Synthesis and DNA interaction studies of Ni(II), Cu(II) and Co(II) complexes with a polyamine ligand containing homopipe
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ORIGINAL PAPER
Synthesis and DNA interaction studies of Ni(II), Cu(II) and Co(II) complexes with a polyamine ligand containing homopiperazine; X‑ray crystal structure of Cu(II) complex Hassan Keypour1 · Parya Jani1 · Masoumeh Mahmoudabadi1 · Sadegh Salehzadeh1 · Farshid Hajibabaei1 · Saeed Faizi1 · Robert William Gable2 Received: 4 November 2019 / Accepted: 15 June 2020 © Institute of Chemistry, Slovak Academy of Sciences 2020
Abstract Macroayclic complexes of Ni(II), Cu(II) and Co(II) were synthesized via the reaction of 1,4-bis(o-aminobenzyl)-1,4-diazacycloheptane (L) with the respective metal salts. The polyamine ligand and the corresponding complexes were characterized by mass spectrometry, elemental analysis and FT-IR and for [CuL](ClO4)2 (2), by a single crystal X-ray structural analysis which revealed the copper was in a square planar environment. The interaction of the ligand and its complexes with calf thymus DNA (ct-DNA) at pH 7.4 was investigated by UV–Vis, competitive fluorescence spectroscopic methods and dynamic viscosity measurements. These results of these experiments supported intercalative mode of binding. The competitive fluorescence studies in the presence of methylene blue (MB) as an intercalator probe showed that the ligand and its complexes were able to release MB from DNA helix. Viscosity measurements were in good agreement with the results of the competitive fluorescence, indicating that all compounds are intercalating species. Keywords Macrocyclic complexes · Homopiperazine · X-ray structure · DNA interaction · Intercalator
Introduction The polyamines (PAs) are aromatic or aliphatic compounds that contain more than one primary amino groups (–NH2). They are essential to a number of biochemical processes in the human body, in animals and in plants (Rezaeivala and Keypour 2014; Gerner and Meyskens 2004; Cohen 1998; Marton and Pegg 1995). The donor centers of these polyamines are potentially able to coordinate to metal ions or form hydrogen bonds with acceptor molecules. Polyamines have Electronic supplementary material The online version of this article (https://doi.org/10.1007/s11696-020-01253-8) contains supplementary material, which is available to authorized users. * Hassan Keypour [email protected] * Sadegh Salehzadeh [email protected] 1
Faculty of Chemistry, Bu-Ali Sina University, 65174 Hamedan, Iran
School of Chemistry, University of Melbourne, Victoria 3010, Australia
2
been used successfully to obtain macroacyclic and macrocyclic complexes (Jastrzab et al. 2017). Metal complexes have been widely used in medicine for centuries, although their molecular mechanism has not yet been fully understood (Kostova 2006; Ott and Gust 2007). The medicinal properties of metal complexes depend on the nature of the metal ions and the ligands (Arjmand et al. 2012). Interest in the preparation of new macrocyclic and macroacyclic metal complexes has included the study of the interaction of metal complexes with DNA for their potential applications in medicine (Chauhan and Arjmand 2006;
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