http://www.cnr.it/ontology/cnr/individuo/prodotto/ID48393

Evaluation of 2-methyl-3-hydroxy-4-pyridinecarboxylic acid as a possible chelating agent for iron and aluminium (Articolo in rivista)

Type

Articolo in rivista (Classe)
Prodotto della ricerca (Classe)

Label

Evaluation of 2-methyl-3-hydroxy-4-pyridinecarboxylic acid as a possible chelating agent for iron and aluminium (Articolo in rivista) (literal)

Anno

2008-01-01T00:00:00+01:00 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi

10.1039/b717269a (literal)

Alternative label

1-Dean A., 2-Ferlin M.G., 3-Castagliuolo I., 3-Brun P., 1-Badocco D., 1-Pastore P., 4-Venzo A., 1-Bombi G.G., 1-Di Marco V.B. (2008)
Evaluation of 2-methyl-3-hydroxy-4-pyridinecarboxylic acid as a possible chelating agent for iron and aluminium
in Dalton transactions (2003. Print); The Royal Society of Chemistry, Cambridge (Regno Unito)
(literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori

1-Dean A., 2-Ferlin M.G., 3-Castagliuolo I., 3-Brun P., 1-Badocco D., 1-Pastore P., 4-Venzo A., 1-Bombi G.G., 1-Di Marco V.B. (literal)

Pagina inizio

1689 (literal)

Pagina fine

1697 (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#url

http://www.rsc.org/dalton (literal)

Rivista

Dalton transactions (Rivista)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#pagineTotali

9 (literal)

Note

ISI Web of Science (WOS) (literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni

1-Dipartimento di Scienze Chimiche, Universit `a di Padova, via Marzolo 1, 35131, Padova, Italy 2-Dipartimento di Scienze Farmaceutiche, Universit`a of Padova, via Marzolo 5, 35131, Padova, Italy 3-Dipartimento di Istologia, Microbiologia e Biotecnologie Mediche, via Gabelli 63, 35121, Padova, Italy 4-CNR-ISTM, via Marzolo 1, 35131, Padova, Italy (literal)

Titolo

Evaluation of 2-methyl-3-hydroxy-4-pyridinecarboxylic acid as a possible chelating agent for iron and aluminium (literal)

Abstract

In view of a possible application to Fe and Al chelation therapy, 2-methyl-3-hydroxy-4-pyridinecarboxylic acid (DT2) was synthesised, and its complex formation, electrochemical and cytotoxic properties were studied. The complexing properties of DT2 towards Fe(III) and Al(III) were investigated in aqueous 0.6 m (Na)Cl at 25oC by means of potentiometric titrations, UV-vis spectrophotometry, and 1H NMR spectroscopy. DT2 is a triprotic acid (H3L+) having pKa1=0.47, pKa2=5.64 and pKa3=11.18. The metal-ligand complexes observed in solution and their corresponding stability constants (logß values) are the following: FeLH (19.38), FeL (16.01), FeLH-1 (12.28), FeL2H2 (37.29), FeL3H3 (53.41), FeL3H2 (47.99), FeL3H (41.21) and FeL3 (34.1); AlLH (17.43), AlL2H2 (33.74), AlL2H (27.6), AlL3H3 (48.72), AlL3H2 (42.67), AlL3H (35.8) and AlL3 (27.92). The complex formation between DT2 and Fe(II) was studied by UV-vis: the weak complex FeLH (logß=15.8) was detected. DT2 shows a lower complexation efficiency with Fe(III) and Al(III) than that of other available chelators, but higher than that of its non-methylated analogue 3-hydroxy-4-pyridinecarboxylic acid (DT0). The electrochemical behaviour of DT2 was investigated by means of cyclic voltammetry, indicating that the oxidation of the ligand proceeds through a two electron process with a CECE mechanism. Voltammetric curves suggest that the oxidation or the reduction of DT2 in vivo is unlikely. According to the thermodynamic data, also the Fe(III)-DT2 complexes do not undergo redox cycling at physiological pH. Amperometric titrations of solutions containing Fe(III) and DT2 at pH = 5 indicated the same Fe(III) : ligand stoichiometric ratio as calculated from potentiometric data. The toxicity of DT2 and of other simple hydroxypyridinecarboxylic acids was investigated in vitro and no cytotoxic activity was observed (IC50 > 0.1 mM) on cancer cell lines and also on primary human cells, following a three day exposure. (literal)

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