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Merck

V116

Sigma-Aldrich

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
MDL number:
MFCD01074990
UNSPSC Code:
12352209
NACRES:
NA.77

Key Documents

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Product Name

Z-VAD-FMK, solid

biological source

synthetic

Quality Level

200

Assay

≥98% (TLC)

form

solid

color

white

solubility

DMSO: 20 mg/mL
H2O: insoluble

storage temp.

−20°C

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

Gene Information

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

Related Categories

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.

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.

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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Disclaimer

Hygroscopic

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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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Articles

Discover Bioactive Small Molecules for Cell Cycle

Cell cycle phases (G1, S, G2, M) regulate cell growth, DNA replication, and division in proliferating cells.

Bioactive Molecules for Apoptosis

Apoptosis regulation involves multiple pathways and molecules for cellular homeostasis.

세포 주기 연구를 위한 생체 활성 저분자

증식하는 세포에서 세포 주기는 4단계로 구성됩니다. Gap 1(G1)은 유사분열과 세포 성장을 특징으로 하는 DNA 복제 사이의 기간입니다. DNA 복제는 합성(S)기에 일어나며, 세포 분열을 위한 성장 및 준비를 하는 Gap 2(G2)가 뒤따릅니다. 이 세 단계는 함께 세포주기의 간기 단계를 구성합니다. 간기 이후에 분열(M)기가 뒤따릅니다.

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