Syntheses of Haptens Containing Dioxaphosphorinan Methoxyacetic Acid Linker Arms for the Production of Antibodies to Organophosphate Pesticides

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Abstract
Four generic heterobifunctional reagents, namely 2-(2-chloro-5-methyl-1,3,2-dioxaphosphorinan-5-yl)methoxyacetic acid methyl ester, p-sulfide, 2-(2-chloro-5-methyl-1,3,2-dioxaphosphorinan-5-yl)methoxyacetic acid methyl ester, p-oxide, 2-(2-mercapto-5-methyl-1,3,2-dioxaphosphorinan-5-yl)methoxyacetic acid bispotassium salt, p-sulfide-, and (2-methoxy-5-methyl-1,3,2-dioxaphosphorinan-5-yl)methoxyacetic acid, methyl ester, have been synthesized and used to prepare organophosphate, thiophosphate, and dithiophosphate haptens containing a functional carboxyl group which can be used to conjugate the haptens to proteins. These hapten−protein conjugates have been used as antigens for preparing polyclonal sera against all classes of organophosphate pesticides. The eight examples used protein−hapten conjugates of chlorpyrifos, parathion, diazinon, paraoxon, azinphos, dimethoate, demeton, and dichlorvos. These were all immunogenic and resulted in sera containing antibodies that recognized the corresponding parent pesticide with high specificity.