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    Carbazole substituted BODIPY dyes: Synthesis, photophysical properties and antitumor activity
    (Elsevier Sci Ltd, 2015) Şengül, İbrahim Fazıl; Okutan, Elif; Kandemir, Hakan; Astarcı, Erhan; Çoşut, Bünyemin
    In this study, two different BODIPYs containing carbazole groups at the mesa position were designed and synthesized. All compounds were fully characterized by elemental analysis, FT-IR, matrix-assisted laser desorption/ionization time-of-flight mass spectrometry, H-1 and C-13 NMR spectroscopy. The photophysical properties of the new compounds were investigated by means of absorption and fluorescence spectroscopies in dilute dichloromethane solutions. We were also interested in the biological activity of these two novel carbazole-linked BODIPYs, particularly concerning their ability to inhibit human colon cancer HT29 cell lines. The photophysical studies revealed strong donor acceptor interaction between carbazole and BODIPY and follow the order compound 5 > compound 4. Also, preliminary assay showed that compound 5 possessed higher cytotoxic activity than compound 4, with IC50 values of 8.3 ng/mL and 21.7 ng/mL respectively. (C) 2015 Elsevier Ltd. All rights reserved.
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    Naked-eye fluorescent sensor for Cu(II) based on indole conjugate BODIPY dye
    (Pergamon-Elsevier Science Ltd, 2016) Oğuz Tümay, Süreyya; Okutan, Elif; Şengül, İbrahim Fazıl; Özcan, Emrah; Kandemir, Hakan; Doruk, Tuğrul; Çoşut, Bünyemin
    A novel on/off fluorescent indole/BODIPY-based Cu2+ chemosensor (3) was synthesized by Knoevenagel condensation of BODIPY derivative 1 with 2-methyl-indole-3-carbaldehyde 2. The identity of compound 3 was confirmed by H-1 NMR, C-13 NMR, FT-IR, matrix-assisted laser desorption/ionization time-of-flight mass spectrometry and single crystal X-ray diffraction techniques. Fluorescent chemosensor (3) is found to be highly selective and sensitive for detection of Cu2+ with a color change from purple to yellow. The optical sensor features for the Cu2+ complex of 3 were investigated by UV-Vis and fluorescence spectroscopy. The addition of Cu2+ caused quenching of fluorescence intensity and the detection limit was calculated to be 0.124 mu M. Also, the stoichiometry ratio of 3+Cu2+ was obtained 2:1 by Job's plot. Live cell image, flow cytometry and cytotoxic properties of compound 3 were examined. (C) 2016 Elsevier Ltd. All rights reserved.