Characterization of Copper(II) Interactions with Sinefungin, a Nucleoside Antibiotic: Combined Potentiometric, Spectroscopic and DFT Studies

Jaworska, Maria; Lodowski, Piotr; Mucha, Ariel; Szczepanik, Wojciech; Valensin, Gianni; Cappannelli, Massimo; Jezowska-Bojczuk, Malgorzata

doi:https://doi.org/10.1155/2007/53521

Bioinorganic Chemistry and Applications

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Research Article | Open Access

Volume 2007 | Article ID 053521 | https://doi.org/10.1155/2007/53521

Characterization of Copper(II) Interactions with Sinefungin, a Nucleoside Antibiotic: Combined Potentiometric, Spectroscopic and DFT Studies

Maria Jaworska,¹Piotr Lodowski,¹Ariel Mucha,²Wojciech Szczepanik,²Gianni Valensin,³Massimo Cappannelli,³and Malgorzata Jezowska-Bojczuk²

Academic Editor: Imre Sóvágó

Received11 Oct 2007

Accepted09 Nov 2007

Published13 Dec 2007

Abstract

Interactions between sinefungin and copper(II) ions were investigated. Stoichiometry and stability constants of the metal-free system and two mononuclear complexes present in solution were determined on the basis of potentiometric data analysis. The results were compared to the Cu(II)-ornithine system due to structural similarities between both molecules. Combined spectroscopic and theoretical studies allowed for determination of coordination pattern for the Cu(II)-sinefungin complexes. At acidic pH, copper is bound in “glycine-like” coordination mode, identical with that of ornithine. This involves α-amino group and the carboxyl oxygen. At higher pH, a “bis-complex” is formed by two sinefungin molecules. The second ligand binds in equatorial position displacing two water molecules, what results in the stable {2N,2O} coordination. Both axial positions are supposed to be occupied by N1 nitrogen donors of adenine moiety, what is confirmed by DFT calculations. They interact indirectly with copper(II) through water molecules as the result of dominant syn conformation of purine.

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Copyright © 2007 Maria Jaworska et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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