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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Abstract
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 | ||||||||
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| 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 |
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| Depositing User: | Krešimir Molčanov | ||||||||
| Date Deposited: | 06 Jul 2023 11:50 | ||||||||
| URI: | http://fulir.irb.hr/id/eprint/8107 | ||||||||
| DOI: | 10.3390/molecules28114499 |
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