Lipophilicity of BODIPY fluorophores and their distribution in 1-octanol–water system
https://doi.org/10.29235/1561-8331-2023-59-2-150-161
Abstract
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.
About the Authors
M. S. Horetski
Research Institute for Physical Chemical Problems of the Belarusian State University
Belarus
Belarus
Horetski Matvey S. – Junior Researcher
14, Leningradskaya Str., 220006, Minsk
N. S. Frolova
Research Institute for Physical Chemical Problems of the Belarusian State University
Russian Federation
Russian Federation
Frolova Nina S. – Researcher
14, Leningradskaya Str., 220006, Minsk
V. M. Shkumatov
Research Institute for Physical Chemical Problems of the Belarusian State University
Russian Federation
Russian Federation
Shkumatov Vladimir M. – Corresponding Member of the
National Academy of Sciences of Belarus, D. Sc. (Biology), Professor, Head of the Laboratory
14, Leningradskaya Str., 220006, Minsk
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