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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.

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
Jie Li et al.
Oncotarget, 5(4), 882-893 (2014-03-25)
Glioblastoma remains one of the deadliest of human cancers, with most patients succumbing to the disease within two years of diagnosis. The available data suggest that simultaneous inactivation of critical nodes within the glioblastoma molecular circuitry will be required for
Kazunori Suzuki et al.
The Journal of pharmacology and experimental therapeutics, 352(3), 471-479 (2014-12-20)
Phosphodiesterase 10A (PDE10A) is a cAMP/cGMP phosphodiesterase highly expressed in medium spiny neurons (MSNs) in the striatum. We evaluated the in vivo pharmacological profile of a potent and selective PDE10A inhibitor, TAK-063 (1-[2-fluoro-4-(1H-pyrazol-1-yl)phenyl]-5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)-pyridazin-4(1H)-one). TAK-063 at 0.3 and 1 mg/kg p.o.
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