CN106928133A - A kind of switching mode bivalent cupric ion fluorescence probe and its preparation and application - Google Patents
A kind of switching mode bivalent cupric ion fluorescence probe and its preparation and application Download PDFInfo
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- CN106928133A CN106928133A CN201710177791.9A CN201710177791A CN106928133A CN 106928133 A CN106928133 A CN 106928133A CN 201710177791 A CN201710177791 A CN 201710177791A CN 106928133 A CN106928133 A CN 106928133A
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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Abstract
The present invention relates to a kind of preparation and application of switching mode bivalent cupric ion fluorescence probe, the fluorescence probe, its molecular formula is C17H11NO3；The preparation of the fluorescence probe has including step：The methoxynaphthalene of (1) 6 acetyl group 2 obtains the hydroxyl naphthalene of 6 acetyl group 2, i.e. compound 1 with triethylamine react, and the reaction of the pyridine carboxylic acid of compound 1 and 2 is obtained the picolyl naphthalene of 6 acetyl of target product 2 by (2)；The application of the fluorescence probe, is that fluorescence probe is reacted with bivalent cupric ion, and the presence or absence of bivalent cupric ion is detected using the color change and change in fluorescence of reaction solution.The synthesis of probe of the present invention only needs to two steps can just be completed, and last handling process is relatively easy.Fluorescent probe molecule of the present invention shows selectivity and sensitivity higher in bivalent cupric ion and other cations coexist system.
Description
Technical field
The invention belongs to detection of heavy metal ion technical field, and in particular to be a kind of switching mode bivalent cupric ion fluorescence
Probe and preparation method thereof.
Background technology
Cu2+As the 3rd abundant transition metal ions, in various physiological processes, such as generation of energy and signal transduction
Process plays vital effect.But the copper ion of excess may cause nerve degenerative diseases, including Parkinson and old
Dementia disease etc..With industry and the development of agricultural, Cu2+Have become a kind of important metal pollutant.Therefore, organism and
The detecting and tracking of copper ion seems increasingly important in environment.
The method for determining copper ion at present is mainly atomic absorption spectrography (AAS), Atomic absorption and AAS, but preceding
Person needs complicated instrument and those skilled in the art and high testing cost, and the latter needs cumbersome operation, and these are not
It is applicable analysis in real-time volume.Compared to the above, fluorescence probe sensitivity is high, the response time is short, low cost and equipment are simple
The advantages of, cause increasing concern.But due to Cu2+Paramagnetic properties, based on coordination the usual table of fluorescence probe
Reveal fluorescent quenching and then spurious results occur.Temperature is needed when the fluorescence probe based on irreversible chemical reaction is detected simultaneously
It is high, time-consuming and the condition such as non-physiological pH.Therefore, in the urgent need to developmental research is quickly and efficiently examined under normal temperature and physiological condition
Survey Cu2+Novel fluorescence probe.
6- acetyl group -2- methylaminos naphthalene is because with typical " push-and-pull " structure, showing excellent optical property.Supplied for electronic
Methylamino on hydroxyl the position of substitution 2, that is, generate 6- acetyl group -2 hydroxy naphthalene, and its " push-and-pull " structure is not changed.When hydroxyl is inhaled
After electron group 2- picolinoyls are protected, the optical property that " pushing away " structure of 6- acetyl group -2 hydroxy naphthalene shows
Will reduce, fluorescent quenching be produced, while picolinic acid group is easy to by Cu2+Hydrolysis.Therefore, bivalent cupric ion of the invention
Probe is using 6- acetyl group -2 hydroxy naphthalene as fluorescent reporter group, using picolyl as the switching mode fluorescence of recognition unit
Probe.Through retrieval without the discovery document close with the application and patent application.
The content of the invention
The purpose of the present invention is directed to the deficiencies in the prior art, by MOLECULE DESIGN, synthesizes a kind of with the response time
Switching mode Cu short and compared with high selectivity2+Fluorescence probe.
Present invention also offers the preparation method of above-mentioned bivalent cupric ion fluorescence probe.
Present invention also offers the application of above-mentioned bivalent cupric ion fluorescence probe.
The present invention solves its technical problem and takes following technical scheme to realize：
A kind of switching mode bivalent cupric ion fluorescence probe, its molecular formula is C17H11NO3, structural formula is as follows：
A kind of preparation method of bivalent cupric ion fluorescence probe as described above, including step is as follows：
(1) 6- acetyl group -2- methoxynaphthalenes obtain 6- acetyl group -2 hydroxy naphthalene, i.e. compound 1 with triethylamine react, its
Structural formula is as follows：
(2) step (1) is obtained into compound 1 and obtains target product 6- acetyl -2- picolyls with the reaction of 2- pyridine carboxylic acids
Naphthalene.
And, the step (1) is specifically completed using following methods：6- acetyl -2- methoxynaphthalenes are dissolved in dichloromethane
Afterwards, dropwise instill in hydrochloric acid solution, stirred in drop, then dropwise instill triethylamine, then stir 4h at 85 DEG C；Reaction is complete
Afterwards, excessive acid is neutralized with NaOH, is extracted with ethyl acetate, and is cleaned with saturated sodium bicarbonate and salt solution, and organic phase is used
Solvent is removed in anhydrous sodium sulfate drying, vacuum distillation, and is purified with silica gel chromatographic column, and petroleum ether and ethyl acetate wash-out are isolated
Compound 1.
And, the ratio of the 6- acetyl -2- methoxynaphthalenes and triethylamine is 1:1.1；The pillar layer separation eluant, eluent
It is ethyl acetate to match:Petroleum ether=1:5.
And, the step (2) is specifically completed using following methods：Compound 1 is dissolved in anhydrous methylene chloride, and uses 2-
Pyridine carboxylic acid, 1- ethyls -3- (3- dimethylamino-propyls) carbodiimide hydrochlorides and DMAP are processed, by institute
The solution for obtaining is stirred at room temperature 2h, argon gas protection；After reaction completely, separate organic phase and washed with hydrochloric acid and saturated brine,
Anhydrous sodium sulfate drying；Water is extracted with dichloromethane, evaporation, obtains thick solid, is crossed silica gel chromatographic column purifying and is obtained compound
2。
And, the compound 1 and 2- pyridine carboxylic acids, 1- ethyls -3- (3- dimethylamino-propyls) carbodiimide hydrochloride
It is 1 with the ratio of DMAP:1.5:1.5:0.6；The pillar layer separation eluant, eluent proportioning is ethyl acetate:Oil
Ether=1:2-4.
A kind of application of bivalent cupric ion fluorescence probe as described above, the application is by fluorescence probe and bivalent cupric ion
Reacted, the presence or absence of bivalent cupric ion is detected using the color change and change in fluorescence of reaction solution.
And, before bivalent cupric ion is not added, the reaction solution is launched for colourless and unstressed configuration, when addition divalence
After copper ion, the reaction solution color becomes blue, and sends fluorescence.
And, the concentrations lower limit of the detection bivalent cupric ion is 8.5nM.
Advantages of the present invention and its effect
The synthesis of probe of the present invention only needs to two steps can just be completed, and last handling process is relatively easy.Fluorescence of the present invention
Probe molecule shows selectivity and sensitivity higher in bivalent cupric ion and other cations coexist system.
Brief description of the drawings
Fig. 1 is compound 2 in case study on implementation 11H NMR spectras；
Fig. 2 is compound 2 in case study on implementation 113C NMR spectras；
Fig. 3 is the ESI-MS collection of illustrative plates of compound 2 in case study on implementation 1；
In Fig. 4 (a) be pH value to the influence schematic diagram of the fluorescence intensity of compound 1 and 2, (b) be pH value to compound 2 with
Cu2+The influence schematic diagram of fluorescence intensity before and after reaction；
(a) is compound 2 and Cu under different spectral conditions in Fig. 52+The change schematic diagram of absorption spectrum intensity after reaction,
B () is compound 2 and Cu at 316nm2+Absorbance changes with time schematic diagram after reaction；
(a) is compound 2 and Cu under different spectral conditions in Fig. 62+The change schematic diagram of fluorescence spectrum after reaction, (b) is
Compound 2 and Cu at 443nm2+Fluorescence intensity changes with time schematic diagram after reaction；
(a) is different Cu in Fig. 72+Compound 2 and Cu under concentration conditions2+After reaction at 443nm fluorescence intensity with the time
Change schematic diagram, (b) is the fluorescence intensity of the compound 2 at 443nm with Cu2+The change schematic diagram of concentration；
Fig. 8 is front and rear with the different metal ions reaction fluorescence intensity change schematic diagram at 443nm of compound 2, (gray columns
Metal ion treatment of the probe only through marking is represented, black post represents probe through Cu2+The metal ion of mark is added after treatment again；1.
Non-metallic ion, 2.Na+, 3.K+, 4.Ca2+, 5.Mg2+, 6.Ag+, 7.Zn2+, 8.Cd2+, 9.Hg2+, 10.Ba2+, 11.Co2+,
12.Ni2+, 13.Mn2+, 14.Pb2+, 15.Al3+, 16.Fe3+, 17.Sn4+, 18.Cu2+)；
Fig. 9 is the Cu of the detection of compound 22+Reaction mechanism schematic diagram.
Specific embodiment
The embodiment of the present invention is further described below：It is emphasized that embodiment of the present invention is explanation
Property, rather than limited, therefore the present invention is not limited to the embodiment described in specific embodiment, every by this area
The other embodiment that technical staff's technology according to the present invention scheme draws, also belongs to the scope of protection of the invention.
Embodiment
(1) preparation of target compound bivalent cupric ion fluorescence probe
(1) synthesis of compound 1
After 6- acetyl -2- methoxynaphthalenes (1.00g, 5mmol) is dissolved in into 4mL dichloromethane, 36% hydrochloric acid is dropwise instilled molten
In liquid (80mL, 0.93mol), stirred in drop, then dropwise instill triethylamine (0.75mL, 5.4mmol), then stirred at 85 DEG C
Mix 4h；After reaction completely, excessive acid is neutralized with NaOH, is extracted with ethyl acetate, and with saturated sodium bicarbonate and salt solution
Cleaning, solvent is removed in organic phase anhydrous sodium sulfate drying, vacuum distillation, and is purified with silica gel chromatographic column, petroleum ether and acetic acid second
Ester wash-out is separated, and eluant, eluent proportioning is ethyl acetate:Petroleum ether=1:5, yield is 90.2%.
(2) synthesis of compound 2
Compound 1 (186.2mg, 1.0mmol) is dissolved in 10mL anhydrous methylene chlorides, and uses 2- pyridine carboxylic acids
(183.2mg, 1.5mmol), 1- ethyls -3- (3- dimethylamino-propyls) carbodiimide hydrochloride (287.6mg, 1.5mmol) and
DMAP (73.3mg, 0.6mmol) is processed, and the solution of gained is stirred at room temperature into 2h, argon gas protection；Instead
After answering completely, separate organic phase and simultaneously washed with hydrochloric acid and saturated brine, anhydrous sodium sulfate drying；Water is mutually with 2 × 20mL dichloromethanes
Alkane is extracted, evaporation, obtains thick solid, crosses silica gel chromatographic column purifying, and eluant, eluent proportioning is ethyl acetate:Petroleum ether=1:2-4, produces
Rate is 78%.
Compound 21H NMR spectras are as shown in Figure 1,1H NMR (400MHz, CDCl3, ppm) δ 8.86 (d, J=4.0Hz,
1H), 8.47 (s, 1H), 8.31 (d, J=7.6Hz, 1H), 8.05 (t, J=9.2Hz, 2H), 7.94 (t, J=7.2Hz, 1H),
7.88 (d, J=8.8Hz, 1H), 7.76 (s, 1H), 7.58 (dd, J1=5.2Hz, J2=7.2Hz, 1H), 7.48 (dd, J1=
7.2Hz, J2=8.8Hz, 1H), 2.71 (s, 3H).
Compound 213C NMR spectras are as shown in Figure 1,13C NMR (100MHz, CDCl3, ppm) and δ 197.88,163.90,
150.67,150.30,137.38,136.21,134.62,131.32,130.77,130.03,128.35,127.72,126.06,
124.82,122.26,118.97,26.77.
The ESI-MS collection of illustrative plates of compound 2 is as shown in Figure 1, ESI-MS m/z for C18H14NO3 +([M+H]+)：calcd：
292.1, found：292.1.
(2) influence of the pH value change to compound 1 and the fluorescence intensity of compound 2
The compound 1 and compound 2 of synthesis are dissolved in dimethyl sulfoxide (DMSO) in Example (), are respectively prepared 2mmol/L
Storing solution.It is at room temperature the photoluminescent property for exciting photo measure compound 1 and 2, fluorescence light with 443nm when pH value is different
Shown in spectrogram such as Fig. 4 (a).Addition Cu2+Front and rear, pH value changes the influence to the fluorescence intensity of compound 2, shown in such as Fig. 4 (b).
Known by Fig. 4 (a) and 4 (b), add Cu2+Before, the fluorescence intensity of compound 2 is basically unchanged, the influence very little of pH value；Addition Cu2+
Afterwards, as pH=5.5-7.0, the fluorescence intensity of compound 2 is rapidly increased to maximum, when pH value continue increase, compound 2 it is glimmering
Luminous intensity is substantially reduced.
(3) the Absorption and fluorescence spectrum research of compound 2
In optimal conditions, i.e. 20mM HEPES, H2O/CH3CN,4:7.0,25 DEG C of 1, v/v, pH, research compound 2
Fluorescence spectrum and absorption spectra property, as a result as shown in Figure 5 and Figure 6, (a) is compound 2 and Cu in Fig. 52+Do not shared the same light after reaction
The change of absorption spectrum intensity under spectral condition, (b) is compound 2 and Cu2+Absorbance after reaction at 316nm with the time change
Change；(a) is compound 2 and Cu in Fig. 62+After reaction under different spectral conditions fluorescence spectrum change, (b) is compound 2 and Cu2 +Fluorescence intensity after reaction at 443nm changes with time.The results show, compound 2 and Cu2+Reaction can cause
The hydrolysis of picolinic acid group, release fluorogen 6- acetyl group -2 hydroxy naphthalene, as shown in Figure 9.Therefore, compound 2 is applied to
Cu2+Quick detection.
(4) detection of compound 2 Cu2+Study of Sensitivity
For test compound 2 detects Cu2+Sensitiveness, different Cu2+Compound 2 and Cu under concentration conditions (0-20 μM)2+Reaction
Fluorescence intensity changes with time the fluorescence intensity of (such as Fig. 7 (a)) and compound 2 at 443nm with Cu at 443nm afterwards2+It is dense
The change (such as Fig. 7 (b)) of degree has all carried out experimental study.Fig. 7 (a) knows, high concentration Cu2+(0-10 μM) provides faster and more drama
The Fluorescence Increasing of property.The detection of compound 2 Cu can be extrapolated by Fig. 7 (b)2+Detection be limited to 8.5nM, far below WHO standard (31
μM) and U.S. environment standard (20 μM).
(5) detection of compound 2 Cu2+Single-minded Journal of Sex Research
For test compound 2 detects Cu2+Selectivity, compound 2 reacts front and rear at 443nm from different heavy metal ion
The change of fluorescence intensity change (such as Fig. 8) and fluorescence color has all carried out experimental study.Known by Fig. 8 and fluorescence color change, its
He potentially competes the presence of metal ion to compound 2 and Cu2+Fluorescence reaction have no significant effect.
Claims (9)
1. a kind of switching mode bivalent cupric ion fluorescence probe, it is characterised in that：Its molecular formula is C17H11NO3, structural formula is as follows：
2. the preparation method of the bivalent cupric ion fluorescence probe described in a kind of claim 1, it is characterised in that as follows including step：
(1) 6- acetyl group -2- methoxynaphthalenes obtain 6- acetyl group -2 hydroxy naphthalene, i.e. compound 1, its structure with triethylamine react
Formula is as follows：
(2) step (1) is obtained into compound 1 and obtains target product 6- acetyl -2- picolyl naphthalenes with the reaction of 2- pyridine carboxylic acids.
3. the preparation method of bivalent cupric ion fluorescence probe according to claim 2, it is characterised in that：The step (1)
Specifically completed using following methods：After 6- acetyl -2- methoxynaphthalenes are dissolved in into dichloromethane, dropwise in instillation hydrochloric acid solution, side
The stirring of drop side, then triethylamine is dropwise instilled, then stir 4h at 85 DEG C；After reaction completely, in excessive acid NaOH
Be extracted with ethyl acetate, and cleaned with saturated sodium bicarbonate and salt solution, organic phase anhydrous sodium sulfate drying, vacuum distillation
Solvent is removed, and is purified with silica gel chromatographic column, petroleum ether and ethyl acetate elute isolated compound 1.
4. the preparation method of bivalent cupric ion fluorescence probe according to claim 3, it is characterised in that the 6- acetyl-
The ratio of 2- methoxynaphthalenes and triethylamine is 1:1.1；The pillar layer separation eluant, eluent proportioning is ethyl acetate:Petroleum ether=1:
5。
5. the preparation method of bivalent cupric ion fluorescence probe according to claim 2, it is characterised in that the step (2)
Specifically completed using following methods：Compound 1 is dissolved in anhydrous methylene chloride, and with 2- pyridine carboxylic acids, 1- ethyls -3- (3- bis-
Methylaminopropyl) carbodiimide hydrochloride and DMAP processed, and the solution of gained is stirred at room temperature into 2h,
Argon gas is protected；After reaction completely, separate organic phase and washed with hydrochloric acid and saturated brine, anhydrous sodium sulfate drying；Water is mutually with two
Chloromethanes is extracted, evaporation, obtains thick solid, is crossed silica gel chromatographic column purifying and is obtained compound 2.
6. the preparation method of bivalent cupric ion fluorescence probe according to claim 5, it is characterised in that the compound 1
Ratio with 2- pyridine carboxylic acids, 1- ethyls -3- (3- dimethylamino-propyls) carbodiimide hydrochlorides and DMAP is
1:1.5:1.5:0.6；The pillar layer separation eluant, eluent proportioning is ethyl acetate:Petroleum ether=1:2-4.
7. the application of the bivalent cupric ion fluorescence probe described in a kind of claim 1, it is characterised in that：The application is to visit fluorescence
Pin is reacted with bivalent cupric ion, and depositing for bivalent cupric ion is detected using the color change and change in fluorescence of reaction solution
Whether.
8. the application of bivalent cupric ion fluorescence probe according to claim 7, it is characterised in that：Do not add cupric from
Before son, the reaction solution is launched for colourless and unstressed configuration, and after bivalent cupric ion is added, the reaction solution color becomes
Indigo plant, and send fluorescence.
9. the application of the bivalent cupric ion fluorescence probe according to claim 7 or 8, it is characterised in that：The detection divalence
The concentrations lower limit of copper ion is 8.5nM.
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| CN111122482A (en) * | 2019-12-27 | 2020-05-08 | 浙江理工大学 | Preparation method of substituted polyacetylene type water-phase divalent copper ion detection probe, product and application thereof |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107629036A (en) * | 2017-10-24 | 2018-01-26 | 贺州学院 | A kind of fluorescence probe of visual detection copper ion and its preparation method and application |
| CN111072644A (en) * | 2018-10-22 | 2020-04-28 | 北京工商大学 | Coumarin copper ion fluorescent probe |
| CN111122482A (en) * | 2019-12-27 | 2020-05-08 | 浙江理工大学 | Preparation method of substituted polyacetylene type water-phase divalent copper ion detection probe, product and application thereof |
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Application publication date: 20170707 |