strains of gram-positive bacteria is obvious;
2. the phenylboronic acid and the derivatives thereof can be used as intermediates for drug synthesis, and have high biological safety when used for activating gold nanoparticles;
3. the antibacterial fiber membrane prepared by the electrostatic spinning method has stable physical and chemical properties and high porosity, can isolate pollutants, is soft and breathable, has good wettability, can be perfectly attached to wounds with different shapes, is prepared by degradable materials, and reduces secondary damage caused by dressing change;
4. the gold nanoparticles activated by the mercaptophenylboronic acid are stable and easy to store, and have high stability, large-scale production potential and wide clinical application prospect after being prepared into the dressing by the electrostatic spinning technology.
Drawings
Embodiments of the invention are described in detail below with reference to the attached drawing figures, wherein:
FIG. 1 shows a schematic diagram of the synthesis of gold nano antibacterial particles activated by mercaptophenylboronic acid and the preparation of antibacterial dressing by electrostatic spinning.
Figure 2 shows the morphological characterization of the mercaptophenylboronic acid-modified gold nanoparticles prepared in examples 1 and 2. FIG. 2A) m-mercaptophenylboronic acid modified gold nanoparticles and B) p-mercaptophenylboronic acid modified gold nanoparticles transmission electron microscopy pictures, C) average diameters and surface charge statistics of m-mercaptophenylboronic acid and p-mercaptophenylboronic acid and their modified gold nanoparticles.
Fig. 3 shows the antibacterial performance characterization of the gold nanoparticles modified with mercaptophenylboronic acid prepared in examples 1 and 2. Fig. 3A) minimum inhibitory concentrations of m-and p-mercaptophenylboronic acid-modified gold nanoparticles; the bacterial turbidity value of the coculture of m-mercaptophenylboronic acid, p-mercaptophenylboronic acid and gold nanoparticles modified by the m-mercaptophenylboronic acid, and penicillin-resistant and staphylococcus aureus-resistant B) sensitive strains (S.a.), C) multidrug-resistant strains (MDR S.a.), D) sensitive strains (S.e.) and E) multidrug-resistant strains (MDR S.e.) is changed.
Fig. 4 shows the antibacterial mechanism characterization of the gold nanoparticles modified with mercaptophenylboronic acid prepared in examples 1 and 2. FIG. 4 is a scanning electron microscope image of the destruction of bacterial cell walls of a) sensitive strain of Staphylococcus aureus by m-mercaptophenylboronic acid-modified gold nanoparticles and p-mercaptophenylboronic acid-modified gold nanoparticles and B) multidrug resistant strain; and D) transmission electron microscope pictures of the gold nanoparticles modified by m-mercaptophenylboronic acid and the gold nanoparticles modified by p-mercaptophenylboronic acid on the bacterial cell wall destruction of C) sensitive strains and D) multidrug resistant strains of staphylococcus aureus.
Figure 5 shows the biosafety characterization of the mercaptophenylboronic acid-modified gold nanoparticles prepared in examples 1 and 2. FIG. 5A) different concentrations of m-mercaptophenylboronic acid modified gold nanoparticles and B) different concentrations of p-mercaptophenylboronic acid modified gold nanoparticles are incubated with red blood cells respectively for hemolysis and 540nm absorbance change, and normal saline and water are negative control and positive control respectively; C) the gold nanoparticles modified by m-mercaptophenylboronic acid and the gold nanoparticles modified by p-mercaptophenylboronic acid are subjected to cell morphological change in co-culture with human umbilical vein endothelial cells (HUVCE) and human aortic fibroblast cells (HAF).
Fig. 6 shows the properties of the polymer nanofiber membranes prepared in examples 1 and 5 and the slow release effect characterization of the supported gold nanoparticles. FIG. 6A) photomicrograph of electrospun PG and PGA fiber membranes and B) scanning electron microscope images; C) the contact angle of the liquid drop on the surface of different materials changes along with time; D) fourier transform infrared spectroscopy of electrospun gelatin, PCL, PG and PGA fiber membranes; E) residual weight change of the electrostatic spinning PGA fiber membrane along with time and accumulated release of gold nanoparticles; F) stress-strain curves of electrospun PG and PGA fiber membranes.
Fig. 7 shows the results of animal experiments on the polymer nanofiber membranes prepared in examples 1 and 5.
Detailed Description
The invention is further illustrated by the following specific examples, which, however, are to be construed as merely illustrative, and not limitative of the remainder of the disclosure in any way whatsoever.
This section generally describes the materials used in the testing of the present invention, as well as the testing methods. Although many materials and methods of operation are known in the art for the purpose of carrying out the invention, the invention is nevertheless described herein in as detail as possible. It will be apparent to those skilled in the art that the materials and methods of operation used in the present invention are well within the skill of the art, provided that they are not specifically illustrated.
The reagents and instrumentation used in the following examples are as follows: reagent:
triethylamine, tween 80, methanol, sodium borohydride, purchased from sigma;
chloroauric acid trihydrate, available from national pharmaceutical group chemical reagents, ltd;
p-mercaptophenylboronic acid, m-mercaptophenylboronic acid, polycaprolactone, gelatin, hexafluoroisopropanol, available from sigma;
filters, available from Millipore corporation;
dialysis bags (14kDa MW cut-off, Solarbio), liquid LB medium, purchased from Beijing Soilebao technologies, Inc.;
sensitive and multidrug resistant strains of staphylococcus aureus (S.a.) and staphylococcus epidermidis (S.e.) were purchased from beijing youan hospital;
human Umbilical Vein Endothelium (HUVEC) and Human Aortic Fibroblast (HAF) were purchased from Changsheng biotechnology, LLC of Beijing ancient cooking.
The instrument comprises the following steps:
transmission Electron microscope, FEI company, USA, model Tecnai G220S-TWIN;
zeta potentiometers, available from Malvern Company, England; model Zetasizer Nano ZS;
an enzyme-linked immunosorbent assay (ELIASA) available from TECAN group of Switzerland, model Tecan infinite M200;
a rotary evaporator, available from central plant import & export of Hunan, type IKA RV10, Germany;
scanning electron microscope, available from Hitachi, Japan, model No. Hitachi S4800+ EDS;
a fully automatic contact angle tester, available from KRUSS, germany, model DSA 100;
a Fourier transform infrared spectrometer, available from Perkin Elmer instruments Inc. model FT-IR Spectrum One;
tensile tester, available from Instron5567, Instron, usa;
example 1
The device designed by the invention is shown in figure 1. This example is used to illustrate the preparation method and performance characterization of gold nanoparticles activated with p-mercaptophenylboronic acid.
(1) In a round-bottomed flask, 0.05 mmol of p-mercaptophenylboronic acid (4MBA molecular weight 153.99, Sigma), 0.05 mmol of chloroauric acid trihydrate (molecular weight 393.83, national pharmaceutical group chemical Co., Ltd.), 50. mu.L of triethylamine and 30 mg of Tween 80 were dissolved in 10 ml of methanol solution and mixed in an ice-water bath for 10 minutes until the molecule was completely dissolved.
(2) 6 mg of sodium borohydride were dissolved in 2 ml of methanol and added dropwise to the round-bottomed flask with vigorous stirring (1000 rpm), the solution in the flask immediately turned brown in color and the reaction was maintained for a further 2 hours.
(3) The obtained p-mercaptophenylboronic acid-activated gold nanoparticles were dialyzed with a dialysis bag (14kDa MW cut-off, Solarbio) for 24 hours to remove untreated chemicals. The nanoparticles were filter sterilized through a 0.22 micron filter (Millipore) and stored in a 4 ℃ freezer for use. Morphology characterization of the mercaptophenylboronic acid-activated gold particles was performed by transmission electron microscopy (TEM, Tecnai G220S-TWIN, FEI company, USA) and observed as shown in FIG. 2A with an average diameter of 2.1nm and a particle size range of 1-5 nm. The Dynamic Light Scattering (DLS) and Zeta potentials of the samples are shown in FIG. 2C by the Zetasizer Nano ZS (Malvern Company, England) test results.
(4) Sensitive strains of staphylococcus aureus (S.a.) and staphylococcus epidermidis (S.e.) and multidrug-resistant strains are cultured in liquid LB culture medium, and the inoculation concentration is 1 × 10 4 CFU/mL. The gold nanoparticles were diluted 2-128 times and added to the culture medium inoculated with the bacteria, respectively, and the Minimum Inhibitory Concentration (MIC) of the bacteria after 24 hours of culture at 37 ℃ was recorded, with the results shown in fig. 3A. And turbidity at 600nm (OD) by testing bacterial suspension 600nm ) The antibacterial activity of the gold nanoparticles was analyzed by the optical density of (2), and compared with penicillin, the antibacterial effect of the gold nanoparticles was more effective in treating multidrug-resistant bacteria, and the results are shown in fig. 3B-E. To further explore the antibiotic mechanism of gold nanoparticles, the inventors oscillated bacteria with different concentrations of gold nanoparticles on a shaker at 260 rpm for 4 hours. The bacteria were centrifuged, fixed, dehydrated, and sliced into ultrathin sections, which were observed by scanning and transmission electron microscopy, and the results are shown in FIGS. 4A-D.
(5) For further clinical applications, the inventors measured the samples at 540nm (OD) by a microplate reader (Tecan infinite M200) 540nm ) The hemolysis performance of gold nanoparticles at different concentrations was tested by human optical density using saline as a negative control and water as a positive control, and the results are shown in fig. 5B. The cytotoxicity of Human Umbilical Vein Endothelial Cells (HUVEC) and Human Aortic Fibroblasts (HAF) in vitro was evaluated by testing their viability under gold nanoparticle treatment, and the results are shown in fig. 5C.
(6) The solvent in the obtained 10 ml p-mercaptophenylboronic acid-activated gold nanoparticles was removed by a rotary evaporator (IKA RV10, germany) at 40 ℃, redissolved in 5.0 ml hexafluoroisopropanol (1,1,1,2,2,2-Hexafluoro-2-propanol, HFIP, Sigma) and mixed well with 0.75 g polycaprolactone (PCL, molecular weight 45000, Sigma) and 0.25 g gelatin (gelatin, type a powder from porcine skin, Sigma), stirred with a magnetic stirrer for 2 hours at normal temperature to prepare a spinning precursor solution.
(7) Sucking the prepared electrostatic spinning precursor solution into an injector fixed on a propelling pump, wherein the optimal spinning parameters are as follows: the diameter of the spinning nozzle is 0.4 mm, the high-voltage direct-current power supply is 14 kilovolts, and the advancing speed of the distance between the spinning nozzle and the collecting electrode is 8 centimeters and is 1.2 milliliters per hour. After 2 hours, the PCL/gelatin composite fiber membrane (PGA) loaded with the antibacterial gold particles can be obtained. The obtained nanofiber membrane was dried in a vacuum dryer for 24 hours to remove the organic solvent that was not completely volatilized. The results of the macroscopic photograph and the observation under a scanning electron microscope of the fiber membrane are shown in FIGS. 6A-B.
(8) The surface wettability of the electrospun nanofiber membrane was evaluated by a static contact angle tester, and the results are shown in fig. 6C, except for the electrospun fiber membrane of PCL, which was hydrophilic and had a contact angle of PCL of 120 degrees. By testing the infrared absorption peaks before and after the gold nanoparticles are loaded on the electrospun composite nanofiber membrane, a new absorption peak is not generated as shown in fig. 6D, which indicates that the doping of the gold nanoparticles has no significant influence on the chemical composition of the polymer matrix. The quality of the spun dry film after being dried by soaking for different time and the content of gold in the soaking liquid were compared to characterize the degradation and release performance of the film, and the results are shown in fig. 6E. The mechanical properties of the electrospun fiber membrane were tested using a tensile tester, and as a result, as shown in fig. 6F, the elongation at break of the fiber membrane exceeded 6%, which has satisfied the requirement of being a support attachment for tissue regeneration material.
(9) The fibrous membrane of this example had antibacterial effect in the skin infection model of SD rats. Four round wounds of 2.0 cm diameter were constructed on the back of each mouse in three groups (n-3), group 1 (gauze group for medical use); group 2 (blank spinning fiber film group); group 3 (gold particle loaded spinning fiber membrane group). The result is shown in fig. 4A, after 10 days after the operation, the size of the wound treated by the gold particle-loaded electrospun fiber membrane is obviously smaller than that of the wound treated by the medical gauze group and the blank spun fiber membrane group, which indicates that the incorporation of the gold nanoparticles has an effective bactericidal effect on the infection of the multi-drug resistant bacteria wound and can achieve better wound healing.
Example 2
This example is used to illustrate the preparation method and performance characterization of m-mercaptophenylboronic acid activated gold nanoparticles.
The method comprises the following steps:
(1) in a round-bottomed flask, 0.05 mmol of m-mercaptophenylboronic acid (3MBA molecular weight 153.99, Sigma), 0.05 mmol of chloroauric acid trihydrate (molecular weight 393.83, national pharmaceutical group chemical Co., Ltd.), 50. mu.l of triethylamine and 30 mg of Tween 80 were dissolved in 10 ml of methanol solution and mixed in an ice-water bath for 10 minutes until the molecule was completely dissolved.
(2) The synthesis of m-mercaptophenylboronic acid modified gold nanoparticles was the same as in example 1, with the results shown in FIGS. 2B-C, the average diameter was 1.8nm, and the particle size range was 1-5 nm.
(3) The antibacterial performance and the antibacterial mechanism characterization of the gold nanoparticles modified by m-mercaptophenylboronic acid are the same as those in example 1, and the results are shown in fig. 3A-E and fig. 4A-D.
(4) The biological safety characterization of the gold nanoparticles modified by m-mercaptophenylboronic acid is the same as that of example 1, and the results are shown in fig. 5A and C.
(5) The spinning stock parameters were the same as in example 1.
Example 3
The method comprises the following steps:
(1) the synthesis and characterization of the gold nanoparticles modified by p-mercaptophenylboronic acid were the same as in example 1.
(2) The solvent in the obtained 10 ml of p-mercaptophenylboronic acid-activated gold nanoparticles was removed by a rotary evaporator (IKA RV10, germany) at 40 ℃, redissolved in 5.0 ml of hexafluoroisopropanol (1,1,1,2,2,2-Hexafluoro-2-propanol, HFIP, Sigma), and mixed well with 1.0 g of polylactic-glycolic acid copolymer (PLGA, 50/50, Sigma) and 0.5 g of gelatin (gelatin, powder type a, from porcine skin, Sigma), and stirred with a magnetic stirrer at normal temperature for 2 hours to prepare a spinning precursor solution.
(3) The antibacterial composite fiber membrane performance characterization is the same as that of example 1.
Example 4
The method comprises the following steps:
(1) the synthesis and characterization of the gold nanoparticles modified by m-mercaptophenylboronic acid were the same as in example 2.
(2) The solvent in the obtained 10 ml of p-mercaptophenylboronic acid-activated gold nanoparticles was removed by a rotary evaporator (IKA RV10, germany) at 40 ℃, redissolved in 5.0 ml of hexafluoroisopropanol (1,1,1,2,2,2-Hexafluoro-2-propanol, HFIP, Sigma), and mixed well with 1.2 g of polylactic-co-glycolic acid (PLGA, 50/50, Sigma) and 0.3 g of collagen (type I, Sigma), and stirred with a magnetic stirrer at room temperature for 2 hours to prepare a spinning precursor solution.
(3) The antibacterial composite fiber membrane performance characterization is the same as that of example 1.
Example 5
This example is a blank control of example 1.
The method comprises the following steps:
(1) in an erlenmeyer flask, 0.75 g of PCL and 0.25 g of gelatin are added into 10 ml of hexafluoroisopropanol, and stirred for 2 hours at normal temperature by a magnetic stirrer, so that the PCL, the gelatin and the inhibitor are dissolved and uniformly mixed in HFIP to prepare a transparent spinning precursor solution.
(2) The spinning process was the same as in example 1.
(3) The performance characterization of the PCL/gelatin composite fiber membrane (PG) was the same as in example 1, and the results are shown in fig. 6.
(4) The animal experiments were the same as in example 1.
Although the present invention has been described to a certain degree, it will be apparent that various modifications may be made without departing from the spirit and scope of the invention. It is to be understood that the invention is not limited to the described embodiments, but is to be accorded the scope consistent with the claims, including equivalents of each element described.
Claims (21)
1. An electrospun dressing, said dressing comprising:
is prepared from linear long-chain natural high-molecular substance with weight average molecular weight of 10 4 ～10 6 The high molecular polymer and the mercapto phenylboronic acid activate gold nano particles to prepare an electrostatic spinning membrane; wherein,
the average particle size of the gold nanoparticles is 1-50 nm.
2. The electrospun dressing of claim 1 wherein the mercaptophenylboronic acid is p-mercaptophenylboronic acid or m-mercaptophenylboronic acid.
3. The electrospun dressing of claim 2, wherein the gold nanoparticles have an average particle size of 1 to 10 nm.
4. The electrospun dressing of claim 3, wherein the gold nanoparticles have an average particle size of 1 to 5 nm.
5. The electrospun dressing of any one of claims 1 to 4, wherein said high molecular polymer is selected from one or more of the following: polyethylene glycol, polylactic acid, polyvinyl alcohol, polycaprolactone, polylactic acid-glycolic acid copolymer;
the natural high molecular substance is selected from one or more of the following substances: fibroin, chitosan, cellulose, gelatin and collagen.
6. The electrospun dressing of claim 5,
the high molecular polymer is polycaprolactone or polylactic acid-glycolic acid copolymer;
the natural polymer is gelatin or collagen.
7. The method of preparing an electrospun dressing according to any one of claims 1 to 6, characterized in that the method comprises the steps of:
(1) adding a high molecular polymer, a natural polymer and mercaptophenylboronic acid activated gold nanoparticles into a solvent, stirring to dissolve and uniformly mix the high molecular polymer, the natural polymer and the gold nanoparticles, and preparing an electrostatic spinning precursor solution;
(2) and (2) sucking the electrostatic spinning precursor solution prepared in the step (1) into an injector fixed on a propulsion pump for electrostatic spinning, and performing vacuum drying to obtain the electrostatic spinning dressing.
8. The method according to claim 7, wherein in the step (1), the method for preparing the mercaptophenylboronic acid-activated gold nanoparticles comprises the following steps:
(a) dissolving mercaptophenylboronic acid, chloroauric acid trihydrate, triethylamine and tween 80 in a methanol solution, and mixing in an ice-water bath until the mercaptophenylboronic acid, the chloroauric acid trihydrate, the triethylamine and the tween 80 are completely dissolved;
(b) dissolving sodium borohydride in methanol, and dropwise adding the solution into the mixed solution obtained in the step (a) to react;
(c) and (c) dialyzing and filtering and sterilizing the product obtained in the step (b) to obtain the gold nanoparticles.
9. The method according to claim 8, wherein in the step (a), the molar ratio of the mercaptophenylboronic acid to the chloroauric acid trihydrate is 1: 0.1-10.
10. The method of claim 9, wherein in step (a), the molar ratio of mercaptophenylboronic acid to chloroauric acid trihydrate is 1: 1.
11. The method according to claim 7, wherein in the step (1), the solvent is selected from one or more of the following: hexafluoroisopropanol, chloroform, acetone, N-dimethylformamide, formic acid, acetic acid, tetrahydrofuran and trifluoroacetic acid;
the mass fraction of solute in the electrostatic spinning precursor solution is 5-20 mass percent.
12. The method according to claim 11, wherein in the step (1), the solvent is hexafluoroisopropanol;
the mass fraction of solute in the electrostatic spinning precursor solution is 10 mass percent.
13. The method according to claim 7, wherein in the electrospinning process in the step (2): the propelling speed of the propelling pump is 0.8-1.5 ml/h, and the flow of the spinning solution is kept stable; the spinning nozzle is a flat needle head with the diameter of 0.2-0.6 mm and is connected with a positive electrode of 10-20 kilovolts of a high-voltage direct-current power supply; the distance between the spinning nozzle and the collecting electrode is 6-10 cm.
14. The method of claim 13, wherein the rate of advancement is 1.2 ml/hour; a 0.4 mm flat needle head of a spinning nozzle; a high voltage power supply of 14 kv; the collection spacing was 8 cm.
15. Use of an electrospun dressing according to any one of claims 1 to 6 or produced according to the process of any one of claims 7 to 14 for the production of an antibacterial material.
16. Use of an electrospun dressing according to any one of claims 1 to 6 or prepared according to the method of any one of claims 7 to 14 for the manufacture of a medical device.
17. Use of an electrospun dressing according to any one of claims 1 to 6 or prepared according to the method of any one of claims 7 to 14 in the manufacture of a medical consumable.
18. Use according to claim 16, wherein the medical device is for clinical wound treatment or cosmetology.
19. The use of claim 16, wherein the medical device is for treating a burn, scald, or decubitus infection.
20. Use according to claim 17, wherein the medical consumable is for clinical wound treatment or cosmetology.
21. Use according to claim 17, wherein the medical consumable is for the treatment of burns, scalds or decubitus infections.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810255084.1A CN110292652B (en) | 2018-03-23 | 2018-03-23 | Mercaptobenzeneboronic acid activated gold nanoparticles as well as preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810255084.1A CN110292652B (en) | 2018-03-23 | 2018-03-23 | Mercaptobenzeneboronic acid activated gold nanoparticles as well as preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN110292652A CN110292652A (en) | 2019-10-01 |
| CN110292652B true CN110292652B (en) | 2022-08-12 |
Family
ID=68026232
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810255084.1A Active CN110292652B (en) | 2018-03-23 | 2018-03-23 | Mercaptobenzeneboronic acid activated gold nanoparticles as well as preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN110292652B (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111020871A (en) * | 2019-12-31 | 2020-04-17 | 苏州卫生职业技术学院 | Nanofiber membrane for enzyme immobilization and preparation method thereof |
| CN111793900A (en) * | 2020-06-15 | 2020-10-20 | 中国人民解放军陆军特色医学中心 | Chitosan/polycaprolactone composite nanofiber membrane material and application thereof |
| CN113412841A (en) * | 2021-06-18 | 2021-09-21 | 国家纳米科学中心 | Modified nano zinc oxide material, preparation method and application |
| CN114177198B (en) * | 2021-10-29 | 2023-06-23 | 广东粤港澳大湾区国家纳米科技创新研究院 | Nano gold antibacterial agent and preparation method and application thereof |
| CN114113592B (en) * | 2021-11-22 | 2023-01-31 | 中国药科大学 | Lateral flow chromatography test paper based on mercaptophenylboronic acid functionalized gold nanoparticles and detection method thereof |
| CN114887121B (en) * | 2022-04-14 | 2023-04-07 | 广东粤港澳大湾区国家纳米科技创新研究院 | Colloidal fluid of artesunate-nanogold compound, preparation method thereof and antibacterial product |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102908653A (en) * | 2012-11-09 | 2013-02-06 | 无锡中科光远生物材料有限公司 | Preparation method of antiseptic dressing for deep infection wound |
| JP2014234349A (en) * | 2013-05-31 | 2014-12-15 | パナソニック株式会社 | Boronic acid compound and sensor |
| CN106139224A (en) * | 2016-07-20 | 2016-11-23 | 国家纳米科学中心 | A kind of containing nanometer gold antiseptic dressing and preparation method thereof |
| CN107602901A (en) * | 2017-08-25 | 2018-01-19 | 中国科学院理化技术研究所杭州研究院 | Antibiont coating material of high density grafting acidic group catalysis bacteria lysis and its preparation method and application |
| CN107722336A (en) * | 2017-10-18 | 2018-02-23 | 德清舒华泡沫座椅有限公司 | The antibacterial sponge and its preparation technology of a kind of environment-friendly degradable |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7368085B2 (en) * | 2003-12-04 | 2008-05-06 | Honeywell International Inc. | Analyte detector |
| CN102453968B (en) * | 2010-11-03 | 2016-01-20 | 广东百合医疗科技股份有限公司 | Containing antibiotic fiber, the fabric and wound dressing and preparation method thereof of nano metal |
| CN103674925B (en) * | 2012-09-14 | 2016-08-10 | 北京大学 | 4-mercaptophenyl boronic acid modify golden nanometer particle and with its detection cell surface sugar labelling method |
| CN107412780B (en) * | 2016-05-23 | 2022-04-15 | 国家纳米科学中心 | Antibacterial agent based on gold nanoparticle surface modified nitrogen heterocyclic micromolecules |
| CN106178079A (en) * | 2016-07-20 | 2016-12-07 | 国家纳米科学中心 | A kind of antibacterial chitosan dressing containing nanometer gold and preparation method thereof |
-
2018
- 2018-03-23 CN CN201810255084.1A patent/CN110292652B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102908653A (en) * | 2012-11-09 | 2013-02-06 | 无锡中科光远生物材料有限公司 | Preparation method of antiseptic dressing for deep infection wound |
| JP2014234349A (en) * | 2013-05-31 | 2014-12-15 | パナソニック株式会社 | Boronic acid compound and sensor |
| CN106139224A (en) * | 2016-07-20 | 2016-11-23 | 国家纳米科学中心 | A kind of containing nanometer gold antiseptic dressing and preparation method thereof |
| CN107602901A (en) * | 2017-08-25 | 2018-01-19 | 中国科学院理化技术研究所杭州研究院 | Antibiont coating material of high density grafting acidic group catalysis bacteria lysis and its preparation method and application |
| CN107722336A (en) * | 2017-10-18 | 2018-02-23 | 德清舒华泡沫座椅有限公司 | The antibacterial sponge and its preparation technology of a kind of environment-friendly degradable |
Non-Patent Citations (2)
| Title |
|---|
| 4-mercaptophenylboronic acid functionalized gold nanoparticles for colorimetric sialic acid detection;Supannee Sankoh等;《Biosensors and Bioelectronics》;20160526;第85卷;第743-750页 * |
| 硼酸化柔性抗菌海绵的制备及其性能研究;李学超等;《纤维素科学与技术》;20170223(第01期);第50-57页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN110292652A (en) | 2019-10-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN110292652B (en) | Mercaptobenzeneboronic acid activated gold nanoparticles as well as preparation method and application thereof | |
| Ali et al. | Antibacterial bi-layered polyvinyl alcohol (PVA)-chitosan blend nanofibrous mat loaded with Azadirachta indica (neem) extract | |
| He et al. | Anti-oxidant electroactive and antibacterial nanofibrous wound dressings based on poly (ε-caprolactone)/quaternized chitosan-graft-polyaniline for full-thickness skin wound healing | |
| Darbasizadeh et al. | Crosslinked-polyvinyl alcohol-carboxymethyl cellulose/ZnO nanocomposite fibrous mats containing erythromycin (PVA-CMC/ZnO-EM): Fabrication, characterization and in-vitro release and anti-bacterial properties | |
| Malmir et al. | Antibacterial properties of a bacterial cellulose CQD-TiO2 nanocomposite | |
| Fahimirad et al. | Naturally-derived electrospun wound dressings for target delivery of bio-active agents | |
| Chen et al. | Recent advances in electrospun nanofibers for wound dressing | |
| Muthukrishnan | An overview on electrospinning and its advancement toward hard and soft tissue engineering applications | |
| Yousefi et al. | An investigation of electrospun Henna leaves extract-loaded chitosan based nanofibrous mats for skin tissue engineering | |
| Cui et al. | Optimizing the chitosan-PCL based membranes with random/aligned fiber structure for controlled ciprofloxacin delivery and wound healing | |
| Konwarh et al. | Electrospun cellulose acetate nanofibers: the present status and gamut of biotechnological applications | |
| Zhou et al. | Quaternized chitin/tannic acid bilayers layer-by-layer deposited poly (lactic acid)/polyurethane nanofibrous mats decorated with photoresponsive complex and silver nanoparticles for antibacterial activity | |
| Mary et al. | Centrifugal spun ultrafine fibrous web as a potential drug delivery vehicle | |
| Sedghi et al. | Electrospun biocompatible core/shell polymer-free core structure nanofibers with superior antimicrobial potency against multi drug resistance organisms | |
| Safdari et al. | Preparation and characterization of Ceftazidime loaded electrospun silk fibroin/gelatin mat for wound dressing | |
| Chen et al. | Preparation and application of chitosan-based medical electrospun nanofibers | |
| CN105908363B (en) | A kind of electrostatic spraying laminated film and preparation method and application | |
| Wei et al. | The multifunctional wound dressing with core–shell structured fibers prepared by coaxial electrospinning | |
| Khan | Applications of electrospun nanofibers in the biomedical field | |
| Shakiba et al. | Development of an antibacterial and antioxidative nanofibrous membrane using curcumin-loaded halloysite nanotubes for smart wound healing: In vitro and in vivo studies | |
| Patel et al. | A review on electrospun nanofibers for multiple biomedical applications | |
| Liu et al. | Antibacterial activity and drug loading of moxifloxacin-loaded poly (vinyl alcohol)/chitosan electrospun nanofibers | |
| de Lima et al. | Electrospinning of hydrogels for biomedical applications | |
| Foroozandeh et al. | Electrospun nylon 6/hyaluronic acid/chitosan bioactive nanofibrous composite as a potential antibacterial wound dressing | |
| Al-Musawi et al. | Electrospun Polyvinylpyrrolidone/Soy protein nanofibers enriched with curcumin-loaded ZIF-8 nanoparticles: Synthesis and evaluation for wound healing application |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |