Literature DB >> 14980686

Penicillin-derived inhibitors that simultaneously target both metallo- and serine-beta-lactamases.

John D Buynak1, Hansong Chen, Lakshminaryana Vogeti, Venkat Rao Gadhachanda, Christine A Buchanan, Timothy Palzkill, Robert W Shaw, James Spencer, Timothy R Walsh.   

Abstract

The synthesis and beta-lactamase inhibitory activity of four 6-(mercaptomethyl)penicillinates and the four corresponding 6-(hydroxymethyl)penicillinates are described. These penicillins include both C6 stereoisomers as well as the sulfide and sulfone oxidation states of the penam thiazolidine sulfur. All compounds were evaluated as inhibitors of representative metallo- and serine-beta-lactamases enzymes. Selected (mercaptomethyl)penicillinates are shown to inactivate both metallo- and serine-beta-lactamases and to display synergism with piperacillin against beta-lactamase producing strains.

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Year:  2004        PMID: 14980686     DOI: 10.1016/j.bmcl.2003.12.037

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


  25 in total

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Authors:  Hanna-Kirsti S Leiros; Pardha S Borra; Bjørn Olav Brandsdal; Kine Susann Waade Edvardsen; James Spencer; Timothy R Walsh; Orjan Samuelsen
Journal:  Antimicrob Agents Chemother       Date:  2012-06-04       Impact factor: 5.191

2.  C4-alkylthiols with activity against Moraxella catarrhalis and Mycobacterium tuberculosis.

Authors:  Maya B Kostova; Carey J Myers; Tim N Beck; Balbina J Plotkin; Jacalyn M Green; Helena I M Boshoff; Clifton E Barry; Jeffrey R Deschamps; Monika I Konaklieva
Journal:  Bioorg Med Chem       Date:  2011-10-01       Impact factor: 3.641

3.  Mechanistic studies on the mononuclear ZnII-containing metallo-beta-lactamase ImiS from Aeromonas sobria.

Authors:  Narayan P Sharma; Christine Hajdin; Sowmya Chandrasekar; Brian Bennett; Ke-Wu Yang; Michael W Crowder
Journal:  Biochemistry       Date:  2006-09-05       Impact factor: 3.162

4.  Modifications of the C6-substituent of penicillin sulfones with the goal of improving inhibitor recognition and efficacy.

Authors:  Micheal Nottingham; Christopher R Bethel; Sundar Ram Reddy Pagadala; Emily Harry; Abishai Pinto; Zachary A Lemons; Sarah M Drawz; Focco van den Akker; Paul R Carey; Robert A Bonomo; John D Buynak
Journal:  Bioorg Med Chem Lett       Date:  2010-11-05       Impact factor: 2.823

Review 5.  Metallo-beta-lactamases: the quiet before the storm?

Authors:  Timothy R Walsh; Mark A Toleman; Laurent Poirel; Patrice Nordmann
Journal:  Clin Microbiol Rev       Date:  2005-04       Impact factor: 26.132

Review 6.  Current challenges in antimicrobial chemotherapy: focus on ß-lactamase inhibition.

Authors:  Carine Bebrone; Patricia Lassaux; Lionel Vercheval; Jean-Sébastien Sohier; Adrien Jehaes; Eric Sauvage; Moreno Galleni
Journal:  Drugs       Date:  2010-04-16       Impact factor: 9.546

Review 7.  Carbapenemases in Klebsiella pneumoniae and other Enterobacteriaceae: an evolving crisis of global dimensions.

Authors:  L S Tzouvelekis; A Markogiannakis; M Psichogiou; P T Tassios; G L Daikos
Journal:  Clin Microbiol Rev       Date:  2012-10       Impact factor: 26.132

Review 8.  Overcoming resistance to β-lactam antibiotics.

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

9.  Regiospecific syntheses of 6alpha-(1R-Hydroxyoctyl)penicillanic acid and 6beta-(1R-hydroxyoctyl)penicillanic acid as mechanistic probes of class D beta-lactamases.

Authors:  Sebastian A Testero; Peter I O'Daniel; Qicun Shi; Mijoon Lee; Dusan Hesek; Akihiro Ishiwata; Bruce C Noll; Shahriar Mobashery
Journal:  Org Lett       Date:  2009-06-18       Impact factor: 6.005

Review 10.  Acinetobacter baumannii: emergence of a successful pathogen.

Authors:  Anton Y Peleg; Harald Seifert; David L Paterson
Journal:  Clin Microbiol Rev       Date:  2008-07       Impact factor: 26.132

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