vestichИзвестия Национальной академии наук Беларуси. Серия химических наукProceedings of the National Academy of Sciences of Belarus, Chemical Series1561-83312524-2342The Republican Unitary Enterprise Publishing House "Belaruskaya Navuka"10.29235/1561-8331-2023-59-2-150-161vestich-813Research ArticleБИООРГАНИЧЕСКАЯ ХИМИЯBIOORGANIC CHEMISTRYЛипофильность BODIPY флуорофоров и их распределение в системе октанол-1–водаLipophilicity of BODIPY fluorophores and their distribution in 1-octanol–water systemХорецкийМ. С.HoretskiM. S.

Хорецкий Матвей Сергеевич – мл. науч. сотрудник

ул. Ленинградская, 14, 220006, Минск

Horetski Matvey S. – Junior Researcher

14, Leningradskaya Str., 220006, Minsk

matvey.horetski@gmail.comФроловаН. С.FrolovaN. S.

Фролова Нина Степановна – науч. сотрудник

ул. Ленинградская, 14, 220006, Минск

Frolova Nina S. – Researcher

14, Leningradskaya Str., 220006, Minsk

ШкуматовВ. М.ShkumatovV. M.

Шкуматов Владимир Макарович – член-корреспондент, д-р биол. наук, профессор, зав. лаб.

ул. Ленинградская, 14, 220006, Минск

Shkumatov Vladimir M. – Corresponding Member of theNational Academy of Sciences of Belarus, D. Sc. (Biology), Professor, Head of the Laboratory

14, Leningradskaya Str., 220006, Minsk

Научно-исследовательский институт физико-химических проблем Белорусского государственного университетаResearch Institute for Physical Chemical Problems of the Belarusian State University202305062023592150161Copyright © Хорецкий М.С., Фролова Н.С., Шкуматов В.М., 20232023Хорецкий М.С., Фролова Н.С., Шкуматов В.М.Horetski M.S., Frolova N.S., Shkumatov V.M.Данная работа распространяется под лицензией Creative Commons Attribution 4.0.This work is licensed under a Creative Commons Attribution 4.0 License.https://vestichem.belnauka.by/jour/article/view/813

Выполнен синтез нескольких BODIPY флуорофоров и рассмотрено их распределение в системе октанол-1–вода. Для оценки эффективности использования расчетных методов при описании липофильности BODIPY производных обсуждены такие подходы, как XLopP3, ALogPS, WLogP, SILICOS-IT и MLogP. С помощью квантово-механических расчетов найдены гидрофобная и полярная площади молекулярных поверхностей соединений. Это позволило установить корреляцию между коэффициентом LogP и топологией молекулярной поверхности, а также определить соответствующие величины инкрементов для метильного, ацетильного и фенильного заместителей.

The work covers synthesis and lipophilicity estimation of several BODIPY dyes. For these compounds, the distribution between 1-octanol and water layers is experimentally described and the corresponding partition coefficients LogP are calculated. The experimental LogP values are compared with popular fragment-based methods XLopP3, ALogPS, WLogP, SILICOS-IT and MLogP. Additionally, the hydrophobic and polar surface areas are found with quantum-mechanical calculations. That allowed to find a correlation between the LogP coefficient and the molecular surface topology, as well as to determine the corresponding incremental values of the methyl, acetyl, and phenyl substituents. 

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The authors declare that there are no conflicts of interest present.