In vitro reactivation of organophosphorus (OP)-inhibited electric eel acetylcholinesterase by novel monoquaternary pyridinium oximes

Article abstract of DOI:10.1007/s00044-012-0128-5

The synthesis of a series of monoquaternary pyridinium oximes bearing either a long-chain alkyloxymethyl or benzyloxymethyl side chain and the corresponding in vitro evaluation for the reactivation of electric eel acetylcholinesterase-inhibited organophosphorus inhibitors viz. sarin, DFP, and VX is reported. The data were compared with that of 2-PAM and obidoxime. Compounds bearing a benzyloxymethyl and 4-methylbenzyloxymethyl side chain showed better reactivation compared to obidoxime. However, none of the newly synthesized oximes bearing an aliphatic side chain could surpass the reactivation potential of 2-PAM. The pKa of the new oximes were determined and correlated with the observed reactivation potential.