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Reversible Off–On Fluorescence Probe for Hypoxia and Imaging of Hypoxia–Normoxia Cycles in Live Cells

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    Reversible Off–On Fluorescence Probe for Hypoxia and Imaging of Hypoxia–Normoxia Cycles in Live Cells
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    ‡ †Faculty of Pharmaceutical Sciences and ‡Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
    § Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama-shi, Kanagawa 226-8501, Japan
    [email protected]
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    Cite this: J. Am. Chem. Soc. 2012, 134, 48, 19588–19591
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    https://doi.org/10.1021/ja310049d
    Published November 16, 2012
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    Abstract

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    We report a fully reversible off–on fluorescence probe for hypoxia. The design employs QSY-21 as a Förster resonance energy transfer (FRET) acceptor and cyanine dye Cy5 as a FRET donor, based on our finding that QSY-21 undergoes one-electron bioreduction to the radical under hypoxia, with an absorbance decrease at 660 nm. At that point, FRET can no longer occur, and the dye becomes strongly fluorescent. Upon recovery of normoxia, the radical is immediately reoxidized to QSY-21, with loss of fluorescence due to restoration of FRET. We show that this probe, RHyCy5, can monitor repeated hypoxia–normoxia cycles in live cells.

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    Full experimental procedures, characterization data for all compounds, spectral properties of cyanine dyes and QSY-21 derivatives, compounds as candidates for a hypoxia-sensing moiety other than QSY-21, ESR spectra, HPLC analyses, and fluorescence imaging under normoxia. This material is available free of charge via the Internet at http://pubs.acs.org.

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    7. Kenneth Yin Zhang, Qi Yu, Huanjie Wei, Shujuan Liu, Qiang Zhao, and Wei Huang . Long-Lived Emissive Probes for Time-Resolved Photoluminescence Bioimaging and Biosensing. Chemical Reviews 2018, 118 (4) , 1770-1839. https://doi.org/10.1021/acs.chemrev.7b00425
    8. Christopher J. Reinhardt and Jefferson Chan . Development of Photoacoustic Probes for in Vivo Molecular Imaging. Biochemistry 2018, 57 (2) , 194-199. https://doi.org/10.1021/acs.biochem.7b00888
    9. Da Xie, Seyong Kim, Vikraant Kohli, Arnab Banerjee, Meng Yu, José S. Enriquez, Jeffrey J. Luci, and Emily L. Que . Hypoxia-Responsive 19F MRI Probes with Improved Redox Properties and Biocompatibility. Inorganic Chemistry 2017, 56 (11) , 6429-6437. https://doi.org/10.1021/acs.inorgchem.7b00500
    10. Jia-nan Liu, Wenbo Bu, and Jianlin Shi . Chemical Design and Synthesis of Functionalized Probes for Imaging and Treating Tumor Hypoxia. Chemical Reviews 2017, 117 (9) , 6160-6224. https://doi.org/10.1021/acs.chemrev.6b00525
    11. Suzan Youssef, Wei Ren, and Hui-wang Ai . A Genetically Encoded FRET Sensor for Hypoxia and Prolyl Hydroxylases. ACS Chemical Biology 2016, 11 (9) , 2492-2498. https://doi.org/10.1021/acschembio.6b00330
    12. Wen Sun, Shigang Guo, Chong Hu, Jiangli Fan, and Xiaojun Peng . Recent Development of Chemosensors Based on Cyanine Platforms. Chemical Reviews 2016, 116 (14) , 7768-7817. https://doi.org/10.1021/acs.chemrev.6b00001
    13. Yan Huang, Fabiao Yu, Jianchao Wang, and Lingxin Chen . Near-Infrared Fluorescence Probe for in Situ Detection of Superoxide Anion and Hydrogen Polysulfides in Mitochondrial Oxidative Stress. Analytical Chemistry 2016, 88 (7) , 4122-4129. https://doi.org/10.1021/acs.analchem.6b00458
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    33. Indrajit Srivastava, Parikshit Moitra, Kurtis M Brent, Kevin Wang, Subhendu Pandit, Esra Altun, Dipanjan Pan. Biodegradable and Switchable Near-Infrared Fluorescent Probes for Hypoxia Detection. Nanomedicine 2023, 18 (16) , 1061-1073. https://doi.org/10.2217/nnm-2023-0095
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    35. Fan Chen, Baoxin Zhang, Zhenjiang Ding, Miao Zhong, Yanan Hou, Fang Zhang, Guodong Hu, Jianguo Fang. Hemin as a General Static Dark Quencher for Constructing Heme Oxygenase‐1 Fluorescent Probes. Angewandte Chemie International Edition 2023, 62 (21) https://doi.org/10.1002/anie.202301598
    36. Wellington Pham. Construction of Molecular Probes and Imaging Applications. 2023, 239-309. https://doi.org/10.1007/978-981-19-5739-0_6
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    38. Bin Fang, Yu Shen, Bo Peng, Hua Bai, Limin Wang, Jiaxin Zhang, Wenbo Hu, Li Fu, Wei Zhang, Lin Li, Wei Huang. Small‐Molecule Quenchers for Förster Resonance Energy Transfer: Structure, Mechanism, and Applications. Angewandte Chemie International Edition 2022, 61 (41) https://doi.org/10.1002/anie.202207188
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    40. Leilei Yao, Caixia Yin, Fangjun Huo. Small-Molecule Fluorescent Probes for Detecting Several Abnormally Expressed Substances in Tumors. Micromachines 2022, 13 (8) , 1328. https://doi.org/10.3390/mi13081328
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    48. Zhen Zhang, Jiangli Fan, Jianjun Du, Xiaojun Peng. Two-channel responsive luminescent chemosensors for dioxygen species: Molecular oxygen, singlet oxygen and superoxide anion. Coordination Chemistry Reviews 2021, 427 , 213575. https://doi.org/10.1016/j.ccr.2020.213575
    49. Rahul T. Kadakia, Da Xie, Hongyu Guo, Bailey Bouley, Meng Yu, Emily L. Que. Responsive fluorinated nanoemulsions for 19 F magnetic resonance detection of cellular hypoxia. Dalton Transactions 2020, 49 (45) , 16419-16424. https://doi.org/10.1039/D0DT01182G
    50. Nicholas G. Taylor, Sang Hun Chung, Albert L. Kwansa, Rob R. Johnson, Aaron J. Teator, Nina J. B. Milliken, Karl M. Koshlap, Yaroslava G. Yingling, Yueh Z. Lee, Frank A. Leibfarth. Partially Fluorinated Copolymers as Oxygen Sensitive 19 F MRI Agents. Chemistry – A European Journal 2020, 26 (44) , 9982-9990. https://doi.org/10.1002/chem.202001505
    51. Luling Wu, Chusen Huang, Ben P. Emery, Adam C. Sedgwick, Steven D. Bull, Xiao-Peng He, He Tian, Juyoung Yoon, Jonathan L. Sessler, Tony D. James. Förster resonance energy transfer (FRET)-based small-molecule sensors and imaging agents. Chemical Society Reviews 2020, 49 (15) , 5110-5139. https://doi.org/10.1039/C9CS00318E
    52. Yawei Liu, Yuyang Gu, Wei Yuan, Xiaobo Zhou, Xiaochen Qiu, Mengya Kong, Qingbing Wang, Wei Feng, Fuyou Li. Quantitative Mapping of Liver Hypoxia in Living Mice Using Time‐Resolved Wide‐Field Phosphorescence Lifetime Imaging. Advanced Science 2020, 7 (11) https://doi.org/10.1002/advs.201902929
    53. Rashmi Kumari, Dhanya Sunil, Raghumani S. Ningthoujam. Hypoxia-responsive nanoparticle based drug delivery systems in cancer therapy: An up-to-date review. Journal of Controlled Release 2020, 319 , 135-156. https://doi.org/10.1016/j.jconrel.2019.12.041
    54. Hemant Sharma, Nian Kee Tan, Natalie Trinh, Jia Hao Yeo, Elizabeth J. New, Frederick M. Pfeffer. A fluorescent naphthalimide NADH mimic for continuous and reversible sensing of cellular redox state. Chemical Communications 2020, 56 (15) , 2240-2243. https://doi.org/10.1039/C9CC09748A
    55. Jieni Liu, Ting Zhu, Xiaoping Yang, Hongfen Chen, Dongliang Shi, Chaoqun Zhu, Desmond Schipper, Richard A. Jones. Construction of a 1-D Sm( iii ) coordination polymer with a long-chain Schiff base ligand: dual-emissive response to metal ions. Inorganic Chemistry Frontiers 2020, 7 (2) , 464-469. https://doi.org/10.1039/C9QI01288E
    56. Rui Wei, Si Liu, Shutian Zhang, Li Min, Shengtao Zhu. Cellular and Extracellular Components in Tumor Microenvironment and Their Application in Early Diagnosis of Cancers. Analytical Cellular Pathology 2020, 2020 , 1-13. https://doi.org/10.1155/2020/6283796
    57. Jieni Liu, Xiaoping Yang, Ting Zhu, Bichen Yuan, Hongfen Chen, Dongliang Shi, Desmond Schipper, Richard A. Jones. Construction of a crystalline 14-metal Zn–Nd rectangular nanocluster with a dual-emissive response towards metal ions. RSC Advances 2019, 9 (68) , 40017-40022. https://doi.org/10.1039/C9RA09409A
    58. Rahul T. Kadakia, Da Xie, Daniel Martinez, Meng Yu, Emily L. Que. A dual-responsive probe for detecting cellular hypoxia using 19 F magnetic resonance and fluorescence. Chemical Communications 2019, 55 (60) , 8860-8863. https://doi.org/10.1039/C9CC00375D
    59. Rashmi Kumari, Dhanya Sunil, Raghumani S. Ningthoujam. Naphthalimides in fluorescent imaging of tumor hypoxia – An up-to-date review. Bioorganic Chemistry 2019, 88 , 102979. https://doi.org/10.1016/j.bioorg.2019.102979
    60. Virginia Spanoudaki, Joshua C. Doloff, Wei Huang, Samuel R. Norcross, Shady Farah, Robert Langer, Daniel G. Anderson. Simultaneous spatiotemporal tracking and oxygen sensing of transient implants in vivo using hot-spot MRI and machine learning. Proceedings of the National Academy of Sciences 2019, 116 (11) , 4861-4870. https://doi.org/10.1073/pnas.1815909116
    61. Zan Li, Zhenzhu Zhu, Zhiwei Sun, Jie Ding, Jinmao You. Design of a multifunctional biotinylated copper complex for visualization and quantification of cancer hypoxia levels. Sensors and Actuators B: Chemical 2019, 282 , 541-548. https://doi.org/10.1016/j.snb.2018.11.119
    62. Thanh Danh Nguyen, Min Seok Song, Nguyễn Hoàng Ly, So Yeong Lee, Sang‐Woo Joo. Nanostars on Nanopipette Tips: A Raman Probe for Quantifying Oxygen Levels in Hypoxic Single Cells and Tumours. Angewandte Chemie 2019, 131 (9) , 2736-2740. https://doi.org/10.1002/ange.201812677
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    64. Xiaofeng Fang, Bo Ju, Zhihe Liu, Fei Wang, Guan Xi, Zezhou Sun, Haobin Chen, Changxiang Sui, Mingxue Wang, Changfeng Wu. Compact Conjugated Polymer Dots with Covalently Incorporated Metalloporphyrins for Hypoxia Bioimaging. ChemBioChem 2019, 20 (4) , 521-525. https://doi.org/10.1002/cbic.201800438
    65. Nan Chen, Yuping Han, Yao Luo, Yanfeng Zhou, Xingjie Hu, Yun Yu, Xiaodong Xie, Min Yin, Jinli Sun, Wenying Zhong, Yun Zhao, Haiyun Song, Chunhai Fan. Nanodiamond-based non-canonical autophagy inhibitor synergistically induces cell death in oxygen-deprived tumors. Materials Horizons 2018, 5 (6) , 1204-1210. https://doi.org/10.1039/C8MH00993G
    66. Jiri Demuth, Radim Kucera, Kamil Kopecky, Zuzana Havlínová, Antonín Libra, Veronika Novakova, Miroslav Miletin, Petr Zimcik. Efficient Synthesis of a Wide‐Range Absorbing Azaphthalocyanine Dark Quencher and Its Application to Dual‐Labeled Oligonucleotide Probes for Quantitative Real‐Time Polymerase Chain Reactions. Chemistry – A European Journal 2018, 24 (38) , 9658-9666. https://doi.org/10.1002/chem.201801319
    67. Min Gao, Rui Wang, Fabiao Yu, Lingxin Chen. Evaluation of sulfane sulfur bioeffects via a mitochondria-targeting selenium-containing near-infrared fluorescent probe. Biomaterials 2018, 160 , 1-14. https://doi.org/10.1016/j.biomaterials.2018.01.011
    68. Zhaoshuai He, Yajie Chou, Hanxin Zhou, Han Zhang, Tanyu Cheng, Guohua Liu. A nitroreductase and acidity detecting dual functional ratiometric fluorescent probe for selectively imaging tumor cells. Organic & Biomolecular Chemistry 2018, 16 (17) , 3266-3272. https://doi.org/10.1039/C8OB00670A
    69. Hai-Tao Feng, Xinggui Gu, Jacky W. Y. Lam, Yan-Song Zheng, Ben Zhong Tang. Design of multi-functional AIEgens: tunable emission, circularly polarized luminescence and self-assembly by dark through-bond energy transfer. Journal of Materials Chemistry C 2018, 6 (33) , 8934-8940. https://doi.org/10.1039/C8TC02504E
    70. Hailey J. Knox, Jamila Hedhli, Tae Wook Kim, Kian Khalili, Lawrence W. Dobrucki, Jefferson Chan. A bioreducible N-oxide-based probe for photoacoustic imaging of hypoxia. Nature Communications 2017, 8 (1) https://doi.org/10.1038/s41467-017-01951-0
    71. Biao Li, Zhaoshuai He, Hanxin Zhou, Han Zhang, Tanyu Cheng. Reversible fluorescent probes for chemical and biological redox process. Chinese Chemical Letters 2017, 28 (10) , 1929-1934. https://doi.org/10.1016/j.cclet.2017.08.055
    72. Rui Lü. Reaction-based small-molecule fluorescent probes for dynamic detection of ROS and transient redox changes in living cells and small animals. Journal of Molecular and Cellular Cardiology 2017, 110 , 96-108. https://doi.org/10.1016/j.yjmcc.2017.07.008
    73. James R.W. Conway, Sean C. Warren, Paul Timpson. Context-dependent intravital imaging of therapeutic response using intramolecular FRET biosensors. Methods 2017, 128 , 78-94. https://doi.org/10.1016/j.ymeth.2017.04.014
    74. Yue Wu, Zhensheng Jiang, Qidong You, Xiaojin Zhang. Application of in-vitro screening methods on hypoxia inducible factor prolyl hydroxylase inhibitors. Bioorganic & Medicinal Chemistry 2017, 25 (15) , 3891-3899. https://doi.org/10.1016/j.bmc.2017.05.026
    75. Toshitada Yoshihara, Yosuke Hirakawa, Masahiro Hosaka, Masaomi Nangaku, Seiji Tobita. Oxygen imaging of living cells and tissues using luminescent molecular probes. Journal of Photochemistry and Photobiology C: Photochemistry Reviews 2017, 30 , 71-95. https://doi.org/10.1016/j.jphotochemrev.2017.01.001
    76. Marie-Caline Z. Abadjian, W. Barry Edwards, Carolyn J. Anderson. Imaging the Tumor Microenvironment. 2017, 229-257. https://doi.org/10.1007/978-3-319-67577-0_15
    77. Dandan Li, Yuqiong Xu, Nannan Zhou, Jianxu Liu, Rui Wang, Tao Cheng, Yun Tang, Weiping Zhu, Yufang Xu, Xuhong Qian. A novel ‘‘donor-two-acceptor’’ type fluorophore-based probe for fast detection and intracellular imaging of nitroreductase. Dyes and Pigments 2017, 136 , 627-632. https://doi.org/10.1016/j.dyepig.2016.09.014
    78. Jinquan Wang, Junfeng Kou, Xiaojuan Hou, Zizhuo Zhao, Hui Chao. A ruthenium(II) anthraquinone complex as the theranostic agent combining hypoxia imaging and HIF-1α inhibition. Inorganica Chimica Acta 2017, 454 , 176-183. https://doi.org/10.1016/j.ica.2016.04.050
    79. Tasuku Hirayama, Hitomi Tsuboi, Masato Niwa, Ayaji Miki, Satoki Kadota, Yukie Ikeshita, Kensuke Okuda, Hideko Nagasawa. A universal fluorogenic switch for Fe( ii ) ion based on N-oxide chemistry permits the visualization of intracellular redox equilibrium shift towards labile iron in hypoxic tumor cells. Chemical Science 2017, 8 (7) , 4858-4866. https://doi.org/10.1039/C6SC05457A
    80. S. Karthik, Avijit Jana, M. Selvakumar, Yarra Venkatesh, Amrita Paul, Sk. Sheriff Shah, N. D. Pradeep Singh. Coumarin polycaprolactone polymeric nanoparticles: light and tumor microenvironment activated cocktail drug delivery. Journal of Materials Chemistry B 2017, 5 (9) , 1734-1741. https://doi.org/10.1039/C6TB02944B
    81. Lu Wang, Dongdong Su, Stuart N. Berry, Jungyeol Lee, Young-Tae Chang. A new approach for turn-on fluorescence sensing of l-DOPA. Chemical Communications 2017, 53 (92) , 12465-12468. https://doi.org/10.1039/C7CC07640A
    82. Xiang Li, Yongheng Yin, Hong Yan, Changsheng Lu, Qiang Zhao. Novel phosphorescent cationic iridium( iii ) complexes with o-carboranylation on the ancillary N^N ligand. Dalton Transactions 2017, 46 (30) , 10082-10089. https://doi.org/10.1039/C7DT02009K
    83. Xiang Li, Yongheng Yin, Pengli Gao, Weijie Li, Hong Yan, Changsheng Lu, Qiang Zhao. A novel phosphorescent iridium( iii ) complex bearing a donor–acceptor-type o-carboranylated ligand for endocellular hypoxia imaging. Dalton Trans. 2017, 46 (40) , 13802-13810. https://doi.org/10.1039/C7DT03097E
    84. Tian-shu Chu, Rui Lü, Bai-tong Liu. Reversibly monitoring oxidation and reduction events in living biological systems: Recent development of redox-responsive reversible NIR biosensors and their applications in in vitro/in vivo fluorescence imaging. Biosensors and Bioelectronics 2016, 86 , 643-655. https://doi.org/10.1016/j.bios.2016.07.039
    85. Xiang Li, Xiao Tong, Hong Yan, Changsheng Lu, Qiang Zhao, Wei Huang. A Convenient Approach To Synthesize o ‐Carborane‐Functionalized Phosphorescent Iridium(III) Complexes for Endocellular Hypoxia Imaging. Chemistry – A European Journal 2016, 22 (48) , 17282-17290. https://doi.org/10.1002/chem.201603340
    86. Weipei Feng, Yuechai Wang, Shizhu Chen, Chao Wang, Shuxiang Wang, Shenghui Li, Hongyan Li, Guoqiang Zhou, Jinchao Zhang. 4-Nitroimidazole-3-hydroxyflavone conjugate as a fluorescent probe for hypoxic cells. Dyes and Pigments 2016, 131 , 145-153. https://doi.org/10.1016/j.dyepig.2016.03.019
    87. Xian‐Sheng Ke, Yingying Ning, Juan Tang, Ji‐Yun Hu, Hao‐Yan Yin, Gao‐Xiang Wang, Zi‐Shu Yang, Jialong Jie, Kunhui Liu, Zhao‐Sha Meng, Zongyao Zhang, Hongmei Su, Chunying Shu, Jun‐Long Zhang. Gadolinium(III) Porpholactones as Efficient and Robust Singlet Oxygen Photosensitizers. Chemistry – A European Journal 2016, 22 (28) , 9676-9686. https://doi.org/10.1002/chem.201601517
    88. Lingli Sun, Yu Chen, Shi Kuang, Guanying Li, Ruilin Guan, Jiangping Liu, Liangnian Ji, Hui Chao. Iridium(III) Anthraquinone Complexes as Two‐Photon Phosphorescence Probes for Mitochondria Imaging and Tracking under Hypoxia. Chemistry – A European Journal 2016, 22 (26) , 8955-8965. https://doi.org/10.1002/chem.201600310
    89. Jacek L. Kolanowski, Amandeep Kaur, Elizabeth J. New. Selective and Reversible Approaches Toward Imaging Redox Signaling Using Small-Molecule Probes. Antioxidants & Redox Signaling 2016, 24 (13) , 713-730. https://doi.org/10.1089/ars.2015.6588
    90. Xiang Li, Hong Yan, Qiang Zhao. Carboranes as a Tool to Tune Phosphorescence. Chemistry – A European Journal 2016, 22 (6) , 1888-1898. https://doi.org/10.1002/chem.201503456
    91. Xiaobo Zhou, Hua Liang, Pengfei Jiang, Kenneth Yin Zhang, Shujuan Liu, Tianshe Yang, Qiang Zhao, Lijuan Yang, Wen Lv, Qi Yu, Wei Huang. Multifunctional Phosphorescent Conjugated Polymer Dots for Hypoxia Imaging and Photodynamic Therapy of Cancer Cells. Advanced Science 2016, 3 (2) https://doi.org/10.1002/advs.201500155
    92. Amandeep Kaur, Jacek L. Kolanowski, Elizabeth J. New. Reversible Fluoreszenzsonden für biologische Redoxzustände. Angewandte Chemie 2016, 128 (5) , 1630-1643. https://doi.org/10.1002/ange.201506353
    93. Amandeep Kaur, Jacek L. Kolanowski, Elizabeth J. New. Reversible Fluorescent Probes for Biological Redox States. Angewandte Chemie International Edition 2016, 55 (5) , 1602-1613. https://doi.org/10.1002/anie.201506353
    94. Dongjian Zhu, Lin Xue, Guoping Li, Hua Jiang. A highly sensitive near-infrared ratiometric fluorescent probe for detecting nitroreductase and cellular imaging. Sensors and Actuators B: Chemical 2016, 222 , 419-424. https://doi.org/10.1016/j.snb.2015.08.093
    95. Sihang Luo, Yingchao Liu, Feiyi Wang, Qiang Fei, Ben Shi, Jiancai An, Chunchang Zhao, Chen-Ho Tung. A fluorescent turn-on probe for visualizing lysosomes in hypoxic tumor cells. The Analyst 2016, 141 (10) , 2879-2882. https://doi.org/10.1039/C6AN00369A
    96. Robert B. P. Elmes. Bioreductive fluorescent imaging agents: applications to tumour hypoxia. Chemical Communications 2016, 52 (58) , 8935-8956. https://doi.org/10.1039/C6CC01037G
    97. Jun Yin, Younghee Kwon, Dabin Kim, Dayoung Lee, Gyoungmi Kim, Ying Hu, Ji-Hwan Ryu, Juyoung Yoon. Preparation of a cyanine-based fluorescent probe for highly selective detection of glutathione and its use in living cells and tissues of mice. Nature Protocols 2015, 10 (11) , 1742-1754. https://doi.org/10.1038/nprot.2015.109
    98. Fabiao Yu, Min Gao, Meng Li, Lingxin Chen. A dual response near-infrared fluorescent probe for hydrogen polysulfides and superoxide anion detection in cells and in vivo. Biomaterials 2015, 63 , 93-101. https://doi.org/10.1016/j.biomaterials.2015.06.007
    99. Pingyu Zhang, Huaiyi Huang, Yu Chen, Jinquan Wang, Liangnian Ji, Hui Chao. Ruthenium(II) anthraquinone complexes as two-photon luminescent probes for cycling hypoxia imaging in vivo. Biomaterials 2015, 53 , 522-531. https://doi.org/10.1016/j.biomaterials.2015.02.126
    100. Jian Xu, Shaobo Sun, Qian Li, Ying Yue, Yingdong Li, Shijun Shao. A rapid response “Turn-On” fluorescent probe for nitroreductase detection and its application in hypoxic tumor cell imaging. The Analyst 2015, 140 (2) , 574-581. https://doi.org/10.1039/C4AN01934B
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    Cite this: J. Am. Chem. Soc. 2012, 134, 48, 19588–19591
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