Library
local_library Home Repository

Effect of charge of quaternary ammonium cations on lipophilicity and electroanalytical parameters

Task for ion transfer voltammetry

Journal Article (2017)
Authors

L. Poltorak (OLD ChemE/Organic Materials and Interfaces)

EJR Sudhölter (OLD ChemE/Organic Materials and Interfaces)

Louis C P M de Smet (Wageningen University & Research, OLD ChemE/Organic Materials and Interfaces)

Research Group
OLD ChemE/Organic Materials and Interfaces
Copyright
© 2017 L. Poltorak, Ernst J. R. Sudhölter, L.C.P.M. de Smet
To reference this document use:
https://doi.org/10.1016/j.jelechem.2017.04.051
More Info
expand_more
Publication Year
2017
Language
English
Copyright
© 2017 L. Poltorak, Ernst J. R. Sudhölter, L.C.P.M. de Smet
Research Group
OLD ChemE/Organic Materials and Interfaces
Volume number
796
Pages (from-to)
66-74
DOI:
https://doi.org/10.1016/j.jelechem.2017.04.051
Reuse Rights

Other than for strictly personal use, it is not permitted to download, forward or distribute the text or part of it, without the consent of the author(s) and/or copyright holder(s), unless the work is under an open content license such as Creative Commons.

Abstract

The electrochemical behavior of three differently charged drug molecules (zwitter-ionic acetylcarnitine, bi-cationic succinylcholine and tri-cationic gallamine) was studied at the interface between two immiscible electrolyte solutions. Tetramethylammonium was used as a model mono cationic molecule and internal reference. The charge and molecular structure were found to play an important role in the drug lipophilicity. The studied drugs gave a linear correlation between the water – octanol (logPoctanol) partition coefficients and the electrochemically measured water – 1,2-dichloroethane (logPDCE) partition coefficients. Comparison with tetraalkylammonium cations indicating that the correlation between logPoctanol and logPDCE is molecular structure dependent. The highest measured sensitivity and lowest limit of detection were found to be 0.543 mA·dm3·mol− 1 and 6.25 μM, respectively, for the tri-cationic gallamine. The sensitivity for all studied ions was found to be a linear function of molecular charge. The dissociation constant of the carboxylic group of zwiter-ionic acetylcarnitine was calculated based on voltammetric parameters and was found to be 4.3. This study demonstrates that electrochemistry at the liquid – liquid interface is powerful technique when it comes to electroanalytical or pharmacokinetic drug assessment.