DNA Oxidative Cleavage Induced by the Novel Peptide Derivatives of 3-(quinoxalin-6-yl)alanine in Combination with Cu(II) or Fe(II) Ions

Author:

Szczepanik Wojciech1,Kucharczyk-Klamińska Marzena1,Stefanowicz Piotr1,Staszewska Anna2,Szewczuk Zbigniew1,Skała Jacek3,Mysiak Andrzej4,Jeżowska-Bojczuk Małgorzata1

Affiliation:

1. Faculty of Chemistry, University of Wrocław, Joliot-Curie 14, 50-383 Wrocław, Poland

2. Institute of Biochemistry and Biophysics, Polish Academy of Sciences, Pawińskiego 5a, 02-106 Warsaw, Poland

3. Microbiological Institute, University of Wrocław, Przybyszewskiego 63, 51-148 Wrocław, Poland

4. Medical University of Wrocław, Pasteura 4, 50-367 Wrocław, Poland

Abstract

Three model dipeptides containing 3-(2,3-di(pyridin-2-yl)quinoxalin-6-yl)alanine, 3-(dipyrido[3,2-a:2,3-c]phenazin-11-yl)alanine, and 3-(2,3-diphenylquinoxalin-6-yl)alanine were studied with respect to their ability to bind selected transition metal ions, such as Cu(II), Fe(II), Ni(II), Co(II), Mn(II), and Cr(III). It was found that only Cu(II) and Fe(II) ions could form stable complex species with the studied compounds. The ability to form the complexes correlated well with DNA damage experiments. Only the ferrous and cupric complexes are capable of generating both single- and double-strand scissions. However, double-strand breakages appear to be dominating lesions in the presence of hydrogen peroxide, especially for copper(II) containing systems. The quantity of breakage products in the presence ofN-(3-(dipyrido[3,2-a:2,3-c]phenazine-11-yl)alanyl)glycine complexes was the highest as compared to the complexes of the remaining compounds. Moreover, this ligand was the only one that cleaved DNA in the absence of either Cu(II) or Fe(II) ions.

Funder

Polish State Committee for Scientific Research

Publisher

Hindawi Limited

Subject

Inorganic Chemistry,Organic Chemistry,Biochemistry

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