SML0429

Ac-YVAD-cmk

Name: Ac-YVAD-cmk
Brand: SIGMA

≥95% (HPLC), selective caspase-1 inhibitor, powder

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 CAS:

178603-78-6

Peso molecular:

540.99

UNSPSC Code:

12352200

PubChem Substance ID:

329825424

NACRES:

NA.77

MDL number:

MFCD00237124

Nombre del producto

Ac-YVAD-cmk, ≥95% (HPLC)

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

assay

≥95% (HPLC)

form

powder

color

white to off-white

shipped in

wet ice

storage temp.

−20°C

Quality Level

100

Categorías relacionadas

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

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 caspase-1 inhibitor.

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.

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Raut P K, et al.

Biochemical Pharmacology, 161, 73-88 (2019)

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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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Xing Y, et al.

Cell Death & Disease, 7(8), e2322-e2322 (2016)

Exposure of cigarette smoke condensate activates NLRP3 inflammasome in THP-1 cells in a stage-specific manner: An underlying role of innate immunity in atherosclerosis.

Sakshi Mehta et al.

Cellular signalling, 72, 109645-109645 (2020-04-20)

Smoking is known to affect all the phases of atherosclerosis, thus is considered as an independent and major risk factor. The underlying mechanism responsible for the atherogenic effects of smoking is still uncertain and a major concern. Recent evidence implicates

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)

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