Synthesis, spectroscopic, and in vitro investigations of 2,6-diiodo-BODIPYs with PDT and bioimaging applications.
Synthesis, spectroscopic, and in vitro investigations of 2,6-diiodo-BODIPYs with PDT and bioimaging applications.
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DOI：
10.1016/j.jphotobiol.2015.02.006
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发表时间：
2015-04
影响因子：
5.4
通讯作者：
Vicente, M. Graca H.
中科院分区：
文献类型：
--
作者：
Gibbs, Jaime H.;Zhou, Zehua;Kessel, David;Fronczek, Frank R.;Pakhomova, Svetlana;Vicente, M. Graca H.
利用Knoevenagel缩合反应合成了一系列含吲哚基、吡咯基、噻吩基和三（乙二醇）苯基的5个单苯乙烯基和它们相应的对称二苯乙烯基-2，6-二碘-BODIPY。使用微波辐射（90 °C，在400 W下1小时），缩合反应的产率提高至40%，这是由于长时间加热时BODIPY的分解较低。研究了BODIPY的光谱、结构（包括二苯乙烯基-2，6-二碘-BODOPY的X射线）和体外性质。通过已知的光毒性2，6-二碘-BODIPY 1的3，5-二甲基的π-缀合的延伸在吸收和发射光谱中产生红移，对于DMSO中的单苯乙烯基-BODIPY为59-125 nm，对于二苯乙烯基-BODIPY为126-220 nm。最大的红移被观察到的吲哚含BODIPY，而最大的荧光量子产率被观察到的三（乙二醇）苯基苯乙烯基-BODIPY。在这一系列中，只有单苯乙烯基-BODIPY具有光毒性（在1.5 J/cm 2下IC 50 = 2-15 µM），并且观察到优先定位于细胞ER和线粒体中。另一方面，发现二苯乙烯基-BODIPY具有低或无光毒性（在1.5 J/cm 2下，IC 50> 100 µM）。在这一系列化合物中，BODIPY 2a显示出最有希望作为PDT中的光敏剂应用。
A series of five mono-styryl and their corresponding symmetric di-styryl-2,6-diiodo-BODIPYs containing indolyl, pyrrolyl, thienyl or tri(ethylene glycol)phenyl groups were synthesized using Knoevenagel condensations. The yields for the condensation reactions were improved up to 40% using microwave irradiation (90 °C for 1 h at 400 W) due to lower decomposition of BODIPYs upon prolonged heating. The spectroscopic, structural (including the X-ray of a di-styryl-2,6-diiodo-BODOPY) and in vitro properties of the BODIPYs were investigated. The extension of π-conjugation through the 3,5-dimethyls of the known phototoxic 2,6-diiodo-BODIPY 1 produced bathochromic shifts in the absorption and emission spectra, in the order of 59–125 nm for the mono-styryl- and 126–220 nm for the di-styryl-BODIPYs in DMSO. The largest red-shifts were observed for the indolyl-containing BODIPYs while the largest fluorescence quantum yields were observed for the tri(ethyleneglycol)phenylstyryl-BODIPYs. Among this series, only the mono-styryl-BODIPYs were phototoxic (IC50 = 2–15 µM at 1.5 J/cm2), and were observed to localize preferentially in the cell ER and mitochondria. On the other hand, the di-styryl-BODIPYs were found to have low or no phototoxicity (IC50 > 100 µM at 1.5 J/cm2). Among this series of compounds BODIPY 2a shows the most promise for application as photosensitizer in PDT.
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影响因子：
46.2
作者：
Kamkaew A;Lim SH;Lee HB;Kiew LV;Chung LY;Burgess K
通讯作者：
Burgess K
影响因子：
4.9
作者：
Atilgan, Serdar;Ekmekci, Zeynep;Akkaya, Engin U.
通讯作者：
Akkaya, Engin U.
影响因子：
7.3
作者：
He, Hui;Lo, Pui-Chi;Ng, Dennis K. P.
通讯作者：
Ng, Dennis K. P.
影响因子：
1.5
作者：
Kessel, D
通讯作者：
Kessel, D
影响因子：
3.5
作者：
Gibbs JH;Robins LT;Zhou Z;Bobadova-Parvanova P;Cottam M;McCandless GT;Fronczek FR;Vicente MG
通讯作者：
Vicente MG