Chemistry:Rebeccamycin

Short description: Chemical compound

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 N
PubChem CID	73110
ChemSpider	65891 Y
UNII	Y96MQM21V9
ChEBI	CHEBI:135511 Y
ChEMBL	ChEMBL370100 Y
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 Y Key:QEHOIJJIZXRMAN-QZQSLCQPSA-N Y
NY (what is this?)  (verify)

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.

Becatecarin (BMS-181176) is a synthetic analog of rebeccamycin.

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.

Further reading

• "Isolation and structure of rebeccamycin-a new antitumor antibiotic from Nocardia aerocoligenes.". Tetrahedron Letters 26 (34): 4011–4014. January 1985. doi:10.1016/S0040-4039(00)89280-1. 
• "Production and biological activity of rebeccamycin, a novel antitumor agent". The Journal of Antibiotics 40 (5): 668–78. May 1987. doi:10.7164/antibiotics.40.668. PMID 3112080. 
• "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". Journal of Medicinal Chemistry 40 (21): 3456–65. October 1997. doi:10.1021/jm9702084. PMID 9341921. 
• "DNA cleavage by topoisomerase I in the presence of indolocarbazole derivatives of rebeccamycin". Biochemistry 36 (13): 3917–29. April 1997. doi:10.1021/bi9624898. PMID 9092822. 
• "Calories from carbohydrates: energetic contribution of the carbohydrate moiety of rebeccamycin to DNA binding and the effect of its orientation on topoisomerase I inhibition". Chemistry & Biology 6 (5): 277–86. May 1999. doi:10.1016/S1074-5521(99)80073-8. PMID 10322124.