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| Content Provider | World Health Organization (WHO)-Global Index Medicus |
|---|---|
| Author | Jiang, Xiong-jie Lo, Pui-chi Yeung, Sin-lui Ng, Dennis K. P. Tsang, Yee-man Fong, Wing-ping |
| Description | Author Affiliation: Jiang XJ ( Department of Chemistry and Center of Novel Functional Molecules, The Chinese University of Hong Kong, Shatin, N.T., Hong Kong.) |
| Abstract | A series of aryl hydroxyamines prepared by reductive amination were treated with silicon(IV) phthalocyanine dichloride in the presence of pyridine to give the diaxially substituted phthalocyanine–polyamine conjugates 1–5. The electronic absorption, fluorescence emission, and efficiency at generating reactive oxygen species of these compounds were all sensitive to the pH environment. Under acidic conditions, the fluorescence quantum yields and the singlet oxygen quantum yields of these compounds were greatly enhanced in DMF as a result of protonation of the amino moieties, which inhibited the photoinduced electron-transfer deactivation pathway. The Q band was diminished and broadened, and the fluorescence intensity decreased as the pH increased in citrate buffer solutions. The rate of superoxide radical formation was also reduced in a higher pH environment. Compound 3, containing a terminal 4-chlorophenyl group at the axial substituent, showed the most desirable pH-responsive properties, which makes it a promising tumor-selective fluorescence probe and photosensitizer for photodynamic therapy. All of the phthalocyanines 1–5 were highly photocytotoxic against HT29 and HepG2 cells with $IC_{50}$ values as low as 0.03 μM. Compound 3 was highly selective toward lysosomes, but not mitochondria of HT29 cells. |
| ISSN | 09476539 |
| e-ISSN | 15213765 |
| Journal | Chemistry - A European Journal |
| Issue Number | 16 |
| Volume Number | 16 |
| Language | English |
| Publisher | Wiley-VCH;ChemPubSoc Europe |
| Publisher Date | 2010-04-26 |
| Publisher Place | Germany |
| Access Restriction | Open |
| Subject Keyword | Antineoplastic Agents Chemistry Pharmacology HT29 Cells Hep G2 Cells Indoles Photosensitizing Agents Polyamines Silicon Compounds Singlet Oxygen Amination Metabolism Cell Line, Tumor Drug Screening Assays, Antitumor Fluorescence Hydrogen-Ion Concentration Toxicity Lysosomes Mitochondria Molecular Structure Photochemistry Photochemotherapy Spectrometry, Fluorescence Research Support, Non-U.S. Gov't |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |
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