Bizelesin

• CAT Number: R049020
• CAS Number: 129655-21-6
• Molecular Formula: C43H36Cl2N8O5
• Molecular Weight: 815.70
• Purity: ≥95%
• Synonyms: 1,3-bis[2-[(8S)-8-(chloromethyl)-4-hydroxy-1-methyl-7,8-dihydro-3H-pyrrolo[3,2-e]indole-6-carbonyl]-1H-indol-5-yl]urea
• InChI: InChI=1S/C43H36Cl2N8O5/c1-19-15-46-39-33(54)11-31-37(35(19)39)23(13-44)17-52(31)41(56)29-9-21-7-25(3-5-27(21)50-29)48-43(58)49-26-4-6-28-22(8-26)10-30(51-28)42(57)53-18-24(14-45)38-32(53)12-34(55)40-36(38)20(2)16-47-40/h3-12,15-16,23-24,46-47,50-51,54-55H,13-14,17-18H2,1-2H3,(H2,48,49,58)/t23-,24-/m1/s1
• InChIKey: FONKWHRXTPJODV-DNQXCXABSA-N
• SMILES: CC1=CNC2=C(C=C3C(=C12)[C@@H](CN3C(=O)C4=CC5=C(N4)C=CC(=C5)NC(=O)NC6=CC7=C(C=C6)NC(=C7)C(=O)N8C[C@H](C9=C1C(=CNC1=C(C=C98)O)C)CCl)CCl)O

Bizelesin（Cat No.:R049020）is a synthetic cyclopropylpyrroloindole (CPI) alkylating agent derived from the natural product CC-1065. It binds to the minor groove of DNA, forming covalent adducts that disrupt DNA replication and transcription, ultimately inducing cell cycle arrest and apoptosis. Bizelesin is highly potent, particularly against rapidly dividing cancer cells, and has been studied for its antitumor activity in preclinical models. Due to its DNA-alkylating mechanism, it exhibits a narrow therapeutic window and significant cytotoxicity, limiting its clinical use. Nonetheless, it remains valuable in cancer pharmacology and DNA-targeted drug research.

Reference

[1]. J M Woynarowski, et al. AT-rich islands in genomic DNA as a novel target for AT-specific DNA-reactive antitumor drugs. J Biol Chem. 2001 Nov 2;276(44):40555-66.
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[2]. J M Woynarowski, et al. Effects of bizelesin (U-77,779), a bifunctional alkylating minor groove binder, on replication of genomic and simian virus 40 DNA in BSC-1 cells. Biochim Biophys Acta. 1997 Jul 17;1353(1):50-60.
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