Fluorescent probes based on side-chain chlorinated benzo[ a ]phenoxazinium chlorides: Studies of interaction with DNA

Abstract

The interaction of DNA with six water soluble benzo[a]phenoxazinium chlorides mono- or di-substituted with 3-chloropropyl groups at the O and N of 2- and 9-positions, along with methyl, hydroxyl and amine terminal groups at 5-positions, was investigated by photophysical techniques. The results indicated that almost all compounds intercalated in DNA base pairs at phosphate to dye ratio higher than 5. At lower values of this ratio, electrostatic binding mode with DNA was observed. Groove binding was detected mainly for the benzo[a]phenoxazinium dye with NH·HBr terminal. The set of six benzo[a]phenoxazinium chlorides proved successful to label the migrating DNA in agarose gel electrophoresis assays. These finding proves the ability of these benzo[a]phenoxazinium dyes to strongly interact with DNA.

Novel Nile Blue Analogue Stains Yeast Vacuolar Membrane, Endoplasmic Reticulum, and Lipid Droplets, Inducing Cell Death through Vacuole Membrane Permeabilization

“…Phenoxazine derivatives are long wavelength fluorescent dyes of great importance as probes since they absorb and emit fluorescence in the 600-900 nm region of the spectrum where there is minimum interference with the biological molecules' autofluorescence [1][2][3][4][5][6]. They have been used in the covalent labeling of amino acids and proteins and in the non-covalent labeling of nucleic acids in various contexts such as blotting experiments, gel electrophoresis, and living cell assays [7][8][9][10][11].…”

New NIR dyes based on quinolizino[1,9-hi]phenoxazin-6-iminium chlorides: synthesis, photophysics and antifungal activity

“…The emerging need of fluorescent probes requires design and strategic synthesis of new fluorescent dyes. Nile Blue (NB) and their derivatives are studied and used as markers due to their fluorescent and solvatochromic characteristics [2][3][4][5][6][7][8][9]. In this context, benzophenoxazinium dyes are structurally compact with high molar extinction coefficients and exhibit strong fluorescence in the near-infrared (NIR) region with high photochemical stability, which indicates the efficacy of these dyes as fluorophores for biological applications [10].…”

“…Keeping in mind the importance and in continuation of our research interest towards the synthesis and applications of benzophenoxazinium salts [2][3][4][5][6][7][8]12,17,18,[35][36][37], we herein report a new series of benzo[a]quinolizino [1,9-hi]phenoxazin-14(5H)-iminium and naphtho [2,3-a]quinolizino [1,9-hi]phenoxazin-14(5H)-iminium chlorides obtained by condensation of nitroso derivative of 8hydroxyjulolidine with naphthalen-1-amine derivatives and anthracen-1-amine, respectively. The introduction of the julolidine nucleous into the polycyclic system is expected to result in maxima absorption and emission wavelengths of fluorophores higher than those obtained from similar unbridged anilines [34].…”

New Nile Blue Derivatives as NIR Fluorescent Probes and Antifungal Agents

“…These probes are an excellent choice to label biological material since its emission will not interfere with the natural fluorescence of biological compounds. Benzo[a]phenoxazinium salts, with Nile Blue being the best known, display fluorescence at around 600 nm and have been used as covalent and non-covalent fluorescent probes for amino acids, proteins and DNA, among other biological material [5][6][7][8][9][10]. In addition, applications as sensors or agents for photodynamic therapy (PDT) have been described [11,12].…”