WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 205951
CAS#: 129655-21-6
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.
MedKoo Cat#: 205951
Name: Bizelesin
CAS#: 129655-21-6
Chemical Formula: C43H36Cl2N8O5
Exact Mass: 814.21857
Molecular Weight: 815.7
Elemental Analysis: C, 63.31; H, 4.45; Cl, 8.69; N, 13.74; O, 9.81
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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
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: soluble in DMSO, not soluble in water.
Shelf Life: >5 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 815.7 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
1: Cao PR, McHugh MM, Melendy T, Beerman T. The DNA minor groove-alkylating cyclopropylpyrroloindole drugs adozelesin and bizelesin induce different DNA damage response pathways in human colon carcinoma HCT116 cells. Mol Cancer Ther. 2003 Jul;2(7):651-9. PubMed PMID: 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 selective DNA-interactive agent, in patients with advanced solid malignancies. Ann Oncol. 2003 May;14(5):775-82. PubMed PMID: 12702533.
3: Pitot HC, Reid JM, Sloan JA, Ames MM, Adjei AA, Rubin J, Bagniewski PG, Atherton P, Rayson D, Goldberg RM, Erlichman C. A Phase I study of bizelesin (NSC 615291) in patients with advanced solid tumors. Clin Cancer 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 an inhibitor. Biochemistry. 1999 Aug 31;38(35):11508-15. PubMed PMID: 10471303.
5: Hidalgo M, Izbicka E, Cerna C, Gomez L, Rowinsky EK, Weitman SD, Von Hoff DD. Comparative activity of the cyclopropylpyrroloindole compounds adozelesin, bizelesin and carzelesin in a human tumor colony-forming assay. Anticancer Drugs. 1999 Mar;10(3):295-302. PubMed PMID: 10327036.
6: Woynarowski JM, Chapman WG, Napier C, Herzig MC. Induction of AT-specific DNA-interstrand crosslinks by bizelesin in genomic and simian 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), 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. 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 agent bizelesin on human, canine and murine myeloid progenitor cells. Cancer Chemother Pharmacol. 1996;39(1-2):143-9. PubMed PMID: 8995512.
10: Woynarowski JM, McHugh MM, Gawron LS, Beerman TA. Effects of bizelesin (U-77779), a bifunctional alkylating minor groove agent, on genomic and simian virus 40 DNA. Biochemistry. 1995 Oct 10;34(40):13042-50. PubMed PMID: 7548063.
