Becatecarin

• CAT Number: I004104
• CAS Number: 119673-08-4
• Molecular Formula: C33H34Cl2N4O7
• Molecular Weight: 669.556
• Purity: ≥95%
• Solubility: Soluble in DMSO, not in water
• Storage: -20°C
• InChI: InChI=1S/C33H34Cl2N4O7/c1-4-37(5-2)12-13-38-31(43)22-20-15-8-6-10-17(34)24(15)36-25(20)27-21(23(22)32(38)44)16-9-7-11-18(35)26(16)39(27)33-29(42)28(41)30(45-3)19(14-40)46-33/h6-11,19,28-30,33,36,40-42H,4-5,12-14H2,1-3H3/t19-,28-,29-,30-,33-/m1/s1
• InChIKey: JSKFWUPVIZYJMR-UDOAKELVSA-N
• SMILES: CCN(CC)CCN1C(=O)C2=C3C4=C(C(=CC=C4)Cl)NC3=C5C(=C2C1=O)C6=C(N5C7C(C(C(C(O7)CO)OC)O)O)C(=CC=C6)Cl

Becatecarin, also known as BMY-27557, XL119 and BMS-181176, is a synthetic diethylaminoethyl analogue of the indolocarbazole glycoside antineoplastic antibiotic rebeccamycin. Becatecarin intercalates into DNA and stabilizes the DNA-topoisomerase I complex, thereby interfering with the topoisomerase I-catalyzed DNA breakage-reunion reaction and initiating DNA cleavage and apoptosis.

Reference

1:Becatecarin (rebeccamycin analog, NSC 655649) is a transport substrate and induces expression of the ATP-binding cassette transporter, ABCG2, in lung carcinoma cells. Robey RW, Obrzut T, Shukla S, Polgar O, Macalou S, Bahr JC, Di Pietro A, Ambudkar SV, Bates SE.Cancer Chemother Pharmacol. 2009 Aug;64(3):575-83. doi: 10.1007/s00280-008-0908-2. Epub 2009 Jan 9. PMID: 19132374 Free PMC Article2:Becatecarin (Helsinn Healthcare). Rewcastle GW.IDrugs. 2005 Oct;8(10):838-47. Review. PMID: 16254805