Structure-Based Design, Synthesis, and Biological Evaluation of Non-Acyl Sulfamate Inhibitors of the Adenylate-Forming Enzyme MenE

Evans, Christopher E.; Si, Yuanyuan; Matarlo, Joe S.; Yin, Yue; French, Jarrod B.; Tonge, Peter J.; Tan, Derek S.

doi:10.1021/acs.biochem.9b00003

Structure-Based Design, Synthesis, and Biological Evaluation of Non-Acyl Sulfamate Inhibitors of the Adenylate-Forming Enzyme MenE

Journal Article · Tue Mar 26 00:00:00 EDT 2019 · Biochemistry

DOI:https://doi.org/10.1021/acs.biochem.9b00003· OSTI ID:1623729

^[1]; Si, Yuanyuan ^[2]; Matarlo, Joe S. ^[3]; Yin, Yue ^[4]; ^[5]; ^[6]; ^[7]

Weill Cornell Graduate School of Medical Sciences, Memorial Sloan Kettering Cancer Center, New York, NY (United States). Pharmacology Program; DOE/OSTI
Stony Brook Univ., NY (United States). Institute of Chemical Biology and Drug Discovery; Stony Brook Univ., NY (United States). Dept. of Chemistry
Stony Brook Univ., NY (United States). Institute of Chemical Biology and Drug Discovery, Stony Brook Univ., NY (United States). Dept. of Biochemistry and Cell Biology
Stony Brook Univ., NY (United States). Institute of Chemical Biology and Drug Discovery; Stony Brook Univ., NY (United States). Dept. of Chemistry
Stony Brook Univ., NY (United States). Institute of Chemical Biology and Drug Discovery; Stony Brook Univ., NY (United States), Dept. of Chemistry; Stony Brook Univ., NY (United States). Dept. of Biochemistry and Cell Biology
Stony Brook Univ., NY (United States). Institute of Chemical Biology and Drug Discovery; Dept. of Chemistry
Weill Cornell Graduate School of Medical Sciences, Memorial Sloan Kettering Cancer Center, New York, NY (United States). Pharmacology Program; Memorial Sloan Kettering Cancer Center. New York, NY (United State). Sloan Kettering Institute and Tri-Institutional Research Program, Chemical Biology Program

N-Acyl sulfamoyladenosines (acyl-AMS) have been used extensively to inhibit adenylate-forming enzymes that are involved in a wide range of biological processes. These acyl-AMS inhibitors are nonhydrolyzable mimics of the cognate acyl adenylate intermediates that are bound tightly by adenylate-forming enzymes. However, the anionic acyl sulfamate moiety presents a pharmacological liability that may be detrimental to cell permeability and pharmacokinetic profiles. We have previously developed the acyl sulfamate OSB-AMS (1) as a potent inhibitor of the adenylate-forming enzyme MenE, an o-succinylbenzoate-CoA (OSB-CoA) synthetase that is required for bacterial menaquinone biosynthesis. Herein, we report the use of computational docking to develop novel, non-acyl sulfamate inhibitors of MenE. A m-phenyl ether-linked analogue (5) was found to be the most potent inhibitor (IC₅₀ = 8 μM; K_d = 244 nM), and its X-ray co-crystal structure was determined to characterize its binding mode in comparison to the computational prediction. This work provides a framework for the development of potent non-acyl sulfamate inhibitors of other adenylate-forming enzymes in the future.

View Accepted Manuscript (DOE)

Research Organization:: Brookhaven National Lab. (BNL), Upton, NY (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

Grant/Contract Number:: AC02-98CH10886

OSTI ID:: 1623729

Alternate ID(s):: OSTI ID: 1689862

Journal Information:: Biochemistry, Journal Name: Biochemistry Journal Issue: 14 Vol. 58; ISSN 0006-2960

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Vitamin K-dependent Proteins, Warfarin, and Vascular Calcification Danziger, John Clinical Journal of the American Society of Nephrology, Vol. 3, Issue 5 https://doi.org/10.2215/CJN.00770208	journal	May 2008
Menaquinones, Bacteria, and the Food Supply: The Relevance of Dairy and Fermented Food Products to Vitamin K Requirements Walther, Barbara; Karl, J. Philip; Booth, Sarah L. Advances in Nutrition, Vol. 4, Issue 4 https://doi.org/10.3945/an.113.003855	journal	July 2013
Menaquinone as a potential target of antibacterial agents Paudel, Atmika; Hamamoto, Hiroshi; Panthee, Suresh Drug Discoveries & Therapeutics, Vol. 10, Issue 3 https://doi.org/10.5582/ddt.2016.01041	journal	January 2016

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