Rebeccamycin

Rebeccamycin, an antitumor antibiotic, inhibits DNA topoisomerase I. Rebeccamycin appears to exert its primary antineoplastic effect by poisoning topoisomerase I and has negligible effect on protein kinase C and topoisomerase II.

Product information

CAS Number: 93908-02-2

Molecular Weight: 570.38

Formula: C27H21Cl2N3O7

Chemical Name: 5, 21-dichloro-23-[(2R, 3R, 4R, 5S, 6R)-3, 4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]-3, 13, 23-triazahexacyclo[14.7.0.0, .0, .0, .0, ]tricosa-1, 4, 6, 8, 10, 15, 17(22), 18, 20-nonaene-12, 14-dione

Smiles: CO[C@@H]1[C@@H](CO)O[C@H]([C@H](O)[C@H]1O)N1C2=C3NC4=C(Cl)C=CC=C4C3=C3C(=O)NC(=O)C3=C2C2=CC=CC(Cl)=C12

InChiKey: QEHOIJJIZXRMAN-QZQSLCQPSA-N

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

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: Soluble in DMSO

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

Rebeccamycin is an antitumor antibiotic produced by the actinomycete Saccharotrix aerocolonigenes with activity against several human tumor cell lines, including A549 (lung adenocarcinoma), HCT-116 (colon carcinoma), and KB (nasopharyngeal carcinoma) . Rebeccamycin shows antibacterial activity against several Gram-positive bacteria, including Staphylococcus aureus and Streptococcus faecalis.

In Vivo:

Rebeccamycin (2-256 mg/kg; i.p.; daily for 9 days) prolongs survival in B16 melanoma, L1210 leukemia.

References:

1. Merchant J, et al. Phase I clinical and pharmacokinetic study of NSC 655649, a rebeccamycin analogue, given in both single-dose and multiple-dose formats. Clin Cancer Res. 2002 Jul;8(7):2193-201.
2. Sánchez C, et al. The biosynthetic gene cluster for the antitumor rebeccamycin: characterization and generation of indolocarbazole derivatives. Chem Biol. 2002 Apr;9(4):519-31.
3. Bush JA, et al. Production and biological activity of rebeccamycin, a novel antitumor agent. J Antibiot (Tokyo). 1987 May;40(5):668-78.

Products are for research use only. Not for human use.