TY - JOUR
T1 - Reasonably constructed NIR fluorescent probes based on dicyanoisophorone skeleton for imaging ONOO− in living cells
AU - Chung, Jeewon
AU - Kim, Heejeong
AU - Li, Haidong
AU - Yoon, Juyoung
N1 - Funding Information:
This study was supported by grants from the National Research Foundation of Korea ( NRF ) funded by the Korean government ( MSIP ) (No. 2012R1A3A2048814 for J. Y). High-resolution mass spectrometer analysis was performed on the Synapt G2-HDMS mass spectrometer (Waters, Manchester, U.K.), which was operated on the MassLynx 4.1 software at KBSI (Korea Basic Science Institue, Ochang, Center of Research Equipment).
Publisher Copyright:
© 2021 Elsevier Ltd
PY - 2021/11
Y1 - 2021/11
N2 - Peroxynitrite (ONOO−), a reactive nitrogen species (RNS), engages in various cellular processes including inflammation, apoptosis, and necrosis. Therefore, the development of a powerful tool for imaging endogenous ONOO− is important with regard to revealing its underlying physiological or pathological functions. In this work, we introduced dihalogen (Cl, Br, and I) at the ortho-positions of the hydroxyl group of a dicyanoisophorone skeleton to adjust its pKa to be more suitable for bio-imaging in the physiological environments with a high signal-to-noise ratio. Based on the optimized spectral results and the requirement of biocompatibility, the fluorescent probe NIR-dCl was successfully designed and fabricated for the detection of ONOO−. Upon the addition of ONOO− in solution, an obvious NIR fluorescent signal at 680 nm was observed. Moreover, the probe NIR-dCl exhibited high selectivity for sensing ONOO−. Cell imaging results confirmed that probe NIR-dCl was capable of imaging exogenous and endogenous ONOO− in live cells. Thus, we believe that probe NIR-dCl could be an effective tool for studying biochemical processes and ONOO−-related diseases.
AB - Peroxynitrite (ONOO−), a reactive nitrogen species (RNS), engages in various cellular processes including inflammation, apoptosis, and necrosis. Therefore, the development of a powerful tool for imaging endogenous ONOO− is important with regard to revealing its underlying physiological or pathological functions. In this work, we introduced dihalogen (Cl, Br, and I) at the ortho-positions of the hydroxyl group of a dicyanoisophorone skeleton to adjust its pKa to be more suitable for bio-imaging in the physiological environments with a high signal-to-noise ratio. Based on the optimized spectral results and the requirement of biocompatibility, the fluorescent probe NIR-dCl was successfully designed and fabricated for the detection of ONOO−. Upon the addition of ONOO− in solution, an obvious NIR fluorescent signal at 680 nm was observed. Moreover, the probe NIR-dCl exhibited high selectivity for sensing ONOO−. Cell imaging results confirmed that probe NIR-dCl was capable of imaging exogenous and endogenous ONOO− in live cells. Thus, we believe that probe NIR-dCl could be an effective tool for studying biochemical processes and ONOO−-related diseases.
KW - Cell imaging
KW - NIR Fluorescent probe
KW - pKa regulation
KW - Reactive nitrogen species
UR - http://www.scopus.com/inward/record.url?scp=85111641736&partnerID=8YFLogxK
U2 - 10.1016/j.dyepig.2021.109665
DO - 10.1016/j.dyepig.2021.109665
M3 - Article
AN - SCOPUS:85111641736
SN - 0143-7208
VL - 195
JO - Dyes and Pigments
JF - Dyes and Pigments
M1 - 109665
ER -