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HomeProduct name listZ-VAD-FMK

Z-VAD-FMK

Synonym(s):caspase 3;caspase 3, apoptosis-related cysteine peptidase;caspase 3, apoptosis-related cysteine protease;N-Benzyloxycarbonyl-Val-Ala-Asp(O-Me) fluoromethyl ketone;Z-VAD (OMe)-FMK

Z-VAD-FMK Structural

What is Z-VAD-FMK?

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.

The Uses of Z-VAD-FMK

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.

The Uses of Z-VAD-FMK

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]

What are the applications of Application

Z-VAD(OMe)-FMK is an irreversible and cell permeable broad-spectrum Caspase Inhibitor that has shown to inhibit caspase-1 and caspase-3

What are the applications of Application

Z-VAD-FMK is Irreversible, cell-permeable, broad-spectrum caspase Inhibitor

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ChEBI: Z-Val-Ala-Asp(OMe)-CH2F is a tripeptide consisting of Z-Val-Ala-Asp(OMe) in which the C-terminal OH group has been replaced by a fluoromethyl group.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

Properties of Z-VAD-FMK

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.
CAS DataBase Reference 187389-52-2

Safety information for Z-VAD-FMK

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
Precautionary Statement Codes P280:Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P332+P313:IF SKIN irritation occurs: Get medical advice/attention.
P337+P313:IF eye irritation persists: Get medical advice/attention.

Computed Descriptors for Z-VAD-FMK

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

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