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J Med Microbiol 55 (2006), 407-415; DOI: 10.1099/jmm.0.46319-0
© 2006 Society for General Microbiology
ISSN 0022-2615

In vitro properties of antimicrobial bromotyrosine alkaloids

Neora Pick1, Mamta Rawat1,2, Dorit Arad1, Jiong Lan3, Junfa Fan3, Andrew S. Kende3 and Yossef Av-Gay1

1 Division of Infectious Diseases, University of British Columbia, Vancouver, BC V5Z 3J5, Canada

2 Department of Biology, California State University – Fresno, Fresno, CA 937401, USA

3 Department of Chemistry, University of Rochester, Rochester, NY 14627-0216, USA

Correspondence
Yossef Av-Gay
yossi{at}interchange.ubc.ca

Received 6 September 2005
Accepted 11 December 2005

A bromotyrosine alkaloid family of antimicrobial agents was synthesized using the known structure of a natural inhibitor of the mycobacterial mycothiol S-conjugate amidase (MCA) as a template. This series of compounds represents a novel class of anti-infective agents against Gram-positive pathogens, including mycobacteria and meticillin- and vancomycin-resistant Staphylococcus aureus. The fact that these compounds are active against mycobacterial strains in which the MCA gene is deleted and against Gram-positive bacteria lacking mycothiol suggests the existence of an alternative target for these compounds. One member of this family, EXEG1706, was identified as the lead compound possessing low MICs (2·5–25 µg ml–1) for several clinical isolates, whilst having low toxicity for THP-1 monocytes and macrophages.

Abbreviations: BCG, Bacille Calmette–Guérin; FACS, fluorescence-activated cell sorting; MCA, mycothiol S-conjugate amidase; MRSA, meticillin-resistant Staphylococcus aureus; MSH, mycothiol; MSSA, meticillin-sensitive Staphylococcus aureus; PI, propidium iodide; PMA, phorbol myristate acetate; TB, tuberculosis; VRSA, vancomycin-resistant Staphylococcus aureus; VRSH, vancomycin-resistant Staphylococcus haemolyticus.




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