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Mar. Drugs 2012, 10(8), 1711-1728; doi:10.3390/md10081711
Article

Evaluation of Pseudopteroxazole and Pseudopterosin Derivatives against Mycobacterium tuberculosis and Other Pathogens

1
,
1,2
,
1
 and
1,2,*
1 Department of Chemistry and Department of Biomedical Sciences, Atlantic Veterinary College, University of Prince Edward Island, Charlottetown, PEI C1A 4P3, Canada 2 Nautilus Biosciences Canada, Inc., Charlottetown, PEI C1A 4P3, Canada
* Author to whom correspondence should be addressed.
Received: 12 June 2012 / Revised: 25 July 2012 / Accepted: 1 August 2012 / Published: 15 August 2012
(This article belongs to the Special Issue Marine Antibiotics)
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Abstract

Pseudopterosins and pseudopteroxazole are intriguing marine natural products that possess notable antimicrobial activity with a commensurate lack of cytotoxicity. New semi-synthetic pseudopteroxazoles, pseudopteroquinoxalines and pseudopterosin congeners along with simple synthetic mimics of the terpene skeleton were synthesized. In order to build structure-activity relationships, a set of 29 new and previously reported compounds was assessed for in vitro antimicrobial and cytotoxic activities. A number of congeners exhibited antimicrobial activity against a range of Gram-positive bacteria including Mycobacterium tuberculosis H37Rv, with four displaying notable antitubercular activity against both replicating and non-replicating persistent forms of M. tuberculosis. One new semi-synthetic compound, 21-((1H-imidazol-5-yl)methyl)-pseudopteroxazole (7a), was more potent than the natural products pseudopterosin and pseudopteroxazole and exhibited equipotent activity against both replicating and non-replicating persistent forms of M. tuberculosis with a near absence of in vitro cytotoxicity. Pseudopteroxazole also exhibited activity against strains of M. tuberculosis H37Rv resistant to six clinically used antibiotics.
Keywords: pseudopteroxazoles; semi-synthesis; Mycobacterium tuberculosis; antibiotic-resistance pseudopteroxazoles; semi-synthesis; Mycobacterium tuberculosis; antibiotic-resistance
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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McCulloch, M.W.B.; Haltli, B.; Marchbank, D.H.; Kerr, R.G. Evaluation of Pseudopteroxazole and Pseudopterosin Derivatives against Mycobacterium tuberculosis and Other Pathogens. Mar. Drugs 2012, 10, 1711-1728.

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