Rebeccamycin

Rebeccamycin (NSC 655649) is a weak topoisomerase I inhibitor isolated from Nocardia sp. It is structurally similar to staurosporine, but does not show any inhibitory activity against protein kinases. It shows significant antitumor properties in vitro (IC₅₀=480nM against mouse B16 melanoma cells and IC₅₀=500nM against P388 leukemia cells). It is an antineoplastic antibiotic and an intercalating agent.

Rebeccamycin

Clinical data
Other names	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
ATC code	none
Identifiers
IUPAC name 1,11-dichloro-12-(4-O-methyl-β-D-glucopyranosyl)-12,13-dihydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione
CAS Number	93908-02-2
PubChem CID	73110
ChemSpider	65891
UNII	Y96MQM21V9
ChEBI	CHEBI:135511
ChEMBL	ChEMBL370100
CompTox Dashboard (EPA)	DTXSID70239880
Chemical and physical data
Formula	C27H21Cl2N3O7
Molar mass	570.38 g·mol^−1
3D model (JSmol)	Interactive image
SMILES CO[C@@H]1[C@H](O[C@H]([C@@H]([C@H]1O)O)N2C3=C(C=CC=C3Cl)C4=C5C(=C6C7=C(C(=CC=C7)Cl)NC6=C42)C(=O)NC5=O)CO
InChI InChI=1S/C27H21Cl2N3O7/c1-38-24-13(8-33)39-27(23(35)22(24)34)32-20-10(5-3-7-12(20)29)15-17-16(25(36)31-26(17)37)14-9-4-2-6-11(28)18(9)30-19(14)21(15)32/h2-7,13,22-24,27,30,33-35H,8H2,1H3,(H,31,36,37)/t13-,22-,23-,24-,27-/m1/s1 Key:QEHOIJJIZXRMAN-QZQSLCQPSA-N
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Becatecarin (BMS-181176) is a synthetic analog of rebeccamycin.[1]

Rebeccamycin and becatecarin have been tested in phase II clinical trials for the treatment of lung cancer, liver cancer, breast cancer, lymphoma, retinoblastoma, kidney cancer, and ovarian cancer.[2]

References

1. https://clinicaltrials.gov/ct2/show/NCT00006017
2. https://clinicaltrials.gov/ct2/results?term=BRN+4732638

• "Isolation and structure of rebeccamycin - a new antitumor antibiotic from nocardia aerocoligenes": D. E. Nettleton, et al.; Tetrahedron Letters 34, 4011 (1985)
• 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)