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Merck

V116

Z-VAD-FMK

≥98% (TLC), solid, Caspase inhibitor

Synonym(s):

N-Benzyloxycarbonyl-Val-Ala-Asp(O-Me) fluoromethyl ketone

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About This Item

Empirical Formula (Hill Notation):
C22H30FN3O7
CAS Number:
187389-52-2
Molecular Weight:
467.49
UNSPSC Code:
12352209
NACRES:
NA.77
MDL number:
MFCD01074990

Key Documents

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Product Name

Z-VAD-FMK, solid

SMILES string

FCC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)OCc1ccccc1)C(C)C)C)CC(=O)OC

InChI

1S/C22H30FN3O7/c1-13(2)19(26-22(31)33-12-15-8-6-5-7-9-15)21(30)24-14(3)20(29)25-16(17(27)11-23)10-18(28)32-4/h5-9,13-14,16,19H,10-12H2,1-4H3,(H,24,30)(H,25,29)(H,26,31)/t14-,16-,19-/m0/s1

InChI key

MIFGOLAMNLSLGH-QOKNQOGYSA-N

biological source

synthetic

assay

≥98% (TLC)

form

solid

color

white

solubility

DMSO: 20 mg/mL
H2O: insoluble

storage temp.

−20°C

Quality Level

200

Gene Information

human ... CASP3(836)
mouse ... CASP3(12367)
rat ... CASP3(25402)

Application

Z-VAD-FMK has been used:
  • to induce mixed-lineage kinase domain-like (MLKL) phosphorylation (p-MLKL) in L929 cells
  • to induce autophagy in Jurkat and K562 cells
  • to revert killing effects of oxaliplatin or oxaliplatin combination with chloroquine (CQ) on HCT116 and SW620 cell lines
  • as a caspase inhibitor to inhibit apoptosis and assess nuclear factor-kB, heat shock protein 70 (Hsp 70), proto-oncogene (cmyc) and tumor suppressor protein p53

Biochem/physiol Actions

Non-selective, cell permeable inhibitor of caspase-1- and caspase-3-related proteases.

Disclaimer

Hygroscopic

Features and Benefits

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Caspases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

General description

Z-VAD-FMK inhibits yeast and mammalian peptide N-glycanase (PNGase). It induces apoptosis. Z-VAD-FMK might be associated with endoplasmic reticulum (ER) stress.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG7963
BCCF8354
BCCD6888
BCCC8336
BCCB8348

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z-VAD-fmk inhibits peptide: N-glycanase and may result in ER stress
Misaghi S, et al.
Cell Death and Differentiation, 13(1), 163-163 (2006)
Increasing colorectal cancer cell sensitivity to oxaliplatin through hyperthermia and chloroquine treatment
Zheng C, et al.
International Journal of Clinical and Experimental Pathology, 9(2), 496-508 (2016)
Apoptosis inhibition can be threatening in Abeta-induced neuroinflammation, through promoting cell proliferation
Abdi A, et al.
Neurochemical Research, 36(1), 39-48 (2011)
Peng Chen et al.
Theranostics, 10(11), 5107-5119 (2020-04-21)
Background and Purpose: RAS mutations limit the effectiveness of anti-epidermal growth factor receptor (EGFR) monoclonal antibodies in combination with chemotherapy for metastatic colorectal cancer (mCRC) patients. Therefore, new cell death forms have focused on identifying indirect targets to inhibit Ras-induced
Deletion of Ripk3 prevents Motor Neuron death in vitro but not in vivo
Dermentzaki G, et al.
eNeuro, ENEURO-EN0308 (2019)
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