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R4900 Sigma

Rebeccamycin

solid, ≥98% (HPLC), from Saccharothrix aerocolonigenes

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Description

Biochem/physiol Actions

Rebeccamycin is an antibiotic composed of a halogenated indolocarbazole chromophore linked via N-glycosidic bond to a glucose derivative. As an antitumor agent,1 it is cytotoxic to tumor cell lines such as human lung adenocarcinoma, colon carcinoma and nasopharyngeal carcinoma, etc.2 Rebeccamycin intercalates into the DNA and is an inhibitor of topoisomerase I. It stabilizes the covalent topoisomerase I-DNA intermediate (the cleavable complex) resulting in increased DNA strand breaks.3

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Safety Information

WGK Germany 
3

Protocols & Articles

Articles

DNA Damage and Repair

Damage to cellular DNA is involved in mutagenesis and the development of cancer. The DNA in a human cell undergoes several thousand to a million damaging events per day, generated by both external (e...
BioFiles 2007, 2.4, 20.
Keywords: AGE, Alkylations, Apoptosis, Applications, Biochemistry, Cancer, Carcinogens, Catalysis, Clinical, DNA replication, Deaminations, Environmental, Error, Events, Gene expression, Metabolites, Methylations, Mutagens, Oxidations, Polymorphisms, Rearrangements, Recombination, Sequences, Substitutions, Transcription, Type

Peer-Reviewed Papers

References

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1. Production and biological activity of rebeccamycin, a novel antitumor agent. Bush J.A. et al. J. Antibiot. 40, 668, (1987)

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2. Weitman, S., et al. J. Pediatr. Hematol. Oncol. 20, 20, (1998)

3. Syntheses and biological activities of rebeccamycin analogues. Introduction of a halogenoacetyl substituent. Moreau, P., et al. J. Med. Chem. 42, 584, (1999)

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Staurosporine and rebeccamycin aglycones are assembled by the oxidative action of StaP, StaC, and RebC on chromopyrrolic acid. Howard-Jones AR and Walsh CT J. Am. Chem. Soc. 128(37), 12289-98, (2006)

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Nonenzymatic oxidative steps accompanying action of the cytochrome P450 enzymes StaP and RebP in the biosynthesis of staurosporine and rebeccamycin. Howard-Jones AR and Walsh CT J. Am. Chem. Soc. 129(36), 11016-7, (2007)

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Flavin redox chemistry precedes substrate chlorination during the reaction of the flavin-dependent halogenase RebH. Yeh E, Cole LJ, Barr EW, et al. Biochemistry 45(25), 7904-12, (2006)

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Phase-II trial of rebeccamycin analog, a dual topoisomerase-I and -II inhibitor, in relapsed "sensitive" small cell lung cancer. Schwandt A, Mekhail T, Halmos B, et al. J. Thorac. Oncol. 7(4), 751-4, (2012)

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Natural product diversification using a non-natural cofactor analogue of S-adenosyl-L-methionine. Zhang C, Weller RL, Thorson JS, et al. J. Am. Chem. Soc. 128(9), 2760-1, (2006)

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Structure and mechanism of the rebeccamycin sugar 4'-O-methyltransferase RebM. Singh S, McCoy JG, Zhang C, et al. J. Biol. Chem. 283(33), 22628-36, (2008)

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Rebeccamycin analog for refractory breast cancer: a randomized phase II trial of dosing schedules. Burstein HJ, Overmoyer B, Gelman R, et al. Invest. New Drugs 25(2), 161-4, (2007)

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Discovery of antitumor indolocarbazoles: rebeccamycin, NSC 655649, and fluoroindolocarbazoles. Long BH, Rose WC, Vyas DM, et al. Curr. Med. Chem. Anticancer Agents 2(2), 255-66, (2002)

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Rebeccamycin and staurosporine biosynthesis: insight into the mechanisms of the flavin-dependent monooxygenases RebC and StaC. Groom K, Bhattacharya A, and Zechel DL ChemBioChem. 12(3), 396-400, (2011)

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Recent developments of rebeccamycin analogues as topoisomerase I inhibitors and antitumor agents. Prudhomme M Curr. Med. Chem. 7(12), 1189-212, (2000)

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Syntheses, biochemical and biological evaluation of staurosporine analogues from the microbial metabolite rebeccamycin. Anizon, F., et al. Bioorg. Med. Chem. 6, 1597, (1998)

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Crystallographic trapping in the rebeccamycin biosynthetic enzyme RebC. Ryan KS, Howard-Jones AR, Hamill MJ, et al. Proc. Natl. Acad. Sci. U. S. A. 104(39), 15311-6, (2007)

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Biosynthetic gene cluster for the cladoniamides, bis-indoles with a rearranged scaffold. Ryan KS PLoS ONE 6(8), e23694, (2011)

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Reevaluation of the violacein biosynthetic pathway and its relationship to indolocarbazole biosynthesis. Sánchez C, Braña AF, Méndez C, et al. ChemBioChem. 7(8), 1231-40, (2006)

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A concise approach to 1,11-didechloro-6-methyl-4'-O-demethyl rebeccamycin and its binding to human serum albumin: fluorescence spectroscopy and molecular modeling method. Cui F, Qin L, Zhang G, et al. Bioorg. Med. Chem. 16(16), 7615-21, (2008)

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Rebeccamycin derivatives as dual DNA-damaging agents and potent checkpoint kinase 1 inhibitors. Marminon C, Anizon F, Moreau P, et al. Mol. Pharmacol. 74(6), 1620-9, (2008)

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Synthesis and biological activities of isogranulatimide analogues. Hugon B, Anizon F, Bailly C, et al. Bioorg. Med. Chem. 15(17), 5965-80, (2007)

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Biosynthesis of indolocarbazole and goadsporin, two different heterocyclic antibiotics produced by actinomycetes. Onaka H Biosci. Biotechnol. Biochem. 73(10), 2149-55, (2009)

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Rebeccamycin analogues as anti-cancer agents. Prudhomme M Eur. J. Med. Chem. 38(2), 123-40, (2003)

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Characterization and functional modification of StaC and RebC, which are involved in the pyrrole oxidation of indolocarbazole biosynthesis. Asamizu S, Shiro Y, Igarashi Y, et al. Biosci. Biotechnol. Biochem. 75(11), 2184-93, (2011)

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Generation of potent and selective kinase inhibitors by combinatorial biosynthesis of glycosylated indolocarbazoles. Sánchez C, Salas AP, Braña AF, et al. Chem. Commun. (Camb.) (27), 4118-20, (2009)

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Molecular cloning, sequence analysis and functional characterization of the gene cluster for biosynthesis of K-252a and its analogs. Chiu HT, Chen YL, Chen CY, et al. Mol. Biosyst. 5(10), 1180-91, (2009)

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Synthesis, biological evaluation, and molecular modeling studies of rebeccamycin analogues modified in the carbohydrate moiety. Animati F, Berettoni M, Bigioni M, et al. ChemMedChem 3(2), 266-79, (2008)

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Engineering biosynthetic pathways to generate antitumor indolocarbazole derivatives. Sánchez C, Méndez C, and Salas JA J. Ind. Microbiol. Biotechnol. 33(7), 560-8, (2006)

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Synthesis and biological evaluation of rebeccamycin analogues modified at the imide moiety. Animati F, Berettoni M, Bigioni M, et al. Bioorg. Med. Chem. Lett. 22(15), 5013-7, (2012)

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Phase 1 study of XL119, a rebeccamycin analog, in patients with refractory hematologic malignancies. Borthakur G, Alvarado Y, Ravandi-Kashani F, et al. Cancer 113(2), 360-6, (2008)

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Synthesis and biological activities of 7-aza rebeccamycin analogues bearing the sugar moiety on the nitrogen of the pyridine ring. Messaoudi S, Anizon F, Peixoto P, et al. Bioorg. Med. Chem. 14(22), 7551-62, (2006)

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Cellular uptake and interaction with purified membranes of rebeccamycin derivatives. Goossens, J.F., et al. Eur. J. Pharmacol. 389, 141, (2000)

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Parenteral formulation and thermal degradation pathways of a potent rebeccamycin based indolocarbazole topoisomerase I inhibitor. Sato Y, Breslin D, Kitada H, et al. Int. J. Pharm. 390(2), 128-33, (2010)

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A three-step synthesis from rebeccamycin of an efficient checkpoint kinase 1 inhibitor. Anizon F, Golsteyn RM, Léonce S, et al. Eur. J. Med. Chem. 44(5), 2234-8, (2009)

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