SML3176

WEHI-539 hydrochloride

≥98% (HPLC)

• Synonym(s): (E)-5-(3-(4-(Aminomethyl)phenoxy)propyl)-2-(8-(2-(benzo[d]thiazol-2-yl)hydrazono)-5,6,7,8-tetrahydronaphthalen-2-yl)thiazole-4-carboxylic acid hydrochloride, 5-[3-[4-(Aminomethyl)phenoxy]propyl]-2-[8-[2-(2-benzothiazolyl)hydrazinylidene]-5,6,7,8-tetrahydro-2-naphthalenyl]-4-thiazolecarboxylic acid hydrochloride, WEHI 539 hydrochloride
• Empirical Formula (Hill Notation): C₃₁H₂₉N₅O₃S₂ · xHCl
• Molecular Weight: 583.72 (free base basis)
• MDL number: MFCD28044305
• UNSPSC Code: 12352200
• NACRES: NA.77

Properties

• Quality Level: 100
• Assay: ≥98% (HPLC)
• form: powder
• storage condition: desiccated
• color: faint yellow to dark orange
• solubility: DMSO: 2 mg/mL, clear
• storage temp.: −20°C
• SMILES string: [s]1c(nc(c1CCCOc6ccc(cc6)CN)C(=O)O)c2cc3c(cc2)CCC=C3NNc4[s]c5c(n4)cccc5
• InChI: 1S/C31H29N5O3S2/c32-18-19-10-14-22(15-11-19)39-16-4-9-27-28(30(37)38)34-29(40-27)21-13-12-20-5-3-7-24(23(20)17-21)35-36-31-33-25-6-1-2-8-26(25)41-31/h1-2,6-8,10-15,17,35H,3-5,9,16,18,32H2,(H,33,36)(H,37,38)

Description

Biochem/physiol Actions

WEHI-539 is an apoptosis inducer that selectively targets the anti-apoptotic Bcl-2 family member Bcl-XL with high affinity (KD = 0.6 nM; 500-fold over Bcl-2 and 400-fold over Bcl-W, Mcl-1 and A1) in a manner distinct from that of ABT-737. WEHI blocks Bcl-XL from targeting the BH3 domain of the pro-apoptotic family member Bim with high potency (IC50 = 1.1 nM), exhibiting no inhibitory potency against Mcl-1-BimBH3 interaction (IC50 >10 μM). WEHI-539 is shown to induce apoptosis in human and murine cultures by selectively antagonizing Bcl-XL prosurvival activity (EC50 <10 nM/Mcl-1-knockout MEF, <0.5 nM/mouse platelets, and <32 nM/human platelets).

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable