| Identification | Back Directory | [Name]
Z-VAD-FMK | [CAS]
187389-52-2 | [Synonyms]
Z-VAD-FMK
HGNC:1504
Z-VAD(OME)-FMK
Z-VA(OME)D-FMK
Z-VAL-ALA-ASP-FMK
CASPASE INHIBITOR I
CASPASE INHIBITOR VI
CASPASE-1, INHIBITOR
Z-VAL-ALA-ASP(OME)-CH2F
Z-VAL-ALA-ASP-(OME)-FMK
Z-VAD-FMK, METHYL ESTER
Z-VAD-FLUOROMETHYLKETONE
Z-VAD-FMK, Non-methylated
Z-VAD-FMK (Cell perMeable)
Z-VAD(OME)-FLUOROMETHYLKETONE
Z-VAL-ALA-ASP-FLUOROMETHYLKETONE
Z-VAL-ALA-DL-ASP-FLUOROMETHYLKETONE
Anti-CASP3 antibody produced in goat
Z-VAL-ALA-ASP(OME)-FLUOROMETHYLKETONE
Z-VAL-ALA-ASP(OCH3)-FLUOROMETHYLKETONE
Z-VAL-ALA-DL-ASP(OME)-FLUOROMETHYLKETONE
PN: WO2005039629 PAGE: 18 claimed protein
3: PN: WO0158526 SEQID: 3 claimed sequence
CASPASE-1 INHIBITOR VI (FLUOROMETHYLKETONE)
caspase 3, apoptosis-related cysteine protease
caspase 3, apoptosis-related cysteine peptidase
N-BENZYLOXYCARBONYL-VAL-ALA-ASP FLUOROMETHYL KETONE
BENZYLOXYCARBONYL-VAL-ALA-ASP(OME)-FLUOROMETHYLKETONE
N-Benzyloxycarbonyl-Val-Ala-Asp(O-Me) fluoromethyl ketone
CARBOBENZOXY-VALYL-ALANYL-ASPARTYL-[O-METHYL]-FLUOROMETHYLKETONE
N-[(Phenylmethoxy)carbonyl]-L-valyl-N-[(1S)-3-fluoro-1-(2-methoxy-2-oxoethyl)-2-oxopropyl]-L-alaninamide
L-Alaninamide, N-[(phenylmethoxy)carbonyl]-L-valyl-N-[(1S)-3-fluoro-1-(2-methoxy-2-oxoethyl)-2-oxopropyl]-
N-[(Phenylmethoxy)carbonyl]-L-valyl-N-[(1S)-3-fluoro-1-(2-methoxy-2-oxoethyl)-2-oxopropyl]-L-alaninamide z-vad-fmk | [Molecular Formula]
C21H28FN3O7 | [MDL Number]
MFCD03452883 | [MOL File]
187389-52-2.mol | [Molecular Weight]
453.46 |
| Chemical Properties | Back Directory | [Melting point ]
>190°C (dec.) | [Boiling point ]
732.4±60.0 °C(Predicted) | [density ]
1.214±0.06 g/cm3 (20 ºC 760 Torr) | [Fp ]
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. | [InChI]
InChI=1S/C22H30FN3O7/c1-13(2)19(25-22(31)33-12-15-8-6-5-7-9-15)21(30)26(14(3)20(24)29)16(17(27)11-23)10-18(28)32-4/h5-9,13-14,16,19H,10-12H2,1-4H3,(H2,24,29)(H,25,31)/t14-,16-,19-/m0/s1 | [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 |
| Hazard Information | Back Directory | [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] | [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 . | [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. | [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. | [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]
Store at -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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