Birinapant

Birinapant is a bivalent mimetic of the Diablo homolog known as second mitochondria-derived activator of caspase (Smac). It is an antagonist of cellular inhibitor of apoptosis 1 (cIAP1, or BIRC2), cIAP2 (BIRC3), and XIAP (BIRC4), binding each at nanomolar concentrations. Birinapant causes rapid cIAP1 degradation, caspase activation, PARP cleavage, and NF-kappaB activation in breast cancer cells. It shows in vivo antitumor activity, inducing apoptosis in several types of cancer xenografts in mice.Formal Name: (2S,2'S)-N,N'-[(6,6'-difluoro[2,2'-bi-1H-indole]-3,3'-diyl)bis[methylene[(2R,4S)-4-hydroxy-2,1-pyrrolidinediyl][(1S)-1-ethyl-2-oxo-2,1-ethanediyl]]]bis[2-(methylamino)]-propanamide. CAS Number: 1260251-31-7. Synonyms: TL-32711. Molecular Formula: C42H56F2N8O6. Formula Weight: 806.9. Purity: >95%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 30 mg/mL, DMSO: 30 mg/mL, DMSO:PBS (pH 7.2) (1:2): 0.33 mg/ml, Ethanol: 30 mg/mL. lambdamax: 232, 285, 298, 331, 346, 365 nm. SMILES: O=C(N1[C@H](CC2=C(C3=C(C[C@H]4N(C([C@@H](NC([C@H](C)NC)=O)CC)=O)C[C@@H](O)C4)C(C=CC(F)=C5)=C5N3)NC6=C2C=CC(F)=C6)C[C@H](O)C1)[C@@H](NC([C@H](C)NC)=O)CC. InChi Code: InChI=1S/C42H56F2N8O6/c1-7-33(49-39(55)21(3)45-5)41(57)51-19-27(53)15-25(51)17-31-29-11-9-23(43)13-35(29)47-37(31)38-32(30-12-10-24(44)14-36(30)48-38)18-26-16-28(54)20-52(26)42(58)34(8-2)50-40(56)22(4)46-6/h9-14,21-22,25-28,33-34,45-48,53-54H,7-8,15-. InChi Key: PKWRMUKBEYJEIX-DXXQBUJASA-N.