Skip to Content
Merck
All Photos(1)

Documents

SML0429

Sigma-Aldrich

Ac-YVAD-cmk

≥95% (HPLC)

Synonym(s):

Ac-Tyr-Val-Ala-Asp-Chloromethylketone, N-Acetyl-L-tyrosyl-L-valyl-N-[(1S)-1-(carboxymethyl)-3-chloro-2-oxopropyl]-L-alaninamide, N-acetyl-tyrosyl-valyl-alanyl-aspartyl chloromethyl ketone

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C24H33ClN4O8
CAS Number:
178603-78-6
Molecular Weight:
540.99
MDL number:
MFCD00237124
UNSPSC Code:
12352200
PubChem Substance ID:
329825424
NACRES:
NA.77

Quality Level

100

Assay

≥95% (HPLC)

form

powder

color

white to off-white

shipped in

wet ice

storage temp.

−20°C

SMILES string

CC(C)[C@H](NC(=O)[C@H](Cc1ccc(O)cc1)NC(C)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(O)=O)C(=O)CCl

InChI

1S/C24H33ClN4O8/c1-12(2)21(24(37)26-13(3)22(35)28-17(10-20(33)34)19(32)11-25)29-23(36)18(27-14(4)30)9-15-5-7-16(31)8-6-15/h5-8,12-13,17-18,21,31H,9-11H2,1-4H3,(H,26,37)(H,27,30)(H,28,35)(H,29,36)(H,33,34)/t13-,17-,18-,21-/m0/s1

InChI key

UOUBHJRCKHLGFB-DGJUNBOTSA-N

Amino Acid Sequence

Ac-Tyr-Val-Ala-Asp-Chloromethylketone

Application

Ac-YVAD-cmk has been used:
  • as an inflammasome inhibitor to add to THP-1 cells or PBMC (peripheral blood mononuclear cell) before stimulation
  • as a caspase-1 inhibitor injected to C57BL/6 mice
  • as a caspase-1 inhibitor, administered into mice before and during hematopoietic stem cell transplantation (HSCT) to evaluate its effect on bone marrow inflammatory injury
  • to abolish the histidine-rich protein II (HRPII) effect on transendothelial electrical resistance (TEER)
  • as caspase 1 inhibitor, to treat MCF-7 tumor xenograft mice, to validate the role of inflammasomes activation in tumor growth in vivo condition

Biochem/physiol Actions

Ac-YVAD-cmk is a selective ireversible inhibitor of caspase-1 (interleukin-1β converting enzyme, ICE) with some activity also against caspase-4. Ac-YVAD-cmk is anti-apoptotic and has anti-inflammatory and neuroprotective effects, thought to result from its preventing caspase-1 activation of the proinflammatory cytokine, Interleukin-1β.

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Plasmodium falciparum histidine-rich protein II compromises brain endothelial barriers and may promote cerebral malaria pathogenesis
Pal P, et al.
mBio, 7(3), e00617-e00616 (2016)
Sakshi Mehta et al.
International immunopharmacology, 88, 107013-107013 (2020-11-14)
Smoking induces excessive inflammation which is associated with all the stages of atherosclerosis. Earlier, we reported Nod-like receptor protein 3 (NLRP3) inflammasome activation as a pro-atherosclerotic property of cigarette smoking. In the present study, we aimed to explore the underlying
Growth of breast cancer cells by leptin is mediated via activation of the inflammasome: Critical roles of estrogen receptor signaling and reactive oxygen species production
Raut P K, et al.
Biochemical Pharmacology, 161, 73-88 (2019)
TLR and NLRP3 inflammasome-dependent innate immune responses to tumor-derived autophagosomes (DRibbles)
Xing Y, et al.
Cell Death & Disease, 7(8), e2322-e2322 (2016)
Yadong Xie et al.
Journal of inflammation research, 14, 3969-3983 (2021-08-26)
Necroptosis is an inflammatory cell death associated with a variety of chronic diseases. Chronic rhinosinusitis with nasal polyps (CRSwNP) is a chronic inflammatory disease accompanied by eosinophil and neutrophil infiltration. The role of necroptosis in the pathogenesis of CRSwNP remains
View All Related Papers

Articles

Caspases Inhibitors and Activators

Agents reported to activate cellular caspases include chemotherapeutic drugs, TNF receptor agonists, and other enzymes. Inhibitors of apoptosis were the first identified endogenous caspase inhibitors.

Caspases Inhibitors and Activators

Agents reported to activate cellular caspases include chemotherapeutic drugs, TNF receptor agonists, and other enzymes. Inhibitors of apoptosis were the first identified endogenous caspase inhibitors.

Caspases Inhibitors and Activators

Agents reported to activate cellular caspases include chemotherapeutic drugs, TNF receptor agonists, and other enzymes. Inhibitors of apoptosis were the first identified endogenous caspase inhibitors.

Caspases Inhibitors and Activators

Agents reported to activate cellular caspases include chemotherapeutic drugs, TNF receptor agonists, and other enzymes. Inhibitors of apoptosis were the first identified endogenous caspase inhibitors.

See All

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service