Z-VAD-FMK peptide

Z-VAD-FMK peptide

• Handling and Storage of Synthetic Peptides
• Material Safety Data Sheets (MSDS)

Batch to batch variation of the purity

Z-VAD-FMK, Benzyloxycarbonyl (Z) at N terminal, Fluoromethylketone (FMK) at C terminal

Benzyloxycarbonyl-Val-Ala-Asp(OMe)-fluoromethylketone

3

95.25%

C₂₂H₃₀FN₃O₇

467.49

Synthetic

Powder

Z-VAD-FMK (Z-Val-Ala-Asp(OMe)-FMK) is a cell-permeable, irreversible pan-caspase inhibitor. Z-VAD-FMK inhibits caspase processing and apoptosis induction in tumour cells in vitro with an IC50 of 0.0015 - 5.8 mM). Z-VAD-FMK is O-methylated in the P1 position on aspartic acid, providing enhanced stability and increased cell permeability. Z-VAD-FMK is active in vivo and can inhibit apoptosis in numerous settings.

Normally, this peptide will be delivered in lyophilized form and should be stored in a freezer at or below -20 °C. For more details, please refer to the manual: Handling and Storage of Synthetic Peptides

• Slee et al (1996) Benzyloxycarbonyl-Val-Ala-Asp (OMe) fluoromethylketone (Z-VAD.FMK) inhibits apoptosis by blocking the processing of CPP32. Biochem.J. 315 21 PMID: 8670109
• Ilangovan et al (2003) Inhibition of apoptosis by Z-VAD-fmk in SMN-depleted S2 cells. J. Biol. Chem. 278(33) 30993 PMID: 12783893
• Simmons et al (2009) Pretreatment with pancaspase inhibitor (Z-VAD-FMK) delays but does not prevent intraperitoneal heat-killed group B Streptococcus-induced preterm delivery in a pregnant mouse model. Infect. Dis. Obstet. Gynecol. 2009 749432 PMID: 20069051

Trifluoroacetic acid (TFA) has a significant impact on peptides due to its role in the peptide synthesis process.

TFA is essential for the protonation of peptides that lack basic amino acids such as Arginine (Arg), Histidine (His), and Lysine (Lys), or ones that have blocked N-termini. As a result, peptides often contain TFA salts in the final product.

TFA residues, when present in custom peptides, can cause unpredictable fluctuations in experimental data. At a nanomolar (nM) level, TFA can influence cell experiments, hindering cell growth at low concentrations (as low as 10 nM) and promoting it at higher doses (0.5–7.0 mM). It can also serve as an allosteric regulator on the GlyR of glycine receptors, thereby increasing receptor activity at lower glycine concentrations.

In an in vivo setting, TFA can trifluoroacetylate amino groups in proteins and phospholipids, inducing potentially unwanted antibody responses. Moreover, TFA can impact structure studies as it affects spectrum absorption.