{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,19]],"date-time":"2026-03-19T22:28:57Z","timestamp":1773959337878,"version":"3.50.1"},"reference-count":38,"publisher":"International Association of Physical Chemists (IAPC)","license":[{"start":{"date-parts":[[2026,3,19]],"date-time":"2026-03-19T00:00:00Z","timestamp":1773878400000},"content-version":"unspecified","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"}],"funder":[{"DOI":"10.13039\/501100004281","name":"Narodowe Centrum Nauki","doi-asserted-by":"publisher","award":["2022\/47\/D\/NZ7\/01043"],"award-info":[{"award-number":["2022\/47\/D\/NZ7\/01043"]}],"id":[{"id":"10.13039\/501100004281","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100018693","name":"HORIZON EUROPE Framework Programme","doi-asserted-by":"publisher","award":["101178074"],"award-info":[{"award-number":["101178074"]}],"id":[{"id":"10.13039\/100018693","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100024109","name":"Uniwersytet Gda\u0144ski","doi-asserted-by":"publisher","award":["EUREKA 533-T000-GE12-25"],"award-info":[{"award-number":["EUREKA 533-T000-GE12-25"]}],"id":[{"id":"10.13039\/501100024109","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["ADMET DMPK"],"abstract":"<jats:p>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\u00a0P\u00a0\/\u00a0log\u00a0D 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\u00a0P\u00a0\/\u00a0log\u00a0D 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.<\/jats:p>","DOI":"10.5599\/admet.3169","type":"journal-article","created":{"date-parts":[[2026,3,19]],"date-time":"2026-03-19T19:01:11Z","timestamp":1773946871000},"page":"3169","source":"Crossref","is-referenced-by-count":0,"title":["Modelling an alternative lipophilicity scale of bisphenols using biomimetic chromatography: Relevance to membrane-driven baseline toxicity"],"prefix":"10.5599","volume":"14","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-6187-6039","authenticated-orcid":false,"given":"Krzesimir","family":"Ciura","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0009-0000-7120-7218","authenticated-orcid":false,"given":"Julia","family":"Nicman","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9640-3810","authenticated-orcid":false,"given":"Szymon","family":"Zdybel","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2964-389X","authenticated-orcid":false,"given":"Giacomo","family":"Russo","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3529-1819","authenticated-orcid":false,"given":"Lucia","family":"Grumetto","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7820-0390","authenticated-orcid":false,"given":"Katarzyna Ewa","family":"Greber","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3288-4309","authenticated-orcid":false,"given":"Anita","family":"Sosnowska","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5595-7764","authenticated-orcid":false,"given":"Joanna","family":"Do\u0142\u017conek","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2730-6873","authenticated-orcid":false,"given":"Karolina","family":"Jagiello","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"3564","published-online":{"date-parts":[[2026,3,19]]},"reference":[{"key":"168813","doi-asserted-by":"crossref","unstructured":"[1] A. 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Screening therapeutics according to their uptake across the blood-brain barrier: A high throughput method based on immobilized artificial membrane liquid chromatography-diode-array-detection coupled to electrospray-time-of-flight mass spectrometry. European Journal of Pharmaceutics and Biopharmaceutics 127 (2018) 72-84. https:\/\/doi.org\/10.1016\/j.ejpb.2018.02.004","DOI":"10.1016\/j.ejpb.2018.02.004"},{"key":"168832","doi-asserted-by":"crossref","unstructured":"[20] S. Kova\u010devi\u0107, M.K. Banjac, N. Milo\u0161evi\u0107, J. \u0106ur\u010di\u0107, D. Marjanovi\u0107, N. Todorovi\u0107, J. Krmar, S. Podunavac-Kuzmanovi\u0107, N. Banjac, G. U\u0161\u0107umli\u0107. 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. Journal of Chromatography A 1628 (2020) 461439. https:\/\/doi.org\/10.1016\/j.chroma.2020.461439","DOI":"10.1016\/j.chroma.2020.461439"},{"key":"168833","doi-asserted-by":"crossref","unstructured":"[21] I. Neri, M. Piccolo, G. Russo, M.G. Ferraro, V. Marotta, R. Santamaria, L. Grumetto. The combined use of biological investigations, bio chromatographic and in silico methods to solve the puzzle of badge and its derivative\u2019s toxicity. Chemosphere 367 (2024) 143640. https:\/\/doi.org\/10.1016\/j.chemosphere.2024.143640","DOI":"10.1016\/j.chemosphere.2024.143640"},{"key":"168834","doi-asserted-by":"crossref","unstructured":"[22] F. Tsopelas, F. Stergiopoulos, A. Tsantili-Kakoulidou. Immobilized artificial membrane chromatography: from medicinal chemistry to environmental sciences. ADMET & DMPK 6 (2018) 225-241. https:\/\/doi.org\/10.5599\/admet.553","DOI":"10.5599\/admet.553"},{"key":"168835","doi-asserted-by":"crossref","unstructured":"[23] C. Stergiopoulos, D. Makarouni, A. Tsantili-Kakoulidou, M. Ochsenk\u00fchn-Petropoulou, F. Tsopelas. Immobilized artificial membrane chromatography as a tool for the prediction of ecotoxicity of pesticides. Chemosphere 224 (2019) 128-139. https:\/\/doi.org\/10.1016\/j.chemosphere.2019.02.075","DOI":"10.1016\/j.chemosphere.2019.02.075"},{"key":"168836","doi-asserted-by":"crossref","unstructured":"[24] A.W. Soba\u0144ska. Affinity of Compounds for Phosphatydylcholine-Based Immobilized Artificial Membrane\u2014A Measure of Their Bioconcentration in Aquatic Organisms. Membranes 12 (2022) 1130. https:\/\/doi.org\/10.3390\/membranes12111130","DOI":"10.3390\/membranes12111130"},{"key":"168837","doi-asserted-by":"crossref","unstructured":"[25] A.W. Soba\u0144ska. RP-18 TLC retention data and calculated physico-chemical parameters as predictors of soil-water partition and bioconcentration of organic sunscreens. Chemosphere 279 (2021) 130527. https:\/\/doi.org\/10.1016\/j.chemosphere.2021.130527","DOI":"10.1016\/j.chemosphere.2021.130527"},{"key":"168838","doi-asserted-by":"crossref","unstructured":"[26] A.W. Soba\u0144ska. Evaluation of drug-likeness and ADME properties of sunscreens and preservatives using reversed-phase thin layer chromatographic retention data and calculated descriptors. Journal of Pharmaceutical and Biomedical Analysis 201 (2021) 114126. https:\/\/doi.org\/10.1016\/j.jpba.2021.114126","DOI":"10.1016\/j.jpba.2021.114126"},{"key":"168839","doi-asserted-by":"crossref","unstructured":"[27] K.L. Valko, T. Zhang. Biomimetic properties and estimated in vivo distribution of chloroquine and hydroxy-chloroquine enantiomers. ADMET & DMPK 9 (2021) 151-165. https:\/\/doi.org\/10.5599\/admet.929","DOI":"10.5599\/admet.929"},{"key":"168840","doi-asserted-by":"crossref","unstructured":"[28] D. Szulczyk, M. Wozi\u0144ski, M. Koli\u0144ski, S. Kmiecik, A. G\u0142ogowska, E. Augustynowicz-Kope\u0107, M.A. Dobrowolski, P. Roszkowski, M. Struga, K. Ciura. Menthol- and thymol-based ciprofloxacin derivatives against Mycobacterium tuberculosis: in vitro activity, lipophilicity, and computational studies. Scientific Reports 13 (2023) 16328. https:\/\/doi.org\/10.1038\/s41598-023-43708-4","DOI":"10.1038\/s41598-023-43708-4"},{"key":"168841","doi-asserted-by":"crossref","unstructured":"[29] S. Ulenberg, K. Ciura, P. Georgiev, M. Pastewska, G. \u015alifirski, M. Kr\u00f3l, F. Herold, T. B\u0105czek. Use of biomimetic chromatography and in vitro assay to develop predictive GA-MLR model for use in drug-property prediction among anti-depressant drug candidates. Microchemical Journal 175 (2022) 107183. https:\/\/doi.org\/10.1016\/j.microc.2022.107183","DOI":"10.1016\/j.microc.2022.107183"},{"key":"168842","doi-asserted-by":"crossref","unstructured":"[30] K. Ciura, S. Kova\u010devi\u0107, M. Pastewska, H. Kapica, M. Kornela, W. Sawicki. 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The effects of bisphenols on the cardiovascular system ex vivo and in vivo. Chemosphere 313 (2023) 137565. https:\/\/doi.org\/10.1016\/j.chemosphere.2022.137565","DOI":"10.1016\/j.chemosphere.2022.137565"},{"key":"168845","doi-asserted-by":"crossref","unstructured":"[33] K.L. Valko, S. Nunhuck, C. Bevan, M.H. Abraham, D.P. Reynolds. Fast gradient HPLC method to determine compounds binding to human serum albumin. Relationships with octanol\/water and immobilized artificial membrane lipophilicity. Journal of Pharmaceutical Sciences 92 (2003) 2236-2248. https:\/\/doi.org\/10.1002\/jps.10494","DOI":"10.1002\/jps.10494"},{"key":"168846","doi-asserted-by":"crossref","unstructured":"[34] K.L. Valko, S. Rava, S. Bunnally, S. Anderson. Revisiting the application of Immobilized Artificial Membrane (IAM) chromatography to estimate in vivo distribution properties of drug discovery compounds based on the model of marketed drugs. ADMET & DMPK 8 (2020) 78-97. https:\/\/doi.org\/10.5599\/admet.757","DOI":"10.5599\/admet.757"},{"key":"168847","doi-asserted-by":"crossref","unstructured":"[35] K. Ciura. Modeling of small molecule affinity to phospholipids using IAM-HPLC and a QSRR approach enhanced by similarity-based machine learning algorithms. Journal of Chromatography A 1714 (2024) 464549. https:\/\/doi.org\/10.1016\/j.chroma.2023.464549","DOI":"10.1016\/j.chroma.2023.464549"},{"key":"168848","doi-asserted-by":"crossref","unstructured":"[36] G. Matteo, K. Leingartner, A. Rowan-Carroll, M. Meier, A. Williams, M.A. Beal, M. Gagn\u00e9, R. Farmahin, S. Wickramasuriya, A.J.F. Reardon, T. Barton-Maclaren, J.C. Corton, C.L. Yauk, E. Atlas. In vitro transcriptomic analyses reveal pathway perturbations, estrogenic activities, and potencies of data-poor BPA alternative chemicals. Toxicological Sciences 191 (2022) 266-275. https:\/\/doi.org\/10.1093\/toxsci\/kfac127","DOI":"10.1093\/toxsci\/kfac127"},{"key":"168849","doi-asserted-by":"crossref","unstructured":"[37] C. Stergiopoulos, L.A. Tsakanika, M. Ochsenk\u00fchn-Petropoulou, A.T. Kakoulidou, F. Tsopelas. Application of micellar liquid chromatography to model ecotoxicity of pesticides. Comparison with immobilized artificial membrane chromatography and n-octanol-water partitioning. Journal of Chromatography A 1696 (2023) 463951. https:\/\/doi.org\/10.1016\/j.chroma.2023.463951","DOI":"10.1016\/j.chroma.2023.463951"},{"key":"168850","doi-asserted-by":"crossref","unstructured":"[38] C. Stergiopoulos, F. Tsopelas, M. Ochsenk\u00fchn-Petropoulou, K. Valko. The use of biomimetic chromatography to predict acute aquatic toxicity of pharmaceutical compounds. 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