Literature DB >> 9545432

Antibiotic sensitization using biphenyl tetrazoles as potent inhibitors of Bacteroides fragilis metallo-beta-lactamase.

J H Toney1, P M Fitzgerald, N Grover-Sharma, S H Olson, W J May, J G Sundelof, D E Vanderwall, K A Cleary, S K Grant, J K Wu, J W Kozarich, D L Pompliano, G G Hammond.   

Abstract

BACKGROUND: High level resistance to carbapenem antibiotics in gram negative bacteria such as Bacteroides fragilis is caused, in part, by expression of a wide-spectrum metallo-beta-lactamase that hydrolyzes the drug to an inactive form. Co-administration of metallo-beta-lactamase inhibitors to resistant bacteria is expected to restore the antibacterial activity of carbapenems.
RESULTS: Biphenyl tetrazoles (BPTs) are a structural class of potent competitive inhibitors of metallo-beta-lactamase identified through screening and predicted using molecular modeling of the enzyme structure. The X-ray crystal structure of the enzyme bound to the BPT L-159,061 shows that the tetrazole moiety of the inhibitor interacts directly with one of the two zinc atoms in the active site, replacing a metal-bound water molecule. Inhibition of metallo-beta-lactamase by BPTs in vitro correlates well with antibiotic sensitization of resistant B. fragilis.
CONCLUSIONS: BPT inhibitors can sensitize a resistant B. fragilis clinical isolate expressing metallo-beta-lactamase to the antibiotics imipenem or penicillin G but not to rifampicin.

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Year:  1998        PMID: 9545432     DOI: 10.1016/s1074-5521(98)90632-9

Source DB:  PubMed          Journal:  Chem Biol        ISSN: 1074-5521


  45 in total

1.  Standard numbering scheme for class B beta-lactamases.

Authors:  M Galleni; J Lamotte-Brasseur; G M Rossolini; J Spencer; O Dideberg; J M Frère
Journal:  Antimicrob Agents Chemother       Date:  2001-03       Impact factor: 5.191

2.  Antifungal properties of substituted 1-phenyl-5-mercaptotetrazoles and their oxidation product, 5-bis-(1-phenyltetrazolyl)disulfide.

Authors:  K Nesmĕrák; M Pospísek; I Nĕmec; K Waisser; J Gabriel
Journal:  Folia Microbiol (Praha)       Date:  2000       Impact factor: 2.099

3.  Role of a solvent-exposed tryptophan in the recognition and binding of antibiotic substrates for a metallo-beta-lactamase.

Authors:  James J A Huntley; Walter Fast; Stephen J Benkovic; Peter E Wright; H Jane Dyson
Journal:  Protein Sci       Date:  2003-07       Impact factor: 6.725

4.  Crystallization and preliminary X-ray analysis of the subclass B3 metallo-β-lactamase SMB-1 that confers carbapenem resistance.

Authors:  Jun-ichi Wachino; Yoshihiro Yamaguchi; Shigetarou Mori; Yuriko Yamagata; Yoshichika Arakawa; Keigo Shibayama
Journal:  Acta Crystallogr Sect F Struct Biol Cryst Commun       Date:  2012-02-23

5.  Docking and scoring of metallo-beta-lactamases inhibitors.

Authors:  Lars Olsen; Ingrid Pettersson; Lars Hemmingsen; Hans-Werner Adolph; Flemming Steen Jørgensen
Journal:  J Comput Aided Mol Des       Date:  2004-04       Impact factor: 3.686

6.  Conformational changes in the metallo-beta-lactamase ImiS during the catalytic reaction: an EPR spectrokinetic study of Co(II)-spin label interactions.

Authors:  Narayan Sharma; Zhenxin Hu; Michael W Crowder; Brian Bennett
Journal:  J Am Chem Soc       Date:  2008-06-04       Impact factor: 15.419

7.  Loss of enzyme activity during turnover of the Bacillus cereus beta-lactamase catalysed hydrolysis of beta-lactams due to loss of zinc ion.

Authors:  Adriana Badarau; Michael I Page
Journal:  J Biol Inorg Chem       Date:  2008-05-01       Impact factor: 3.358

Review 8.  Fragment-based inhibitor discovery against β-lactamase.

Authors:  Derek A Nichols; Adam R Renslo; Yu Chen
Journal:  Future Med Chem       Date:  2014-03       Impact factor: 3.808

9.  N-arylsulfonyl hydrazones as inhibitors of IMP-1 metallo-beta-lactamase.

Authors:  Stefan Siemann; Darryl P Evanoff; Laura Marrone; Anthony J Clarke; Thammaiah Viswanatha; Gary I Dmitrienko
Journal:  Antimicrob Agents Chemother       Date:  2002-08       Impact factor: 5.191

Review 10.  Tetrazoles via Multicomponent Reactions.

Authors:  Constantinos G Neochoritis; Ting Zhao; Alexander Dömling
Journal:  Chem Rev       Date:  2019-02-01       Impact factor: 60.622

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