Evaluation of 4-hydroxy-6-methyl-3-pyridinecarboxylic acid and 2,6-dimethyl-4-hydroxy-3-pyridinecarboxylic acid as chelating agents for iron and aluminium (Articolo in rivista)

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  • Evaluation of 4-hydroxy-6-methyl-3-pyridinecarboxylic acid and 2,6-dimethyl-4-hydroxy-3-pyridinecarboxylic acid as chelating agents for iron and aluminium (Articolo in rivista) (literal)
Anno
  • 2011-01-01T00:00:00+01:00 (literal)
Alternative label
  • Dean A., Ferlin M.G., Brun P., Castagliuolo I., Yokel R.A., Venzo A., Bombi G.G., Di Marco V.B. (2011)
    Evaluation of 4-hydroxy-6-methyl-3-pyridinecarboxylic acid and 2,6-dimethyl-4-hydroxy-3-pyridinecarboxylic acid as chelating agents for iron and aluminium
    in Inorganica Chimica Acta (Testo stamp.)
    (literal)
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  • Dean A., Ferlin M.G., Brun P., Castagliuolo I., Yokel R.A., Venzo A., Bombi G.G., Di Marco V.B. (literal)
Pagina inizio
  • 179 (literal)
Pagina fine
  • 185 (literal)
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  • doi: 10.1016/j.ica.2011.04.009 (literal)
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  • 373 (literal)
Rivista
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  • pubblicazione scientifica (literal)
Note
  • ISI Web of Science (WOS) (literal)
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  • Dipartimento di Scienze Chimiche, Università di Padova, via Marzolo 1, 35131 Padova, Italy Dipartimento di Scienze Farmaceutiche, Università of Padova, via Marzolo 5, 35131 Padova, Italy Dipartimento di Istologia, Microbiologia e Biotecnologie Mediche, via Gabelli 63, 35121 Padova, Italy Pharmaceutical Sciences Department, 511C Multidisciplinary Science Building, University of Kentucky Academic Medical Center, Rose Street, Lexington, KY 40536-0082, USA CNR, Istituto di Scienze e Tecnologie Molecolari, via Marzolo 1, 35131 Padova, Italy (literal)
Titolo
  • Evaluation of 4-hydroxy-6-methyl-3-pyridinecarboxylic acid and 2,6-dimethyl-4-hydroxy-3-pyridinecarboxylic acid as chelating agents for iron and aluminium (literal)
Abstract
  • 4-Hydroxy-6-methyl-3-pyridinecarboxylic acid (DQ6) and the new compound 2,6-dimethyl-4-hydroxy-3-pyridinecarboxylic acid (DQ726) were evaluated for possible application for iron (Fe) and aluminium (Al) chelation therapy. Metal/ligand solution chemistry, cytotoxicity, octanol/water partitioning (Do/w), and chelation efficiency were studied. The solution chemistry of the two ligands with Fe(III) and Al(III) was investigated in aqueous 0.6 m (Na)Cl at 25 ºC by means of potentiometric titrations, UV–Vis spectrophotometry, and 1H NMR spectroscopy. DQ6 exhibited a high coordination efficiency towards Al(III). Fe(III)/DQ6, Al(III)/DQ726, and Fe(III)/DQ726 complexes were less stable. These results were confirmed by chelation efficiency measurements performed in an octanol/aqueous solution. Accordingly, the effects of the substitution at various ring positions of 4-hydroxy-3-pyridinecarboxylic acid were rationalised. Partitioning experiments at pH 7.4 showed both DQ6 and DQ726, and their Fe(III) and Al(III) complexes, to be hydrophilic. The toxicity of DQ6 and of DQ726 was investigated with human cancer cell lines and normal human primary cells: no cytotoxic effects were observed up to 0.1 mM, following a 3 days exposure. According to our results, DQ6 has the favourable properties to be a chelating agent for Al. (literal)
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