| Highly photocytotoxic glucosylated silicon(IV) phthalocyanines. Effects of peripheral chloro substitution on the photophysical and photodynamic properties. | |
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MedLine Citation:
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PMID: 17394299 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Two novel glucoconjugated silicon(IV) phthalocyanines (compounds 3 and 4) have been prepared and examined for their photophysical and biological properties. With two axial 1,2:5,6-di-O-isopropylidene-alpha-d-glucofuranose substituents linked to the silicon center through the tetraethylene glycol chain, both compounds are highly soluble and remain nonaggregated in N,N-dimethylformamide. The dichloro-substituted phthalocyanine 4 exhibits a weaker fluorescence emission and higher efficiency to generate singlet oxygen compared with the nonchlorinated counterpart 3 as a result of the heavy atom effect. Both compounds are highly photocytotoxic against HT29 human colorectal carcinoma and HepG2 human hepatocarcinoma cells, particularly the nonchlorinated phthalocyanine 3, of which the IC50 values are as low as 6 nM. The lower photodynamic activity of the chlorinated derivative (IC50 = 17-21 nM) can be attributed to its higher aggregation tendency in the biological media, leading to a lower efficiency to generate reactive oxygen species inside the cells. Fluorescence microscopic studies have also revealed that compound 3 has a high and selective affinity to the lysosomes, but not the mitochondria, of HT29 cells. |
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Authors:
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Pui-Chi Lo; Crystal M H Chan; Jian-Yong Liu; Wing-Ping Fong; Dennis K P Ng |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't Date: 2007-03-30 |
Journal Detail:
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Title: Journal of medicinal chemistry Volume: 50 ISSN: 0022-2623 ISO Abbreviation: J. Med. Chem. Publication Date: 2007 May |
Date Detail:
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Created Date: 2007-04-26 Completed Date: 2007-06-26 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 9716531 Medline TA: J Med Chem Country: United States |
Other Details:
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Languages: eng Pagination: 2100-7 Citation Subset: IM |
Affiliation:
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Department of Chemistry, Department of Biochemistry, and Center of Novel Functional Molecules, The Chinese University of Hong Kong, Shatin, N.T., Hong Kong, China. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Antineoplastic Agents
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chemical synthesis*,
chemistry,
pharmacology Cell Line, Tumor Chlorine* Drug Screening Assays, Antitumor Glycosides / chemical synthesis*, chemistry, pharmacology Humans Indoles / chemical synthesis*, pharmacology Lysosomes / metabolism Mitochondria / metabolism Organosilicon Compounds / chemical synthesis*, chemistry, pharmacology Photosensitizing Agents / chemical synthesis*, chemistry, pharmacology Singlet Oxygen / metabolism Structure-Activity Relationship |
| Chemical | |
Reg. No./Substance:
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0/Antineoplastic Agents; 0/Glycosides; 0/Indoles; 0/Organosilicon Compounds; 0/Photosensitizing Agents; 17778-80-2/Singlet Oxygen; 7782-50-5/Chlorine |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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