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SML0429

Sigma-Aldrich

Ac-YVAD-cmk

≥95% (HPLC)

Sinónimos:

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

Fórmula empírica (notación de Hill):
C24H33ClN4O8
Número de CAS:
178603-78-6
Peso molecular:
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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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
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)
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
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