engleski

The benzothiazine core as a novel motif for DNA-binding small molecules

New series of 4H-1, 3-benzothiazine dyes were prepared and fully characterized in aqueous medium. Benzothiazine salts were synthesized either by classical synthetic pathway using Buchwald-Hartwig amination or the economical and environmentally friendly electrochemical synthesis. The latest synthetic approach employs successful electrochemical intramolecular dehy- drogenative cyclization of N- benzylbenzenecarbothioamides to form 4H-1, 3- benzothiazines. 4H-1, 3-benzothiazines were evaluated as novel DNA/RNA probes. Through the use of several methods such as UV/Vis spectrophotometric titrations, circular dichroism and thermal melting experiments, the binding of 4 benzothiazine based molecules to polynucleotides was examined. Compounds 1 and 2 acted as DNA/RNA groove binders thus suggesting the potential of these compounds as novel DNA/RNA probes. This is a proof of concept study and will be expanded with SAR/QSAR studies included.

4H-1,3-benzothiazines; electrochemical dehydrogenative cyclization; DNA/RNA binding; UV/Vis spectroscopy; circular dichroism

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