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

Mlakić, Milena; Čipor, Ivona; Kovačec, Petra; Kragol, Goran; Ratković, Ana; Kovačević, Tatjana; Zadravec, Rahela; Milašinović, Valentina; Molčanov, Krešimir; Piantanida, Ivo; Škorić, Irena (2023) The benzothiazine core as a novel motif for DNA-binding small molecules. Molecules, 28 . ISSN 1420-3049

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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.

Item Type: Article
Uncontrolled Keywords: 4H-1 ; 3-benzothiazines ; electrochemical dehydrogenative cyclization, DNA/RNA binding ; UV/Vis spectroscopy ; circular dichroism
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Division of Organic Chemistry and Biochemistry
Division of Physical Chemistry
Project titleProject leaderProject codeProject type
Višekromoforne probe za prepoznavanje pojedinih struktura DNA, RNA i proteinaPiantanida, IvoIP-2018-01-5475HRZZ
Depositing User: Krešimir Molčanov
Date Deposited: 06 Jul 2023 11:50
DOI: 10.3390/molecules28114499

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