Comparative chemometric and quantitative structure-retention relationship analysis of anisotropic lipophilicity of 1-arylsuccinimide derivatives determined in high-performance thin-layer chromatography system with aprotic solvents

Strahinja Kovačević; Milica Karadžić Banjac; Nataša Milošević; Jelena Ćurčić; Dunja Marjanović; Nemanja Todorović; Jovana Krmar; Sanja Podunavac-Kuzmanović; Nebojša Banjac; Gordana Ušćumlić

doi:10.1016/j.chroma.2020.461439

Comparative chemometric and quantitative structure-retention relationship analysis of anisotropic lipophilicity of 1-arylsuccinimide derivatives determined in high-performance thin-layer chromatography system with aprotic solvents

J Chromatogr A. 2020 Sep 27:1628:461439. doi: 10.1016/j.chroma.2020.461439. Epub 2020 Jul 29.

Affiliations

¹ University of Novi Sad, Faculty of Technology Novi Sad, Bulevar cara Lazara 1, 21000 Novi Sad, Serbia.
² University of Novi Sad, Faculty of Technology Novi Sad, Bulevar cara Lazara 1, 21000 Novi Sad, Serbia. Electronic address: mkaradza@uns.ac.rs.
³ University of Novi Sad, Faculty of Medicine, Department of Pharmacy, Hajduk Veljkova 3, 21000 Novi Sad, Serbia.
⁴ University of Novi Sad, Faculty of Medicine, Department of Pharmacy, Hajduk Veljkova 3, 21000 Novi Sad, Serbia; University Business Academy in Novi Sad, Faculty of Pharmacy Novi Sad, Trg Mladenaca 5, 21000 Novi Sad, Serbia.
⁵ University of Belgrade, Faculty of Pharmacy, Department of Drug Analysis, Vojvode Stepe 450, 11221 Belgrade, Serbia.
⁶ University of Belgrade, Faculty of Agriculture, 11081 Belgrade-Zemun, Nemanjina 6, Serbia.
⁷ University of Belgrade, Faculty of Technology and Metallurgy, Karnegijeva 4, 11000 Belgrade, Serbia.

PMID: 32822979
DOI: 10.1016/j.chroma.2020.461439

Abstract

Numerous structurally different amides and imides including succinimide derivatives exhibit diverse bioactive potential. The development of new compounds requires rationalization in the design in order to provide structural changes that guarantee favorable physico-chemical properties, pharmacological activity and safety. In the present research, a comprehensive study with comparison of the chromatographic lipophilicity and other physico-chemical properties of five groups of 1-arylsuccinimide derivatives was conducted. The chemometric analysis of their physico-chemical properties was carried out by using unsupervised (hierarchical cluster analysis and principal component analysis) and supervised pattern recognition methods (linear discriminant analysis), while the correlations between the in silico molecular features and chromatographic lipophilicity were examined applying linear and non-linear Quantitative Structure-Retention Relationship (QSRR) approaches. The main aim of the conducted research was to determine similarities and dissimilarities among the studied 1-arylsuccinimides, to point out the molecular features which have significant influence on their lipophilicity, as well as to establish high-quality QSRR models which can be used in prediction of chromatographic lipophilicity of structurally similar 1-arylsuccinimides. This study is a continuation of analysis and determination of the physico-chemical properties of 1-arylsuccinimides which could be important guidelines in further in vitro and eventually in vivo studies of their biological potential.

Keywords: Chemometrics; Chromatography; Lipophilicity; QSRR; Succinimide derivatives.

MeSH terms

Chemistry Techniques, Analytical / methods*
Chromatography, Thin Layer*
Cluster Analysis
Computer Simulation
Principal Component Analysis
Quantitative Structure-Activity Relationship*
Solvents / chemistry*
Succinimides / chemistry*

Substances

Solvents
Succinimides