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

The purines and among them inosine synthetic nucleoside derivatives and ana logues belong to a group of compounds to which the attention is being paid because of their biological activities. Relationships of their various para meters are being investigated because of their effect on biological (antine oplastic, virostatic, immunosuppressive) properties. Hydrophobicity paramet ers expressed as the logarithm of the partition coefficient (log P) and the capacity factor k' for naturally occurring inosine, 2'-deoxyinosine, 2'-de oxyadenosine and 2'-deoxyguanosine and for inosine synthetic analogues 5'-d eoxyinosine, 5'-chloro-5'-deoxyinosine and 2',3'-dideoxyinosine were measur ed. 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 exa mined. 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 derivat ives as the k' Values were almost unchanged at various pH of the mobile pha se used. The stability of the all investigated compounds was investigated i n basic, neutral and acidic conditions. The values of the reaction constant k(I) were calculated and effects of nucleoside structural characteristic o n stability are discussed. (C) 2000 Elsevier Science B.V. All rights reserv ed.