engleski

New dicationic derivatives of dibenzotetraaza[14]annulene: tuning of the DNA/RNA binding properties

Four new water-soluble derivatives of dibenzotetraaza14]annulene have been synthesized bearing meso substituents different in structure and dimensions: 3-(N, N, N-trimethylammonium)propyl, 3-(N-pyridinium-1-yl)propyl, 2-[3-(N, N, N-trimethylammonium)propoxy]benzoyl and 2-[3-(N-pyridinium-1-yl)propoxy]benzoyl. The crystal structures of 3-(trimethylammonium)propyl and (N, N, N-trimethylammonium)propoxy]benzoyl derivatives have been determined by single crystal X-Ray analysis. According to the UV-Vis titrations, thermal denaturation experiments and ethidium bromide displacements assays all here presented compounds strongly interact with double stranded (ct-) DNA. The product equipped with 3-(trimethylammonium)propyl pendant groups and two positive charges interacts with DNA by one dominant binding mode, whereas other three derivatives revealed more complex mixed-type of non-covalent interactions. The results have been discussed in terms of dimensions, geometry and electronic properties of evaluated compounds on the basis of corresponding crystallographic data.

dibenzotetraaza[14]annulene ; synthesis ; crystal structure ; DNA binding ; UV/Vis titration ; DNA thermal denaturation ; ethidium bromide displacement

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