In vitro and in vivo imaging of peroxynitrite by a ratiometric boronate-based fluorescent probe.
Peroxynitrite (ONOO-) is an important species involved in many physiopathological processes. Progresses have been made in developing novel fluorescent probes to detect peroxynitrite with relatively high sensitivity and specificity. Herein, we report the synthesis, characterization and biological applications of a new boronate-based fluorescent probe, 4-MB. The studies showed that 4-MB exhibits a dual ratiometric and calorimetric response toward peroxynitrite due to ONOO--triggered oxidative reaction. A possible mechanism of the oxidation reaction was proposed and the reaction product was isolated and characterized using different spectroscopic methods. We have thoroughly demonstrated the utility of 4-MB for intracellular peroxynitrite imaging. Further, we showed that 4-MB can be potentially employed to visualize exogenous and endogenous peroxynitrite in RAW264.7 macrophages, EAhy926 cells, zebrafish and in live tissues from a high-fat diet-induced obese mouse model.
Department of Biological Science and Technology, Institute of Molecular Medicine and Bioengineering, National Chiao Tung University, 75 Bo-Ai Street, Hsinchu 300, Taiwan.
Sathyadevi
S
Palanisamy
Department of Biological Science and Technology, Institute of Molecular Medicine and Bioengineering, National Chiao Tung University, 75 Bo-Ai Street, Hsinchu 300, Taiwan.
Pei-Yu
PY
Wu
Department of Biological Science and Technology, Institute of Molecular Medicine and Bioengineering, National Chiao Tung University, 75 Bo-Ai Street, Hsinchu 300, Taiwan.
Shou-Cheng
SC
Wu
Department of Biological Science and Technology, Institute of Molecular Medicine and Bioengineering, National Chiao Tung University, 75 Bo-Ai Street, Hsinchu 300, Taiwan.
Yu-Jen
YJ
Chen
Department of Biological Science and Technology, Institute of Molecular Medicine and Bioengineering, National Chiao Tung University, 75 Bo-Ai Street, Hsinchu 300, Taiwan.
Shey-Cherng
SC
Tzou
Department of Biological Science and Technology, Institute of Molecular Medicine and Bioengineering, National Chiao Tung University, 75 Bo-Ai Street, Hsinchu 300, Taiwan.
Chih-Hong
CH
Wang
Department of Medical Imaging, Kaohsiung Medical University Hospital, Kaohsiung, Taiwan; Department of Radiology, Faculty of Medicine, College of Medicine, Kaohsiung Medical University, Kaohsiung, Taiwan.
Chiao-Yun
CY
Chen
Department of Biological Science and Technology, Institute of Molecular Medicine and Bioengineering, National Chiao Tung University, 75 Bo-Ai Street, Hsinchu 300, Taiwan; Department of Biomedical Science and Environmental Biology, Kaohsiung Medical University, Kaohsiung 807, Taiwan. Electronic address: ymwang@mail.nctu.edu.tw.
Yun-Ming
YM
Wang
D000818:Animals; D015374:Biosensing Techniques / Q000379:methods; D001897:Boronic Acids / Q000737:chemistry*; D002460:Cell Line; D005456:Fluorescent Dyes / Q000737:chemistry*; D008264:Macrophages / Q000737:chemistry / Q000166:cytology; D008297:Male; D051379:Mice; D008810:Mice, Inbred C57BL; D009765:Obesity / Q000473:pathology; D061848:Optical Imaging / Q000379:methods*; D030421:Peroxynitrous Acid / Q000032:analysis*; D000067996:RAW 264.7 Cells; D013050:Spectrometry, Fluorescence / Q000379:methods
D001897:Boronic Acids; D005456:Fluorescent Dyes; D030421:Peroxynitrous Acid
Fluorescence; Imaging; Peroxynitrite; Sensor