D0879

Diisopropylfluorophosphate

Name: Diisopropylfluorophosphate
Brand: SIGMA

synthetic (organic), serine proteases and acetylcholinesterase inhibitor, liquid

Sinónimos:

DFP, DIFP, Diisopropyl phosphorofluoridate, Phosphoric acid diisopropyl ester fluoride

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Fórmula lineal:

[(CH₃)₂CHO]₂POF

Número CAS:

55-91-4

Peso molecular:

184.15

NACRES:

NA.77

PubChem Substance ID:

24893303

UNSPSC Code:

12352200

EC Number:

200-247-6

MDL number:

MFCD00008873

Beilstein/REAXYS Number:

1723307

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Nombre del producto

Diisopropylfluorophosphate,

SMILES string

CC(C)OP(F)(=O)OC(C)C

InChI key

MUCZHBLJLSDCSD-UHFFFAOYSA-N

InChI

1S/C6H14FO3P/c1-5(2)9-11(7,8)10-6(3)4/h5-6H,1-4H3

biological source

synthetic (organic)

vapor pressure

0.58 mmHg ( 20 °C)

form

liquid

refractive index

n20/D 1.385 (lit.)

bp

62 °C/9 mmHg (lit.)

mp

−82 °C (lit.)

solubility

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.)

density

1.06 g/mL at 25 °C (lit.)

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria

mode of action

protein synthesis | interferes

storage temp.

2-8°C

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Este artículo	P7626	T4376	537462
Sigma-Aldrich D0879 Diisopropylfluorophosphate	Sigma-Aldrich P7626 Phenylmethanesulfonyl fluoride	Sigma-Aldrich T4376 N-p-Tosyl-L-phenylalanine chloromethyl ketone	Sigma-Aldrich 537462 Isopropyl acetate
biological source synthetic (organic)	biological source synthetic	biological source synthetic	biological source -
Gene Information human ... ACHE(43), PTGS1(5742), PTGS2(5743)	Gene Information -	Gene Information human ... NFKB1(4790), NKAP(79576), NKRF(55922), NOS2(4843), PTGS2(5743)	Gene Information -
Quality Level 100	Quality Level 300	Quality Level 200	Quality Level 200
form liquid	form powder	form powder	form liquid
storage temp. 2-8°C	storage temp. -	storage temp. −20°C	storage temp. -
solubility 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.)	solubility dry solvents (ethanol, methanol, and 2-propanol): 200 mM (Stock solution are stable for months at 4°C.), H₂O: unstable	solubility DMSO: >10 mg/mL (stable for several months at 4°C.), ethanol: 20 mg/mL	solubility water: soluble 31.9 g/L at 20 °C

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

Biochem/physiol Actions

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.

Analysis Note

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

Other Notes

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.

pictograms

GHS06

signalword

Danger

hcodes

H300 + H310 + H330

pcodes

P260 - P262 - P264 - P280 - P302 + P352 + P310 - P304 + P340 + P310

Hazard Classifications

Acute Tox. 1 Oral - Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation

Clase de almacenamiento

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Identification of a novel splice variant isoform of TREM-1 in human neutrophil granules

Baruah S, et al.

Journal of Immunology, 195(12), 5725-5731 (2015)

Inhibition of the prostaglandin EP2 receptor is neuroprotective and accelerates functional recovery in a rat model of organophosphorus induced status epilepticus

Rojas A, et al.

Neuropharmacology, 93, 15-27 (2015)

Accurate MS-based Rab10 Phosphorylation Stoichiometry Determination as Readout for LRRK2 Activity in Parkinson's Disease.

Özge Karayel et al.

Molecular & cellular proteomics : MCP, 19(9), 1546-1560 (2020-07-01)

Pathogenic mutations in the Leucine-rich repeat kinase 2 (LRRK2) are the predominant genetic cause of Parkinson's disease (PD). They increase its activity, resulting in augmented Rab10-Thr73 phosphorylation and conversely, LRRK2 inhibition decreases pRab10 levels. Currently, there is no assay to

Recombinant human thrombomodulincsa+: a tool for analyzing Plasmodium falciparum adhesion to chondroitin-4-sulfate

Parzy D, et al.

Microbes and Infection, 2(7), 779-788 (2000)

Urethane attenuates early neuropathology of diisopropylfluorophosphate-induced status epilepticus in rats.

Asheebo Rojas et al.

Neurobiology of disease, 140, 104863-104863 (2020-04-14)

Seizures can be evident within minutes of exposure to an organophosphorus (OP) agent and often progress to status epilepticus (SE) resulting in a high mortality if left untreated. Effective medical countermeasures are necessary to sustain patients suffering from OP poisoning

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