Phosphinate–benzoindocyanin fluorescent probe for endogenous mitochondrial peroxynitrite detection in living cells and gallbladder access in inflammatory zebrafish animal models

• Published in: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy Molecular and biomolecular spectroscopy, 2022-02, Vol.267, p.120568, Article 120568
• Main Authors: Sonawane, Prasad M., Lee, Woohyun, Kim, Yunsu, Roychaudhury, Arkaprava, Bhosale, Vikas K., Kim, Donghyeon, Park, Hee-Sung, Kim, Cheol-Hee, Churchill, David G.
• Format: Article
• Language: English
• Subjects: Cell imaging; Diphenyl phosphinate; Mitochondria-accessing; ONOO; Zebrafish
• ISSN: 1386-1425
• DOI: 10.1016/j.saa.2021.120568

[Display omitted] •Mitochondria-selective and ICT-based specific probing of ONOO− fluorogenic probe was developed.•The detection limit for ONOO− is nanomolar; highly photostable and large red shifting is exhibited.•It displays capability to track fluctuations of ONOO− levels in endogenous RAW 264.7 cells.•The probe remarkably and distinctly demonstrates visualization of ONOO− in inflammatory zebrafish models. Potent oxidants such as peroxynitrite (ONOO−) play important roles in the regulation of different physiopathological processes; their overproduction is thought to potentially cause several diseases in living organisms. Hence, the precise and selective monitoring of ONOO− is imperative for elucidating its interplay and roles in pathological and physiological processes. Herein, we present a novel diphenyl phosphinate-masked benzoindocyanin “turn-on” fluorogenic probe to help detect mitochondrial ONOO− in living cells and zebrafish models. A pale yellow color solution of BICBzDP turns rose-red upon the addition of ONOO−, selectively, contrary to that of other competitive bioactive molecules. BICBzDP displays an ultra-sensitivity detection limit (47.8 nM) with outstanding selectivity and sensitivity towards mitochondrial ONOO− and possesses a notable 68-fold fluorescence enhancement involving a large redshift of 91 nm. Importantly, further biological experimental investigations with BICBzDP indicate specific sensitivity and reliability of the probe to track the ONOO− level, not only in live cells, but also demonstrates dynamic fluctuations in the inflammatory zebrafish animal models. Thus, BICBzDP could be employed as a future potential biological tool for exploiting the role of ONOO− in a variety of different physiological systems.