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NMR determination of Electrophorus electricus acetylcholinesterase inhibition and reactivation by neutral oximes.

Abstract：

:Neurotoxic organophosphorus compounds (OPs), which are used as pesticides and chemical warfare agents lead to more than 700,000 intoxications worldwide every year. The main target of OPs is the inhibition of acetylcholinesterase (AChE), an enzyme necessary for the control of the neurotransmitter acetylcholine (ACh). The control of ACh function is performed by its hydrolysis with AChE, a process that can be completely interrupted by inhibition of the enzyme by phosphylation with OPs. Compounds used for reactivation of the phosphylated AChE are cationic oximes, which usually possess low membrane and hematoencephalic barrier permeation. Neutral oximes possess a better capacity for hematoencephalic barrier permeation. NMR spectroscopy is a very confident method for monitoring the inhibition and reactivation of enzymes, different from the Ellman test, which is the common method for evaluation of inhibition and reactivation of AChE. In this work (1)H NMR was used to test the effect of neutral oximes on inhibition of AChE and reactivation of AChE inhibited with ethyl-paraoxon. The results confirmed that NMR is a very efficient method for monitoring the action of AChE, showing that neutral oximes, which display a significant AChE inhibition activity, are potential drugs for Alzheimer disease. The NMR method showed that a neutral oxime, previously indicated by the Ellman test as better in vitro reactivator of AChE inhibited with paraoxon than pralidoxime (2-PAM), was much less efficient than 2-PAM, confirming that NMR is a better method than the Ellman test.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

da Cunha Xavier Soares SF,Vieira AA,Delfino RT,Figueroa-Villar JD

doi

10.1016/j.bmc.2013.05.063

subject

Has Abstract

pub_date

2013-09-15 00:00:00

pages

5923-30

issue

18

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(13)00532-4

journal_volume

21

pub_type

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