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Inhibitor Report for: DFP

Inhibitor of cholinesterases and many serine hydrolases (not only alpha/beta hydrolases but also trypsin chymotrypsin etc.). DFP is a parasympathomimetic drug used in ophthalmology as a miotic agent in treatment of chronic glaucoma, as a miotic in veterinary medicine, and as an experimental agent in neuroscience because of its acetylcholinesterase inhibitory properties and ability to induce delayed peripheral neuropathy. DFP can phosphorylate other residues than active serine (tyrosine, lysine) see pdb 1TRN and Grigoryan et al. BChE appears to be about 100-200 times as sensitive as AChE to DFP and DFP was used to distinguish AChE and BChE before BW284C51 and Iso-OMPA were discovered. DFP is the oxygen analogue of Mipafox.(Structures of not alpha/beta hydrolases inhibited by DFP include: 4V08, 4H1D, 3VTA, 3TT7, 3TXT, 3MH5, 3MH6, 1RS0, 1CI9, 1DUI, 1AT3, 1SUE, 1DFP, 2TGD, 4PKA, 3LH3, 3GCN, 3GCO, 3GDS, 3GDU, 3GDV, 2RCE, 2Z2X, 1PPZ, 1GNV, 1A2Q, 5PTP)



General
Type: Organophosphate
Chemical_Nomenclature: Diisopropylphosphorofluoridate
Canonical SMILES: CC(C)OP(=O)(OC(C)C)F
InChI: InChI=1S/C6H14FO3P/c1-5(2)9-11(7,8)10-6(3)4/h5-6H,1-4H3
InChIKey: MUCZHBLJLSDCSD-UHFFFAOYSA-N
Other name(s): Diisopropylphosphorofluoridate ; Dyflos ; Diflupyl ; Floropyl ; isofluorophate ; Fluostigmine ; Isoflurophate ; Difluorophate ; Diflurphate ; Dyphlos ; isofluorphate ; Neoglaucit ; PF-3 ; PF3 ; T-1703 ; TL 466
MW: 184.1
Formula: C6H14FO3P
CAS_number: 55-91-4
PubChem: 5936
IUPHAR:

Target families

Stucture of targets
13 structures (e.g. : 2DFP, 5HCU, 5DTG... more)

Protein target

References
Search PubMed for references concerning: DFP

46 more
    Title: Site-directed mutagenesis of active site residues reveals plasticity of human butyrylcholinesterase in substrate and inhibitor interactions
    Gnatt A, Loewenstein Y, Yaron A, Schwarz M, Soreq H
    Ref: Journal of Neurochemistry, 62:749, 1994 : PubMed

            

    Title: Mechanisms involved in the development of tolerance to DFP toxicity
    Gupta RC, Patterson GT, Dettbarn WD
    Ref: Fundamental & Applied Toxicology, 5:S17, 1985 : PubMed

            

    Title: Evaluation of cytotoxic responses caused by selected organophosphorus esters in chick sympathetic ganglia cultures
    Obersteiner EJ, Sharma RP
    Ref: Can J Comp Med, 42:80, 1978 : PubMed

            


human-BCHE
MutationKiKsiIc50SubstrateConditionPaper
> Mutations for human-BCHE (8)

WT Kinetics
Kinetic parametersKiKsiIc50SubstrateConditionsPapers
human-BCHE--0.02 uM Butyrylthiocholine100mM Na phosphate pH7.4 T22C Gnatt_1994_J.Neurochem_62_749