Nitric oxide turn-on fluorescent probe based on deamination of aromatic primary monoamines

Tsun Wei Shiue, Yen Hao Chen, Chi Ming Wu, Gyan Singh, Hsing Yin Chen, Chen Hsiung Hung, Wen Feng Liaw, Yun-Ming Wang*

*Corresponding author for this work

Research output: Contribution to journalArticle

75 Scopus citations

Abstract

The stable, water-soluble, and nonfluorescent FA-OMe can sense nitric oxide (NO) and form the intensely fluorescent product dA-FA-OMe via reductive deamination of the aromatic primary amine. The reaction is accompanied by a notable increase of the fluorescent quantum yield from 1.5 to 88.8%. The deamination mechanism of FA-OMe with NO was proposed in this study. The turn-on fluorescence signals were performed by suppression of photoinduced electron transfer (PeT), which was demonstrated by density functional theory (DFT) calculations of the components forming FA-OMe and dA-FA-OMe. Furthermore, FA-OMe showed water solubility and good stability at physiological pHs. Moreover, the selectivity study indicated that FA-OMe had high specificity for NO over other reactive oxygen/nitrogen species. In an endogenously generated NO detection study, increasing the incubation time of FA-OMe with lipopolysaccharide (LPS) pretreated Raw 264.7 murine macrophages could cause an enhanced fluorescence intensity image. In addition, a diffusion/localization cell imaging study showed that FA-OMe could be trapped in Raw 264.7 cells. These cell imaging results demonstrated that FA-OMe could be used as a turn-on fluorescent sensor for the detection of endogenously generated NO.

Original languageEnglish
Pages (from-to)5400-5408
Number of pages9
JournalInorganic Chemistry
Volume51
Issue number9
DOIs
StatePublished - 7 May 2012

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    Shiue, T. W., Chen, Y. H., Wu, C. M., Singh, G., Chen, H. Y., Hung, C. H., Liaw, W. F., & Wang, Y-M. (2012). Nitric oxide turn-on fluorescent probe based on deamination of aromatic primary monoamines. Inorganic Chemistry, 51(9), 5400-5408. https://doi.org/10.1021/ic300379u