Dual-Channel Fluorescent Probe for the Simultaneous Monitoring of Peroxynitrite and Adenosine-5′-triphosphate in Cellular Applications

Luling Wu, Jihong Liu, Xue Tian, Robin R. Groleau, Beidou Feng, Yonggang Yang, Adam C. Sedgwick, Hai Hao Han, Yang Wang, Han Min Wang, Fang Huang, Steven D. Bull, Hua Zhang, Chusen Huang, Yi Zang, Jia Li, Xiao Peng He, Ping Li, Bo Tang, Tony D. JamesJonathan L. Sessler

Research output: Contribution to journalArticlepeer-review

22 Citations (SciVal)

Abstract

Changes in adenosine triphosphate (ATP) and peroxynitrite (ONOO-) concentrations have been correlated in a number of diseases including ischemia-reperfusion injury and drug-induced liver injury. Herein, we report the development of a fluorescent probe ATP-LW, which enables the simultaneous detection of ONOO- and ATP. ONOO- selectively oxidizes the boronate pinacol ester of ATP-LW to afford the fluorescent 4-hydroxy-1,8-naphthalimide product NA-OH (λex = 450 nm, λem = 562 nm or λex = 488 nm, λem = 568 nm). In contrast, the binding of ATP to ATP-LW induces the spirolactam ring opening of rhodamine to afford a highly emissive product (λex = 520 nm, λem = 587 nm). Due to the differences in emission between the ONOO- and ATP products, ATP-LW allows ONOO- levels to be monitored in the green channel (λex = 488 nm, λem = 500-575 nm) and ATP concentrations in the red channel (λex = 514 nm, λem = 575-650 nm). The use of ATP-LW as a combined ONOO- and ATP probe was demonstrated using hepatocytes (HL-7702 cells) in cellular imaging experiments. Treatment of HL-7702 cells with oligomycin A (an inhibitor of ATP synthase) resulted in a reduction of signal intensity in the red channel and an increase in that of the green channel as expected for a reduction in ATP concentrations. Similar fluorescence changes were seen in the presence of SIN-1 (an exogenous ONOO- donor).

Original languageEnglish
Pages (from-to)174-183
Number of pages10
JournalJournal of the American Chemical Society
Volume144
Issue number1
Early online date21 Dec 2021
DOIs
Publication statusPublished - 12 Jan 2022

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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