A DNA topoisomerase I inhibitor
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Rebeccamycin

Item No. 17914

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
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
CAS Number
93908-02-2
Synonyms
  • BRN 4732638
  • NSC 359079
Molecular Formula
C27H21Cl2N3O7
Formula Weight
570.4
Purity
≥99%
Formulation
A lyophilisate
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: Soluble
SMILES
O=C(NC1=O)C2=C1C(C(C=CC=C3Cl)=C3N4[C@]5([H])O[C@H](CO)[C@@H](OC)[C@H](O)[C@H]5O)=C4C6=C2C7=C(C(Cl)=CC=C7)N6
InChi Code
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
InChi Key
QEHOIJJIZXRMAN-QZQSLCQPSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $196

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    2.5 mg

    $873

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    Cayman Chemical
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    Product Description

    Rebeccamycin is an indolocarbazole antibiotic produced by S. aerocolonigenes ATCC39243 that weakly inhibits DNA topoisomerase I.1,2 It is cytotoxic to human lung adenocarcinoma, colon carcinoma, and nasopharyngeal carcinoma cell lines (IC50s range from 0.4-98 µM), producing single-strand breaks in the DNA of these tumor cells.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Long, B.H., Rose, W.C., Vyas, D.M., et al. Discovery of antitumor indolocarbazoles: Rebeccamycin, NSC 655649, and fluoroindolocarbazoles. Curr. Med. Chem. Anticancer Agents 2(2), 255-266 (2002).

    2. Sánchez, C., Butovich, I.A., Braña, A.F., et al. The biosynthetic gene cluster for the antitumor rebeccamycin: Characterization and generation of indolocarbazole derivatives. Chem. Biol. 9(4), 519-531 (2002).

    3. Bush, J.A., Long, B.H., Catino, J.J., et al. Production and biological activity of rebeccamycin, a novel antitumor agent. J. Antibiot. (Tokyo) 40(5), 668-678 (1987).