Literature DB >> 25147614

Alkylidene Oxapenem β-Lactamase Inhibitors Revisited: Potent Broad Spectrum Activity but New Stability Challenges.

Matthew D Miller1, Manoj Kale2, Kishore Reddy2, Sharon Tentarelli1, Mark Zambrowski1, Minli Zhang1, Tiffany Palmer1, John Breen1, Sushmita Lahiri1, Pravin S Shirude2, Jeroen C Verheijen1.   

Abstract

We present a comprehensive study of C6-alkylidene containing oxapenems. We show that this class of β-lactamase inhibitors possesses an unprecedented spectrum with activity against class A, C, and D enzymes. Surprisingly, this class of compounds displayed significant photolytic instability in addition to the known hydrolytic instability. Quantum mechanical calculations were used to develop models to predict the stability of new analogues.

Entities:  

Keywords:  Gram-negative infections; Oxapenems; quantum mechanical calculations; stability; β-lactamase inhibitors

Year:  2014        PMID： 25147614      PMCID： PMC4137382          DOI： 10.1021/ml5001855

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  11 in total

1.  In vitro and in vivo activities of AM-112, a novel oxapenem.

Authors:  Conor E Jamieson; Peter A Lambert; Iain N Simpson
Journal:  Antimicrob Agents Chemother       Date:  2003-05       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.  Understanding the longevity of the beta-lactam antibiotics and of antibiotic/beta-lactamase inhibitor combinations.

Authors:  John D Buynak
Journal:  Biochem Pharmacol       Date:  2005-12-13       Impact factor: 5.858

4.  Kinetics of avibactam inhibition against Class A, C, and D β-lactamases.

Authors:  David E Ehmann; Haris Jahic; Philip L Ross; Rong-Fang Gu; Jun Hu; Thomas F Durand-Réville; Sushmita Lahiri; Jason Thresher; Stephania Livchak; Ning Gao; Tiffany Palmer; Grant K Walkup; Stewart L Fisher
Journal:  J Biol Chem       Date:  2013-08-02       Impact factor: 5.157

Review 5.  New β-lactam antibiotics and β-lactamase inhibitors.

Authors:  Karen Bush; Mark J Macielag
Journal:  Expert Opin Ther Pat       Date:  2010-10       Impact factor: 6.674

Review 6.  The future of the β-lactams.

Authors:  Leticia I Llarrull; Sebastian A Testero; Jed F Fisher; Shahriar Mobashery
Journal:  Curr Opin Microbiol       Date:  2010-09-29       Impact factor: 7.934

7.  Avibactam is a covalent, reversible, non-β-lactam β-lactamase inhibitor.

Authors:  David E Ehmann; Haris Jahić; Philip L Ross; Rong-Fang Gu; Jun Hu; Gunther Kern; Grant K Walkup; Stewart L Fisher
Journal:  Proc Natl Acad Sci U S A       Date:  2012-07-02       Impact factor: 11.205

8.  In vitro activities of novel oxapenems, alone and in combination with ceftazidime, against gram-positive and gram-negative organisms.

Authors:  Conor E Jamieson; Peter A Lambert; Iain N Simpson
Journal:  Antimicrob Agents Chemother       Date:  2003-08       Impact factor: 5.191

Review 9.  Three decades of beta-lactamase inhibitors.

Authors:  Sarah M Drawz; Robert A Bonomo
Journal:  Clin Microbiol Rev       Date:  2010-01       Impact factor: 26.132

10.  Establishment of in vitro susceptibility testing methodologies and comparative activities of piperacillin in combination with the penem {beta}-lactamase inhibitor BLI-489.

Authors:  Peter J Petersen; C Hal Jones; Aranapakam M Venkatesan; Tarek S Mansour; Steven J Projan; Patricia A Bradford
Journal:  Antimicrob Agents Chemother       Date:  2008-11-10       Impact factor: 5.191
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