New N4-Donor Ligands as Supramolecular Guests for DNA and RNA: Synthesis, Structural Characterization, In Silico, Spectrophotometric and Antimicrobial Studies
New N4-Donor Ligands as Supramolecular Guests for DNA and RNA: Synthesis, Structural Characterization, In Silico, Spectrophotometric and Antimicrobial Studies(126 views) Ewert E, Pospieszna-markiewicz I, Szymańska M, Kurkiewicz A, Belter A, Kubicki M, Patroniak V, Fik-jaskółka MA, Roviello GN
1 Faculty of Chemistry, Adam Mickiewicz University in Pozna ´n, Uniwersytetu Pozna ´nskiego 8,61-614 Pozna ´n, Poland2Institute of Bioorganic Chemistry, Polish Academy of Science, Noskowskiego 12/14, 61-704 Pozna ´n, Poland3Institute of Biostructures and Bioimaging, Italian National Council for Research (IBB-CNR), Area di Ricercasite and Headquarters, Via Pietro Castellino 111, 80131 Naples, Italy* Correspondence: martafik@amu.edu.pl (M.A.F.-J.); giroviel@unina.it (G.N.R.)
References: Not available.
New N4-Donor Ligands as Supramolecular Guests for DNA and RNA: Synthesis, Structural Characterization, In Silico, Spectrophotometric and Antimicrobial Studies
The present work reports the synthesis of new N4-donor compounds carrying p-xylyl
spacers in their structure. Different Schiff base aliphatic N-donors were obtained synthetically and
subsequently evaluated for their ability to interact with two models of nucleic acids: calf-thymus
DNA (CT-DNA) and the RNA from yeast Saccharomyces cerevisiae (herein simply indicated as
RNA). In more detail, by condensing p-xylylenediamine and a series of aldehydes, we obtained
the following Schiff base ligands: 2-thiazolecarboxaldehyde (L1), pyridine-2-carboxaldehyde (L2),
5-methylisoxazole-3-carboxaldehyde (L3), 1-methyl-2-imidazolecarboxaldehyde (L4), and quinoline2-carboxaldehyde (L5). The structural characterisation of the ligands L1-L5 (X-ray, 1H NMR, 13C
NMR, elemental analysis) and of the coordination polymers {[CuL1]PF6}n (herein referred to as
Polymer1) and {[AgL1]BF4}n, (herein referred to as Polymer2, X-ray, 1H NMR, ESI-MS) is herein
described in detail. The single crystal X-ray structures of complexes Polymer1 and Polymer2 were
also investigated, leading to the description of one-dimensional coordination polymers. The spectroscopic and in silico evaluation of the most promising compounds as DNA and RNA binders, as
well as the study of the influence of the 1D supramolecular polymers Polymer1 and Polymer2 on the
proliferation of Escherichia coli bacteria, were performed in view of their nucleic acid-modulating and
antimicrobial applications. Spectroscopic measurements (UV–Vis) combined with molecular docking
calculations suggest that the thiazolecarboxaldehyde derivative L1 is able to bind CT-DNA with a
mechanism different from intercalation involving the thiazole ring in the molecular recognition and
shows a binding affinity with DNA higher than RNA. Finally, Polymer2 was shown to slow down
the proliferation of bacteria much more effectively than the free Ag(I) salt.
New N4-Donor Ligands as Supramolecular Guests for DNA and RNA: Synthesis, Structural Characterization, In Silico, Spectrophotometric and Antimicrobial Studies
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New N4-Donor Ligands as Supramolecular Guests for DNA and RNA: Synthesis, Structural Characterization, In Silico, Spectrophotometric and Antimicrobial Studies