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A6664

Sigma-Aldrich

4-Amidinophenylmethanesulfonyl fluoride hydrochloride

serine protease inhibitor

Synonym(s):

4-Amidinobenzylsulfonyl fluoride hydrochloride, p-APMSF

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About This Item

Empirical Formula (Hill Notation):
C8H9FN2O2S · HCl
CAS Number:
74938-88-8
Molecular Weight:
252.69
Beilstein:
9083148
MDL number:
MFCD00078902
UNSPSC Code:
12352202
PubChem Substance ID:
24891118
NACRES:
NA.77

Assay

≥97% (silver nitrate titration)

form

powder

mp

190-191 ºC

solubility

H2O: 50 mM (Stable when aliquoted at −20°C. Half-life = 6 minutes in pH 7.0 buffer systems.)

storage temp.

−20°C

SMILES string

Cl[H].NC(=N)c1ccc(CS(F)(=O)=O)cc1

InChI

1S/C8H9FN2O2S.ClH/c9-14(12,13)5-6-1-3-7(4-2-6)8(10)11;/h1-4H,5H2,(H3,10,11);1H

InChI key

KHLLRHIUKOJXLL-UHFFFAOYSA-N

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General description

4-Amidinophenylmethanesulfonyl fluoride hydrochloride is relatively nontoxic.

Application

4-Amidinophenylmethanesulfonyl fluoride hydrochloride has been used:
  • as a component of inhibitor cocktail for whole blood collection and separation of plasma
  • as a component of sodium dodecyl sulfate (SDS) sample buffer to prepare whole-cell extract
  • as a trypsin inhibitor to measure its inhibition efficiency and to determine the efficacy of the quantum dot fluorescence resonance energy transfer (FRET)-based enzymatic probes

Biochem/physiol Actions

4-Amidinophenylmethanesulfonyl fluoride hydrochloride (p-APMSF) can inhibit the trypsin-like proteinase produced by Fusarium culmorum. It is also capable of blocking bovine Factor Xa, human plasmin, and the human complement proteases, C1r and C1s.
Irreversible inhibitor of serine proteases with lysine or arginine substrate specificities. Effective concentration 10-100 μM. Frequently used to characterize newly discovered proteases.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Lifang Shi et al.
Analytical chemistry, 79(1), 208-214 (2006-12-30)
The paper describes the development and characterization of analytical properties of quantum dot-based probes for enzymatic activity and for screening enzyme inhibitors. The luminescent probes are based on fluorescence resonance energy transfer (FRET) between luminescent quantum dots that serve as
Anja I Pekkarinen et al.
Journal of agricultural and food chemistry, 50(13), 3849-3855 (2002-06-13)
The fungal disease Fusarium head blight occurs on wheat (Triticum spp.) and barley (Hordeum vulgare L.) and is one of the worldwide problems of agriculture. It can be caused by various Fusarium species. We are characterizing the proteinases of F.
Yoshihiro Hayashi et al.
Cancer discovery, 8(11), 1438-1457 (2018-08-25)
Myelodysplastic syndromes (MDS) are heterogeneous hematopoietic disorders that are incurable with conventional therapy. Their incidence is increasing with global population aging. Although many genetic, epigenetic, splicing, and metabolic aberrations have been identified in patients with MDS, their clinical features are
R Laura et al.
Biochemistry, 19(21), 4859-4864 (1980-10-14)
p-(Amidinophenyl)methanesulfonyl fluoride (p-APMSF) has been synthesized and shown to be a specific, irreversible inhibitor of the class of plasma serine proteases which demonstrate substrate specificity for the positively charged side chains of the amino acid lysine or arginine. In equimolar
Lacramioara Ivanciu et al.
Blood, 124(11), 1705-1714 (2014-05-30)
The membrane-dependent interaction of factor Xa (FXa) with factor Va (FVa) forms prothrombinase and drives thrombin formation essential for hemostasis. Activated platelets are considered to provide the primary biological surface to support prothrombinase function. However, the question of how other
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