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Details

Stereochemistry ACHIRAL
Molecular Formula C7H7FO2S
Molecular Weight 174.193
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENYLMETHANESULFONYL FLUORIDE

SMILES

FS(=O)(=O)CC1=CC=CC=C1

InChI

InChIKey=YBYRMVIVWMBXKQ-UHFFFAOYSA-N
InChI=1S/C7H7FO2S/c8-11(9,10)6-7-4-2-1-3-5-7/h1-5H,6H2

HIDE SMILES / InChI

Description

Phenylmethanesulfonyl fluoride is an irreversible inhibitor of serine proteases commonly used in the preparation of cell lysates. Phenylmethanesulfonyl fluoride has been used as a supplement in nuclear protein extraction and inhibitor of cholesterol esterase (CE) and pseudocholinesterase (PCE). Administration of PMSF produces analgesia unrelated to its anticholinesterase effect and prolongs the analgesic effect of centrally administered β-endorphin. The physiological and toxicological properties of this compound have not been evaluated in humans.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
52161.0 nM [IC50]
833.0 nM [IC50]
19230.0 nM [IC50]
13000.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

Sample Use Guides

In Vivo Use Guide
LD50 for mice = 215mg/kg
Route of Administration: Intraperitoneal
In Vitro Use Guide
The purified enzymes PR3 and HNE were used for activity evaluation. The enzymatic activity of free PR3 and HNE was measured in triplicate in 50 mM HEPES, 750 mM NaCl, supplemented with 0.05% Igepal CA 630 (v/v) at pH 7.4. Purified PR3 (0.5nM) was incubated with 6 μM of the Phenylmethanesulfonyl fluoride for 30 min at room temperature. The same protocol was used for PMSF and α1-PI, while PR3 alone was used as a control. The reaction was started by adding 5 μM of the substrate N-EYFRET to the reaction buffer (20 μL total volume) in 384-well black nonbinding plates (Greiner bio-one #784900). The progress of the hydrolytic reaction was determined by measuring the fluorescence for 30 min at 37 °C with an EnSpire multimode plate reader (PerkinElmer) with 320 and 420 nm excitation and emission wavelengths, respectively, at 37 °C. Similarly, 0.5 nM HNE was incubated for 30 min at room temperature with 6 μM of the above-mentioned inhibitors.