Becatecarin

For research use only. Not for therapeutic Use.

  • CAT Number: I004104
  • CAS Number: 119673-08-4
  • Molecular Formula: C33H34Cl2N4O7
  • Molecular Weight: 669.556
  • Purity: ≥95%
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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.


Catalog Number I004104
CAS Number 119673-08-4
Synonyms

BMS-181176; BMS 181176; BMS181176; BMY-27557; BMY27557; BMY 27557; XL119; XL 119; XL-119; Becatecarin.;1,11-dichloro-6-(2-(diethylamino)ethyl)-12-((2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxytetrahydro-2H-pyran-2-yl)-12,13-dihydro-5H-in

Molecular Formula C33H34Cl2N4O7
Purity ≥95%
Target Topoisomerase
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
Reference

</br>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 Article</br>2:Becatecarin (Helsinn Healthcare). Rewcastle GW.IDrugs. 2005 Oct;8(10):838-47. Review. PMID: 16254805

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