Synthesis and in vitro photodynamic activity of mono-substituted amphiphilic zinc(II) phthalocyanines.
A series of novel zinc(II) phthalocyanines mono-substituted with a 1,3-bis(dimethylamino)-2-propoxy group at the alpha- or beta-position, and the corresponding di-N-methylated derivatives, have been synthesized. All these compounds can generate singlet oxygen effectively and exhibit high in vitro photodynamic activities toward HT29 human colorectal carcinoma cells with IC(50) values down to 0.08microM. The dicationic derivatives have a higher affinity to the cell membrane compared with the non-ionic counterparts.
Lo
Pui-Chi
PC
Department of Chemistry and Center of Novel Functional Molecules, The Chinese University of Hong Kong, Shatin, NT, Hong Kong, China.
Zhao
Baozhong
B
Duan
Wubiao
W
Fong
Wing-Ping
WP
Ko
Wing-Hung
WH
Ng
Dennis K P
DK
D002462:Cell Membrane / Q000187:drug effects / Q000378:metabolism; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D019073:HT29 Cells; D006801:Humans; D007202:Indicators and Reagents; D008856:Microscopy, Fluorescence; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000494:pharmacology*; D010778:Photochemotherapy; D017319:Photosensitizing Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D013050:Spectrometry, Fluorescence; D015032:Zinc / Q000494:pharmacology*
D007202:Indicators and Reagents; D009942:Organometallic Compounds; D017319:Photosensitizing Agents; D015032:Zinc