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Synthesis and biological evaluation of purpurealidin E-derived marine Sponge metabolites : aplysamine-2, aplyzanzine A, suberedamines A and B.

Kottakota, S.K. and Evangelopoulos, D. and Alnimr, A. and Bhakta, S. and McHugh, T.D. and Gray, M. and Groundwater, P.W. and Marrs, E.C.L. and Perry, J.D. and Spilling, C.D. and Harburn, J.J. (2012) 'Synthesis and biological evaluation of purpurealidin E-derived marine Sponge metabolites : aplysamine-2, aplyzanzine A, suberedamines A and B.', Journal of natural products., 75 (6). pp. 1090-1101.

Abstract

Five purpurealidin-derived marine secondary sponge metabolies have been synthesized through the carbodiimide coupling of an appropriate bromotyrosine unit. The structure elucidations have been confirmed through direct comparison with spectroscopic data of isolated natural products. Aplyzanzine A has been shown to be the most active product against a broad bacterial and fungal screen, demonstrating MIC values 2 to 4 times lower than the other metabolites in this study. Compounds 2, 3, 4a, and 5-7 exhibit a modest inhibition against slow growing mycobacteria (MIC 25-50 μg/mL), including Mycobacterium tuberculosis. iso-Anomoian A and suberedamine B showed antitumor activity in the NCI-DTP60 cell line screen at single-digit micromolar concentrations, with iso-anomoian A inhibiting 53 cell lines. These molecules present novel scaffolds for further optimization. New value: Five purpurealidin-derived marine secondary sponge metabolies have been synthesized through the carbodiimide coupling of an appropriate bromotyrosine unit. The structure elucidations have been confirmed through direct comparison with spectroscopic data of isolated natural products. Aplyzanzine A has been shown to be the most active product against a broad bacterial and fungal screen, demonstrating MIC values 2 to 4 times lower than the other metabolites in this study. Compounds 2, 3, 4a, and 5-7 exhibit a modest inhibition against slow growing mycobacteria (MIC 25-50 μg/mL), including Mycobacterium tuberculosis. iso-Anomoian A and suberedamine B showed antitumor activity in the NCI-DTP60 cell line screen at single-digit micromolar concentrations, with iso-anomoian A inhibiting 53 cell lines. These molecules present novel scaffolds for further optimization.

Item Type:Article
Full text:Full text not available from this repository.
Publisher Web site:http://dx.doi.org/10.1021/np300102z
Record Created:29 Oct 2012 13:20
Last Modified:10 Apr 2013 13:16

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