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Acta poloniae pharmaceutica

Lipophilicity parameter from high-performance liquid chromatography on an immobilized artificial membrane column and its relationships to bioactivity of the group of 2,4-dihydroxythiobenzanilides.


PMID 12602794

Abstract

Several groups of 2,4-dihydroxythiobenzanilide derivatives are extensively studied in our laboratories as potential antifungal or antibacterial agents. Previous papers showed that their biological activities are closely correlated with the lipophilicity determined in HPLC experiments using on octadecylsilyl stationary phase (RP-18). In the present paper we attempted to measure chromatographic indices of 2,4-dihydroxythiobenzanilides, using a silica-based immobilized artificial membrane (IAM) column especially designed to evaluating biological lipophilicity. The theoretical (extrapolated) retention in pure water the log k(w)(IAM) parameter for 23 derivatives was determined during poly-cratic experiments. Statistical analysis exhibited good correlations between the log k(w)(IAM) parameter and the biological data concerning bacteriostatic activity of these compounds. Retention on the IAM phase can be used as predictor of biological membrane permeability and biological lipophilicity of 2,4-dihydroxythiobenzanilides in spite of the acidic properties of this group of compounds.

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