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A6191

Sigma-Aldrich

Antipain dihydrochloride from microbial source

protease inhibitor

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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
MDL number:
MFCD00135957
PubChem Substance ID:
24891067

biological source

Streptomyces sp.

Quality Level

300

form

lyophilized powder

potency

1.4 μM Ki

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

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

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

InChI key

YAHXZYICKJUJEO-BXLPLHKWSA-N

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General description

Chemical structure: peptide

Application

Antipain dihydrochloride from microbial source has been used in the preparation of adipocyte proteins for western blotting and in protease inhibitor cocktail for isolating nuclear extracts for gelshift analysis.
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 Ki = 1.4 μM

Biochem/physiol Actions

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

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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The adipose tissue phenotype of hormone-sensitive lipase deficiency in mice
Wang S, et al.
Obesity Research, 9(2), 119-128 (2001)
Wenjie Xia et al.
Foods (Basel, Switzerland), 9(6) (2020-07-02)
In this study, a novel method called selective proteolysis was applied to the glycinin component of soy protein isolate (SPI), and a degraded glycinin hydrolysate (DGH) was obtained. The effects of high-intensity ultrasound (HIU) treatment (20 kHz at 400 W
Beynon, R.J. and Bond, J.S., ed.
Proteolytic Enzymes: A Practical Approach, 242-242 (1989)
Methods for Protein Analysis: A Practical Guide for Laboratory Protocols, 23-23 (2013)
Dawson, R., ed.
Data for Biochemical Research, 328-328 (1987)
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