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Integrated chromatographic and chemometric evaluation of lipophilicity in steroidal hydrazone derivatives across multiple mobile phase systems.

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Τίτλος: Integrated chromatographic and chemometric evaluation of lipophilicity in steroidal hydrazone derivatives across multiple mobile phase systems.
Συγγραφείς: Mosić MD; University of Belgrade - Faculty of Chemistry, Studentski trg 12-16, 11158, Belgrade, Serbia. Electronic address: mosicm@chem.bg.ac.rs., Nastić MA; University of Niš, Faculty of Sciences and Mathematics, Department of Biology and Ecology, Višegradska 33, 18000, Niš, Serbia., Živković MB; University of Belgrade - Institute of Chemistry, Technology and Metallurgy, Department of Chemistry, Njegoševa 12, 11000, Belgrade, Serbia., Mitreski KL; University of Belgrade - Faculty of Chemistry, Studentski trg 12-16, 11158, Belgrade, Serbia., Šegan SB; University of Belgrade - Institute of Chemistry, Technology and Metallurgy, Department of Chemistry, Njegoševa 12, 11000, Belgrade, Serbia. Electronic address: sandra.segan@ihtm.bg.ac.rs.
Πηγή: Journal of chromatography. A [J Chromatogr A] 2026 Oct 11; Vol. 1786, pp. 467342. Date of Electronic Publication: 2026 Aug 07.
Τύπος έκδοσης: Journal Article
Γλώσσα: English
Στοιχεία περιοδικού: Publisher: Elsevier Country of Publication: Netherlands NLM ID: 9318488 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1873-3778 (Electronic) Linking ISSN: 00219673 NLM ISO Abbreviation: J Chromatogr A Subsets: MEDLINE
Imprint Name(s): Original Publication: Amsterdam ; New York : Elsevier, 1993-
Ιατρικοί όροι (MeSH): Steroids*/chemistry , Hydrazones*/chemistry, Chromatography, Thin Layer/methods ; Chromatography, Reverse-Phase/methods ; Emulsions/chemistry ; Hydrophobic and Hydrophilic Interactions ; Micelles ; Acetonitriles
Περίληψη: The retention behavior of structurally related steroidal semicarbazones, thiadiazolines, thiazolidin-4-ones, and monoethyl carbazate esters was investigated using thin-layer chromatography on octadecyl-silica (RP18) under reversed-phase (RP), micellar, microemulsion, and acetonitrile/phosphate-buffered saline (pH 7.4) mobile phase conditions. Classical binary methanol-water and acetone-water systems were used to determine RM0, C0, and PC1, while RM values obtained in micellar, microemulsion, and acetonitrile/phosphate-buffered saline (pH 7.4) systems were employed as lipophilicity-related descriptors. Micellar systems containing sodium dodecyl sulfate (SDS) and n-butanol enabled evaluation of pseudophase-mediated solubilization, whereas microemulsions, additionally incorporating n-octanol or n-heptane, introduced multiphase partitioning among aqueous, micellar, oil, and stationary phases. The buffered acetonitrile-based system provided a non-organized reference medium under physiologically relevant conditions. The relationships among chromatographic descriptors, chromatographic systems, and in silico lipophilicity estimates were assessed using the Sum of Ranking Differences (SRD) method and Hierarchical Cluster Analysis (HCA), with an average RM-based reference ranking applied in SRD. Conventional RP and buffered systems showed the closest relationship with descriptors reflecting binary partitioning behavior, indicating dominant hydrophobic partitioning. In contrast, micellar and microemulsion systems formed distinct clusters, reflecting pseudophase and multiphase distribution effects. These findings demonstrate that organized mobile phases create mechanistically distinct retention environments, while the buffered system serves as a transitional, non-supramolecular reference medium bridging conventional reversed-phase and organized multiphase environments. This integrative chemometric framework enables statistically supported comparison of chromatographic systems and evaluation of their complementary contribution to lipophilicity.
(Copyright © 2026 Elsevier B.V. All rights reserved.)
Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
Contributed Indexing: Keywords: Lipophilicity; Micellar liquid chromatography (MLC); Microemulsion liquid chromatography (MELC); Reversed-phase thin-layer chromatography (RP-TLC); Steroidal hydrazone derivatives
Substance Nomenclature: 0 (Steroids)
0 (Hydrazones)
0 (Micelles)
0 (Emulsions)
Z072SB282N (acetonitrile)
0 (Acetonitriles)
Entry Date(s): Date Created: 20260811 Date Completed: 20260907 Latest Revision: 20260907
Update Code: 20260908
DOI: 10.1016/j.chroma.2026.467342
PMID: 42580232
Βάση Δεδομένων: MEDLINE
Περιγραφή
ISSN:1873-3778
DOI:10.1016/j.chroma.2026.467342