Abstract
DFP (diisopropylfluorophosphate) [(C3H7)2-P(O)-F] is a dialkyl fluorophosphate synthesized in the 1930s by procedures patented looking either for insecticides, mold control, warfare agents, or fluorine compounds for dental protection. It has been extensively used in research as a model compound of an acetylcholinesterase inhibitor and in other toxicological, pharmacological, and biomedical studies, and also as an analog of a warfare nerve agent. However, DFP has never been produced for chemical warfare and is not used as an insecticide. The main chemical reactivity is based on the nucleophilic reaction on the PO group, with fluoride being the leaving group. This chemical property can explain foremost its environmental and toxicological properties: (1) spontaneous degradation in water, (2) the hydrolysis by A-esterases (i.e., DFPase is not present in humans), and (3) the binding to B-type esterases with tyrosine residue as albumin and to the serine residue on cholinesterases, neuropathy target esterase, to serine-proteases and other unidentified esterases. These reactions can explain its biodegradation and toxicity properties. The lower toxicity of DFP in mammals compared to other F-containing nerve agents makes it a suitable model compound for research studies of the biotransformation, toxicity, therapy, and biotechnological disposal of F-containing nerve agents.
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