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D0879

Sigma-Aldrich

Diisopropylfluorophosphate

Sinônimo(s):

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

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About This Item

Fórmula linear:
[(CH3)2CHO]2POF
Número CAS:
55-91-4
Peso molecular:
184.15
Beilstein:
1723307
Número CE:
200-247-6
Número MDL:
MFCD00008873
Código UNSPSC:
12352200
ID de substância PubChem:
24893303
NACRES:
NA.77

fonte biológica

synthetic (organic)

Nível de qualidade

100

pressão de vapor

0.58 mmHg ( 20 °C)

Formulário

liquid

índice de refração

n20/D 1.385 (lit.)

p.e.

62 °C/9 mmHg (lit.)

pf

−82 °C (lit.)

solubilidade

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.)

densidade

1.06 g/mL at 25 °C (lit.)

espectro de atividade do antibiótico

Gram-negative bacteria
Gram-positive bacteria

Modo de ação

protein synthesis | interferes

temperatura de armazenamento

2-8°C

cadeia de caracteres 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

chave InChI

MUCZHBLJLSDCSD-UHFFFAOYSA-N

Informações sobre genes

human ... ACHE(43) , PTGS1(5742) , PTGS2(5743)

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Aplicação

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

Ações bioquímicas/fisiológicas

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.

Nota de análise

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

Outras notas

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.

Pictogramas

Skull and crossbones
GHS06

Palavra indicadora

Danger

Frases de perigo

H300 + H310 + H330

Classificações de perigo

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

Código de classe de armazenamento

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

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

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

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Certificados de análise (COA)

Lot/Batch Number
MKCX2209
BCCL7784
MKCV7644
MKCW1604
MKCT0584

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Diisopropyl chlorophosphate 97%

Sigma-Aldrich

672114

Diisopropyl chlorophosphate

Dichlorvos PESTANAL®, analytical standard

Supelco

45441

Dichlorvos

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)
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)
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
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)
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
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