A6191

Antipain dihydrochloride

lyophilized powder

• Synonym(s): N-(Nα-Carbonyl-Arg-Val-Arg-al)-Phe
• Empirical Formula (Hill Notation): C₂₇H₄₄N₁₀O₆ · 2 HCl
• CAS Number: 37682-72-7
• Molecular Weight: 677.62
• UNSPSC Code: 12352202
• PubChem Substance ID: 24891067
• NACRES: NA.77
• MDL number: MFCD00135957

Properties

• Product Name: Antipain dihydrochloride from microbial source, protease inhibitor
• SMILES string: Cl[H].Cl[H].[H]C(=O)C(CCCNC(N)=N)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=N)NC(=O)NC(Cc1ccccc1)C(O)=O)C(C)C
• InChI key: YAHXZYICKJUJEO-BXLPLHKWSA-N
• InChI: 1S/C27H44N10O6.2ClH/c1-16(2)21(23(40)34-18(15-38)10-6-12-32-25(28)29)37-22(39)19(11-7-13-33-26(30)31)35-27(43)36-20(24(41)42)14-17-8-4-3-5-9-17;;/h3-5,8-9,15-16,18-21H,6-7,10-14H2,1-2H3,(H,34,40)(H,37,39)(H,41,42)(H4,28,29,32)(H4,30,31,33)(H2,35,36,43);2*1H/t18?,19-,20?,21-;;/m0../s1
• biological source: Streptomyces sp.
• form: lyophilized powder
• potency: 1.4 μM K_i
• solubility: H₂O: 50 mg/mL; 1-butanol: soluble; 1-propanol: soluble; DMSO: soluble; ethanol: soluble; methanol: soluble
• mode of action: enzyme | inhibits
• storage temp.: −20°C
• Quality Level: 300

Description

Application

Antipain dihydrochloride from microbial source has been used in the preparation of adipocyte proteins for western blotting[1] and in protease inhibitor cocktail for isolating nuclear extracts for gelshift analysis.[2]

Concentrations for 50% inhibition (μg/ml):
papain, 0.16
trypsin, 0.26
cathepsin A, 1.19
cathepsin B, 0.59
cathepsin D, 125
plasmin, >93
chymotrypsin and pepsin, >250
It also has been reported to inhibit calpain I, (porcine) with K_i = 1.4 μM

Biochem/physiol Actions

Antipain dihydrochloride also inhibits the action of papain and cathespsin B.[3]

Non-selective serine and cysteine protease inhibitor.

Reversible inhibitor of serine/cysteine proteases and some trypsin-like serine proteases. Its action resembles leupeptin; however, its plasmin inhibition is less and its cathepsin A inhibition is more than that observed with leupeptin. Chronic administration of antipain can reduce the frequency of chemically induced transformation in BALB/c-/3T3 cells.

General description

Chemical structure: peptide

Preparation Note

Solubility testing at 50 mg/ml in water yields a clear to slightly hazy yellow solution. It is reportedly soluble in methanol, water, and DMSO; less soluble in ethanol, butanol, and propanol; insoluble in benzene, hexane, and chloroform.⁸ A stock solution in water or buffer is stable for about a month at -20 °C.

Dilute solutions should be stored on ice and kept for only a day because of the terminal aldehyde, which is subject to oxidation and racemization.

Stock solutions in water or buffer stable for 1 week at 4 °C, 1 month at −20 °C.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)