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Pentalysine β‐Carbonylphthalocyanine Zinc: An Effective Tumor‐Targeting Photosensitizer for Photodynamic Therapy
Author(s) -
Chen Zhuo,
Zhou Shanyong,
Chen Jincan,
Deng Yicai,
Luo Zhipu,
Chen Hongwei,
Hamblin Michael R.,
Huang Mingdong
Publication year - 2010
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.201000042
Subject(s) - photosensitizer , photodynamic therapy , phototoxicity , singlet oxygen , phthalocyanine , zinc , chemistry , combinatorial chemistry , cationic polymerization , quantum yield , photochemistry , biophysics , in vitro , organic chemistry , oxygen , biochemistry , fluorescence , biology , physics , quantum mechanics
Unsymmetrical phthalocyanine derivatives have been widely studied as photosensitizers for photodynamic therapy (PDT), targeting various tumor types. However, the preparation of unsymmetrical phthalocyanines is always a challenge due to the presence of many possible structural isomers. Herein we report a new unsymmetrical zinc phthalocyanine, pentalysine β‐carbonylphthalocyanine zinc (ZnPc‐(Lys) 5 ), that was prepared in large quantity and high purity. This is a water‐soluble cationic photosensitizer and maintains a high quantum yield of singlet oxygen generation similar to that of unsubstituted zinc phthalocyanine (ZnPc). Compared with anionic ZnPc counterparts, ZnPc‐(Lys) 5 shows a higher level cellular uptake and 20‐fold higher phototoxicity toward tumor cells. Pharmacokinetics and PDT studies of ZnPc‐(Lys) 5 in S180 tumor‐bearing mice showed a high ratio of tumor versus skin retention and significant tumor inhibition. This new molecular framework will allow synthetic diversity in the number of lysine residues incorporated and will facilitate future QSAR studies.