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

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• 作者：M. Laine^aAuthor Vitae ; N.A. Barbosa^aAuthor Vitae ; A. Kochel^aAuthor Vitae ; B. Osiecka^bAuthor Vitae ; G. Szewczyk^cAuthor Vitae ; T. Sarna^cAuthor Vitae ; P. Zió ; łkowski^bAuthor Vitae ; R. Wieczorek^aAuthor Vitae ; A. Filarowski^a ; ^d ; ^{aleksander.filarowski@chem.uni.wroc.pl" class="auth_mail" title="E-mail the corresponding author}Author Vitae
• 关键词：BODIPY dye ; Colon cancer SW 480 cell ; DFT ; TD-DFT ; EPR spin-trapping
• 刊名：Sensors & Actuators: B. Chemical
• 出版年：2017
• 出版时间：January 2017
• 年：2017
• 卷：238
• 期：Complete
• 页码：548-555
• 全文大小：1671 K

文摘

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.