SML0429

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
• 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

Properties

• 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

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.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable