Symplocamide A, a Potent Cytotoxin and Chymotrypsin Inhibitor from the Marine Cyanobacterium Symploca sp.
- 29 December 2007
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Natural Products
- Vol. 71 (1) , 22-27
- https://doi.org/10.1021/np070280x
Abstract
Investigation of a Symploca sp. from Papua New Guinea has led to the isolation of symplocamide A (1), a potent cancer cell cytotoxin, which also inhibits serine proteases with a 200-fold greater inhibition of chymotrypsin over trypsin. The complete stereostructure of symplocamide A was determined by detailed NMR and MS analysis as well as chiral HPLC analysis of the component amino acid residues. The presence of several unusual structural features in symplocamide A provides new insights into the pharmacophore model for protease selectivity in this drug class and may underlie the potent cytotoxicity of this compound to H-460 lung cancer cells (IC50 = 40 nM) as well as neuro-2a neuroblastoma cells (IC50 = 29 nM).Keywords
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