Literature DB >> 22921080

2-Substituted 4,5-dihydrothiazole-4-carboxylic acids are novel inhibitors of metallo-β-lactamases.

Pinhong Chen1, Lori B Horton, Rose L Mikulski, Lisheng Deng, Sandeep Sundriyal, Timothy Palzkill, Yongcheng Song.   

Abstract

Bacterial resistance to β-lactam antibiotics caused by class B metallo-β-lactamases (MBL), especially for certain hospital-acquired, Gram-negative pathogens, poses a significant threat to public health. We report several 2-substituted 4,5-dihydrothiazole-4-carboxylic acids to be novel MBL inhibitors. Structure activity relationship (SAR) and molecular modeling studies were performed and implications for further inhibitor design are discussed.
Copyright © 2012 Elsevier Ltd. All rights reserved.

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Year:  2012        PMID: 22921080      PMCID: PMC3463135          DOI: 10.1016/j.bmcl.2012.08.012

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN: 0960-894X            Impact factor:   2.823


  22 in total

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Authors:  Isabel C Materon; Anne Marie Queenan; Theresa M Koehler; Karen Bush; Timothy Palzkill
Journal:  Antimicrob Agents Chemother       Date:  2003-06       Impact factor: 5.191

Review 2.  Bacterial resistance to beta-lactam antibiotics: compelling opportunism, compelling opportunity.

Authors:  Jed F Fisher; Samy O Meroueh; Shahriar Mobashery
Journal:  Chem Rev       Date:  2005-02       Impact factor: 60.622

Review 3.  Metallo-beta-lactamases: novel weaponry for antibiotic resistance in bacteria.

Authors:  Michael W Crowder; James Spencer; Alejandro J Vila
Journal:  Acc Chem Res       Date:  2006-10       Impact factor: 22.384

4.  Coordination chemistry based approach to lipophilic inhibitors of 1-deoxy-D-xylulose-5-phosphate reductoisomerase.

Authors:  Lisheng Deng; Sandeep Sundriyal; Valentina Rubio; Zheng-zheng Shi; Yongcheng Song
Journal:  J Med Chem       Date:  2009-11-12       Impact factor: 7.446

5.  Succinic acids as potent inhibitors of plasmid-borne IMP-1 metallo-beta-lactamase.

Authors:  J H Toney; G G Hammond; P M Fitzgerald; N Sharma; J M Balkovec; G P Rouen; S H Olson; M L Hammond; M L Greenlee; Y D Gao
Journal:  J Biol Chem       Date:  2001-06-04       Impact factor: 5.157

Review 6.  Metallo-beta-lactamase inhibitors: promise for the future?

Authors:  Jeffrey H Toney; Joseph G Moloughney
Journal:  Curr Opin Investig Drugs       Date:  2004-08

7.  Crystal structure of the IMP-1 metallo beta-lactamase from Pseudomonas aeruginosa and its complex with a mercaptocarboxylate inhibitor: binding determinants of a potent, broad-spectrum inhibitor.

Authors:  N O Concha; C A Janson; P Rowling; S Pearson; C A Cheever; B P Clarke; C Lewis; M Galleni; J M Frère; D J Payne; J H Bateson; S S Abdel-Meguid
Journal:  Biochemistry       Date:  2000-04-18       Impact factor: 3.162

8.  Analysis of the functional contributions of Asn233 in metallo-β-lactamase IMP-1.

Authors:  Nicholas G Brown; Lori B Horton; Wanzhi Huang; Sompong Vongpunsawad; Timothy Palzkill
Journal:  Antimicrob Agents Chemother       Date:  2011-09-06       Impact factor: 5.191

Review 9.  Metallo-beta-lactamases (classification, activity, genetic organization, structure, zinc coordination) and their superfamily.

Authors:  Carine Bebrone
Journal:  Biochem Pharmacol       Date:  2007-06-02       Impact factor: 5.858

10.  Discovery of 4-substituted methoxybenzoyl-aryl-thiazole as novel anticancer agents: synthesis, biological evaluation, and structure-activity relationships.

Authors:  Yan Lu; Chien-Ming Li; Zhao Wang; Charles R Ross; Jianjun Chen; James T Dalton; Wei Li; Duane D Miller
Journal:  J Med Chem       Date:  2009-03-26       Impact factor: 7.446

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  11 in total

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

2.  Heteroaryl Phosphonates as Noncovalent Inhibitors of Both Serine- and Metallocarbapenemases.

Authors:  Orville A Pemberton; Priyadarshini Jaishankar; Afroza Akhtar; Jessie L Adams; Lindsey N Shaw; Adam R Renslo; Yu Chen
Journal:  J Med Chem       Date:  2019-09-13       Impact factor: 7.446

Review 3.  Overcoming resistance to β-lactam antibiotics.

Authors:  Roberta J Worthington; Christian Melander
Journal:  J Org Chem       Date:  2013-03-28       Impact factor: 4.354

Review 4.  Diversity and Proliferation of Metallo-β-Lactamases: a Clarion Call for Clinically Effective Metallo-β-Lactamase Inhibitors.

Authors:  Anou M Somboro; John Osei Sekyere; Daniel G Amoako; Sabiha Y Essack; Linda A Bester
Journal:  Appl Environ Microbiol       Date:  2018-08-31       Impact factor: 4.792

5.  Spectroscopic and biochemical characterization of metallo-β-lactamase IMP-1 with dicarboxylic, sulfonyl, and thiol inhibitors.

Authors:  Huan Zhang; Kundi Yang; Zishuo Cheng; Caitlyn Thomas; Abbie Steinbrunner; Cecily Pryor; Maya Vulcan; Claire Kemp; Diego Orea; Chathura Paththamperuma; Allie Y Chen; Seth M Cohen; Richard C Page; David L Tierney; Michael W Crowder
Journal:  Bioorg Med Chem       Date:  2021-05-01       Impact factor: 3.461

Review 6.  Metallo-β-Lactamase Inhibitors Inspired on Snapshots from the Catalytic Mechanism.

Authors:  Antonella R Palacios; María-Agustina Rossi; Graciela S Mahler; Alejandro J Vila
Journal:  Biomolecules       Date:  2020-06-03

7.  N-Aryl mercaptoacetamides as potential multi-target inhibitors of metallo-β-lactamases (MBLs) and the virulence factor LasB from Pseudomonas aeruginosa.

Authors:  Samir Yahiaoui; Katrin Voos; Jörg Haupenthal; Thomas A Wichelhaus; Denia Frank; Lilia Weizel; Marco Rotter; Steffen Brunst; Jan S Kramer; Ewgenij Proschak; Christian Ducho; Anna K H Hirsch
Journal:  RSC Med Chem       Date:  2021-07-29

8.  "Stormy waters ahead": global emergence of carbapenemases.

Authors:  Gopi Patel; Robert A Bonomo
Journal:  Front Microbiol       Date:  2013-03-14       Impact factor: 5.640

9.  The intrinsic resistome of bacterial pathogens.

Authors:  Jorge Olivares; Alejandra Bernardini; Guillermo Garcia-Leon; Fernando Corona; Maria B Sanchez; Jose L Martinez
Journal:  Front Microbiol       Date:  2013-04-30       Impact factor: 5.640

10.  Assay platform for clinically relevant metallo-β-lactamases.

Authors:  Sander S van Berkel; Jürgen Brem; Anna M Rydzik; Ramya Salimraj; Ricky Cain; Anil Verma; Raymond J Owens; Colin W G Fishwick; James Spencer; Christopher J Schofield
Journal:  J Med Chem       Date:  2013-08-16       Impact factor: 7.446

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