Oxime-induced reactivation of acetylcholinesterase inhibited by phosphoramidates.

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  • Additional Information
    • Source:
      Publisher: Elsevier Country of Publication: Netherlands NLM ID: 7709027 Publication Model: Print Cited Medium: Print ISSN: 0378-4274 (Print) Linking ISSN: 03784274 NLM ISO Abbreviation: Toxicol Lett Subsets: MEDLINE
    • Publication Information:
      Publication: Amsterdam : Elsevier
      Original Publication: Amsterdam, Elsevier/North Holland.
    • Subject Terms:
      Acetylcholinesterase/*metabolism ; Cholinesterase Inhibitors/*pharmacology ; Cholinesterase Reactivators/*pharmacology ; Organophosphorus Compounds/*pharmacology ; Oximes/*pharmacology; Acetylcholinesterase/blood ; Cholinesterase Reactivators/chemistry ; Erythrocytes/drug effects ; Erythrocytes/enzymology ; Humans ; Kinetics ; Oximes/chemistry ; Pyridinium Compounds/pharmacology ; Trimedoxime/pharmacology
    • Abstract:
      The reaction of human erythrocyte acetylcholinesterase (AChE) with a set of structurally related phosphoramidates was studied in order to investigate the properties of phosphorylated enzyme and the effects of 4 oximes PAM-2, TMB-4, HI-6 and BDB-106 on the reactivation of inhibited AChE. Second-order rate constant of the phosphorylation reaction of the compounds towards the active site of AChE range between 5.0 x 10(2) and 4.9 x 10(6) M-1min-1 and their inhibitory power (I50) was from 7.3 x 10(-5) to 5.7 x 10(-9) M for 20 min incubation at 37 degrees C. The oximes used were weak reactivators of inhibited AChE except for (C4H9O)(NH2)P(O)DCP (DCP, -O-2,5-dichlorphenyl group) and (C6H13O)(NH2)P(O)SCH3 where we have obtained good reactivation. Imidazole oxime BDB-106 proved to be a potent reactivator of tabun-inhibited AChE.
    • Accession Number:
      0 (Cholinesterase Inhibitors)
      0 (Cholinesterase Reactivators)
      0 (Organophosphorus Compounds)
      0 (Oximes)
      0 (Pyridinium Compounds)
      56-97-3 (Trimedoxime)
      EC 3.1.1.7 (Acetylcholinesterase)
      HUV88P6SJS (asoxime chloride)
    • Publication Date:
      Date Created: 19960401 Date Completed: 19960607 Latest Revision: 20190819
    • Publication Date:
      20221213
    • Accession Number:
      10.1016/0378-4274(96)03634-x
    • Accession Number:
      8619258