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Application of Thin-Layer Chromatography to the Lipophilicity Analysis of Selected Anticancer Quinobenzothiazine Derivatives

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Summary

The aim of this work was the application of thin-layer chromatography to the lipophilicity analysis of selected quinobenzothiazine derivatives. These are newly synthesized compounds, which were previously analyzed taking into consideration biological activity and their antiproliferative activity. Experimental lipophilicity parameters (RM0 and log PTLC) were determined by use of thin-layer chromatography, and also some theoretical values of lipophilicity were calculated by use of computer programs. The correlation between the experimental and the theoretical values of lipophilicity was found. Also, cluster analysis was performed for the data obtained. Phenothiazine derivatives were modified mainly by introduction of substituents into the nitrogen atom of the thiazine ring. The computer programs applied based on different theoretical approaches gave different values of lipophilicity parameters depending on the kind of substituent in the quinobenzothiazine system. None of the computer programs took into consideration the influence of substituents in a structure of the tested compounds, and in this case, the calculated lipophilicity parameter had the same value for all isomers with the same substituent. Also, none of the computer programs gave values of lipophilicity parameters close to these obtained by experimental method. The results of log Pcalc for the compounds 1–13 were quite different according to the computer program used (log Pcalc = 1.69–5.98). No computer programs gave values of log Pcalc close to values of log PTLC obtained experimentally. The reason can be the specific special structure of the tested phenothiazine derivatives consisting of tetracyclic system with additional nitrogen atom. It shows that calculation methods can be useless for the preliminary lipophilicity determination of such a kind of compounds.

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Authors and Affiliations

  1. Department of Organic Chemistry, School of Pharmacy and the Division of Laboratory Medicine, Medical University of Silesia in Katowice, Jagiellońska 4, 41-200, Sosnowiec, Poland

    Andrzej Zięba

  2. Department of Analytical Chemistry, School of Pharmacy and the Division of Laboratory Medicine, Medical University of Silesia in Katowice, Jagiellońska 4, 41-200, Sosnowiec, Poland

    Katarzyna Bober

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  1. Andrzej Zięba
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  2. Katarzyna Bober
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Correspondence to Katarzyna Bober.

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Zięba, A., Bober, K. Application of Thin-Layer Chromatography to the Lipophilicity Analysis of Selected Anticancer Quinobenzothiazine Derivatives. JPC-J Planar Chromat 31, 105–111 (2018). https://doi.org/10.1556/1006.2018.31.2.2

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