Hydrates of Quaternary Ammonium Aldehydes as Potential Reactivators of Sarin-Inhibited Acetylcholinesterase

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Title:Hydrates of Quaternary Ammonium Aldehydes as Potential Reactivators of Sarin-Inhibited Acetylcholinesterase
Creators:
Cabal, Jiří
Hampl, František
Liška, František
Patočka, Jiří
Riedl, František
Ševčíková, Kateřina
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 63, 7, pp. 1021-1030
Uncontrolled Keywords:Organophosphorus inhibitors, Reactivators of phosphonylated acetylcholinesterase, Phosphonates, Sarin, Pyridinium salts, Acetylcholinesterase

Abstract

Synthesis of 2- (<strong>5a</strong>), 3- (<strong>5b</strong>) and 4-formyl-1-methylpyridinium iodides (<strong>5c</strong>) and (2,2-dihydroxyethyl)trimethylammonium chloride (<strong>6a</strong>) is described. In aqueous solution aldehydes<strong> 5</strong> exist predominantly as hydrates - geminal diols <strong>7</strong>. The ability of the geminal diols <strong>6a</strong> and <strong>7</strong> to reactivate acetylcholinesterase inhibited by isopropyl methylfluorophosphonate (Sarin) was tested <i>in vitro</i>. Although compounds <strong>6a</strong> and <strong>7</strong> exhibit an affinity towards the acetylcholinesterase bonding site comparable with that of the natural substrate acetylcholine, their reactivation ability was negligible. Second-order rate constants for cleavage of 4-nitrophenyl diphenyl phosphate (PNPDPP) with anions of the studied geminal diols were measured in order to determine their nucleophilicity.

Title:Hydrates of Quaternary Ammonium Aldehydes as Potential Reactivators of Sarin-Inhibited Acetylcholinesterase
Creators:
Cabal, Jiří
Hampl, František
Liška, František
Patočka, Jiří
Riedl, František
Ševčíková, Kateřina
Uncontrolled Keywords:Organophosphorus inhibitors, Reactivators of phosphonylated acetylcholinesterase, Phosphonates, Sarin, Pyridinium salts, Acetylcholinesterase
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:63
Number:7
Page Range:pp. 1021-1030
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19981021UNSPECIFIED
ID Code:1361
Item Type:Article
Deposited On:06 Feb 2009 17:08
Last Modified:06 Feb 2009 16:08

Citation

Cabal, Jiří; Hampl, František; Liška, František; Patočka, Jiří; Riedl, František; Ševčíková, Kateřina (1998) Hydrates of Quaternary Ammonium Aldehydes as Potential Reactivators of Sarin-Inhibited Acetylcholinesterase. Collection of Czechoslovak Chemical Communications, 63 (7). pp. 1021-1030. ISSN 0010-0765

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