Synthesis, structural, spectroscopic, computational and cytotoxic studies of BODIPY dyes

Three 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dyes have been synthesized and investigated by biological, spectroscopic, crystallographic and computational methods. The spectroscopic and structural properties of the dyes have been investigated with UV, steady-state fluorimetry and X-ray m...

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Bibliographic Details
Published in:Sensors and actuators. B, Chemical Chemical, 2017-01, Vol.238, p.548-555
Main Authors: Laine, M., Barbosa, N.A., Kochel, A., Osiecka, B., Szewczyk, G., Sarna, T., Ziółkowski, P., Wieczorek, R., Filarowski, A.
Format: Article
Language:English
Subjects:
Anions
Biological computing
BODIPY dye
Cancer
Chemical synthesis
Colon
Colon cancer SW 480 cell
Colorectal cancer
Computation
Crystallography
Cytotoxicity
DFT
Dyes
Electron paramagnetic resonance
Electron spin
EPR spin-trapping
Fluorimetry
Phosphorescence
Singlet oxygen
Spectroscopy
Spectrum analysis
Synthesis
TD-DFT
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Summary:Three 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dyes have been synthesized and investigated by biological, spectroscopic, crystallographic and computational methods. The spectroscopic and structural properties of the dyes have been investigated with UV, steady-state fluorimetry and X-ray methods. The spectral features have been characterized with respect to DFT and TD-DFT calculations. The cytotoxic and photocytotoxic abilities of the synthesized BODIPYs have been investigated in vitro using colon cancer SW480 cells. The cytotoxic effect of 4,4-difluoro-8-[4-(methoxycarbonyl)-phenyl]-1,3,5,7-tetramethyl-2-formyl-3a,4a-diaza-4-bora-s-indacene (1) after its addition and incubation with the cells has been examined by confocal spectroscopy. The photocytotoxicity of compound 1 has been tested on the colon cancer SW480 cells under varying the light dose and concentration of the added dye. The ability of the synthesized compounds to photogenerate singlet oxygen and superoxide anion has been measured by time-resolved near-infrared phosphorescence and electron paramagnetic resonance (EPR) spin-trapping, respectively.
ISSN:0925-4005
1873-3077
DOI:10.1016/j.snb.2016.07.103