Rebeccamycin

Rebeccamycin
Clinical data
Other names7,10-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
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC27H21Cl2N3O7
Molar mass570.38 g·mol−1
3D model (JSmol)
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 checkY
  • Key:QEHOIJJIZXRMAN-QZQSLCQPSA-N checkY
 ☒NcheckY (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.[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

  • "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)


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