Synthesis, Characterization, and in vitro Photodynamic Activity of Novel Amphiphilic Zinc(II) Phthalocyanines Bearing Oxyethylene-Rich Substituents
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AbstractThree novel zinc(II) phthalocyanines substituted with one or two 3,4,5-tris(3,6,9-trioxadecoxy)benzoxy group(s) have been prepared and spectroscopically characterized. These compounds are highly soluble and remain nonaggregated in �� , �� -dimethylformamide. Upon excitation, they exhibit a relatively weak fluorescence emission and high efficiency to generate singlet oxygen compared with the unsubstituted zinc(II) phthalocyanine. These amphiphilic photosensitizers formulated with Cremophor EL are highly photocytotoxic against HT29 human colon adenocarcinoma and HepG2 human hepatocarcinoma cells. The mono- �� -substituted analogue 4 is particularly potent with I C 5 0 values as low as 0.02  �� M. The higher photodynamic activity of this compound can be attributed to its lower aggregation tendency in the culture media as shown by absorption spectroscopy and higher cellular uptake as suggested by the stronger intracellular fluorescence, resulting in a higher efficiency to generate reactive oxygen species inside the cells.
All Author(s) ListLIU Jian-yong, JIANG Xiong-jie, FONG Wing Ping, NG Kee Pui Dennis
Journal nameMetal-Based Drugs
Year2008
Volume Number2008
PublisherHindawi
Article number284691
ISSN0793-0291
eISSN1687-5486
LanguagesEnglish-United Kingdom
KeywordsPhthalocyanines, Photodynamic Therapy, Photosensitizers

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