Tryptamine-Derived Schiff Bases: Potent Antimicrobial Agents and Evaluation of Cytotoxicity, ADME and DNA Binding Properties.

Autor: Marjanović JS; University of Kragujevac, Faculty of Science, Department of Chemistry, Radoja Domanovica 12, 34 000, Kragujevac, Serbia., Petrović N; University of Kragujevac, Faculty of Science, Department of Biology and Ecology, 34 000, Kragujevac, Serbia., Kosanić M; University of Kragujevac, Faculty of Science, Department of Biology and Ecology, 34 000, Kragujevac, Serbia., Košarić J; University of Kragujevac, Institute for Information Technologies, Jovana, Cvijića, bb 34 000, Kragujevac, Serbia., Mirić A; University of Kragujevac, Institute for Information Technologies, Jovana, Cvijića, bb 34 000, Kragujevac, Serbia., Milivojević N; University of Kragujevac, Institute for Information Technologies, Jovana, Cvijića, bb 34 000, Kragujevac, Serbia., Kostić MD; University of Kragujevac, Institute for Information Technologies, Jovana, Cvijića, bb 34 000, Kragujevac, Serbia., Divac VM; University of Kragujevac, Faculty of Science, Department of Chemistry, Radoja Domanovica 12, 34 000, Kragujevac, Serbia.
Jazyk: angličtina
Zdroj: Chemistry & biodiversity [Chem Biodivers] 2024 Oct 28, pp. e202401699. Date of Electronic Publication: 2024 Oct 28.
DOI: 10.1002/cbdv.202401699
Abstrakt: Inspired by the fact that the introduction of indole pharmacophore in organic scaffolds could enable interesting pharmacological properties, the series of novel tryptamine-derived Schiff bases was synthetized. Tryptamine was used as a source of indole pattern, as well as an example of biogenic amines which chemical transformations lead to the compounds with prominent biological activities. The obtained results for antimicrobial activity against a range of bacterial and fungal strains and cytotoxic activities have revealed that Schiff base TSB4 combining the tryptamine and p-nitro aryl patterns in the structure showed better antifungal activity at low concentrations than standard drug Fluconazole, while compound TSB6 with molecular scaffold composed from tryptamine and quinoline moieties showed certain cytotoxic effect on HCT-116 cell line with a strongly expressed selectivity about healthy fibroblast cells, MRC-5. For these two selected compounds, additional ADME analysis and DNA interactions were performed. to obtain better insight into their pharmacokinetics and determination of binding mode for DNA molecules. As results suggested, strong binding of examined compounds to CT-DNA was observed, while the ADME screening showed that selected compounds possess suitable physicochemical properties for oral bioavailability and druglikeness.
(© 2024 Wiley-VHCA AG, Zurich, Switzerland.)
Databáze: MEDLINE
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