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
- CAS NO.:187389-52-2
- Empirical Formula: C22H30FN3O7
- Molecular Weight: 467.49
- MDL number: MFCD03452883
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-18 21:14:07
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ChEBI: Z-Val-Ala-Asp(OMe)-CH2F is a tripeptide consisting of Z-Val-Ala-Asp(OMe) in which the C-terminal OH group has been replaced by a fluoromethyl group.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) |
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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