Literature DB >> 29614332

New therapeutic approaches and novel alternatives for organophosphate toxicity.

Francine S Katz1, Stevan Pecic2, Laura Schneider3, Zhengxiang Zhu3, Ashley Hastings3, Michal Luzac3, Joanne Macdonald4, Donald W Landry3, Milan N Stojanovic3.   

Abstract

Organophosphate compounds (OPCs) are commonly used as pesticides and were developed as nerve agents for chemical warfare. Exposure to OPCs results in toxicity due to their covalent binding and inhibition of acetylcholinesterase (AChE). Treatment for toxicity due to OPC exposure has been largely focused on the reactivation of AChE by oxime-based compounds via direct nucleophilic attack on the phosphorous center. However, due to the disadvantages to existing oxime-based reactivators for treatment of OPC poisoning, we considered non-oxime mechanisms of reactivation. A high throughput screen of compound libraries was performed to discover previously unidentified reactivation compounds, followed by studies on their analogs. In the process, we discovered multiple non-oxime classes of compounds, the most robust of which we have already reported [1]. Herein, we report other classes of compounds we identified in our screen that are efficient at reactivation. During biochemical characterization, we also found some compounds with other activities that may inspire novel therapeutic approaches to OPC toxicity. Specifically, we found compounds that [1] increase the rate of substrate hydrolysis by AChE and, [2] protect the enzyme from inhibition by OPC. Further, we discovered that a subset of reactivator compounds recover activity from both AChE and the related enzyme butyrylcholinesterase (BuChE). We now report these compounds, their activities and discuss how each relates to therapeutic approaches that would provide alternatives to traditional oxime-based reactivation.
Copyright © 2018 Elsevier B.V. All rights reserved.

Entities:  

Keywords:  Acetylcholinesterase (AChE); Butyrylcholinesterase (BuChE); Non-oxime reactivators; Organophosphate compounds (OPCs); Structure activity relationship (SAR) study

Mesh:

Substances:

Year:  2018        PMID: 29614332      PMCID: PMC5955786          DOI: 10.1016/j.toxlet.2018.03.028

Source DB:  PubMed          Journal:  Toxicol Lett        ISSN: 0378-4274            Impact factor:   4.372


  47 in total

1.  Discovery of New Classes of Compounds that Reactivate Acetylcholinesterase Inhibited by Organophosphates.

Authors:  Francine S Katz; Stevan Pecic; Timothy H Tran; Ilya Trakht; Laura Schneider; Zhengxiang Zhu; Long Ton-That; Michal Luzac; Viktor Zlatanic; Shivani Damera; Joanne Macdonald; Donald W Landry; Liang Tong; Milan N Stojanovic
Journal:  Chembiochem       Date:  2015-09-09       Impact factor: 3.164

2.  Acetylcholinesterase. XI. Reversibility of tetraethyl pyrophosphate.

Authors:  I B WILSON
Journal:  J Biol Chem       Date:  1951-05       Impact factor: 5.157

3.  Production of the butyrylcholinesterase knockout mouse.

Authors:  Bin Li; Ellen G Duysen; Thomas L Saunders; Oksana Lockridge
Journal:  J Mol Neurosci       Date:  2006       Impact factor: 3.444

4.  Differential sensitivity of plasma carboxylesterase-null mice to parathion, chlorpyrifos and chlorpyrifos oxon, but not to diazinon, dichlorvos, diisopropylfluorophosphate, cresyl saligenin phosphate, cyclosarin thiocholine, tabun thiocholine, and carbofuran.

Authors:  Ellen G Duysen; John R Cashman; Lawrence M Schopfer; Florian Nachon; Patrick Masson; Oksana Lockridge
Journal:  Chem Biol Interact       Date:  2011-12-24       Impact factor: 5.192

5.  The bioactivation of amodiaquine by human polymorphonuclear leucocytes in vitro: chemical mechanisms and the effects of fluorine substitution.

Authors:  M D Tingle; H Jewell; J L Maggs; P M O'Neill; B K Park
Journal:  Biochem Pharmacol       Date:  1995-09-28       Impact factor: 5.858

Review 6.  Design, evaluation and structure-activity relationship studies of the AChE reactivators against organophosphorus pesticides.

Authors:  Kamil Musilek; Martin Dolezal; Frank Gunn-Moore; Kamil Kuca
Journal:  Med Res Rev       Date:  2009-12-21       Impact factor: 12.944

7.  Butyrylcholinesterase as a therapeutic drug for protection against percutaneous VX.

Authors:  David E Lenz; Edward D Clarkson; Susan M Schulz; Douglas M Cerasoli
Journal:  Chem Biol Interact       Date:  2010-06-01       Impact factor: 5.192

Review 8.  Unequal efficacy of pyridinium oximes in acute organophosphate poisoning.

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

Review 9.  Entry of oximes into the brain: a review.

Authors:  D E Lorke; H Kalasz; G A Petroianu; K Tekes
Journal:  Curr Med Chem       Date:  2008       Impact factor: 4.530

10.  Design and expression of organophosphorus acid anhydride hydrolase activity in human butyrylcholinesterase.

Authors:  C B Millard; O Lockridge; C A Broomfield
Journal:  Biochemistry       Date:  1995-12-12       Impact factor: 3.162

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  4 in total

Review 1.  Resurrection and Reactivation of Acetylcholinesterase and Butyrylcholinesterase.

Authors:  Andrew J Franjesevic; Sydney B Sillart; Jeremy M Beck; Shubham Vyas; Christopher S Callam; Christopher M Hadad
Journal:  Chemistry       Date:  2019-02-13       Impact factor: 5.236

2.  Synthesis, kinetic evaluation and molecular docking studies of donepezil-based acetylcholinesterase inhibitors.

Authors:  Makar Makarian; Michael Gonzalez; Stephanie M Salvador; Shahrokh Lorzadeh; Paula K Hudson; Stevan Pecic
Journal:  J Mol Struct       Date:  2021-09-03       Impact factor: 3.196

3.  Role of penehyclidine in acute organophosphorus pesticide poisoning.

Authors:  Shi-Yuan Yu; Yan-Xia Gao; Joseph Walline; Xin Lu; Li-Na Zhao; Yuan-Xu Huang; Jiang Tao; An-Yong Yu; Na Ta; Ren-Ju Xiao; Yi Li
Journal:  World J Emerg Med       Date:  2020

4.  Discovery of Novel Non-Oxime Reactivators Showing In Vivo Antidotal Efficiency for Sarin Poisoned Mice.

Authors:  Zhao Wei; Xinlei Zhang; Huifang Nie; Lin Yao; Yanqin Liu; Zhibing Zheng; Qin Ouyang
Journal:  Molecules       Date:  2022-02-07       Impact factor: 4.411

  4 in total

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