| Photooxidation and Phototoxicity of pi-extended squaraines. | |
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MedLine Citation:
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PMID: 20131844 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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This paper describes the synthesis of pi-extended squaraines and their photooxidation properties and gives an in-depth characterization of these molecules as photosensitizing agents. Squaraines show a strong absorption in the tissue transparency window (600-800 nm), and upon irradiation, they undergo a photooxidation process, leading to the formation of peroxide and hydroperoxide radicals according to a type I radical chain process. Confocal laser microscopy demonstrates that the designed squaraines efficiently internalize in the cytoplasm and not in the nucleus of the cell. In the dark, they are scarcely cytotoxic, but after irradition, they promote a strong dose-dependent phototoxic effect in four different cancer cells. In HeLa and MCF-7 cells, squaraines 4 and 5, thanks to their hydrocarbon tails, associate to the membranes and induce lipid peroxidation, as indicated by a marked increase of malonyldialdehyde after photodynamic treatment, in agreement with in vitro photooxidation studies. FACS, caspase-3/7 assays and time-lapse microscopy demonstrate that the designed squaraines cause cell death primarily by necrosis. |
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Authors:
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Valentina Rapozzi; Luca Beverina; Patrizio Salice; Giorgio A Pagani; Monica Camerin; Luigi E Xodo |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Journal of medicinal chemistry Volume: 53 ISSN: 1520-4804 ISO Abbreviation: J. Med. Chem. Publication Date: 2010 Mar |
Date Detail:
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Created Date: 2010-03-04 Completed Date: 2010-04-01 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: 2188-96 Citation Subset: IM |
Affiliation:
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Department of Biomedical Science and Technology, University of Udine, Ple Kolbe 4, I-33100 Udine, Italy. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Antineoplastic Agents
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chemical synthesis*,
chemistry,
pharmacology Benzothiazoles / chemical synthesis*, chemistry, pharmacology Cell Proliferation / drug effects Cyclobutanes / chemical synthesis*, chemistry, pharmacology Dermatitis, Phototoxic / metabolism* Flow Cytometry Gas Chromatography-Mass Spectrometry Hela Cells Humans Inhibitory Concentration 50 Lipid Peroxides / metabolism* Microscopy, Confocal Photosensitizing Agents / chemical synthesis*, chemistry, pharmacology Thiobarbituric Acid Reactive Substances / analysis |
| Chemical | |
Reg. No./Substance:
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0/Antineoplastic Agents; 0/Benzothiazoles; 0/Cyclobutanes; 0/Lipid Peroxides; 0/Photosensitizing Agents; 0/Thiobarbituric Acid Reactive Substances |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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