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Merck

11004646001

Roche

Antipain dihydrochloride

crystalline, suitable for cell culture, pkg of 10 mg

Synonym(s):

Antipain dihydrochloride from microbial source, N-(Nα-Carbonyl-Arg-Val-Arg-al)-Phe

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About This Item

Empirical Formula (Hill Notation):
C27H44N10O6 · 2 HCl
CAS Number:
37682-72-7
Molecular Weight:
677.62
UNSPSC Code:
12352202
PubChem Substance ID:
329749271
MDL number:
MFCD00135957
NACRES:
NA.54

Product Name

Antipain dihydrochloride, crystalline, suitable for cell culture, pkg of 10 mg

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

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

form

crystalline

mol wt

Mr = 677.63

packaging

pkg of 10 mg

manufacturer/tradename

Roche

technique(s)

cell culture | mammalian: suitable

mp

209-217 °C

solubility

DMSO: 20 mg/mL
methanol: 20 mg/mL
water: 20 mg/mL
benzene: insoluble
chloroform: insoluble
ethanol: sparingly soluble
hexane: insoluble

storage temp.

2-8°C

Quality Level

100

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Application

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

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

Antipain is a protease inhibitor isolated from actinomycetes. It inhibits thrombokinase and blood coagulation.

Other Notes

For life science research only. Not for use in diagnostic procedures.

Preparation Note

Formula: C27H44N10O6 x 2 HCl
Working concentration: 50 μg/ml

Working solution: Soluble in water, methanol, or DMSO to 20 mg/ml. Sparingly soluble in ethanol, propanol, or butanol. Insoluble in benzene, chloroform (CHCl3), hexane, or petroleum and ethyl ethers.
Storage conditions (working solution): -15 to -25 °C
Dilute solutions should be stored frozen in aliquots at -15 to -25 °C. Growth of microorganisms and repeated freezing should be avoided. Stable for approximately one month.
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.
Soluble in water, methanol, or DMSO to 20 mg/ml. Sparingly soluble in ethanol, propanol, or butanol. Insoluble in benzene, chloroform (CHCl3), hexane, or petroleum and ethyl ethers. Dilute solutions should be stored frozen in aliquots at -15 to -25 °C. Stable for approximately one month.
CAUTION: DMSO (Dimethyl sulfoxide) will permeate the skin, carrying solubilized protease inhibitors. Always wear appropriate protection for eyes, skin, etc.

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
65303420
10075748
10068997
10041421
10041420

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Antipain, a new protease inhibitor isolated from agtinomycetes
Suda H, et al.
The Journal of Antibiotics, 25(4), 263-265 (1972)
Reddy Peera Kommaddi et al.
The Journal of biological chemistry, 300(2), 105619-105619 (2024-01-06)
Protein kinase-B (Akt) and the mechanistic target of rapamycin (mTOR) signaling pathways are implicated in Alzheimer's disease (AD) pathology. Akt/mTOR signaling pathways, activated by external inputs, enable new protein synthesis at the synapse and synaptic plasticity. The molecular mechanisms impeding
Antipain, a new protease inhibitor isolated from actinomycetes.
H Suda et al.
The Journal of antibiotics, 25(4), 263-266 (1972-04-01)
Davia Prischich et al.
iScience, 26(10), 107899-107899 (2023-09-28)
Clathrin-mediated endocytosis (CME) is an essential cellular process, conserved among eukaryotes. Yeast constitutes a powerful genetic model to dissect the complex endocytic machinery, yet there is a lack of specific pharmacological agents to interfere with CME in these organisms. TL2
Silvia Magalhães-Novais et al.
Autophagy, 16(2), 313-333 (2019-04-17)
Given the relatively long life of stem cells (SCs), efficient mechanisms of quality control to balance cell survival and resistance to external and internal stress are required. Our objective was to test the relevance of cell quality control mechanisms for
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