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SML0429

Ac-YVAD-cmk

Name: Ac-YVAD-cmk
Brand: SIGMA

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

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

UNSPSC Code:

12352200

PubChem Substance ID:

329825424

NACRES:

NA.77

MDL number:

MFCD00237124

Assay:

≥95% (HPLC)

Form:

powder

Quality level:

100

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Properties

Product Name

Ac-YVAD-cmk, ≥95% (HPLC)

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

Description

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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)

Molecular insights of cigarette smoke condensate-activated NLRP3 inflammasome in THP-1 cells in a stage-specific atherogenesis.

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)

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