{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,25]],"date-time":"2026-09-25T18:35:22Z","timestamp":1790361322347,"version":"4.1.0"},"reference-count":43,"publisher":"MDPI AG","issue":"6","license":[{"start":{"date-parts":[[2023,3,21]],"date-time":"2023-03-21T00:00:00Z","timestamp":1679356800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/100007771","name":"Medical University of Silesia Katowice","doi-asserted-by":"publisher","award":["PCN-1-009\/N\/2\/F"],"award-info":[{"award-number":["PCN-1-009\/N\/2\/F"]}],"id":[{"id":"10.13039\/100007771","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Lipophilicity in addition to the solubility, acid-base character and stability is one of the most important physicochemical parameters of a compound required to assess the ADMET properties (absorption, distribution, metabolism, excretion and toxicity) of a bioactive molecule. Therefore, the subject of this work was to determine the lipophilicity parameters of selected antimicrobial and immunosuppressive compounds such as delafloxacin, linezolid, sutezolid, ceftazidime, everolimus and zotarolimus using thin-layer chromatography in reversed phase system (RP-TLC). The chromatographic parameters of lipophilicity (RMW) for tested compounds were determined on different stationary phases: RP18F254, RP18WF254 and RP2F254 using ethanol, acetonitrile, and propan-2-ol as organic modifiers of mobile phases used. Chromatographically established RMW values were compared with partition coefficients obtained by different computational methods (AlogPs, AClogP, AlogP, MlogP, XlogP2, XlogP3, logPKOWWIN, ACD\/logP, milogP). Both cluster and principal component analysis (CA and PCA) of the received results allowed us to compare the lipophilic nature of the studied compounds. The sum of ranking differences analysis (SRD) of all lipophilicity parameters was helpful to select the most effective method of determining the lipophilicity of the investigated compounds. The presented results demonstrate that RP-TLC method may be a good tool in determining the lipophilic properties of studied substances. Obtained lipophilic parameters of the compounds can be valuable in the design of their new derivatives as efficient antimicrobial and immunosuppressive agents.<\/jats:p>","DOI":"10.3390\/molecules28062820","type":"journal-article","created":{"date-parts":[[2023,3,21]],"date-time":"2023-03-21T04:48:01Z","timestamp":1679374081000},"page":"2820","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":23,"title":["Assessment of Lipophilicity Parameters of Antimicrobial and Immunosuppressive Compounds"],"prefix":"10.3390","volume":"28","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-2852-1647","authenticated-orcid":false,"given":"Dawid","family":"Wardecki","sequence":"first","affiliation":[{"name":"Faculty of Pharmaceutical Sciences in Sosnowiec, Doctoral School, Medical University of Silesia in Katowice, 41-200 Sosnowiec, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0425-5468","authenticated-orcid":false,"given":"Ma\u0142gorzata","family":"Do\u0142owy","sequence":"additional","affiliation":[{"name":"Department of Analytical Chemistry, Faculty of Pharmaceutical Sciences in Sosnowiec, Medical University of Silesia in Katowice, 41-200 Sosnowiec, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5150-0396","authenticated-orcid":false,"given":"Katarzyna","family":"Bober-Majnusz","sequence":"additional","affiliation":[{"name":"Department of Analytical Chemistry, Faculty of Pharmaceutical Sciences in Sosnowiec, Medical University of Silesia in Katowice, 41-200 Sosnowiec, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2023,3,21]]},"reference":[{"key":"ref_1","first-page":"1047","article-title":"Lipophilicity, methods of determination and its role in biological effect of chemical substances","volume":"55","year":"2001","journal-title":"Wiad. Chem."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"12156","DOI":"10.1021\/acs.jmedchem.9b01813","article-title":"Integrating the impact of lipophilicity on potency and pharmacokinetic parameters enables the use of diverse chemical space during small molecule drug optimization","volume":"63","author":"Miller","year":"2020","journal-title":"J. Med. Chem."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"261","DOI":"10.1080\/17460441.2020.1691995","article-title":"Is there enough focus on lipophilicity in drug discovery?","volume":"15","author":"Lobo","year":"2019","journal-title":"Expert Opin. Drug Discov."},{"key":"ref_4","doi-asserted-by":"crossref","unstructured":"Soares, J., Santos, \u00c1., Fernandes, C., and Pinto, M.M. (2022). Liquid chromatography on the different methods for the determination of lipophilicity: An essential analytical tool in medicinal chemistry. Chemosensors, 10.","DOI":"10.3390\/chemosensors10080340"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"54","DOI":"10.1016\/j.trac.2019.01.011","article-title":"State of the art and prospects of methods for determination of lipophilicity of chemical compounds","volume":"113","author":"Chmiel","year":"2019","journal-title":"Trends Anal. Chem."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"28","DOI":"10.1016\/j.trac.2015.02.009","article-title":"Recent advances in lipophilicity measurement by reversed-phase high-performance liquid chromatography","volume":"68","author":"Liang","year":"2015","journal-title":"Trends Anal. Chem."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"70","DOI":"10.1016\/j.jpba.2017.10.034","article-title":"The comparative study of micellar TLC and RP-TLC as potential tools for lipophilicity assessment based on QSRR approach","volume":"149","author":"Ciura","year":"2018","journal-title":"J. Pharm. Biomed. Anal."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"885","DOI":"10.1080\/17460441.2017.1344210","article-title":"Lipophilicity and biomimetic properties to support drug discovery","volume":"12","author":"Tsopelas","year":"2017","journal-title":"Expert Opin. Drug Discov."},{"key":"ref_9","doi-asserted-by":"crossref","unstructured":"Janicka, M., Mycka, A., Sztanke, M., and Sztanke, K. (2021). Predicting pharmacokinetic properties of potential anticancer agents via their chromatographic behavior on different reversed phase materials. Int. J. Mol. Sci., 22.","DOI":"10.3390\/ijms22084257"},{"key":"ref_10","doi-asserted-by":"crossref","unstructured":"Ciura, K., Fedorowicz, J., Andri\u0107, F., \u017duvela, P., Greber, K.E., Baranowski, P., Kawczak, P., Nowakowska, J., B\u0105czek, T., and S\u0105czewski, J. (2019). Lipophilicity determination of antifungal Isoxazolo[3,4-b]pyridin-3(1H)-ones and their N1-substituted derivatives with chromatographic and computational methods. Molecules, 24.","DOI":"10.3390\/molecules24234311"},{"key":"ref_11","doi-asserted-by":"crossref","unstructured":"Wardecki, D., Do\u0142owy, M., Bober-Majnusz, K., and Jampilek, J. (2023). Comparative study of the lipophilicity of selected anti-androgenic and blood uric acid lowering compounds. Molecules, 28.","DOI":"10.3390\/molecules28010166"},{"key":"ref_12","doi-asserted-by":"crossref","unstructured":"Ciura, K., Fedorowicz, J., Kapica, H., Pastewska, M., Sawicki, W., and S\u0105czewski, J. (2021). Interaction between antifungal isoxazolo[3,4-b]pyridin 3(1H)-one derivatives and human serum proteins analyzed with biomimetic chromatography and QSAR approach. Processes, 9.","DOI":"10.3390\/pr9030512"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"462552","DOI":"10.1016\/j.chroma.2021.462552","article-title":"Multivariate assessment of anticancer oleanane triterpenoids lipophilicity","volume":"1656","author":"Pastewska","year":"2021","journal-title":"J. Chromatogr. A"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"462666","DOI":"10.1016\/j.chroma.2021.462666","article-title":"Prediction of the chromatographic hydrophobicity index with immobilized artificial membrane chromatography using simple molecular descriptors and artificial neural networks","volume":"1660","author":"Ciura","year":"2021","journal-title":"J. Chromatogr. A"},{"key":"ref_15","doi-asserted-by":"crossref","unstructured":"Ciura, K., Fedorowicz, J., Andri\u0107, F., Greber, K.E., Gurgielewicz, A., Sawicki, W., and S\u0105czewski, J. (2019). Lipophilicity determination of quaternary(fluoro)quinolones by chromatographic and theoretical approaches. Int. J. Mol. Sci., 20.","DOI":"10.3390\/ijms20215288"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"461439","DOI":"10.1016\/j.chroma.2020.461439","article-title":"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","volume":"1628","author":"Banjac","year":"2020","journal-title":"J. Chromatogr. A"},{"key":"ref_17","doi-asserted-by":"crossref","unstructured":"Kadela-Tomanek, M., Jastrz\u0119bska, M., Chrobak, E., and B\u0119benek, E. (2023). Lipophilicity and ADMET analysis of quinoline-1,4-quinone hybrids. Pharmaceutics, 15.","DOI":"10.3390\/pharmaceutics15010034"},{"key":"ref_18","first-page":"615","article-title":"Application of chemometric methods for determination of the lipophilicity of pentacyclic triterpene derivatives","volume":"79","author":"Chrobak","year":"2022","journal-title":"Acta Pol. Pharm."},{"key":"ref_19","doi-asserted-by":"crossref","unstructured":"Do\u0142owy, M., Jampilek, J., and Bober-Majnusz, K. (2021). A Comparative study of the lipophilicity of metformin and phenformin. Molecules, 26.","DOI":"10.3390\/molecules26216613"},{"key":"ref_20","first-page":"671","article-title":"Evaluation of lipophilic properties of betamethasone and related compounds","volume":"72","author":"Pyka","year":"2015","journal-title":"Acta Pol. Pharm."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"1452","DOI":"10.1080\/10826076.2015.1050502","article-title":"Determination of lipophilicity of allyl thiosemicarbazide, N-1-thiocarbamylamidrazone derivatives, and their cyclic products by RP-HPLC, RP-TLC, and theoretical methods: Effects of selected compounds on the CNS of mice","volume":"38","author":"Strzemecka","year":"2015","journal-title":"J. Liq. Chromatogr. Relat. Technol."},{"key":"ref_22","first-page":"927","article-title":"A TLC study of the lipophilicity of thirty-two acetylcholinesterase inhibitors\u20141,2,3,4-tetrahydroacridine and 2,3-dihydro-1H-cyclopenta[b]quinoline derivatives","volume":"11","author":"Liszka","year":"2013","journal-title":"Cent. Eur. J. Chem."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"1759","DOI":"10.1002\/bmc.3490","article-title":"Lipophilicity study of eight cephalosporins by reversed-phase thin-layer chromatographic method","volume":"29","author":"Komsta","year":"2015","journal-title":"Biomed. Chromatogr."},{"key":"ref_24","doi-asserted-by":"crossref","unstructured":"Constantinescu, T., Lungu, C.N., and Lung, I. (2019). Lipophilicity as a central component of drug-like properties of chalchones and flavonoid derivatives. Molecules, 24.","DOI":"10.3390\/molecules24081505"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"99","DOI":"10.1016\/j.ejps.2017.05.006","article-title":"A comparative study of chromatographic behavior and lipophilicity of selected natural styryl lactones, their derivatives and analogues","volume":"105","author":"Popsavin","year":"2017","journal-title":"Eur. J. Pharm. Sci."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"58","DOI":"10.1016\/j.forc.2016.07.004","article-title":"Rapid experimental and computational determination of phenethylamine drug analogue lipophilicity","volume":"1","author":"Kretsch","year":"2016","journal-title":"Forensic Chem."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"934","DOI":"10.1093\/chromsci\/bmx054","article-title":"Chromatographic and computational assessment of lipophilicity of new anticancer acetylenequinoline derivatives","volume":"55","author":"Marciniec","year":"2017","journal-title":"J. Chromatogr. Sci."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"128318","DOI":"10.1016\/j.bmcl.2021.128318","article-title":"Estimation of the lipophilicity of purine-2,6-dione-based TRPA1 antagonists and PDE4\/7 inhibitors with analgesic activity","volume":"49","author":"Starek","year":"2021","journal-title":"Bioorg. Med. Chem."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"1481","DOI":"10.1007\/s40265-017-0790-5","article-title":"Delafloxacin: First global approval","volume":"77","author":"Markham","year":"2017","journal-title":"Drugs"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"1759","DOI":"10.2147\/DDDT.S164515","article-title":"Linezolid: A review of its properties, function, and use in critical care","volume":"12","author":"Hashemian","year":"2018","journal-title":"Drug Des Devel Ther."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"680","DOI":"10.1021\/jm950956y","article-title":"Identification of a novel oxazolidinone (U-100480) with potent antimycobacterial activity","volume":"39","author":"Barbachyn","year":"1996","journal-title":"J. Med. Chem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"270","DOI":"10.1128\/AAC.01691-15","article-title":"Contribution of oxazolidinones to the efficacy of novel regimens containing bedaquiline and pretomanid in a mouse model of tuberculosis","volume":"60","author":"Tasneen","year":"2016","journal-title":"Antimicrob. Agents Chemother."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"00172","DOI":"10.1002\/prp2.172","article-title":"Randomized pharmacokinetic and drug-drug interaction studies of ceftazidime, avibactam, and metronidazole in healthy subjects","volume":"3","author":"Das","year":"2015","journal-title":"Pharmacol. Res. Perspect."},{"key":"ref_34","unstructured":"(2022, December 28). European Medicines Agency. Available online: https:\/\/www.ema.europa.eu\/en."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"101","DOI":"10.1007\/978-3-319-91442-8_8","article-title":"Everolimus","volume":"211","author":"Hasskarl","year":"2018","journal-title":"Recent Results Cancer Res."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"913","DOI":"10.1080\/14737175.2019.1635457","article-title":"Everolimus as adjunctive therapy for tuberous sclerosis complex-associated partial-onset seizures","volume":"19","author":"Lechuga","year":"2019","journal-title":"Expert Rev. Neurother."},{"key":"ref_37","doi-asserted-by":"crossref","unstructured":"Chang, G.R., Kuo, C.Y., Tsai, M.Y., Lin, W.L., Lin, T.C., Liao, H.J., Chen, C.H., and Wang, Y.C. (2021). Anti-cancer effects of zotarolimus combined with 5-fluorouracil treatment in HCT-116 colorectal cancer-bearing BALB\/c nude mice. Molecules, 26.","DOI":"10.3390\/molecules26154683"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"3793","DOI":"10.1111\/bph.13168","article-title":"Rapamycin impairs HPD-induced beneficial effects on glucose homeostasis","volume":"172","author":"Chang","year":"2015","journal-title":"Br. J. Pharmacol."},{"key":"ref_39","unstructured":"Stanisz, A. (2007). Przyst\u0119pny Kurs Statystyki z Zastosowaniem STATISTICA PL na Przyk\u0142adach Medycyny, Vol. 3, Analizy Wielowymiarowe, Stat Soft Polska."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"20150202","DOI":"10.1098\/rsta.2015.0202","article-title":"Principal component analysis: A review and recent developments","volume":"374","author":"Jolliffe","year":"2016","journal-title":"Phil. Trance. R. Soc."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"183","DOI":"10.1016\/j.jpba.2015.07.006","article-title":"Towards better understanding of lipophilicity: Assessment of in silico and chromatographic logP measures for pharmaceutically important compounds by nonparametric rankings","volume":"115","year":"2015","journal-title":"J. Pharm. Biomed. Anal."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"130","DOI":"10.1016\/j.chroma.2014.12.073","article-title":"Chromatographic and computational assessment of lipophilicity using sum of ranking differences and generalized pair-correlation","volume":"1380","year":"2015","journal-title":"J. Chromatogr. A"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"81","DOI":"10.1016\/j.jpba.2016.04.001","article-title":"Multivariate assessment of lipophilicity scales\u2014Computational and reversed phase thin-layer chromatographic indices","volume":"127","author":"Bajusz","year":"2016","journal-title":"J. Pharm. Biomed. Anal."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/6\/2820\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T18:59:30Z","timestamp":1760122770000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/6\/2820"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,3,21]]},"references-count":43,"journal-issue":{"issue":"6","published-online":{"date-parts":[[2023,3]]}},"alternative-id":["molecules28062820"],"URL":"https:\/\/doi.org\/10.3390\/molecules28062820","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,3,21]]}}}