Z-VAD-FMK

• CAT Number: I002423
• CAS Number: 187389-52-2
• Molecular Formula: C₂₂H₃₀N₃O₇F
• Molecular Weight: 467.5
• Purity: ≥95%
• Synonyms: methyl (3S)-5-fluoro-3-[[(2S)-2-[[(2S)-3-methyl-2-(phenylmethoxycarbonylamino)butanoyl]amino]propanoyl]amino]-4-oxopentanoate
• Target: Caspase
• Solubility: DMSO: ≥ 30 mg/mL
• Storage: 3 years -20C powder
• InChI: InChI=1S/C22H30FN3O7/c1-13(2)19(26-22(31)33-12-15-8-6-5-7-9-15)21(30)24-14(3)20(29)25-16(17(27)11-23)10-18(28)32-4/h5-9,13-14,16,19H,10-12H2,1-4H3,(H,24,30)(H,25,29)(H,26,31)
• InChIKey: MIFGOLAMNLSLGH-UHFFFAOYSA-N
• SMILES: CC(C)C(C(=O)NC(C)C(=O)NC(CC(=O)OC)C(=O)CF)NC(=O)OCC1=CC=CC=C1

Z-VAD-FMK (CAT: I002423) is a synthetic peptide-based compound and a potent irreversible inhibitor of caspases, which are a family of cysteine proteases involved in apoptosis (programmed cell death). The “Z” in the compound’s name refers to the benzyloxy carbonyl (Z) protecting group. VAD stands for valine-alanine-aspartate, which is the recognition motif for caspases. FMK stands for fluoromethyl ketone, which is the reactive group that irreversibly binds to the active site of caspases. By inhibiting caspase activity, Z-VAD-FMK can prevent apoptosis and has been widely used as a tool compound in research to investigate the role of caspases in various biological processes, including cell death, inflammation, and immune responses.

Reference

[1]. Slee EA, et al. Benzyloxycarbonyl-Val-Ala-Asp (OMe) fluoromethylketone (Z-VAD.FMK) inhibits apoptosis by blocking the processing of CPP32. Biochem J. 1996 Apr 1;315 ( Pt 1):21-4.
[2]. Shimizu T, et al. Camptothecin-induced apoptosis in p53-null human leukemia HL60 cells and their isolated nuclei: effects of the protease inhibitors Z-VAD-fmk and dichloroisocoumarin suggest an involvement of both caspases and serine proteases. Leukemia. 1997 Aug;11(8):1238-44.
[3]. Ilangovan R, et al. Inhibition of apoptosis by Z-VAD-fmk in SMN-depleted S2 cells. J Biol Chem. 2003 Aug 15;278(33):30993-9.