Rebeccamycin

Drugbox
IUPAC_name = 7,10-dichloro-8-(3,4-dihydroxy-6-(hydroxymethyl)-5-methoxytetrahydro-2H-
pyran-2-yl)-8,9-dihydro-1H-indolo [2,3-a] pyrrolo [3,4-c] carbazole-1,3(2H)-dione


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CAS_number= 93908-02-2
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DrugBank=
C=27 | H=21 | Cl=2 | N=3 | O=7
molecular_weight = 570.38
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Rebeccamycin is a weak topoisomerase I inhibitor isolated from "Streptomyces sp." structurally similar to staurosporine. Does not show any inhibitory activity against protein kinases. Shows significant antitumor properties in vitro (IC₅₀=480nM against mouse B16 melanoma cells and IC₅₀=500nM against P388 leukemia cells).

References

*"Production and biological activity of rebeccamycin, a novel antitumor agent": J.A. Bush, et al.; J. Antibiot. (Tokyo) 40, 668 (1987)
*"Syntheses and biological activities (topoisomerase inhibition and antitumor and antimicrobial properties) of rebeccamycin analogues bearing modified sugar moieties and substituted on the imide nitrogen with a methyl group" F. Anizon, et al.; J. Med. Chem. 40, 3456 (1997)
*"DNA cleavage by topoisomerase I in the presence of indolocarbazole derivatives of rebeccamycin": C. Bailly, et al.; Biochemistry 36, 3917 (1997)
*"Calories from carbohydrates: energetic contribution of the carbohydrate moiety of rebeccamycin to DNA binding and the effect of its orientation on topoisomerase I inhibition": C. Bailly, et al.; Chem. Biol. 6, 277 (1999)