D0879

Diisopropylfluorophosphate

• Synonyme(s) : DFP, DIFP, Diisopropyl phosphorofluoridate, Phosphoric acid diisopropyl ester fluoride
• Formule linéaire : [(CH₃)₂CHO]₂POF
• CAS Number: 55-91-4
• Poids moléculaire : 184.15
• Beilstein: 1723307
• Numéro CE : 200-247-6
• Numéro MDL: MFCD00008873
• Code UNSPSC : 12352200
• ID de substance PubChem : 24893303
• Nomenclature NACRES : NA.77

Propriétés

• Source biologique: synthetic (organic)
• Niveau de qualité: 100
• Pression de vapeur: 0.58 mmHg ( 20 °C)
• Forme: liquid
• Indice de réfraction: n20/D 1.385 (lit.)
• pb: 62 °C/9 mmHg (lit.)
• Pf: −82 °C (lit.)
• Solubilité: anhydrous isopropanol: 0.1-0.5 M (stable for months if stored at -70 °C); H₂O: 1.5% at 25 °C (very unstable (at pH 7.5, half-life = 1 hr); decomposed by alkali.)
• Densité: 1.06 g/mL at 25 °C (lit.)
• Spectre d'activité de l'antibiotique: Gram-negative bacteria; Gram-positive bacteria
• Mode d’action: protein synthesis | interferes
• Température de stockage: 2-8°C
• Chaîne SMILES: CC(C)OP(F)(=O)OC(C)C
• InChI: 1S/C6H14FO3P/c1-5(2)9-11(7,8)10-6(3)4/h5-6H,1-4H3
• Clé InChI: MUCZHBLJLSDCSD-UHFFFAOYSA-N
• Informations sur le gène: human ... ACHE(43), PTGS1(5742), PTGS2(5743)

Description

Application

Diisopropylfluorophosphate has been used:

• in combination with inactivated thrombin in Affi-Gel 10 column for the purification of recombinant human thrombomodulin with its chondroitin sulfate chain (shrTMCSA)
• for inducing status epilepticus (SE) in adult rats
• as an irreversible serine protease inhibitor in human neutrophil subcellular fractions

Actions biochimiques/physiologiques

Potent inhibitor of serine proteases and acetylcholinesterase; inhibits cathepsin G, cholinesterase, coagulation factor Xa, leucocyte elastase, pancreatic elastase, tissue kallikrein, plasmin, subtilisin, and thrombin. Inhibits apoptosis induced by ricin and bacterial toxins.

Potent inhibitor of serine proteases such as trypsin and chymotrypsin, and of acetylcholinesterase; also inhibits cathepsin G, cholinesterase, coagulation factor Xa, leucocyte elastase, pancreatic elastase, tissue kallikrein, plasmin, subtilisin, and thrombin. Inhibition of acetylcholinesterase makes this compound especially toxic. Inhibits apoptosis induced by ricin and bacterial toxins.

Remarque sur l'analyse

Typically used at a concentration of 0.10 mM. A safer alternative inhibitor for serine protease is phenylmethylsulfonyl fluoride (PMSF).

Autres remarques

Stored properly at 2-8°C, in an unopened bottle, DIFP should be stable for a minimum of two years. DIFP
is unstable when exposed to moisture. DIFP will develop a dark yellow color upon decomposition.

Informations sur la sécurité

• Pictogrammes: GHS06
• Mention d'avertissement: Danger
• Mentions de danger: H300 + H310 + H330
• Conseils de prudence: P260 - P262 - P264 - P280 - P302 + P352 + P310 - P304 + P340 + P310
• Classification des risques: Acute Tox. 1 Oral - Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation
• Code de la classe de stockage: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable
• Équipement de protection individuelle: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter