Original scientific paper

https://doi.org/10.5599/admet.3169

Modelling an alternative lipophilicity scale of bisphenols using biomimetic chromatography: Relevance to membrane-driven baseline toxicity

Krzesimir Ciura orcid.org/0000-0001-6187-6039 ; Department of Physical Chemistry, Faculty of Pharmacy, Medical University of Gdańsk, Al. Gen. J. Hallera 107, 80-416, Gdańsk, Poland and Laboratory of Environmental Chemoinformatics, Faculty of Chemistry, University of Gdansk, Wita Stwosza 63, 80-308, Gdansk, Poland *
Julia Nicman ; Department of Physical Chemistry, Faculty of Pharmacy, Medical University of Gdańsk, Al. Gen. J. Hallera 107, 80-416, Gdańsk, Poland
Szymon Zdybel ; Laboratory of Environmental Chemoinformatics, Faculty of Chemistry, University of Gdansk, Wita Stwosza 63, 80-308, Gdansk, Poland and QSAR Lab Ltd., Trzy Lipy 3 St., 80-172 Gdańsk, Poland
Giacomo Russo orcid.org/0000-0002-2964-389X ; School of Applied Sciences, Sighthill Campus, Edinburgh Napier University, 9 Sighthill Ct, EH11 4BN Edinburgh, United Kingdom
Lucia Grumetto orcid.org/0000-0002-3529-1819 ; Department of Pharmacy, School of Medicine and Surgery, University of Naples Federico II, Via D. Montesano, 49, 80131, Naples, Italy
Katarzyna Ewa Greber ; Department of Physical Chemistry, Faculty of Pharmacy, Medical University of Gdańsk, Al. Gen. J. Hallera 107, 80-416, Gdańsk, Poland
Anita Sosnowska ; Laboratory of Environmental Chemoinformatics, Faculty of Chemistry, University of Gdansk, Wita Stwosza 63, 80-308, Gdansk, Poland and QSAR Lab Ltd., Trzy Lipy 3 St., 80-172 Gdańsk, Poland
Joanna Dołżonek ; Department of Environmental Analysis, Faculty of Chemistry, University of Gdansk, Wita Stwosza 63, 80-308, Gdansk, Poland
Karolina Jagiello ; Laboratory of Environmental Chemoinformatics, Faculty of Chemistry, University of Gdansk, Wita Stwosza 63, 80-308, Gdansk, Poland and QSAR Lab Ltd., Trzy Lipy 3 St., 80-172 Gdańsk, Poland

* Corresponding author.

Abstract

Background and purpose: Bisphenol A and its structural analogues are ubiquitous environmental contaminants and potential endocrine disruptors, creating a need for mechanistically relevant descriptors that support early hazard assessment. This study asked whether lipophilicity indices derived from biomimetic chromatography better reflect baseline toxicity and membrane-relevant behaviour of bisphenols than commonly used in silico log P / log D descriptors. Experimental approach: A set of 18 bisphenol derivatives was analysed using phosphatidylcholine- and sphingomyelin-functionalised stationary phases and a conventional C18 column to obtain chromatographic hydrophobicity indices, which were then compared with predicted log P / log D values and related to mechanistically diverse toxicity endpoints (in vitro cytotoxicity in mammalian cells, ex vivo cardiotoxicity assessed as vasodilation, and aquatic toxicity towards Daphnids). Key results: Biomimetic chromatographic indices showed consistently stronger and more coherent relationships with biological activity than theoretical descriptors. They also uniquely captured structural effects, such as positional isomerism, which were largely indistinguishable using theoretical lipophilicity indices. Conclusion: These findings support biomimetic chromatography as an early-tier IATA tool, providing membrane-relevant experimental indices linking bisphenol lipophilicity with baseline toxicity.

Keywords

Immobilized artificial membrane; phospholipid affinity; endocrine disruptors; baseline toxicity; sphingomyelin column

Hrčak ID:

346786

URI

https://hrcak.srce.hr/346786

Publication date:

19.3.2026.

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