LIPOPHILIC CHARACTER OF PYRIMIDINIC NUCLEOSIDE DERIVATIVES: CORRELATION BETWEEN SHAKE FLASK, CHROMATOGRAPHIC (RP-TLC AND RP-HPLC) AND THEORETICAL METHODS

Abstract

Chromatographic R_Mw and log k'_w parameters have been used as alternatives to the shake flask n-octanol/water partition coefficient method to study the lipophilic character of several known pyrimidinic nucleoside derivatives and two novel ones. The R_M and log k' values were measured by means of reversed-phase thin-layer chromatography (RP-TLC) and reversed-phase high performance liquid chromatography (RP-HPLC) respectively. Good linear relationships were observed between log P values obtained from the classical shake flask method (log P_o/w) and each one of those obtained by chromatographic techniques (log P_RP-TLC and log P_RP-HPLC) and by theoretical calculations using the CLOGP program (log P_CLOGP). The R_Mw and log k'_w values have proven to be reliable parameters for describing the lipophilic properties of this family of compounds.

ACKNOWLEDGMENTS

The authors thank the Consejo de Investigaciones de la Provincia de Córdoba (CONICOR), the Secretaria de Ciencia y Técnica de la Universidad Nacional de Córdoba (SECyT-UNC) and the Consejo Nacional de Investigaciones Científicas y Técnicas (CONICET), Argentina, for financial support. M.I.M. and G.M. acknowledge receipt of a fellowship granted by SECyT-UNC and CONICOR, respectively.