Indole‐Based Long‐Wavelength Fluorescent Probes for Bioimaging of S‐Nitrosylation in Mitochondria. Issue 58 (26th August 2022)

• Record Type: Journal Article
• Authors: Yu, Jinfeng; Gan, Lu; Zhou, Yani; Xu, Jingyao; Yun, Chengyu; Fang, Tong; Cai, Xiaoqing
• Is Part Of: Chemistry. Volume 28:Issue 58(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-08-26
• Subjects: fluorescent probe -- indole -- long-wavelength -- mitochondria-targeting -- S-nitrosylation; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.202201494
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: S ‐Nitrosylation has been found to play an important role in regulating mitochondrial function. However, probes for detection of protein S ‐nitrosylation in mitochondria remain unexplored. Herein, a novel 4‐(pyridin‐4‐yl)vinyl‐substituted indole was designed, exhibiting a long‐wavelength emission and a high fluorescent quantum yield. Functionalization of the 7‐position of the indole ring with an arylphosphine ester resulted with probes with efficient mitochondria‐targeting ability. Furthermore, the indole‐arylphosphine displayed a significant fluorescence enhancement upon exposure to S ‐nitrosoglutathione (GSNO) at low micromolar concentrations in A431 cells. Taken together, this study provides a new indole‐based fluorescent probe with a unique long‐wavelength emission for direct detection of S ‐nitrosylation in mitochondria, which may represent a powerful tool for understanding the critical roles of S ‐nitrosylation within mitochondria of living organisms. Abstract : A novel indole‐based fluorophore was designed and synthesized, exhibiting long‐wavelength emission and high quantum yield. Functionalization of the 7‐position of the indole ring with an arylphosphine ester resulted with a unique mitochondria‐targeting fluorescent probe for direct detection of S ‐nitrosylation within mitochondria of living cells.