On the possibility of theoretical prediction of benzanthrone dye lipophilicity
Keywords:
benzanthrone dyes, lipophilicity, correlation coefficientAbstract
The present study was aimed at comparing the prediction power of several computational methods in
evaluating the lipophilicity (logP) of a series of newly synthesized benzanthrone derivatives, tentatively
divided into three groups: 1) aminobenzanthrones, 2) amidinobenzanthrones, and 3) bromine-containing
amidinobenzanthrones. Experimental partition coefficients (log p K ) were derived from fluorescence
titration experiments. Analysis of the correlation coefficients between the experimental and theoretically
predicted lipophilicity values showed that generally log p K rather poorly correlates with logP of the
examined compounds. The best agreement between calculated and experimental lipophilicities was
observed for KOWWIN (group1), XLOGP3 (group2) and ALOGPs (group 3) methods, pointing to the
importance of different structure- and property-based factors in determining the dye lipophilicity. It is
concluded that computed logP, with careful choice of calculation method, can be effectively used for
prediction of membrane partition properties of benzanthrones, in combination with other molecular and
quantum-chemical descriptors.
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