Development of Azo-Based Fluorescent Probes to Detect Different Levels of Hypoxia†
Wen Piao
Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
Search for more papers by this authorSatoru Tsuda
Department of Ophthalmology, Tohoku University, Graduate School of Medicine, 1-1 Seiryo-machi, Aoba-ku, Sendai, Miyagi 980-8574 (Japan)
Search for more papers by this authorDr. Yuji Tanaka
Department of Ophthalmology, Tohoku University, Graduate School of Medicine, 1-1 Seiryo-machi, Aoba-ku, Sendai, Miyagi 980-8574 (Japan)
Search for more papers by this authorDr. Satoshi Maeda
Department of Chemistry, Faculty of Science, Hokkaido University, Kita 10 Nishi 8, Kita-ku, Sapporo, Hokkaido 060-0808 (Japan)
Search for more papers by this authorDr. Fengyi Liu
Fukui Institute for Fundamental Chemistry, Kyoto University, 34-4 Takano Nishihiraki-cho, Sakyo, Kyoto 606-8103 (Japan)
Search for more papers by this authorShodai Takahashi
Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
Search for more papers by this authorYu Kushida
Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
Search for more papers by this authorDr. Toru Komatsu
Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
Search for more papers by this authorDr. Tasuku Ueno
Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
Search for more papers by this authorDr. Takuya Terai
Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
Search for more papers by this authorProf. Toru Nakazawa
Department of Ophthalmology, Tohoku University, Graduate School of Medicine, 1-1 Seiryo-machi, Aoba-ku, Sendai, Miyagi 980-8574 (Japan)
Search for more papers by this authorProf. Masanobu Uchiyama
Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
Advanced Elements Chemistry Laboratory, RIKEN 2-1 Hirosawa, Wako-shi, Saitama 351-0198 (Japan)
Search for more papers by this authorProf. Keiji Morokuma
Fukui Institute for Fundamental Chemistry, Kyoto University, 34-4 Takano Nishihiraki-cho, Sakyo, Kyoto 606-8103 (Japan)
Search for more papers by this authorProf. Tetsuo Nagano
Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
Search for more papers by this authorCorresponding Author
Dr. Kenjiro Hanaoka
Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)===Search for more papers by this authorWen Piao
Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
Search for more papers by this authorSatoru Tsuda
Department of Ophthalmology, Tohoku University, Graduate School of Medicine, 1-1 Seiryo-machi, Aoba-ku, Sendai, Miyagi 980-8574 (Japan)
Search for more papers by this authorDr. Yuji Tanaka
Department of Ophthalmology, Tohoku University, Graduate School of Medicine, 1-1 Seiryo-machi, Aoba-ku, Sendai, Miyagi 980-8574 (Japan)
Search for more papers by this authorDr. Satoshi Maeda
Department of Chemistry, Faculty of Science, Hokkaido University, Kita 10 Nishi 8, Kita-ku, Sapporo, Hokkaido 060-0808 (Japan)
Search for more papers by this authorDr. Fengyi Liu
Fukui Institute for Fundamental Chemistry, Kyoto University, 34-4 Takano Nishihiraki-cho, Sakyo, Kyoto 606-8103 (Japan)
Search for more papers by this authorShodai Takahashi
Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
Search for more papers by this authorYu Kushida
Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
Search for more papers by this authorDr. Toru Komatsu
Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
Search for more papers by this authorDr. Tasuku Ueno
Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
Search for more papers by this authorDr. Takuya Terai
Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
Search for more papers by this authorProf. Toru Nakazawa
Department of Ophthalmology, Tohoku University, Graduate School of Medicine, 1-1 Seiryo-machi, Aoba-ku, Sendai, Miyagi 980-8574 (Japan)
Search for more papers by this authorProf. Masanobu Uchiyama
Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
Advanced Elements Chemistry Laboratory, RIKEN 2-1 Hirosawa, Wako-shi, Saitama 351-0198 (Japan)
Search for more papers by this authorProf. Keiji Morokuma
Fukui Institute for Fundamental Chemistry, Kyoto University, 34-4 Takano Nishihiraki-cho, Sakyo, Kyoto 606-8103 (Japan)
Search for more papers by this authorProf. Tetsuo Nagano
Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
Search for more papers by this authorCorresponding Author
Dr. Kenjiro Hanaoka
Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)===Search for more papers by this authorThis work was supported in part by MEXT (Specially Promoted Research Grant 22000006 to T.N., 24689003 and 24659042 to K.H., and 24655147 to T.K.) and SENTAN and JST( K.H.). K.H. was also supported by The Asahi Glass Foundation, The Uehara Memorial Foundation, the Tokyo Biochemical Research Foundation, the Inoue Foundation for Science, the Takeda Science Foundation, and The Cosmetology Research Foundation. The authors thank Mr. Yu Harabuchi of Hokkaido University for helpful discussions on photoreactions of azobenzene. Some of the theoretical calculations were carried out using the computational resources of the Institute for Molecular Science, Okazaki (Japan). W.P. was supported by a Grant-in-Aid for JSPS Fellows.
Graphical Abstract
Let it shine: New hypoxia-sensitive fluorescent probes were developed; they consist of a rhodamine moiety with an azo group directly conjugated to the fluorophore. Because of an ultrafast conformational change around the NN bond, the compounds are nonfluorescent under normoxia. However, under hypoxia, the azo group is reduced, and a strongly fluorescent rhodamine derivative is released.
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