For research use only. Not for therapeutic Use.
Rebeccamycin（Cat No.:R030133）is a naturally occurring antibiotic and antitumor agent derived from the bacterium Streptomyces hygroscopicus. It exhibits potent cytotoxicity against a variety of cancer cell lines by inhibiting topoisomerase I, an enzyme crucial for DNA replication and transcription. By stabilizing the enzyme-DNA complex, rebeccamycin induces DNA breaks, leading to cell cycle arrest and apoptosis. Its unique structure and mechanism of action make it a valuable compound in cancer research. While not widely used in clinical practice, rebeccamycin and its analogs are being investigated for potential therapeutic applications in oncology.
| Catalog Number | R030133 |
| CAS Number | 93908-02-2 |
| Synonyms | 1,11-Dichloro-12,13-dihydro-12-(4-O-methyl-β-D-glucopyranosyl)-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione; (+)-Rebeccamycin; NSC 359079? |
| Molecular Formula | C27H21Cl2N3O7 |
| Purity | ≥95% |
| Storage | -20°C |
| IUPAC Name | 5,21-dichloro-3-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-1,4(9),5,7,10,15,17(22),18,20-nonaene-12,14-dione |
| 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 |
| InChIKey | QEHOIJJIZXRMAN-QZQSLCQPSA-N |
| 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 |
| Reference | Discovery of antitumor indolocarbazoles: rebeccamycin, NSC 655649, and fluoroindolocarbazoles. Long B. H., et al. , Curr. Med. Chem. Anticancer Agents, 2002, 2, 255.<br/><br/>Active site mutations in DNA topoisomerase I distinguish the cytotoxic activities of camptothecin and the indolocarbazole, rebeccamycin. Woo M. H., et al. , J. Biol. Chem., 2002, 277, 3813.<br/><br/>Production and biological activity of rebeccamycin, a novel antitumor agent. Bush J. A., et al. , J. Antibiot., 1987, 40, 668.</span></p> |
