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Micellar liquid chromatography for lipophilicity determination of new biologically active 1,3-purinodiones

Kawczak, Piotr, Vander Heyden, Yvan, Nasal, Antoni, Bączek, Tomasz, Drabczyñska, Anna, Kieć-Kononowicz, Katarzyna, Kaliszan, Roman
Journal of separation science 2010 v.33 no.11 pp. 1546-1557
1-propanol, adenosine, anticonvulsants, hydrophobicity, liquid chromatography, receptors
A series of newly synthesized 1,3-purinodiones with potential anticonvulsant activity, exhibiting affinity to adenosine A₁ and/or A₂A receptors, were subjected to micellar LC (MLC) with SDS as micelle-forming agent and n-propanol as organic modifier. Two C18 silica-based columns were employed in MLC: a particle one and a monolithic. In parallel, those derivatives were also analyzed in RP-LC on four silica-based columns and on an immobilized artificial membrane column. The correlations between the relevant logarithms of the retention factors of analytes obtained in MLC, immobilized artificial membrane and RP-LC systems on the one hand, and the calculated log P (clog P) and log D values (clog D) on the other, were examined. The level of the correlations of retention data from MLC and RP-LC systems with clog P and clog D obtained is similar but it could be stressed that MLC allows increasing the speed of analysis and using only one mobile phase. Moreover, there is no need of applying an extrapolation procedure in lipophilicity determination. Therefore, the MLC systems, providing chromatographic data in a fast and efficient manner, were demonstrated as promising alternatives to the classical RP-LC systems to estimate the lipophilicity of drugs and drug candidates.