SML2900

AZD5582

≥98% (HPLC)

• Synonym(s): 3,3′-[2,4-Hexadiyne-1,6-diylbis[oxy[(1S,2R)-2,3-dihydro-1H-indene-2,1-diyl]]]bis[N-methyl-L-alanyl-(2S)-2-cyclohexylglycyl-L-prolinamide], AZD 5582, AZD-5582
• Empirical Formula (Hill Notation): C₅₈H₇₈N₈O₈
• CAS Number: 1258392-53-8
• Molecular Weight: 1015.29
• MDL number: MFCD28411397
• UNSPSC Code: 12352200
• NACRES: NA.77

Properties

• Quality Level: 100
• Assay: ≥98% (HPLC)
• form: powder
• color: white to beige
• storage temp.: −20°C
• SMILES string: CN[C@@H](C)C(N[C@@H](C1CCCCC1)C(N2[C@H](C(N[C@H]3C4=C(C=CC=C4)C[C@H]3OCC#CC#CCO[C@@H]5CC6=C(C=CC=C6)[C@@H]5NC([C@@H]7CCCN7C([C@H](C8CCCCC8)NC([C@H](C)NC)=O)=O)=O)=O)CCC2)=O)=O

Description

Biochem/physiol Actions

AZD5582 is a divalent AVPI motif-based Smac (DIABLO) mimetic (SMC) that acts a potent apoptosis protein repeat (BIR) domain-targeting antagonist against inhibitor of apoptosis proteins (IAPs) cIAP1/2 (BIR3 IC₅₀ = 15/21 nM against 2.5 nM AbuRPFK-5FAM) and XIAP (BIR2/3 IC₅₀ = 21/15 nM). AZD5582 abolishes cellular XIAP-caspase-9 interaction (1 μM, 4 hrs), induces cIAP1/2 degradation (EC₅₀ = 0.1 nM, 1 hr) and apoptosis (GI₅₀ <60 pM, 48 hrs) in MDA-MB-231 breast cancer cultures. AZD5582 causes substantial tumor regression by inducing cIAP1 degradation and apoptosis in tumor cells in MDA-MB-231 xenograft-bearing mice in vivo (3.0 mg/kg/wk i.v.).

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3