Literature DB >> 17960099

Targeted synthesis of 1-(4-hydroxyiminomethylpyridinium)-3-pyridiniumpropane dibromide--a new nerve agent reactivator.

Kamil Kuca1, Kamil Musilek, Martin Paar, Daniel Jun, Petr Stodulka, Martina Hrabinova, Jan Marek.   

Abstract

Preparation of 1-(4-hydroxy-iminomethylpyridinium)-3-pyridiniumpropane dibromide is described. This compound represents a new acetylcholinesterase (AChE) reactivator, which has no substituents on the second pyridinium ring as found in other commonly used AChE reactivators. The reactivation ability of this reactivator was tested on tabun- and cyclosarin-inhibited AChE. According to the results obtained, the new compound (without substitution and with decreased molecule size) showed increased reactivation potency in case of cyclosarin inhibited AChE. A potent oxime for treatment of tabun and cyclosarin-caused intoxications was thus obtained via slight modification of the reactivator structure (compared to trimedoxime and K027).

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Year:  2007        PMID: 17960099      PMCID: PMC6149109          DOI: 10.3390/12081964

Source DB:  PubMed          Journal:  Molecules        ISSN: 1420-3049            Impact factor:   4.411


  25 in total

Review 1.  Health and environmental threats associated with the destruction of chemical weapons.

Authors:  Jirí Matousek
Journal:  Ann N Y Acad Sci       Date:  2006-09       Impact factor: 5.691

Review 2.  Organophosphates/nerve agent poisoning: mechanism of action, diagnosis, prophylaxis, and treatment.

Authors:  Jirí Bajgar
Journal:  Adv Clin Chem       Date:  2004       Impact factor: 5.394

3.  Synthesis of the novel series of bispyridinium compounds bearing (E)-but-2-ene linker and evaluation of their reactivation activity against chlorpyrifos-inhibited acetylcholinesterase.

Authors:  Kamil Musilek; Kamil Kuca; Daniel Jun; Vlastimil Dohnal; Martin Dolezal
Journal:  Bioorg Med Chem Lett       Date:  2005-11-08       Impact factor: 2.823

4.  Potency of new structurally different oximes to reactivate cyclosarin-inhibited human brain acetylcholinesterases.

Authors:  Kamil Kuca; Jiri Cabal; Daniel Jun; Jiri Bajgar; Martina Hrabinova
Journal:  J Enzyme Inhib Med Chem       Date:  2006-12       Impact factor: 5.051

5.  Crystal structures of acetylcholinesterase in complex with HI-6, Ortho-7 and obidoxime: structural basis for differences in the ability to reactivate tabun conjugates.

Authors:  Fredrik Ekström; Yuan-Ping Pang; Malin Boman; Elisabet Artursson; Christine Akfur; Susanne Börjegren
Journal:  Biochem Pharmacol       Date:  2006-07-31       Impact factor: 5.858

6.  In vitro and in vivo evaluation of pyridinium oximes: mode of interaction with acetylcholinesterase, effect on tabun- and soman-poisoned mice and their cytotoxicity.

Authors:  Maja Calić; Ana Lucić Vrdoljak; Bozica Radić; Dubravko Jelić; Daniel Jun; Kamil Kuca; Zrinka Kovarik
Journal:  Toxicology       Date:  2005-12-05       Impact factor: 4.221

7.  Pretreatment with pyridinium oximes improves antidotal therapy against tabun poisoning.

Authors:  Ana Lucić Vrdoljak; Maja Calić; Bozica Radić; Suzana Berend; Daniel Jun; Kamil Kuca; Zrinka Kovarik
Journal:  Toxicology       Date:  2006-08-18       Impact factor: 4.221

8.  [QUATERNARY HYDROXYIMINOMETHYLPYRIDINIUM SALTS. THE DISCHLORIDE OF BIS-(4-HYDROXYIMINOMETHYL-1-PYRIDINIUM-METHYL)-ETHER (LUEH6), A NEW REACTIVATOR OF ACETYLCHOLINESTERASE INHIBITED BY ORGANIC PHOSPHORIC ACID ESTERS].

Authors:  A LUETTRINGHAUS; I HAGEDORN
Journal:  Arzneimittelforschung       Date:  1964-01

9.  Quaternary salts of 4,3' and 4,4' bis-pyridinium monooximes. Part 2: synthesis and biological activity.

Authors:  Chennamaneni Srinivas Rao; Vobalaboina Venkateswarlu; Garlapati Achaiah
Journal:  Bioorg Med Chem Lett       Date:  2006-02-14       Impact factor: 2.823

Review 10.  Structural requirements of acetylcholinesterase reactivators.

Authors:  Kamil Kuca; Daniel Juna; Kamil Musilek
Journal:  Mini Rev Med Chem       Date:  2006-03       Impact factor: 3.862

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  2 in total

1.  Differential binding of bispyridinium oxime drugs with acetylcholinesterase.

Authors:  Manoj K Kesharwani; Bishwajit Ganguly; Amit Das; Tusar Bandyopadhyay
Journal:  Acta Pharmacol Sin       Date:  2010-02-08       Impact factor: 6.150

2.  Effect of seven newly synthesized and currently available oxime cholinesterase reactivators on cyclosarin-intoxicated rats.

Authors:  Jana Zdarova Karasova; Jiri Kassa; Kamil Musilek; Miroslav Pohanka; Ladislav Novotny; Kamil Kuca
Journal:  Int J Mol Sci       Date:  2009-07-07       Impact factor: 6.208

  2 in total

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