Z-VAD-FMK Chemical Properties

Melting point:

>190°C (dec.)

Boiling point:

732.4±60.0 °C(Predicted)

Density 

1.214±0.06 g/cm3 (20 ºC 760 Torr)

Flash point:

396.7℃

storage temp. 

-20°C

solubility 

DMSO: 20 mg/mL

form 

powder

pka

11.05±0.46(Predicted)

color 

white

Stability:

Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 week.

InChIKey

MIFGOLAMNLSLGH-QOKNQOGYSA-N

SMILES

C(N)(=O)[C@H](C)N(C(=O)[C@H](C(C)C)NC(OCC1=CC=CC=C1)=O)[C@@H](CC(OC)=O)C(=O)CF

CAS DataBase Reference

187389-52-2

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

HS Code 

29145090

MSDS

• Language:English Provider:SigmaAldrich

Z-VAD-FMK Usage And Synthesis

Description

Z-VAD-FMK (187389-52-2), cell-permeable, methyl ester form. Potent, irreversible pan-caspase inhibitor. Inhibits caspase activity and apoptosis induction in a variety of cell types (IC50 = 1.5 μM). Active in vivo.

Uses

Z-VAD(OMe)-FMK is a cell-permeable, competitive, and irreversible inhibitor of all caspases. Through this action, it inhibits cleavage of poly(ADP-ribose) polymerase, preventing apoptosis when used at 10-50 μM. It also blocks caspase-mediated apoptosis in vivo. Z-VAD(OMe)-FMK effectively prevents caspase action in inflammasomes.[Cayman Chemical]

Uses

Z-VAD-FMK is a caspase inhibitor that inhibits apoptosis and caspase processing in Jurkat T cells treated with low concentrations of z-FA-CMK.

Definition

ChEBI: Z-Val-Ala-Asp(OMe)-CH2F is a tripeptide consisting of Z-Val-Ala-Asp(OMe) in which the C-terminal OH group has been replaced by a fluoromethyl group. An irreversible pan-caspase inhibitor. It has a role as an apoptosis inhibitor and a protease inhibitor. It is a carbamate ester, a tripeptide and an organofluorine compound.

General Description

A cell-permeable, irreversible, pan-caspase inhibitor. Shown to enhance the freeze-thaw survival of human embryonic stem cells. Inhibits Fas-mediated apoptosis in Jurkat T cells. Also reported to inhibit Peptide: N-glycanse (PNGase) in vitro amd in vivo. When using with a purified recombinant enzyme, pretreatment with an esterase is required.

Biological Activity

Cell-permeable, irreversible pan-caspase inhibitor. Inhibits caspase processing and apoptosis induction in tumor cells in vitro (IC 50 = 0.0015-5.8 mM). Active in vivo .

Biochem/physiol Actions

Cell permeable: yes

Enzyme inhibitor

This tripeptide halomethyl ketone (FWfree-acid = 467.49 g/mol; Soluble to 9.35 mg/ml in DMSO; CAS RegistryNumber = 187389-52-2), also known as Z-VAD-FMK and caspase inhibitor VI, is a broad-spectrum caspase inhibitor that blocks caspase-mediated apoptosis. Z-VAD-FMK inhibits caspase processing (IC50 = 0.0015–5.8 mM, depending on enzyme and cell type). The aspartate methyl ester derivative (FW = 467.49 g/mol), also known as caspase inhibitor I, is far more cell-permeable. Target (s) : caspases; caspase-1; caspase-2; caspase-3; caspase-4 ; caspase 5; caspase-6; caspase-7; caspase-8 ; caspase-9; caspase-10.

storage

-20°C

References

1) 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 2) Kunstle et al. (1997), ICE-protease inhibitors block murine liver injury and apoptosis caused by CD95 or by TNF-alpha; Immunol. Lett., 55 5 3) Garcia-Calvo et al. (1998), Inhibition of human caspases by peptide based and macromolecular inhibitors; J. Biol. Chem., 273 32608

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