Literature DB >> 16288867

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

Kamil Musilek1, Kamil Kuca, Daniel Jun, Vlastimil Dohnal, Martin Dolezal.   

Abstract

Six potential AChE reactivators were synthesized using modification of currently known synthetic pathways. Their potency to reactivate AChE inhibited by insecticide chlorpyrifos was tested in vitro. According to the results, (E)-1-(2-hydroxyiminomethylpyridinium)-4-(4-hydroxyiminomethylpyridinium)-but-2-ene dibromide seems to be the most potent AChE reactivator. The reactivation potency of these compounds depends on structural factors such as constitution of the linking chain between both pyridinium rings, position of the oxime moiety at the pyridinium ring and presence of quaternary nitrogens.

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Year:  2005        PMID: 16288867     DOI: 10.1016/j.bmcl.2005.10.059

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN: 0960-894X            Impact factor:   2.823


  9 in total

1.  Two step synthesis of a non-symmetric acetylcholinesterase reactivator.

Authors:  Kamil Musilek; Kamil Kuca; Vlastimil Dohnal; Daniel Jun; Jan Marek; Vit Koleckar
Journal:  Molecules       Date:  2007-08-07       Impact factor: 4.411

2.  Bisquaternary pyridinium oximes: Comparison of in vitro reactivation potency of compounds bearing aliphatic linkers and heteroaromatic linkers for paraoxon-inhibited electric eel and recombinant human acetylcholinesterase.

Authors:  Sandip B Bharate; Lilu Guo; Tony E Reeves; Douglas M Cerasoli; Charles M Thompson
Journal:  Bioorg Med Chem       Date:  2009-11-27       Impact factor: 3.641

Review 3.  Unequal efficacy of pyridinium oximes in acute organophosphate poisoning.

Authors:  Biljana Antonijevic; Milos P Stojiljkovic
Journal:  Clin Med Res       Date:  2007-03

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

Authors:  Kamil Kuca; Kamil Musilek; Martin Paar; Daniel Jun; Petr Stodulka; Martina Hrabinova; Jan Marek
Journal:  Molecules       Date:  2007-08-20       Impact factor: 4.411

5.  New series of monoquaternary pyridinium oximes: Synthesis and reactivation potency for paraoxon-inhibited electric eel and recombinant human acetylcholinesterase.

Authors:  Sandip B Bharate; Lilu Guo; Tony E Reeves; Douglas M Cerasoli; Charles M Thompson
Journal:  Bioorg Med Chem Lett       Date:  2009-07-10       Impact factor: 2.823

6.  In vitro reactivation potency of acetylcholinesterase reactivators--K074 and K075--to reactivate tabun-inhibited human brain cholinesterases.

Authors:  Kamil Kuca; Jiri Cabal; Daniel Jun; Kamil Musilek
Journal:  Neurotox Res       Date:  2007-02       Impact factor: 3.911

7.  A newly developed oxime K203 is the most effective reactivator of tabun-inhibited acetylcholinesterase.

Authors:  Kamil Kuca; Kamil Musilek; Daniel Jun; Jana Zdarova-Karasova; Eugenie Nepovimova; Ondrej Soukup; Martina Hrabinova; John Mikler; Tanos C C Franca; Elaine F F Da Cunha; Alexandre A De Castro; Martin Valis; Teodorico C Ramalho
Journal:  BMC Pharmacol Toxicol       Date:  2018-02-21       Impact factor: 2.483

8.  In Vitro Evaluation of Neutral Aryloximes as Reactivators for Electrophorus eel Acetylcholinesterase Inhibited by Paraoxon.

Authors:  Daniel A S Kitagawa; Samir F de A Cavalcante; Reuel L de Paula; Rafael B Rodrigues; Leandro B Bernardo; Munique C J da Silva; Thiago N da Silva; Wellington V Dos Santos; José M Granjeiro; Joyce S F D de Almeida; Marcos C Barcellos; Ana Beatriz de A Correa; Tanos C C França; Kamil Kuča; Alessandro B C Simas
Journal:  Biomolecules       Date:  2019-10-08

9.  Charged pyridinium oximes with thiocarboxamide moiety are equally or less effective reactivators of organophosphate-inhibited cholinesterases compared to analogous carboxamides.

Authors:  Zuzana Kohoutova; David Malinak; Rudolf Andrys; Jana Svobodova; Miroslav Psotka; Monika Schmidt; Lukas Prchal; Kamil Musilek
Journal:  J Enzyme Inhib Med Chem       Date:  2022-12       Impact factor: 5.051

  9 in total

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