Imidazopyridinium cations: A new family of azonia aromatic heterocycles with applications as DNA intercalators. (March 2017)

• Record Type: Journal Article
• Authors: Bosch, Pedro; García, Verónica; Bilen, Başak S.; Sucunza, David; Domingo, Alberto; Mendicuti, Francisco; Vaquero, Juan J.
• Is Part Of: Dyes and pigments. Volume 138(2017)
• Page Start: 135
• Page End: 146
• Publication Date: 2017-03
• Subjects: Imidazopyridinium cations -- Azonia aromatic heterocycles -- DNA intercalation -- Cell staining; Dyes and dyeing -- Periodicals; Pigments -- Periodicals; 667.2
• DOI: 10.1016/j.dyepig.2016.11.041
• Languages: English
• ISSNs: 0143-7208

Abstract

Abstract: Two novel imidazopyridinium cations formed by a hexacyclic azonia aromatic system have been synthesized. Spectrofluorimetric titrations, circular dichroism measurements, theoretical simulations and fluorescence-based thermal denaturation experiments on these materials have shown the interesting fluorescence properties and DNA-binding ability by intercalation, with a marked preference for AT-rich sequences. Compound2 presents the highest fluorescence quantum yield (0.32 in 5% DMSO/water and 0.46 in MeOH) and affinity for DNA (binding constant of ∼4.5 × 10 5 M −1 ). Moreover, the potential of these compounds for cell staining has been investigated in living HeLa cells by confocal microscopy imaging. This analysis showed the remarkable capacity of both compounds for uptake and accumulation by living cells. Graphical abstract: