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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,*
Received: 12 June 2012; in revised form: 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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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.

AMA Style

McCulloch MWB, Haltli B, Marchbank DH, Kerr RG. Evaluation of Pseudopteroxazole and Pseudopterosin Derivatives against Mycobacterium tuberculosis and Other Pathogens. Marine Drugs. 2012; 10(8):1711-1728.

Chicago/Turabian Style

McCulloch, Malcolm W. B.; Haltli, Brad; Marchbank, Douglas H.; Kerr, Russell G. 2012. "Evaluation of Pseudopteroxazole and Pseudopterosin Derivatives against Mycobacterium tuberculosis and Other Pathogens." Mar. Drugs 10, no. 8: 1711-1728.



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