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Intramolecular .pi.-.pi. stacking interactions in aqueous solution in mixed-ligand copper (II) complexes formed by heteroaromatic amines and the nucleotide analogue (PME2AP), an isomer of the antivirally active (PMEA)

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    0326309 - ÚOCHB 2010 RIV NL eng J - Journal Article
    Fernández-Botello, A. - Holý, Antonín - Moreno, V. - Operschall, B. P. - Sigel, H.
    Intramolecular .pi.-.pi. stacking interactions in aqueous solution in mixed-ligand copper (II) complexes formed by heteroaromatic amines and the nucleotide analogue (PME2AP), an isomer of the antivirally active (PMEA).
    Inorganica chimica acta. Roč. 362, č. 3 (2009), s. 799-810. ISSN 0020-1693. E-ISSN 1873-3255
    R&D Projects: GA MŠMT 1M0508
    Institutional research plan: CEZ:AV0Z40550506
    Keywords : antiviral activity * intramolecular equilibria * isomeric complexes * phosphonate complexes
    Subject RIV: CC - Organic Chemistry
    Impact factor: 2.322, year: 2009

    Stability constants of the mixed-ligand complexes formed between Cu(Arm)2+, where Arm = 2,20-bipyridine (Bpy) or 1,10-phenanthroline (Phen), and the monoanion or the dianion of 9-[2-(phosphonomethoxy)ethyl]-2-aminopurine (PME2AP) were determined by potentiometric pH titrations in aqueous solution at 25 ºC and I = 0.1M (NaNO3). Speculatively, the reduced stacking intensity, together with a different hydrogen-bonding pattern, could well lead to a different positioning of the 2-aminopurine moiety (compared to the adenine residue) in the active site cavity of nucleic acid polymerases and thus be responsible for the reduced antiviral activity of PME2AP compared with that of PMEA.
    Permanent Link: http://hdl.handle.net/11104/0173450

     
     
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