Probing functional diversity in pactamycin toward antibiotic, antitumor, and antiprotozoal activity.

Abstract

A total of eight new analogs of pactamycin were prepared and tested alongside pactamycin and three of its natural congeners for antibacterial, anticancer, and antiprotozoal activities. The present study highlights the effects of changing the urea and aniline groups especially with regard to anticancer and antiprotozoal activities.

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References

Articles referenced by this article (35)

Synthesis and Biological Activity of Natural Aminocyclopentitol Glycosidase Inhibitors: Mannostatins, Trehazolin, Allosamidins, and Their Analogues.
Berecibar A, Grandjean C, Siriwardena A
Chem Rev, (3):779-844 1999
MED: 11749432
Synthesis of cyclopentitols by ring-closing approaches.
Kurteva VB, Afonso CA
Chem Rev, (12):6809-6857 2009
MED: 19772301
Title not supplied
Argoudelis
Antimicrob. Agents Chemother. 1962
The structure of pactamycin.
Wiley PF, Jahnke HK, MacKellar F, Kelly RB, Argoudelis AD
J Org Chem, (5):1420-1425 1970
MED: 5440331
8''-Hydroxypactamycin and 7-deoxypactamycin, new members of the pactamycin group.
Dobashi K, Isshiki K, Sawa T, Obata T, Hamada M, Naganawa H, Takita T, Takeuchi T, Umezawa H, Bei HS
J Antibiot (Tokyo), (12):1779-1783 1986
MED: 3818452
Carbon-13 nuclear magnetic resonance assignments of pactamycin and related compounds.
Weller DD, Haber A, Rinehart KL Jr, Wiley PF
J Antibiot (Tokyo), (10):997-1006 1978
MED: 711622
Duchamp, D. J. Abstract J. Am. Crystal. Assoc. Winter Meeting. Albuquerque, 1972, April, p. 23.
Title not supplied
Bhuyan
Antimicrob. Agents Chemother. 1962
Pactamycin, an antibiotic that inhibits protein synthesis.
Bhuyan BK
Biochem Pharmacol, (8):1411-1420 1967
MED: 4963460
Determination of the gene sequence of poliovirus with pactamycin.
Summers DF, Maizel JV Jr
Proc Natl Acad Sci U S A, (11):2852-2856 1971
MED: 4330946

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Chemical Modification of Pactamycin Leads to New Compounds with Retained Antimicrobial Activity and Reduced Toxicity.
Tsirogianni A, Ntinou N, Karampatsou K, Dinos G, Kournoutou GG, Athanassopoulos CM
Molecules, 29(17):4169, 03 Sep 2024
Cited by: 0 articles | PMID: 39275017 | PMCID: PMC11397182
This article is in the Europe PMC Open access subset. Refer to the copyright information in the article for licensing details.
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The chemistry and biology of natural ribomimetics and related compounds.
Tsunoda T, Tanoeyadi S, Proteau PJ, Mahmud T
RSC Chem Biol, 3(5):519-538, 07 Apr 2022
Cited by: 1 article | PMID: 35656477 | PMCID: PMC9092360
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Strategies for the Syntheses of Pactamycin and Jogyamycin.
Gerstner NC, Nicastri KA, Schomaker JM
Angew Chem Int Ed Engl, 60(26):14252-14271, 18 Jan 2021
Cited by: 3 articles | PMID: 32392399 | PMCID: PMC7655678
Review Free full text in Europe PMC
Recent Advances in the Discovery of Novel Antiprotozoal Agents.
Lee SM, Kim MS, Hayat F, Shin D
Molecules, 24(21):E3886, 28 Oct 2019
Cited by: 27 articles | PMID: 31661934 | PMCID: PMC6864685
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Stereocontrolled Synthesis of the Aminocyclopentitol Core of Jogyamycin via an Ichikawa Rearrangement Reaction.
Gerstner NC, Schomaker JM
J Org Chem, 84(21):14092-14100, 16 Oct 2019
Cited by: 2 articles | PMID: 31578059 | PMCID: PMC6944531
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Small molecules (chemicals) in ChEMBL (Showing 10 of 32)

Plasmodium falciparum(CHEMBL - CHEMBL364)
Acinetobacter baumannii(CHEMBL - CHEMBL614425)
Pactamycate(CHEMBL - CHEMBL2337348)
de-6-methylsalicylyl pactamycate(CHEMBL - CHEMBL2337349)
3-((1R,2R,3S,4S,5S)-4-((3-Acetylphenyl)amino)-5-amino-2,3-dihydroxy-1-((S)-1-hydroxyethyl)-3-(hydroxymethyl)-2-methylcyclopentyl)-1,1-diethylurea(CHEMBL - CHEMBL2337350)
N-((1R,2R,3S,4S,5S)-4-((3-Acetylphenyl)amino)-5-amino-2,3-dihydroxy-1-((S)-1-hydroxyethyl)-3-(hydroxymethyl)-2-methylcyclopentyl)pyrrolidine-1-carboxamide(CHEMBL - CHEMBL2337351)
N-((1R,2R,3S,4S,5S)-4-((3-Acetylphenyl)amino)-5-amino-2,3-dihydroxy-1-((S)-1-hydroxyethyl)-3-(hydroxymethyl)-2-methylcyclopentyl)piperidine-1-carboxamide(CHEMBL - CHEMBL2337352)
N-((1R,2R,3S,4S,5S)-4-((3-Acetylphenyl)amino)-5-amino-2,3-dihydroxy-1-((S)-1-hydroxyethyl)-3-(hydroxymethyl)-2-methylcyclopentyl)morpholine-4-carboxamide(CHEMBL - CHEMBL2337353)
3-((1R,2R,3S,4S,5S)-5-Amino-2,3-dihydroxy-1-((S)-1-hydroxyethyl)-3-(hydroxymethyl)-2-methyl-4-(phenylamino)cyclopentyl)-1,1-dimethylurea(CHEMBL - CHEMBL2337354)
3-((1R,2R,3S,4S,5S)-5-amino-4-(3-fluorophenylamino)-2,3-dihydroxy-1-((S)-1-hydroxyethyl)-3-(hydroxymethyl)-2-methylcyclopentyl)-1,1-diethylurea(CHEMBL - CHEMBL2337355)

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Abstract

Full text links

References

Synthesis and Biological Activity of Natural Aminocyclopentitol Glycosidase Inhibitors: Mannostatins, Trehazolin, Allosamidins, and Their Analogues.

Synthesis of cyclopentitols by ring-closing approaches.

Title not supplied

The structure of pactamycin.

8''-Hydroxypactamycin and 7-deoxypactamycin, new members of the pactamycin group.

Carbon-13 nuclear magnetic resonance assignments of pactamycin and related compounds.

Duchamp, D. J. Abstract J. Am. Crystal. Assoc. Winter Meeting. Albuquerque, 1972, April, p. 23.

Title not supplied

Pactamycin, an antibiotic that inhibits protein synthesis.

Determination of the gene sequence of poliovirus with pactamycin.

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Impact metrics

Citations of article over time

Smart citations by scite.ai
Explore citation contexts and check if this article has been supported or disputed.
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Article citations

Chemical Modification of Pactamycin Leads to New Compounds with Retained Antimicrobial Activity and Reduced Toxicity.

The chemistry and biology of natural ribomimetics and related compounds.

Strategies for the Syntheses of Pactamycin and Jogyamycin.

Recent Advances in the Discovery of Novel Antiprotozoal Agents.

Stereocontrolled Synthesis of the Aminocyclopentitol Core of Jogyamycin via an Ichikawa Rearrangement Reaction.

Data

Data that cites the article

Small molecules (chemicals) in ChEMBL (Showing 10 of 32)

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Search life-sciences literature (45,094,167 articles, preprints and more)

Probing functional diversity in pactamycin toward antibiotic, antitumor, and antiprotozoal activity.

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Abstract

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References

Title not supplied

Duchamp, D. J. Abstract J. Am. Crystal. Assoc. Winter Meeting. Albuquerque, 1972, April, p. 23.

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Funding

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NSERC

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