Identification of borinic esters as inhibitors of bacterial cell growth and bacterial methyltransferases, CcrM and MenH

Benkovic, Stephen J., Baker, Stephen J., Alley, M.R.K., Woo, Youn-Hi, Zhang, Yong-Kang, Akama, Tsutomu, Mao, Weimin, Baboval, Justin, Rajagopalan, P.T. Ravi, Wall, Mark, Kahng, Lyn Sue, Tavassoli, Ali and Shapiro, Lucy (2005) Identification of borinic esters as inhibitors of bacterial cell growth and bacterial methyltransferases, CcrM and MenH. Journal of Medicinal Chemistry, 48, (23), 7468-7476. (doi:10.1021/jm050676a).


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As bacteria continue to develop resistance toward current antibiotics, we find ourselves in a continual battle to identify new antibacterial agents and targets. We report herein a class of boron-containing compounds termed borinic esters that have broad spectrum antibacterial activity with minimum inhibitory concentrations (MIC) in the low microgram/mL range. These compounds were identified by screening for inhibitors against Caulobacter crescentus CcrM, an essential DNA methyltransferase from gram negative alpha-proteobacteria. In addition, we demonstrate that borinic esters inhibit menaquinone methyltransferase in gram positive bacteria using a new biochemical assay for MenH from Bacillus subtilis. Our data demonstrate the potential for further development of borinic esters as antibacterial agents as well as leads to explore more specific inhibitors against two essential bacterial enzymes.

Item Type: Article
Digital Object Identifier (DOI): doi:10.1021/jm050676a
ISSNs: 0022-2623 (print)
Related URLs:
Keywords: anti-bacterial agents, chemical synthesis/chemistry/pharmacology bacillus subtilis/drug effects/enzymology borinic acids, chemical synthesis/chemistry/pharmacology caulobacter crescentus/drug effects/enzymology dna modification methylases, antagonists & inhibitors/chemistry esters/chemical synthesis/chemistry/pharmacology gram-negative bacteria, drug effects/enzymology/growth & development gram-positive bacteria, drug effects/enzymology/growth & development kinetics microbial sensitivity tests proteobacteria/enzymology structure-activity relationship
Subjects: Q Science > QD Chemistry
Q Science > QR Microbiology
Divisions : University Structure - Pre August 2011 > School of Chemistry
ePrint ID: 45309
Accepted Date and Publication Date:
Date Deposited: 20 Mar 2007
Last Modified: 31 Mar 2016 12:19

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