Naslov
Dicationic derivatives of dinaphtotetraaza[14]annulene: Synthesis, crystal structures and the preliminary evaluation of their DNA binding properties

Autori
Kaźmierska, Alicja ; Gryl, Marlena ; Stadnicka, Katarzyna ; Sieroń, Lesław ; Eilmes, Andrzej ; Matković, Marija ; Radić-Stojković, Marijana ; Piantanida, Ivo ; Eilmes, Julita

Izvornik
Tetrahedron (0040-4020) 71 (2015), 24; 4163-4173

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
dinaphtotetraaza[14]annulene; synthesis; crystal structure; fluorescence; UV-vis spectra; DFT calculation; DNA binding; CD and UV/Vis spectroscopy; DNA thermal denaturation

Sažetak
Four new water-soluble, fluorescent derivatives of dinaphthotetraaza[14]annulene have been synthesized varying in the structure, dimensions and spatial arrangements of their meso side groups: 2-[4-(N, N, N-trimethyloammonium)butoxy]benzoyl, 2-[3-(N-pyridinium-1-yl)propoxy]benzoyl, 2-[4-(N-pyridinium-1-yl)butoxy]benzoyl and 3-(N-pyridinium-1-yl)propyl. The new products have been carefully characterized by elemental analyses and spectroscopy. Quantum-chemical calculations employing DFT methodology were used to study the electronic structure of DNTAA derivatives and differences between their absorption spectra. Crystal structures showed that the new compounds represent molecules with large planar aromatic cores, differing mainly in the exposure of the central π plane to external access. Directional arrangements of the charged side groups and dimensions of the molecules are discussed in terms of their potential intercalative and groove binding abilities. One representative product of a new DNTAA series was tested for DNA binding, revealing ds-DNA intercalation as a dominant binding mode, similarly to previously studied DBTAA analogue. However, at variance to non-fluorescent DBTAA analogues, new DNTAA derivatives show 3-fold fluorescence increase upon DNA binding, and offer intriguing new applications as fluorescence DNA/RNA dyes.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA