Issue 37, 2012

Syntheses of mycobactin analogs as potent and selective inhibitors of Mycobacterium tuberculosis

Abstract

Three analogs of mycobactin T, the siderophore secreted by Mycobacterium tuberculosis (Mtb) were synthesized and screened for their antibiotic activity against Mtb H37Rv and a broad panel of Gram-positive and Gram-negative bacteria. The synthetic mycobactins were potent (MIC90 0.02–0.88 μM in 7H12 media) and selective Mtb inhibitors, with no inhibitory activity observed against any other of the microorganisms tested. The maleimide-containing analog 40 represents a versatile platform for the development of mycobactin-drug conjugates, as well as other applications.

Graphical abstract: Syntheses of mycobactin analogs as potent and selective inhibitors of Mycobacterium tuberculosis

Supplementary files

Article information

Article type
Paper
Submitted
04 Jun 2012
Accepted
02 Aug 2012
First published
03 Aug 2012

Org. Biomol. Chem., 2012,10, 7584-7593

Syntheses of mycobactin analogs as potent and selective inhibitors of Mycobacterium tuberculosis

R. E. Juárez-Hernández, S. G. Franzblau and M. J. Miller, Org. Biomol. Chem., 2012, 10, 7584 DOI: 10.1039/C2OB26077H

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