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A New bis-3-hydroxy-4-pyrone as a potential therapeutic iron chelating agent: effect of connecting and side chains on the complex structures and metal ion selectivity

Nurchi, Valeria Marina and Crisponi, Guido and Arca, Massimiliano and Crespo Alonso, Miriam and Lachowicz, Joanna Izabela and Mansoori, Delara and Toso, Leonardo and Pichiri, Giuseppina and Santos, M. Amelia and Marques, Sergio M. and Niclós-Gutiérrez, Juan and González Pérez, Josefa M. and Domínguez Martín, Alicia and Choquesillo Lazarte, Duane and Szewczuk, Zbigniew and Zoroddu, Maria Antonietta and Peana, Massimiliano Francesco (2014) A New bis-3-hydroxy-4-pyrone as a potential therapeutic iron chelating agent: effect of connecting and side chains on the complex structures and metal ion selectivity. Journal of inorganic biochemistry, Vol. 141 , p. 132-143. ISSN 0162-0134. eISSN 1873-3344. Article.

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DOI: 10.1016/j.jinorgbio.2014.09.002

Abstract

This work reports the synthesis, characterization and study of complex formation equilibria of the new ligand 6,6′-(2-(diethylamino)ethylazanediyl)bis(methylene)bis(5-hydroxy-2-hydroxymethyl-4H-pyran-4-one) with FeIII, AlIII, CuII and ZnII. On the basis of previous encouraging results with tetradentate bis-kojic acid chelators, this ligand was designed to improve the pharmacokinetic properties: increase the solubility, neutral at physiological pH 7.4, and enhancement of membrane crossing ability. FeIII and AlIII complexation gave evidence of high metal-sequestering capacity of L9. Cellular assays showed that the ligand is capable of crossing cellular membranes and it does not present toxic effects. Complex formation equilibria with the essential metal ions CuII and ZnII have been furthermore studied to evaluate disturbances of this chelator on the homeostatic equilibria of these essential metal ions. A variety of techniques (potentiometry, UV–visible spectrophotometry, 1D and 2D NMR spectroscopy, ESI–MS (electrospray ionization–mass spectrometry), quantum mechanical calculations and X-ray diffraction) have facilitated the characterization of the ligand, and the corresponding iron and zinc complexes, together with an exhaustive analysis of the protonation and complex equilibria.

Item Type:Article
ID Code:10643
Status:Published
Refereed:Yes
Subjects:Area 03 - Scienze chimiche > CHIM/03 Chimica generale e inorganica
Divisions:001 Università di Sassari > 01-a Nuovi Dipartimenti dal 2012 > Chimica e Farmacia
Publisher:Elsevier
ISSN:0162-0134
eISSN:1873-3344
Additional Information:X-ray structures, iron chelators, complex formation, equilibria, speciation, NMR
Deposited On:19 Jan 2015 15:14

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