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    Effect of electron donors on the photophysical and theoretical properties of BODIPY dyes based on tetrazolo[1,5-a]quinoline
    (Elsevier, 2022) Arslan, Baris Seckin; Derin, Yavuz; Misir, Bursa Albayrak; Kaya, Savas; Sisman, Ilkay; Tutar, Ahmet; Nebioglu, Mehmet
    Novel tetrazolo[1,5-a] quinoline-based BODIPY dyes ( 6b-d ) were synthesized and characterized by photo -physical and theoretical methods. Except for 6c , fluorescence quantum yield of the dyes increased paral-lelly with the solvent viscosity due to hindrance of free rotation at meso position. Fluorescence quantum yield of 6c is higher than 6d , although the number of electron-donating groups of the former is less than that of the latter. The fluorophores exhibited apparent responses in the fluorescence intensities with increasing water ratio in ethanol owing to their aggregation-induced emission (AIE) characteristics. In a separate study, NBO analysis and DFT calculations were also performed for dyes 6a-d . Various quantum chemical parameters from frontier orbital energies to polarizability were calculated and discussed in de-tail. The theoretical calculations showed that compound 6d is the most stable. These results demonstrate that tetrazolo[1,5-a] quinoline-based fluorophores would have potential application in water detection systems.(c) 2022 Elsevier B.V. All rights reserved.
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    Novel diarylated tacrine derivatives: Synthesis, characterization, anticancer, antiepileptic, antibacterial, and antifungal activities
    (Wiley, 2024) Misir, Busra A.; Derin, Yavuz; Okten, Salih; Aydin, Ali; Kocyigit, Umit M.; Sahin, Hatice; Tutar, Ahmet
    In this study, our goal was to synthesize novel aryl tacrine derivatives and assess their potential as anticancer, antibacterial agents, and enzyme inhibitors. We adopted a two-step approach, initiating with the synthesis of dibromotacrine derivatives 3 and 4 through the Friedlander reaction. These intermediates underwent further transformation into diarylated tacrine derivatives 3a-e and 4a-e using a Suzuki-Miyaura cross-coupling reaction. Thorough characterization of these novel diarylated tacrines was achieved using various spectroscopic techniques. Our findings highlighted the potent anticancer effects of these innovative compounds across a range of cancer cell lines, including lung, gynecologic, bone, colon, and breast cancers, while demonstrating low cytotoxicity against normal cells. Notably, these compounds surpassed the control drug, 5-Fluorouracil, in terms of antiproliferative activity in numerous cancer cell lines. Moreover, our investigation included an analysis of the inhibitory properties of these novel compounds against various microorganisms and cytosolic carbonic anhydrase enzymes. The results suggest their potential for further exploration as cancer-specific, enzyme inhibitory, and antibacterial therapeutic agents. Notably, four compounds, namely, 5,7-bis(4-(methylthio)phenyl)tacrine (3d), 5,7-bis(4-(trifluoromethoxy)phenyl)tacrine (3e), 2,4-bis(4-(trifluoromethoxy)phenyl)-7,8,9,10-tetrahydro-6H-cyclohepta[b]quinolin-11-amine (4e), and 6,8-dibromotacrine (3), emerged as the most promising candidates for preclinical studies. The novel aryl substituted tacrine were efficiently synthesized and their anticancer potentials were highlighted in this study. Their inducing apoptosis, cell migration, and mitochondrial membrane potentials were screened. image