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MedKoo Cat#: 461193 | Name: Rebeccamycin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Rebeccamycin is a microbial metabolite and a well-known topoisomerase I inhibitor. It is used as an antitumor drug.

Chemical Structure

Rebeccamycin
Rebeccamycin
CAS#93908-02-2

Theoretical Analysis

MedKoo Cat#: 461193

Name: Rebeccamycin

CAS#: 93908-02-2

Chemical Formula: C27H21Cl2N3O7

Exact Mass: 569.0757

Molecular Weight: 570.37

Elemental Analysis: C, 56.86; H, 3.71; Cl, 12.43; N, 7.37; O, 19.63

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Rebeccamycin;
IUPAC/Chemical Name
1,11-dichloro-12-((2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxytetrahydro-2H-pyran-2-yl)-12,13-dihydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione
InChi Key
QEHOIJJIZXRMAN-QZQSLCQPSA-N
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
SMILES Code
O=C1NC(C2=C1C3=C(C4=C2C5=C(N4[C@H]6[C@@H]([C@H]([C@@H]([C@@H](CO)O6)OC)O)O)C(Cl)=CC=C5)NC7=C3C=CC=C7Cl)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 570.37 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Van Arnam EB, Ruzzini AC, Sit CS, Currie CR, Clardy J. A Rebeccamycin Analog Provides Plasmid-Encoded Niche Defense. J Am Chem Soc. 2015 Nov 18;137(45):14272-4. doi: 10.1021/jacs.5b09794. Epub 2015 Nov 10. PubMed PMID: 26535611; PubMed Central PMCID: PMC4735871. 2: Spolitak T, Ballou DP. Evidence for catalytic intermediates involved in generating the chromopyrrolic acid scaffold of rebeccamycin by RebO and RebD. Arch Biochem Biophys. 2015 May 1;573:111-9. doi: 10.1016/j.abb.2015.03.020. Epub 2015 Mar 30. PubMed PMID: 25837855. 3: Animati F, Berettoni M, Bigioni M, Binaschi M, Cipollone A, Irrissuto C, Nardelli F, Olivieri L. Synthesis and biological evaluation of rebeccamycin analogues modified at the imide moiety. Bioorg Med Chem Lett. 2012 Aug 1;22(15):5013-7. doi: 10.1016/j.bmcl.2012.06.016. Epub 2012 Jun 15. PubMed PMID: 22749423. 4: Sánchez C, Butovich IA, Braña AF, Rohr J, Méndez C, Salas JA. The biosynthetic gene cluster for the antitumor rebeccamycin: characterization and generation of indolocarbazole derivatives. Chem Biol. 2002 Apr;9(4):519-31. PubMed PMID: 11983340. 5: Berg SL, Aleksic A, McGuffey L, Dauser R, Nuchtern J, Bernacky B, Blaney SM. Plasma and cerebrospinal fluid pharmacokinetics of rebeccamycin (NSC 655649) in nonhuman primates. Cancer Chemother Pharmacol. 2004 Aug;54(2):127-30. Epub 2004 May 18. PubMed PMID: 15150671. 6: Prudhomme M. Rebeccamycin analogues as anti-cancer agents. Eur J Med Chem. 2003 Feb;38(2):123-40. Review. PubMed PMID: 12620658. 7: Groom K, Bhattacharya A, Zechel DL. Rebeccamycin and staurosporine biosynthesis: insight into the mechanisms of the flavin-dependent monooxygenases RebC and StaC. Chembiochem. 2011 Feb 11;12(3):396-400. doi: 10.1002/cbic.201000580. Epub 2011 Jan 11. PubMed PMID: 21290541. 8: Schwandt A, Mekhail T, Halmos B, O'Brien T, Ma PC, Fu P, Ivy P, Dowlati A. Phase-II trial of rebeccamycin analog, a dual topoisomerase-I and -II inhibitor, in relapsed "sensitive" small cell lung cancer. J Thorac Oncol. 2012 Apr;7(4):751-4. doi: 10.1097/JTO.0b013e31824abca2. PubMed PMID: 22425925; PubMed Central PMCID: PMC3310884. 9: Burstein HJ, Overmoyer B, Gelman R, Silverman P, Savoie J, Clarke K, Dumadag L, Younger J, Ivy P, Winer EP. Rebeccamycin analog for refractory breast cancer: a randomized phase II trial of dosing schedules. Invest New Drugs. 2007 Apr;25(2):161-4. Epub 2006 Sep 13. PubMed PMID: 16969707. 10: Watari A, Hasegawa M, Yagi K, Kondoh M. Checkpoint Kinase 1 Activation Enhances Intestinal Epithelial Barrier Function via Regulation of Claudin-5 Expression. PLoS One. 2016 Jan 4;11(1):e0145631. doi: 10.1371/journal.pone.0145631. eCollection 2016. PubMed PMID: 26727128; PubMed Central PMCID: PMC4699696. 11: Bush JA, Long BH, Catino JJ, Bradner WT, Tomita K. Production and biological activity of rebeccamycin, a novel antitumor agent. J Antibiot (Tokyo). 1987 May;40(5):668-78. PubMed PMID: 3112080. 12: Anizon F, Moreau P, Sancelme M, Laine W, Bailly C, Prudhomme M. Rebeccamycin analogues bearing amine substituents or other groups on the sugar moiety. Bioorg Med Chem. 2003 Aug 15;11(17):3709-22. PubMed PMID: 12901916. 13: Goossens JF, Hénichart JP, Anizon F, Prudhomme M, Dugave C, Riou J, Bailly C. Cellular uptake and interaction with purified membranes of rebeccamycin derivatives. Eur J Pharmacol. 2000 Feb 18;389(2-3):141-6. PubMed PMID: 10688977. 14: Long BH, Rose WC, Vyas DM, Matson JA, Forenza S. Discovery of antitumor indolocarbazoles: rebeccamycin, NSC 655649, and fluoroindolocarbazoles. Curr Med Chem Anticancer Agents. 2002 Mar;2(2):255-66. Review. PubMed PMID: 12678746. 15: Onaka H, Taniguchi S, Igarashi Y, Furumai T. Characterization of the biosynthetic gene cluster of rebeccamycin from Lechevalieria aerocolonigenes ATCC 39243. Biosci Biotechnol Biochem. 2003 Jan;67(1):127-38. PubMed PMID: 12619684. 16: Langevin AM, Bernstein M, Kuhn JG, Blaney SM, Ivy P, Sun J, Chen Z, Adamson PC; Children's Oncology Group. A phase II trial of rebeccamycin analogue (NSC #655649) in children with solid tumors: a Children's Oncology Group study. Pediatr Blood Cancer. 2008 Mar;50(3):577-80. PubMed PMID: 17610262. 17: Lam KS, Schroeder DR, Veitch JM, Matson JA, Forenza S. Isolation of a bromo analog of rebeccamycin from Saccharothrix aerocolonigenes. J Antibiot (Tokyo). 1991 Sep;44(9):934-9. PubMed PMID: 1938615. 18: Nishizawa T, Grüschow S, Jayamaha DH, Nishizawa-Harada C, Sherman DH. Enzymatic assembly of the bis-indole core of rebeccamycin. J Am Chem Soc. 2006 Jan 25;128(3):724-5. PubMed PMID: 16417354. 19: Messaoudi S, Anizon F, Peixoto P, David-Cordonnier MH, Golsteyn RM, Léonce S, Pfeiffer B, Prudhomme M. Synthesis and biological activities of 7-aza rebeccamycin analogues bearing the sugar moiety on the nitrogen of the pyridine ring. Bioorg Med Chem. 2006 Nov 15;14(22):7551-62. Epub 2006 Aug 4. PubMed PMID: 16889964. 20: Moreau P, Anizon F, Sancelme M, Prudhomme M, Bailly C, Sevère D, Riou JF, Fabbro D, Meyer T, Aubertin AM. Syntheses and biological activities of rebeccamycin analogues. Introduction of a halogenoacetyl substituent. J Med Chem. 1999 Feb 25;42(4):584-92. PubMed PMID: 10052965.