Preparation and Photodynamic Activities of Silicon(IV) Phthalocyanines Substituted with Permethylated beta-Cyclodextrins
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摘要A series of silicon(IV) phthalocyanines linked to two permethylated beta-cyclodextrin moieties through different spacers at the axial positions have been synthesized and characterized. The effects of these spacers on the photophysical properties and in vitro photodynamic activities have also been examined. Having two bulky hydrophilic substituents, all of these compounds are soluble and essentially non-aggregated in DMF and even in aqueous media. The fluorescence and singlet oxygen quantum yields in DMF are lower for the analogue with the shortest separation between the amino group in the spacer and the phthalocyanine ring. The fluorescence quantum yield of this compound increases in water probably due to protonation of the amino group, which inhibits the reductive quenching process. This series of compounds also exhibit pho-tocytotoxicity toward HT29 human colon adenocarcinoma and HepG2 human hepatocarcinoma cells with IC50 values in the range of 0.04-1.32 mu M. The analogue with an alpha,omega-aminohydroxypentyl linker shows the highest potency, which can be ascribed to its high cellular uptake and high efficiency in generating intracellular reactive oxygen species. This compound also shows preferential localization in the lysosome, induces cell death mainly through apoptosis, and inhibits the growth of tumor in vivo. The results suggest that it is a promising photosensitizer for photodynamic therapy.
著者Lau JTF, Lo PC, Fong WP, Ng DKP
期刊名稱Chemistry - A European Journal
出版年份2011
月份6
日期1
卷號17
期次27
出版社WILEY-V C H VERLAG GMBH
頁次7569 - 7577
國際標準期刊號0947-6539
電子國際標準期刊號1521-3765
語言英式英語
關鍵詞antitumor agents; cyclodextrins; photodynamic therapy; photosensitizers; phthalocyanines
Web of Science 學科類別Chemistry; Chemistry, Multidisciplinary; CHEMISTRY, MULTIDISCIPLINARY

上次更新時間 2020-21-10 於 00:33