Molecular recognition of guanosine and 2-acetylaminofluorene-modified guanosine. A comparative study

Abstract The ability of an abiotic receptor, 7-acetylamino-2-methyl–1,8-naphthyridine, to bind to guanosine was analysed by a combination of NMR determinations and molecular modeling studies. The results indicate that this receptor simulates the base-pairing properties of cytidine in its Watson-Crick interaction with guanosine. Binding of the same receptor to N-(guanosin-8-yl)-2-acetylaminofluorene, the guanosine adduct containing the carcinogen 2-acetylaminofluorene, was found to occur in a similar manner. The calculated binding energies show that the molecular recognition of the adduct is lower than that of the unmodified guanosine. The theoretical studies suggest that the predominance of an abnormal low energy syn conformation for the adduct is the main structural feature accounting for the observed decrease of the host-guest interaction.