Reasonably constructed NIR fluorescent probes based on dicyanoisophorone skeleton for imaging ONOO in living cells

Jeewon Chung, Heejeong Kim, Haidong Li, Juyoung Yoon

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

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.

Original languageEnglish
Article number109665
JournalDyes and Pigments
Volume195
DOIs
StatePublished - Nov 2021

Keywords

  • Cell imaging
  • NIR Fluorescent probe
  • pKa regulation
  • Reactive nitrogen species

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