Inosine and 2′-deoxyinosine and their synthetic analogues: lipophilicity in the relation to their retention in reversed-phase liquid chromatography and the stability characteristics

Abstract

The purines and among them inosine synthetic nucleoside derivatives and analogues belong to a group of compounds to which the attention is being paid because of their biological activities. Relationships of their various parameters are being investigated because of their effect on biological (antineoplastic, virostatic, immunosuppressive) properties. Hydrophobicity parameters expressed as the logarithm of the partition coefficient (log P) and the capacity factor k′ for naturally occurring inosine, 2′-deoxyinosine, 2′-deoxyadenosine and 2′-deoxyguanosine and for inosine synthetic analogues 5′-deoxyinosine, 5′-chloro-5′-deoxyinosine and 2′,3′-dideoxyinosine were measured. The effect of methanol percentage in the mobile phase and its pH on the retention of the studied compounds in a reversed-phase system was also examined. There was a good correlation between the lipophilicity expressed as log P and capacity factor k′. It was also determined that dissociation has a marginal effect on capacity factor k′ in this group of nucleoside derivatives as the k′ values were almost unchanged at various pH of the mobile phase used. The stability of the all investigated compounds was investigated in basic, neutral and acidic conditions. The values of the reaction constant k 1 were calculated and effects of nucleoside structural characteristic on stability are discussed.