pH-Responsive Cy5 dyes having nucleophilic substituents for molecular imaging |
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Authors: | Masahiro Oe Koji Miki Huiying Mu Hiroshi Harada Akiyo Morinibu Kouichi Ohe |
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Affiliation: | 1. Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan;2. Laboratory of Cancer Cell Biology, Radiation Biology Center, Kyoto University, Yoshida Konoe-cho, Sakyo-ku, Kyoto 606-8501, Japan |
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Abstract: | pH-Responsive fluorescent pentamethine cyanine (Cy5) derivatives having nucleophilic substituents were synthesized. Cy5 derivatives 1-O having mercaptopropyl, hydroxypropyl, and aminopropyl groups on an indole nitrogen atom showed pH-dependent equilibria between a fluorescent open-ring structure (1-O) and a non-fluorescent closed-ring structure (1-C) in pH ranges 3–7, 6–7.5, and 8–9, respectively. pH-Responsive dyes 1a-C having a 1,3-thiazinane structure were easily internalized into A549 cells and converted to open-ring structure 1a-O in response to the relatively low pH of acidic compartments in the cells. |
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Keywords: | pH-response Fluorescence Cyanine dye Molecular imaging |
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