A Chemiluminescent Probe for HNO Quantification and Real-Time Monitoring in Living Cells

Weiwei An, Lucas S. Ryan, Audrey G. Reeves, Kevin J. Bruemmer, Lyn Mouhaffel, Jeni L. Gerberich, Alexander Winters, Ralph P Mason, Alexander R. Lippert

Research output: Contribution to journalArticle

14 Scopus citations

Abstract

Azanone (HNO) is a reactive nitrogen species with pronounced biological activity and high therapeutic potential for cardiovascular dysfunction. A critical barrier to understanding the biology of HNO and furthering clinical development is the quantification and real-time monitoring of its delivery in living systems. Herein, we describe the design and synthesis of the first chemiluminescent probe for HNO, HNOCL-1, which can detect HNO generated from concentrations of Angeli's salt as low as 138 nm with high selectivity based on the reaction with a phosphine group to form a self-cleavable azaylide intermediate. We have capitalized on this high sensitivity to develop a generalizable kinetics-based approach, which provides real-time quantitative measurements of HNO concentration at the picomolar level. HNOCL-1 can monitor dynamics of HNO delivery in living cells and tissues, demonstrating the versatility of this method for tracking HNO in living systems.

Original languageEnglish (US)
Pages (from-to)1361-1365
Number of pages5
JournalAngewandte Chemie - International Edition
Volume58
Issue number5
DOIs
StatePublished - Jan 28 2019

Keywords

  • bioanalysis
  • chemiluminescence
  • nitroxyl
  • phosphine

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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    An, W., Ryan, L. S., Reeves, A. G., Bruemmer, K. J., Mouhaffel, L., Gerberich, J. L., Winters, A., Mason, R. P., & Lippert, A. R. (2019). A Chemiluminescent Probe for HNO Quantification and Real-Time Monitoring in Living Cells. Angewandte Chemie - International Edition, 58(5), 1361-1365. https://doi.org/10.1002/anie.201811257