@misc{
author = "Šegan, Sandra B. and Jevtić, Ivana I. and Tosti, Tomislav and Penjišević, Jelena and Šukalović, Vladimir and Kostić-Rajačić, Slađana and Milojković-Opsenica, Dušanka",
year = "2022",
abstract = "Lipophilicity and ionization constant of sixteen fentanyl analogues were investigated by reversed-phase thin-layer chromatography (RP-TLC). Fourteen compounds have nitrogen containing groups at C-3 position of thepiperidine ring and two compounds are 3-carbomethoxy derivatives of fentanyl. Among them, five are diaste-reomeric cis/trans couples and six novel trans diastereomers. In addition, the lipophilicity and ionization constantof fentanyl were also determined by the same method, as a reference. The physicochemical property, lip-ophilicity, expressed as retention indices RM0 , b, and C0, as well as PC1, was determined and correlated with insilico values. Ionization constants were determined on the basis of the relationships between analyte’s retentionexpressed as RF and mobile phase pH. Calculated structural descriptors together with the retention indices, weresubjected to the principal component analysis – PCA and hierarchical cluster analysis – HCA, in order to providebasic insights into the similarities among the studied compounds. The blood – brain barrier (BBB) permeationwas investigated in the function of experimentally obtained values of lipophilicity, polar surface area and mo-lecular weight. In general, results of the present research corroborate well with previously determined anti-nociceptive activities of the investigated compounds, pointing out that besides the cis/trans isomerism, anotherset of important parameters should be taken into account when designing new derivatives of C-3 substitutedfentanyl, especially lipophilicity, voluminosity and HBD/A character of the substituents. Accordingly, RP-TLCcan be considered as a valuable asset in the ligand-based drug design",
publisher = "Elsevier",
journal = "Journal of Chromatography B",
title = "Supplementary material for: Šegan, S., Jevtić, I., Tosti, T., Penjišević, J., Šukalović, V., Kostić-Rajačić, S.,& Milojković-Opsenica, D.. (2022). Determination of lipophilicity and ionization of fentanyl and its 3‑substituted analogs by reversed-phase thin-layer chromatography. in Journal of Chromatography B Elsevier., 1211, 123481. https://doi.org/10.1016/j.jchromb.2022.123481",
volume = "1211",
pages = "123481",
url = "https://hdl.handle.net/21.15107/rcub_cherry_5650"
}