Hydrophobicity parameters of 2-chloro-2′-deoxyadenosine and some related analogues and retention in reversed-phase liquid chromatography

Abstract

Hydrophobicity parameters expressed as the logarithm of the partition coefficient (log P) and ionization constants (p K a) for 2-chloro-2′-deoxyadenosine and some related nucleoside analogues (2-fluoroarabinosyladenine, 2-chloroadenosine and 5′-chloro-5′-deoxyadenosine) are reported. The effects of methanol concentration and the pH of the mobile phase on the retention of the studied compounds in a reversed-phase system were examined. The relationship between hydrophobicity parameters and the retention in the HPLC system was investigated. A fairly good linear correlation was obtained when log k′ values ( r = 0.960) and/or log k′ w values (extrapolated from the relationship between log k′ and the percentage of methanol to 100% water) ( r = 0.959 and 0.967, respectively) were correlated with log P values.