Lipophilicity of 5′‐Carbonates of Lamivudine with Antiretroviral Activity. Correlation Between Different Methods

Abstract

This study reports on the lipophilicity of novel 5′‐carbonates of lamivudine with anti‐HIV activity. Reversed‐phase thin layer chromatography (RP‐TLC), reversed‐phase high performance liquid chromatography (RP‐HPLC), conventional shake flask (log P_oct), and the theoretical CLOGP methods were used, in order to establish if the linear relationships between the conventional and chromatographic methods permit an extrapolation procedure. The nature of the organic modifiers used in the chromatographic techniques did not substantially affect the measurement of lipophilicity, since a good correlation between experimental log P_oct and extrapolated RP‐TLC and RP‐HPLC values (R_Mw and log k′_w, respectively) supported the validity of the extrapolation technique.

Keywords:

• Lipophilicity
• 5′‐Carbonates of lamivudine
• RP‐TLC
• RP‐HPLC
• log P_oct
• CLOGP

Acknowledgments

The authors gratefully acknowledge FONCYT, the Secretaría de Ciencia y Técnica de la Universidad Nacional de Córdoba (SECYT‐UNC) and the Consejo Nacional de Investigaciones Científicas y Tecnológicas (CONICET) of Argentina for financial support. The authors also wish to express their sincere thanks to L. Alassia (FILAXIS Laboratories, Buenos Aires, Argentina) for supplying lamivudine. S.R. acknowledges receipt of a fellowship granted by SECyT‐UNC.