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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

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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

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’.

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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)
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
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)
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
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