Abstract：
: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/cm(2)) 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.
journal_name
Bioorg Med Chemjournal_title
Bioorganic & medicinal chemistryauthors
Gibbs JH,Robins LT,Zhou Z,Bobadova-Parvanova P,Cottam M,McCandless GT,Fronczek FR,Vicente MGdoi
10.1016/j.bmc.2013.07.017subject
Has Abstractpub_date
2013-09-15 00:00:00pages
5770-81issue
18eissn
0968-0896issn
1464-3391pii
S0968-0896(13)00628-7journal_volume
21pub_type
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