Molecular recognition of guanosine and 2-acetylaminofluorene-modified guanosine. A comparative study |
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| Authors: | M Amélia Santos Teresa Ferreira M Alexandra Esteves Michael G Drew Frederick A Beland M Matilde Marques |
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| Institution: | 1. Centro de Química Estrutural, Complexo I, Instituto Superior Técnico , Av. Rovisco Pais, 1096, Lisboa Codex, Portugal;2. Department of Chemistry , University of Reading , Whiteknights, Reading, RG6 2AD, UK;3. Division of Biochemical Toxicology, National Center for Toxicological Research , Jefferson, AR, 72079, USA |
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| Abstract: | 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. |
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| Keywords: | Crystal structures molecular mechanics aza-macrocycles protonations |
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