Determining the Effect of pH on the Partitioning of Neutral, Cationic and Anionic Chemicals to Artificial Sebum: New Physicochemical Insight and QSPR Model

Yang, S, Li, L, Chen, Tao, Han, L and Lian, Guoping (2018) Determining the Effect of pH on the Partitioning of Neutral, Cationic and Anionic Chemicals to Artificial Sebum: New Physicochemical Insight and QSPR Model Pharmaceutical Research, 35, 141.

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Abstract

Purpose:

Sebum is an important shunt pathway for transdermal permeation and targeted delivery, but there have been limited studies on its permeation properties. Here we report a measurement and modelling study of solute partition to artificial sebum.

Methods:

Equilibrium experiments were carried out for the sebum-water partition coefficients of 23 neutral, cationic and anionic compounds at different pH.

Results:

Sebum-water partition coefficients not only depend on the hydrophobicity of the chemical but also on pH. As pH increases from 4.2 to 7.4, the partition of cationic chemicals to sebum increased rapidly. This appears to be due to increased electrostatic attraction between the cationic chemical and the fatty acids in sebum. Whereas for anionic chemicals, their sebum partition coefficients are negligibly small, which might result from their electrostatic repulsion to fatty acids. Increase in pH also resulted in a slight decrease of sebum partition of neutral chemicals.

Conclusions:

Based on the observed pH impact on the sebum-water partition of neutral, cationic and anionic compounds, a new quantitative structure-property relationship (QSPR) model has been proposed. This mathematical model considers the hydrophobic interaction and electrostatic interaction as the main mechanisms for the partition of neutral, cationic and anionic chemicals to sebum.

Item Type:	Article
Divisions :	Faculty of Engineering and Physical Sciences > Chemical and Process Engineering
Authors :	Name Email ORCID Yang, S Li, L Chen, Tao T.Chen@surrey.ac.uk Han, L Lian, Guoping g.lian@surrey.ac.uk
Date :	14 May 2018
DOI :	10.1007/s11095-018-2411-8
Copyright Disclaimer :	This is a post-peer-review, pre-copyedit version of an article published in Pharmaceutical Research. The final authenticated version is available online at: http://dx.doi.org/10.1007/s11095-018-2411-8
Uncontrolled Keywords :	partition coefficient; pH; physicochemical; QSPR; mathematical model
Depositing User :	Melanie Hughes
Date Deposited :	17 Apr 2018 14:05
Last Modified :	09 Sep 2019 08:47
URI:	http://epubs.surrey.ac.uk/id/eprint/846244

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