A 3,7-Dihydroxyphenoxazine-based Fluorescent Probe for Selective Detection of Intracellular Hydrogen Peroxide

Zhiqiang Han; Xiao Liang; Xuejiao Ren; Luqing Shang; Zheng Yin

doi:10.1002/asia.201501304

A 3,7-Dihydroxyphenoxazine-based Fluorescent Probe for Selective Detection of Intracellular Hydrogen Peroxide

Chem Asian J. 2016 Mar 18;11(6):818-22. doi: 10.1002/asia.201501304. Epub 2016 Feb 10.

Authors

Zhiqiang Han^{1

2}, Xiao Liang^{1

2}, Xuejiao Ren^{1

2}, Luqing Shang^{3

4}, Zheng Yin^{5

6}

Affiliations

¹ College of Pharmacy & State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin, 300071, China.
² Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin, 300071, China.
³ College of Pharmacy & State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin, 300071, China. shanglq@nankai.edu.cn.
⁴ Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin, 300071, China. shanglq@nankai.edu.cn.
⁵ College of Pharmacy & State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin, 300071, China. zheng_yin@nankai.edu.cn, zheng_yin@nankai.edu.cn.
⁶ Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin, 300071, China. zheng_yin@nankai.edu.cn, zheng_yin@nankai.edu.cn.

PMID: 26807851
DOI: 10.1002/asia.201501304

Abstract

A novel N-borylbenzyloxycarbonyl-3,7-dihydroxyphenoxazine fluorescent probe (NBCD) for detecting H2O2 in living cells is described. The probe could achieve high selectivity for detecting H2O2 over other biological reactive oxygen species (ROS). In addition, upon addition of H2O2, NBCD exhibited color change from colorless to pink, which makes it a "naked-eye" probe for H2O2 detection. NBCD could not only be used to detect enzymatically generated H2O2 but also to detect H2O2 in living systems by using fluorescence spectroscopy, with a detection limit of 2 μm. Importantly, NBCD enabled the visualization of epidermal growth factor (EGF)-stimulated H2O2 generation inside the cells.

Keywords: N-protected 3,7-dihydroxyphenoxazine; fluorescent probes; hydrogen peroxide; imaging agents; reactive oxygen species; sensors.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Fluorescent Dyes / chemistry*
Humans
Hydrogen Peroxide / analysis*
Phenazines / chemistry*
Reactive Oxygen Species / analysis
Spectrometry, Fluorescence

Substances

Fluorescent Dyes
Phenazines
Reactive Oxygen Species
dihydroxyphenoxazine
Hydrogen Peroxide