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Multivariate assessment of anticancer oleanane triterpenoids lipophilicity.

Monika Pastewska¹, Barbara Bednarczyk-Cwynar², Strahinja Kovačević³

¹Department of Physical Chemistry, Medical University of Gdańsk, Al. Gen. Hallera 107, 80-416 Gdańsk, Poland.

Journal of Chromatography. A

|September 27, 2021

Summary

This summary is machine-generated.

Oleanolic acid derivatives show antitumor potential. This study correlates chromatographic and computational lipophilicity, finding ionization potential and polarizability are key to retention behavior in chromatography.

Keywords:

Chemometrics IAM Lipophilicity Oleanane triterpenoids RP-HPLC

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Area of Science:

Medicinal Chemistry
Computational Chemistry
Analytical Chemistry

Background:

Naturally occurring molecules, like oleanolic acid (OA) derivatives, are valuable sources for novel drug leads.
Previously synthesized OA derivatives exhibit promising antitumor activity, warranting further investigation into their properties.

Purpose of the Study:

To evaluate the lipophilicity of OA derivatives using both chromatographic and computational methods.
To elucidate the molecular mechanisms governing the retention behavior of these compounds in different chromatographic systems.
To compare and correlate lipophilicity indices derived from experimental and in silico approaches.

Main Methods:

Utilized reversed-phase liquid chromatography (RP-HPLC) and immobilized artificial membrane chromatography (IAM-HPLC) for retention data acquisition.
Employed chemometric tools including cluster analysis, principal component analysis, and sum of ranking differences for data analysis.
Performed quantitative structure-retention relationship (QSRR) analysis using genetic algorithm coupled with multiple linear regression (GA-MLR).

Main Results:

Significant differences were observed between computationally predicted and chromatographically determined lipophilicity indices.
Ionization potential was identified as a major factor influencing retention in RP-HPLC.
Polarizability-related descriptors were found to be crucial for retention mechanisms in IAM-HPLC.

Conclusions:

Chromatographic and computational methods provide complementary insights into OA derivative lipophilicity.
Understanding the molecular drivers of retention is essential for optimizing chromatographic separation and predicting drug behavior.
The study highlights the importance of considering multiple molecular descriptors for accurate lipophilicity assessment.