An inhibitor of caspase-1
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Ac-YVAD-CHO

Item No. 10016

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-acetyl-L-tyrosyl-L-valyl-N-[(1S)-2-carboxyl-1-formylethyl]-L-alaninamide
CAS Number
143313-51-3
Synonyms
  • Caspase-1 Inhibitor I
  • L 709049
  • N-Ac-Tyr-Val-Ala-Asp-CHO
Molecular Formula
C23H32N4O8
Formula Weight
492.5
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlPBS (pH 7.2): 5 mg/ml
SMILES
CC(N([H])[C@@H](CC1=CC=C(O)C=C1)C(N([H])[C@@H](C(C)C)C(N([H])[C@@H](C)C(N([H])[C@@H](CC(O)=O)C([H])=O)=O)=O)=O)=O
InChi Code
InChI=1S/C23H32N4O8/c1-12(2)20(23(35)24-13(3)21(33)26-16(11-28)10-19(31)32)27-22(34)18(25-14(4)29)9-15-5-7-17(30)8-6-15/h5-8,11-13,16,18,20,30H,9-10H2,1-4H3,(H,24,35)(H,25,29)(H,26,33)(H,27,34)(H,31,32)/t13-,16-,18-,20-/m0/s1
InChi Key
LPIARALSGDVZEP-SJVNDZIOSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Ac-YVAD-CHO is an inhibitor of caspase-1/interleukin-1β converting enzyme (ICE; Ki = 0.76 nM) and an acetylated form of the caspase-1 inhibitor YVAD-CHO (Item No. 27420).1,2 It is selective for caspase-1 over caspase-4, -5, -8, -9, and -10 (Kis = 163-970 nM), as well as over caspase-2, -3, -6, and -7 (Kis = >10,000 nM for all).2 It inhibits activation of caspase-1 and IL-1β in a cell-free assay using LPS-treated THP-1 cell homogenates when used at a concentration of 5 µM.3 Ac-YVAD-CHO (12.5 µmol/kg) reduces pancreatic levels of IL-18 and serum levels of IL-1β, as well as reduces pyroptosis of pancreatic cells, in a mouse model of cerulein-induced acute pancreatitis but does not decrease pancreatic expression of NOD-like receptor protein 3 (NLRP3).4 It increases susceptibility to lethal E. coli infection but prevents LPS-induced death in C3H/HeN mice when administered at doses of 5 and 10 mg/kg, respectively.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Chapman, K.T. Synthesis of a potent, reversible inhibitor of interleukin-1β converting enzyme. Bioorg. Med. Chem. Lett. 2(6), 613-618 (1992).

    2. Garcia-Calvo, M., Peterson, E.P., Leiting, B., et al. Inhibition of human caspases by peptide-based and macromolecular inhibitors. The Journal of Biological Chemisty 273(49), 32608-32613 (1998).

    3. Walsh, J.G., Logue, S.E., Lüthi, A.U., et al. Caspase-1 promiscuity is counterbalanced by rapid inactivation of processed enzyme. The Journal of Biological Chemisty 286(37), 32513-32524 (2011).

    4. Wang, J., Wang, L., Zhang, X., et al. Cathepsin B aggravates acute pancreatitis by activating the NLRP3 inflammasome and promoting the caspase-1-induced pyroptosis. Int. Immunopharmacol. 94, 107496 (2021).

    5. Joshi, V.D., Kalvakolanu, D.V., Hebel, J.R., et al. Role of caspase 1 in murine antibacterial host defenses and lethal endotoxemia. Infect. Immun. 70(12), 6896-6903 (2002).