Bizelesin

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

Description:Bizelesin is a synthetic cyclopropylpyrroloindole antineoplastic antibiotic. Bizelesin binds to the minor groove of DNA and induces interstrand cross-linking of DNA, thereby inhibiting DNA replication and RNA synthesis. Bizelesin also enhances p53 and p21 induction and triggers G2/M cell-cycle arrest, resulting in cell senescence without apoptosis.

Price and Availability

Bizelesin, purity > 98%, is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.

Chemical Structure

Theoretical Analysis

MedKoo Cat#: 205951Name: BizelesinCAS#: 129655-21-6Chemical Formula: C43H36Cl2N8O5Exact Mass: 814.21857Molecular Weight: 815.7Elemental Analysis: C, 63.31; H, 4.45; Cl, 8.69; N, 13.74; O, 9.81

Synonym:U77779; U-77779; U 77779; Bizelesin.

IUPAC/Chemical Name:1,3-bis(2-((S)-1-(chloromethyl)-5-hydroxy-8-methyl-1,2,3,6-tetrahydropyrrolo[3,2-e]indole-3-carbonyl)-1H-indol-5-yl)urea

InChi Key:FONKWHRXTPJODV-DNQXCXABSA-N

InChi Code: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

SMILES Code:O=C(NC1=CC2=C(NC(C(N3C[C@@H](CCl)C4=C3C=C(O)C5=C4C(C)=CN5)=O)=C2)C=C1)NC6=CC7=C(NC(C(N8C[C@@H](CCl)C9=C8C=C(O)C%10=C9C(C)=CN%10)=O)=C7)C=C6

Technical Data

Additional Information

References

1: Cao PR, McHugh MM, Melendy T, Beerman T. The DNAminor groove-alkylating cyclopropylpyrroloindole drugs adozelesin andbizelesin induce different DNA damage response pathways in human coloncarcinoma HCT116 cells. Mol Cancer Ther. 2003 Jul;2(7):651-9. PubMedPMID: 12883038.

2: Schwartz GH, Patnaik A, Hammond LA, Rizzo J, Berg K, Von Hoff DD,Rowinsky EK. A phase I study of bizelesin, a highly potent and selectiveDNA-interactive agent, in patients with advanced solid malignancies. AnnOncol. 2003 May;14(5):775-82. PubMed PMID: 12702533.

3: Pitot HC, Reid JM, Sloan JA, Ames MM, Adjei AA, Rubin J, BagniewskiPG, Atherton P, Rayson D, Goldberg RM, Erlichman C. A Phase I study ofbizelesin (NSC 615291) in patients with advanced solid tumors. ClinCancer Res. 2002 Mar;8(3):712-7. PubMed PMID: 11895900.

4: McHugh MM, Kuo SR, Walsh-O"Beirne MH, Liu JS, Melendy T, Beerman TA.Bizelesin, a bifunctional cyclopropylpyrroloindole alkylating agent,inhibits simian virus 40 replication in trans by induction of aninhibitor. Biochemistry. 1999 Aug 31;38(35):11508-15. PubMed PMID:10471303.

5: Hidalgo M, Izbicka E, Cerna C, Gomez L, Rowinsky EK, Weitman SD, VonHoff DD. Comparative activity of the cyclopropylpyrroloindole compoundsadozelesin, bizelesin and carzelesin in a human tumor colony-formingassay. Anticancer Drugs. 1999 Mar;10(3):295-302. PubMed PMID: 10327036.

6: Woynarowski JM, Chapman WG, Napier C, Herzig MC. Induction ofAT-specific DNA-interstrand crosslinks by bizelesin in genomic andsimian virus 40 DNA. Biochim Biophys Acta. 1999 Feb 16;1444(2):201-17.PubMed PMID: 10023060.

7: Woynarowski JM, Beerman TA. Effects of bizelesin (U-77,779), abifunctional alkylating minor groove binder, on replication of genomicand simian virus 40 DNA in BSC-1 cells. Biochim Biophys Acta. 1997 Jul17;1353(1):50-60. PubMed PMID: 9256064.

8: Carter CA, Waud WR, Li LH, DeKoning TF, McGovren JP, Plowman J.Preclinical antitumor activity of bizelesin in mice. Clin Cancer Res.1996 Jul;2(7):1143-9. PubMed PMID: 9816280.

9: Volpe DA, Tomaszewski JE, Parchment RE, Garg A, Flora KP, Murphy MJ,Grieshaber CK. Myelotoxic effects of the bifunctional alkylating agentbizelesin on human, canine and murine myeloid progenitor cells. CancerChemother Pharmacol. 1996;39(1-2):143-9. PubMed PMID: 8995512.

10: Woynarowski JM, McHugh MM, Gawron LS, Beerman TA. Effects ofbizelesin (U-77779), a bifunctional alkylating minor groove agent, ongenomic and simian virus 40 DNA. Biochemistry. 1995 Oct10;34(40):13042-50. PubMed PMID: 7548063.