Application of capillary electrophoresis technique for the enantioseparation of bioactive ferrocene-based compounds versus DFT calculated data

Snegur, L.V.; Borisov, Y.A.; Ermolenko, Y.V.; Safronova, V.N.; Kiselev, S.S.; Kochetkov, K.A.; Simenel, A.A.

Авторы: Snegur Lubov V., Borisov Yurii A., Ermolenko Yuliya V., Safronova Viktoriya N., Kiselev Sergey S., Kochetkov Konstantin A., Simenel Alexander A.
Журнал: Electrophoresis
Том: 41
Год издания: 2020
Издательство: John Wiley & Sons Ltd.
Местоположение издательства: United Kingdom
Первая страница: 1969
Последняя страница: 1979
DOI: 10.1002/elps.202000154
Аннотация: Herein, a series of bioactive ferrocene-modified N-heterocycles with alkyl linkers was prepared in good to quantitative yields starting from easy accessible ferrocene alcohols and heterocycles under acidic or neutral (for imidazole) conditions in racemic forms. The analytical resolution of a number of bioactive racemic ferrocene azoles 1-6 (where azole = imidazole, pyrazole, benzotriazole derivatives) into enantiomers was first carry out by capillary electrophoresis (CE) using sulfobuthylether-β-cyclodextrin (captisol) as a chiral selector. The analytical approaches to highly enantiomeric-enriched ferrocene derivatives are based on the formation of their inclusion complexes. The best chiral separation was achieved using zone capillary electrophoresis in a quartz capillary. The affinity capillary electrophoresis (ACE) was used to evaluate the stability constants of captisol complexes with enantiomeric forms of two ferrocene derivatives 1, FcCHMe-Imidazole, and 6, FcCHMe-Benzotriazole. The optimal conditions for the resolution of the studied (R,S)-ferrocene compounds 1, 2 , and 6 were predicted on the basis of the performed quantum chemical (QC) calculations and then implemented by the electrophoretic method. A high correlation between DFT calculation results and experimental electrophoresis data was obtained. Successful enantioseparation of racemic mixtures is of great importance for the characterization and further applications of drug candidates in enantiopure forms and in the development of clinical treatment. The advantages of the CE procedure make it possible to have important practical value and significance for determining the purity and enantiomeric excess of other ferrocene-containing compounds.
Добавил в систему: Сименел Александр Александрович

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Application of capillary electrophoresis technique for the enantioseparation of bioactive ferrocene-based compounds versus DFT calculated dataстатья

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