Literature DB >> 17101678

Pyrazinoic acid and its n-propyl ester inhibit fatty acid synthase type I in replicating tubercle bacilli.

Oren Zimhony1, Catherine Vilchèze, Masayoshi Arai, John T Welch, William R Jacobs.   

Abstract

The activity of different analogs of pyrazinamide on Mycobacterium tuberculosis fatty acid synthase type I (FASI) in replicating bacilli was studied. Palmitic acid biosynthesis was diminished by 96% in bacilli treated with n-propyl pyrazinoate, 94% in bacilli treated with 5-chloro-pyrazinamide, and 97% in bacilli treated with pyrazinoic acid, the pharmacologically active agent of pyrazinamide. We conclude that the minimal structure of pyrazine ring with an acyl group is sufficient for FASI inhibition and antimycobacterial activity.

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Year:  2006        PMID： 17101678      PMCID： PMC1797748          DOI： 10.1128/AAC.01369-06

Source DB:  PubMed          Journal:  Antimicrob Agents Chemother        ISSN： 0066-4804            Impact factor:   5.191


  18 in total

1.  Quantitative structure-activity relationships for the in vitro antimycobacterial activity of pyrazinoic acid esters.

Authors:  K E Bergmann; M H Cynamon; J T Welch
Journal:  J Med Chem       Date:  1996-08-16       Impact factor: 7.446

2.  Pyrazinamide and pyrazinoic acid activity against tubercle bacilli in cultured human macrophages and in the BACTEC system.

Authors:  M Salfinger; A J Crowle; L B Reller
Journal:  J Infect Dis       Date:  1990-07       Impact factor: 5.226

3.  Role of acid pH and deficient efflux of pyrazinoic acid in unique susceptibility of Mycobacterium tuberculosis to pyrazinamide.

Authors:  Y Zhang; A Scorpio; H Nikaido; Z Sun
Journal:  J Bacteriol       Date:  1999-04       Impact factor: 3.490

4.  Pyrazinamide inhibits the eukaryotic-like fatty acid synthetase I (FASI) of Mycobacterium tuberculosis.

Authors:  O Zimhony; J S Cox; J T Welch; C Vilchèze; W R Jacobs
Journal:  Nat Med       Date:  2000-09       Impact factor: 53.440

5.  In vitro antimycobacterial activity of 5-chloropyrazinamide.

Authors:  M H Cynamon; R J Speirs; J T Welch
Journal:  Antimicrob Agents Chemother       Date:  1998-02       Impact factor: 5.191

6.  Mutations in pncA, a gene encoding pyrazinamidase/nicotinamidase, cause resistance to the antituberculous drug pyrazinamide in tubercle bacillus.

Authors:  A Scorpio; Y Zhang
Journal:  Nat Med       Date:  1996-06       Impact factor: 53.440

7.  Activity of n-propyl pyrazinoate against pyrazinamide-resistant Mycobacterium tuberculosis: investigations into mechanism of action of and mechanism of resistance to pyrazinamide.

Authors:  R J Speirs; J T Welch; M H Cynamon
Journal:  Antimicrob Agents Chemother       Date:  1995-06       Impact factor: 5.191

8.  Determination of pyrazinamide MICs for Mycobacterium tuberculosis at different pHs by the radiometric method.

Authors:  M Salfinger; L B Heifets
Journal:  Antimicrob Agents Chemother       Date:  1988-07       Impact factor: 5.191

9.  Lipophilic N-acylpyrazinamide derivatives: synthesis, physicochemical characterization, liposome incorporation, and in vitro activity against Mycobacterium avium-intracellulare.

Authors:  Z Z Liu; X D Guo; L E Straub; G Erdos; R J Prankerd; R J Gonzalez-Rothi; H Schreier
Journal:  Drug Des Discov       Date:  1991-11

10.  Pyrazinoic acid esters with broad spectrum in vitro antimycobacterial activity.

Authors:  M H Cynamon; R Gimi; F Gyenes; C A Sharpe; K E Bergmann; H J Han; L B Gregor; R Rapolu; G Luciano; J T Welch
Journal:  J Med Chem       Date:  1995-09-29       Impact factor: 7.446
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  31 in total

1.  Evaluation of colorimetric methods using nicotinamide for rapid detection of pyrazinamide resistance in Mycobacterium tuberculosis.

Authors:  Niuris C Mirabal; Sergio L Yzquierdo; Dihadenys Lemus; Mariela Madruga; Yoslaine Milián; Miguel Echemendía; Howard Takiff; Anandi Martin; Patrick Van der Stuyf; Juan Carlos Palomino; Ernesto Montoro
Journal:  J Clin Microbiol       Date:  2010-06-16       Impact factor: 5.948

2.  Mutually exclusive genotypes for pyrazinamide and 5-chloropyrazinamide resistance reveal a potential resistance-proofing strategy.

Authors:  Anthony D Baughn; Jiaoyu Deng; Catherine Vilchèze; Angelica Riestra; John T Welch; William R Jacobs; Oren Zimhony
Journal:  Antimicrob Agents Chemother       Date:  2010-09-27       Impact factor: 5.191

3.  Pharmacokinetics-pharmacodynamics of pyrazinamide in a novel in vitro model of tuberculosis for sterilizing effect: a paradigm for faster assessment of new antituberculosis drugs.

Authors:  Tawanda Gumbo; Chandima S W Siyambalapitiyage Dona; Claudia Meek; Richard Leff
Journal:  Antimicrob Agents Chemother       Date:  2009-05-18       Impact factor: 5.191

Review 4.  The Bewildering Antitubercular Action of Pyrazinamide.

Authors:  Elise A Lamont; Nicholas A Dillon; Anthony D Baughn
Journal:  Microbiol Mol Biol Rev       Date:  2020-03-04       Impact factor: 11.056

5.  A High-Throughput Assay for Developing Inhibitors of PhoP, a Virulence Factor of Mycobacterium tuberculosis.

Authors:  Liqin Wang; Miao Xu; Noel Southall; Wei Zheng; Shuishu Wang
Journal:  Comb Chem High Throughput Screen       Date:  2016       Impact factor: 1.339

6.  Pyrazinamide Resistance Is Caused by Two Distinct Mechanisms: Prevention of Coenzyme A Depletion and Loss of Virulence Factor Synthesis.

Authors:  Pooja Gopal; Michelle Yee; Jickky Sarathy; Jian Liang Low; Jansy P Sarathy; Firat Kaya; Véronique Dartois; Martin Gengenbacher; Thomas Dick
Journal:  ACS Infect Dis       Date:  2016-08-08       Impact factor: 5.084

7.  Synthesis and biological activity of alkynoic acids derivatives against mycobacteria.

Authors:  Catherine Vilchèze; Lawrence W Leung; Robert Bittman; William R Jacobs
Journal:  Chem Phys Lipids       Date:  2015-08-06       Impact factor: 3.329

8.  Inhibition of isolated Mycobacterium tuberculosis fatty acid synthase I by pyrazinamide analogs.

Authors:  Silvana C Ngo; Oren Zimhony; Woo Jin Chung; Halimah Sayahi; William R Jacobs; John T Welch
Journal:  Antimicrob Agents Chemother       Date:  2007-05-07       Impact factor: 5.191

9.  Searching for the Optimal Predictor of Ciprofloxacin Resistance in Klebsiella pneumoniae by Using In Vitro Dynamic Models.

Authors:  Elena N Strukova; Yury A Portnoy; Andrey V Romanov; Mikhail V Edelstein; Stephen H Zinner; Alexander A Firsov
Journal:  Antimicrob Agents Chemother       Date:  2015-12-07       Impact factor: 5.191

10.  Pantothenate and pantetheine antagonize the antitubercular activity of pyrazinamide.

Authors:  Nicholas A Dillon; Nicholas D Peterson; Brandon C Rosen; Anthony D Baughn
Journal:  Antimicrob Agents Chemother       Date:  2014-09-22       Impact factor: 5.191
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