Spectroscopic, computational modeling and cytotoxicity of a series of meso-phenyl and meso-thienyl-BODIPYs.
Spectroscopic, computational modeling and cytotoxicity of a series of meso-phenyl and meso-thienyl-BODIPYs.
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DOI：
10.1016/j.bmc.2013.07.017
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发表时间：
2013-09-15
影响因子：
3.5
通讯作者：
Vicente MG
中科院分区：
文献类型：
--
作者：
Gibbs JH;Robins LT;Zhou Z;Bobadova-Parvanova P;Cottam M;McCandless GT;Fronczek FR;Vicente MG
合成了一系列22个BODIPY化合物，含有不同的meso-苯基和meso-噻吩基基团，并使用实验和计算方法研究了它们的光谱和结构性质。探索了通过在2，6-吡咯位置处的碘化的BODIPY框架的进一步官能化，以确定这些重原子对内消旋-芳基-BODIPY的生物物理学和细胞毒性的影响。带有meso-噻吩基取代基的BODIPY显示出最大的红移吸收和发射以及降低的荧光量子产率。BODIPY在人癌HEp 2细胞中的光毒性取决于碘的存在和内消旋芳基的性质。与非碘化BODIPY相比，研究的11种2，6-二碘-BODIPY中有6种显示出至少7倍的光毒性增强（IC 50 = 3.5-28 μM，1.5 J/cm 2），而其他化合物没有显示出细胞毒性，而它们的单线态氧量子产率范围为0.02至0.76。在所研究的系列中，具有供电子meso-二甲氧基苯基取代基的BODIPY 2a和4a显示出最高的光毒性和暗/光毒性比，因此最有希望用于PDT。
A series of twenty-two BODIPY compounds were synthesized, containing various meso-phenyl and meso-thienyl groups, and their spectroscopic and structural properties were investigated using both experimental and computational methods. Further functionalization of the BODIPY framework via iodination at the 2,6-pyrrolic positions was explored in order to determine the effect of these heavy atoms on the photophysical and cytotoxicity of the meso-aryl-BODIPYs. BODIPYs bearing meso-thienyl substituents showed the largest red-shifted absorptions and emissions and reduced fluorescence quantum yields. The phototoxicity of the BODIPYs in human carcinoma HEp2 cells depends on both the presence of iodines and the nature of the meso-aryl groups. Six of the eleven 2,6-diiodo-BODIPYs investigated showed at least a sevenfold enhancement in phototoxicity (IC50 = 3.5–28 μM at 1.5 J/cm2) compared with the non-iodinated BODIPYs, while the others showed no cytotoxicity, while their singlet oxygen quantum yields ranged from 0.02 to 0.76. Among the series investigated, BODIPYs 2a and 4a bearing electron-donating meso-dimethoxyphenyl substituents showed the highest phototoxicity and dark/phototoxicity ratio, and are therefore the most promising for application in PDT.
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