EVALUATION OF THE LIPOPHILICTY OF SELECTED URIDINE DERIVATIVES BY USE OF RP-TLC, SHAKE-FLASK, AND COMPUTATIONAL METHODS

Abstract

The lipophilicity parameters R _Mw of twenty-one uridine derivatives were determined by reverse phase thin layer chromatography (RP-TLC). Experiments were performed on RP-18 F₂₅₄ plates with mixtures of methanol/water as the mobile phases. Amounts of methanol as an organic modifier were in the range 60–85% (v/v) in 5% increments. For nine compounds, logP_exp values were determined by shake-flask method. A good correlation was found between logP_exp and R _Mw (r 0.96). Theoretical logP values for the studied compounds were calculated using nine different algorithms. A correlation matrix was formed to compare the experimental lipophilicity parameters: R _Mw , logP_exp and theoretical logP values. A good agreement between two experimental methods and theoretical logP values was achieved. The best agreement was obtained between AC/logP vs. logP_exp, and R _Mw (r 0.98 and 0.96, respectively).

Keywords:

• calculated partition coefficients
• correlation between experimental & calculated lipophilicity parameters
• lipophilicity
• RP-TLC
• shake-flask method
• uridine

ACKNOWLEDGMENT

Publication partly financed by the European Union within the European Regional Development Fund (POIG. 01.01.02-14-102/09).