Electrochemical Sensors for the Estimation of the Inhibitory Effect of Phenylcarbamates to Cholinesterase

Abstract

Abstract:The inhibitory effect of nine phenylcarbamates with various substituents was studied. For this purpose, electrochemical sensors were applied under two different conditions: if an enzyme was present in the solution or if the enzyme was immobilized onto the electrode surface. In both cases, 3-[(ethoxycarbonyl)amino]phenyl (4-chlorophenyl)carbamate was found as the most effective inhibitor for butyrylcholinesterase. The best inhibitors for acetylcholinesterase were determined as well, depending on the used method. Thus, 3-[(butoxycarbonyl)-amino]phenyl phenylcarbamate with the enzyme present in the solution and 3-[(ethoxycarbonyl)amino]phenyl (3-methylphenyl)carbamate when the enzyme was immobilized onto the electrode surface were evaluated as the most effective inhibitors. Michaelis constants as well as maximum reaction rates were calculated and assessed.

Cholinesterase-based biosensors

“…Du et al adsorbed AChE onto the multi-walled carbon nanotubes 130 . Vorčáková et al immobilized AChE via adsorption onto the surface of screen-printed three-electrode sensors for determination of cholinesterase inhibition in the presence of some substituted phenylcarbamates 131 .…”

Synthesis, characterization andin vitroevaluation of substitutedN-(2-phenylcyclopropyl)carbamates as acetyl- and butyrylcholinesterase inhibitors

“…Many of the potential or approved commercially available pharmaceutical substances acting as AChE inhibitors contain carbamate functional group among others 16,32 ; for instance, human drug Rivastigmin 33,34 , which is used in the therapy of patients in the early or middle stage of AD. Besides this, many of differently substituted carbamate derivatives are described in literature [35][36][37][38][39][40][41][42][43][44][45][46] , which embody significant inhibition activity against AChE and/or BChE. Unfortunately, the clinical applicability of these compounds is limited with regard to many side effects or demerits, e.g.…”