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P7626

Sigma-Aldrich

Phenylmethanesulfonyl fluoride

powder, ≥98.5% (GC)

Synonim(y):

α-Toluenesulfonyl fluoride, Benzylsulfonyl fluoride, PMSF, Phenylmethylsulfonyl fluoride

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About This Item

Wzór empiryczny (zapis Hilla):
C7H7FO2S
Numer CAS:
329-98-6
Masa cząsteczkowa:
174.19
Beilstein:
2088311
Numer WE:
206-350-2
Numer MDL:
MFCD00007424
Kod UNSPSC:
12352202
Identyfikator substancji w PubChem:
24898863
NACRES:
NA.77

product name

Phenylmethanesulfonyl fluoride, ≥98.5% (GC)

pochodzenie biologiczne

synthetic

Próba

≥98.5% (GC)

Postać

powder

mp

91-94 °C

rozpuszczalność

dry solvents (ethanol, methanol, and 2-propanol): 200 mM (Stock solution are stable for months at 4°C.)
H2O: unstable

ciąg SMILES

FS(=O)(=O)Cc1ccccc1

InChI

1S/C7H7FO2S/c8-11(9,10)6-7-4-2-1-3-5-7/h1-5H,6H2

Klucz InChI

YBYRMVIVWMBXKQ-UHFFFAOYSA-N

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Opis ogólny

Phenylmethanesulfonyl fluoride (PMSF) is a widely used serine protease inhibitor, effective against such enzymes as chymotrypsin, thrombin, and trypsin. PMSF acts as an inhibitor via sulfonation of the hydroxyl residues of serine residues at the reactive sites of serine proteases.

Zastosowanie

PMSF is often used in lysis buffer to assist in preserving proteins of interest during protein isolation and sample preparation, by inhibiting proteases that would otherwise degrade proteins after cell or tissue lysis. PMSF is unstable in aqueous media. Thus stock solutions of PMSF are generally prepared in anhydrous organic solvents (e.g. 100% ethanol, or anhydrous isopropanol) prior to use in aqueous media.

Noted general features and benefits of PMSF include the following:
  • Inhibits serine proteases such as trypsin and chymotrypsin
  • Also inhibits cysteine proteases (reversible by reduced thiols) and mammalian acetylcholinesterase
  • Not as effective or as toxic as DFP
  • Effective concentration 0.1-1 mM
  • Half-life = 1 hr. at pH 7.5
Phenylmethanesulfonyl fluoride has been used in following applications:
  • cell fractionation.
  • used as a supplement in nuclear protein extraction.
  • inhibitor of cholesterol esterase (CE) and pseudocholinesterase (PCE).
  • used for the collection of blood prior to centrifugation to quantify plasma ANP levels.

Działania biochem./fizjol.

Administration of PMSF produces analgesia unrelated to its anticholinesterase effect, and prolongs the analagesic effect of centrally administered β-endorphin.

Inne uwagi

2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research
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Odwiedź Bibliotekę dokumentów

Estrogen receptors activate atrial natriuretic peptide in the rat heart.
Jankowski M, et al.
Proceedings of the National Academy of Sciences of the USA, 98(20), 11765-11770 (2001)
Salivary esterase activity and its association with the biodegradation of dental composites.
Finer Y and Santerre JP.
Journal of Dental Research, 83(1), 22-26 (2004)
C Pinsky et al.
Life sciences, 31(12-13), 1193-1196 (1982-09-20)
Intraperitoneal (IP) injection of the serine proteinase inhibitor phenylmethylsulfonyl fluoride (PMSF) produced dose-dependent analgesia in Sprague-Dawley rats. AD50 was 2.9 +/- 1.4 (S.E.) mg kg-1, the analgesia was antagonized by naloxone but unaffected by atropine. PMSF significantly enhanced the analgesic
Löms Ziegler-Heitbrock et al.
Journal of immunology (Baltimore, Md. : 1950), 171(1), 285-290 (2003-06-21)
The anti-inflammatory cytokine IL-10 can be induced by type I IFNs, but the molecular mechanisms involved have remained elusive. With in silico analysis of the human IL-10 promoter we identified a module consisting of an IFN regulatory factor 1 (IRF-1)
Rui Chen et al.
The Journal of biological chemistry, 287(36), 30800-30811 (2012-07-19)
Hypoxia-inducible factors (HIFs) are oxygen-sensitive transcription factors. HIF-1α plays a prominent role in hypoxic gene induction. HIF-2α target genes are more restricted but include erythropoietin (Epo), one of the most highly hypoxia-inducible genes in mammals. We previously reported that HIF-2α
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