Z-VAD-FMK Property

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

Safety Statements 

22-24/25

WGK Germany 

3

HS Code 

29145090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

Z-VAD-FMK Chemical Properties,Usage,Production

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ChEBI: Z-Val-Ala-Asp(OMe)-CH2F is a tripeptide consisting of Z-Val-Ala-Asp(OMe) in which the C-terminal OH group has been replaced by a fluoromethyl group.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