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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)

forma

liquid

índice de refração

n20/D 1.385 (lit.)

pb

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

Certificados de análise (COA)

Busque Certificados de análise (COA) digitando o Número do Lote do produto. Os números de lote e remessa podem ser encontrados no rótulo de um produto após a palavra “Lot” ou “Batch”.

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Sigma-Aldrich

672114

Diisopropyl chlorophosphate

Dichlorvos PESTANAL®, analytical standard

Supelco

45441

Dichlorvos

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)
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)
A molecular probe for the highly selective chromogenic detection of DFP, a mimic of Sarin and Soman nerve agents.
Raúl Gotor et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 17(43), 11994-11997 (2011-09-17)
Yonggang Li et al.
Toxicology and applied pharmacology, 262(2), 194-204 (2012-05-16)
Current medical countermeasures against organophosphate (OP) nerve agents are effective in reducing mortality, but do not sufficiently protect the CNS from delayed brain damage and persistent neurological symptoms. In this study, we examined the efficacy of neuregulin-1 (NRG-1) in protecting
A V Terry et al.
Neurotoxicology and teratology, 34(1), 1-8 (2011-10-26)
The acute toxicity of organophosphates (OPs) has been studied extensively; however, much less attention has been given to the subject of repeated exposures that are not associated with overt signs of toxicity (i.e., subthreshold exposures). The objective of this study
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Artigos

Elastase

Enzyme Explorer Product Application Index for Elastase. Leukocyte elastase is a 29KDa serine endoprotease of the Proteinase S1 Family. It exists as a single 238 amino acid-peptide chain with four disulfide bonds.

Chymotrypsin

Analytical Enzyme Chymotrypsin: Chymotrypsin is produced in the acinar cells of the pancreas as the inactive precursor, chymotrypsinogen.

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