AC-YVAD-CHO CAS 143313-51-3

Introduction：Basic information about AC-YVAD-CHO CAS 143313-51-3, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

AC-YVAD-CHO Basic information

• Product Name: AC-YVAD-CHO
• Synonyms: N-ACETYL-L-TYROSYL-L-VALYL-N-[(1S)-2-CARBOXYL-1-FORMYLETHYL]-L-ALANINAMIDE;N-ACETYL-TYR-VAL-ALA-ASP-CHO (ALDEHYDE);N-ACETYL-TYR-VAL-ALA-GLU-AL;N-AC-TYR-VAL-ALA-ASP-CHO;N-ACETYL-ALA-ALA-VAL-ALA-LEU-LEU-PRO-ALA-VAL-LEU-LEU-ALA-LEU-LEU-ALA-PRO-TYR-VAL-ALA-ASP-CHO (ALDEHYDE);TYR-VAL-ALA-ASP-CHO;YVAD-CHO;ICE INHIBITOR
• CAS: 143313-51-3
• MF: C23H32N4O8
• MW: 492.52
• Product Categories: Caspases/Apoptosis;peptide;Pepetides;peptides
• Mol File: 143313-51-3.mol

AC-YVAD-CHO Chemical Properties

• Boiling point: 937.7±65.0 °C(Predicted)
• density: 1.276±0.06 g/cm3(Predicted)
• storage temp.: −20°C
• solubility: DMF:30.0(Max Conc. mg/mL);60.91(Max Conc. mM) DMSO:30.0(Max Conc. mg/mL);60.91(Max Conc. mM) Ethanol:30.0(Max Conc. mg/mL);60.91(Max Conc. mM) PBS (pH 7.2):5.0(Max Conc. mg/mL);10.15(Max Conc. mM)
• pka: 4.20±0.10(Predicted)
• form: Powder
• color: White to off-white
• Sensitive: Moisture Sensitive
• InChIKey: KQCBPHUOVBKBPQ-SJVNDZIOSA-N
• SMILES: N([C@@H](CC(=O)O)C=O)[C@@H](C)C(=O)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)C)Cc1ccc(cc1)O)C(C)C

Safety Information

• WGK Germany: 3
• Storage Class: 11 - Combustible Solids

AC-YVAD-CHO Usage And Synthesis

Description

Ac-YVAD-CHO is an inhibitor of caspase-1/interleukin-1β converting enzyme (ICE; K_i = 0.76 nM) and an acetylated form of the caspase-1 inhibitor YVAD-CHO . It is selective for caspase-1 over caspase-4, -5, -8, -9, and -10 (K_is = 163-970 nM), as well as over caspase-2, -3, -6, and -7 (K_is = >10,000 nM for all). 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. 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). 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.

Uses

A potent, specific, and reversible inhibitor of caspases-1, -4 and -5

in vivo

Ac-YVAD-CHO (30 mg/kg; i.p.; 6 hours) suppresses IL-1β levels in blood of P. acnes-sensitized mice^[1].
Ac-YVAD-CHO (2-8 μg, intrastriatal infusion) attenuates Quinolinic acid (QA)-induced apoptosis in rat striatum^[2].
Ac-YVAD-CHO (10 and 50 mg/kg; i.p.; 1 hour) is cleared from the blood rapidly, and drops precipitously to approximately 1 and 0.2 μM at 30 and 60 minutes after injection^[1].

• Animal Model: P. acnes-sensitized mice^[1]
• Dosage: 50 mg/kg
• Administration: I.p.;
• Result: Suppressed IL-1β levels in blood.

• Animal Model: Quinolinic acid-treated Rats^[2]
• Dosage: 2-8 μg
• Administration: Intrastriatal infusion.
• Result: Attenuated Quinolinic acid (QA)-induced increases in p53 and apoptosis in rat striatum. Inhibited QA-induced increases in caspase-1 activity and p53 protein levels, with no effect on QA-induced IκB-α degradation, NF-κB or AP-1 activation.

IC 50

IL-1β; Caspase-1

References

[1] CHAPMAN K T. Synthesis of a potent, reversible inhibitor of interleukin-1β converting enzyme[J]. Bioorganic & Medicinal Chemistry Letters, 1992, 2 6: Pages 613-618. DOI: 10.1016/s0960-894x(01)81209-9
[2] JOHN G WALSH. Caspase-1 promiscuity is counterbalanced by rapid inactivation of processed enzyme.[J]. The Journal of Biological Chemistry, 2011: 32513-32524. DOI: 10.1074/jbc.m111.225862
[3] JIANHUA WANG . Cathepsin B aggravates acute pancreatitis by activating the NLRP3 inflammasome and promoting the caspase-1-induced pyroptosis[J]. International immunopharmacology, 2021, 94: Article 107496. DOI: 10.1016/j.intimp.2021.107496
[4] VISHWAS D JOSHI. Role of caspase 1 in murine antibacterial host defenses and lethal endotoxemia.[J]. Infection and Immunity, 2002, 70 12: 6896-6903. DOI: 10.1128/iai.70.12.6896-6903.2002