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Theoretical and Experimental Studies on the Near-Infrared Photoreaction Mechanism of a Silicon Phthalocyanine Photoimmunotherapy Dye : Photoinduced Hydrolysis by Radical Anion Generation

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Title: Theoretical and Experimental Studies on the Near-Infrared Photoreaction Mechanism of a Silicon Phthalocyanine Photoimmunotherapy Dye : Photoinduced Hydrolysis by Radical Anion Generation
Authors: Kobayashi, Masato Browse this author
Harada, Mei Browse this author
Takakura, Hideo Browse this author
Ando, Kanta Browse this author
Goto, Yuto Browse this author
Tsuneda, Takao Browse this author
Ogawa, Mikako Browse this author
Taketsugu, Tetsuya Browse this author →KAKEN DB
Keywords: bond dissociation
cancer photoimmunotherapy
density functional calculation
near-infrared dyes
radical anions
silicon phthalocyanine
Issue Date: 1-Jul-2020
Publisher: Wiley-Blackwell
Journal Title: ChemPlusChem
Publisher DOI: 10.1002/cplu.202000338
Abstract: Ligand release from IR700, a silicon phthalocyanine dye used in near-infrared (NIR) photoimmunotherapy, initiates cancer cell death after NIR absorption, although its photochemical mechanism has remained unclear. This theoretical study reveals that the direct Si-ligand dissociation by NIR light is difficult to activate because of the high dissociation energy even in excited states, i. e., >1.30 eV. Instead, irradiation generates the IR700 radical anion, leading to acid-base reactions with nearby water molecules (i. e., calculated pK(b) for the radical anion is 7.7) to produce hydrophobic ligand-released dyes. This suggests two possibilities: (1) water molecules participate in ligand release and (2) light is not required for Si-ligand dissociation as formation of the IR700 radical anion is sufficient. Experimental evidence confirmed possibility (1) by using O-18-labeled water as the solvent, while (2) is supported by the pH dependence of ligand exchange, providing a complete description of the Si-ligand bond dissociation mechanism.
Rights: https://creativecommons.org/licenses/by/4.0/
Type: article
URI: http://hdl.handle.net/2115/78733
Appears in Collections:理学院・理学研究院 (Graduate School of Science / Faculty of Science) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

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