Water-soluble Hantzsch ester as switch-on fluorescent probe for efficiently detecting nitric oxide.
A water soluble Hantzsch ester derivative of coumarin, DHPS, was synthesized and successfully applied in the fluorescent sensing nitric oxide (NO) in aqueous solution. The fluorescence of probe DHPS is extremely weak, while its fluorescence was greatly switched on upon the addition of NO solution and showed high selectivity and sensitivity to NO. The limitation of the detection was calculated to be 18nM. The NO-induced aromatization of dihydropyridine in DHPS to pyridine derivative (PYS) proved to be the switching mechanism for the fluorescent sensing process, which was confirmed through spectra characterization and computation study. Cytotoxicity assay demonstrated both DHPS and PYS are biocompatible, the DHPS was successfully applied to track the endogenously produced NO in the RAW 264.7 cells.
National Institute for Food and Drug Control, Beijing 100050, China.
Hui-Li
HL
Wang
College of Chemistry, Beijing Normal University, Beijing 100875, China.
Fu-Tao
FT
Liu
College of Chemistry, Beijing Normal University, Beijing 100875, China.
Ai-Xiang
AX
Ding
College of Chemistry, Beijing Normal University, Beijing 100875, China.
Su-Fang
SF
Ma
National Institute for Food and Drug Control, Beijing 100050, China. Electronic address: helan1961@aliyun.com.
Lan
L
He
National Institute for Food and Drug Control, Beijing 100050, China. Electronic address: lanlin@yeah.net.
Lan
L
Lin
College of Chemistry, Beijing Normal University, Beijing 100875, China. Electronic address: luzl@bnu.edu.cn.
Zhong-Lin
ZL
Lu
D000818:Animals; D003374:Coumarins / Q000737:chemistry*; D004952:Esters / Q000737:chemistry; D005453:Fluorescence; D005456:Fluorescent Dyes / Q000737:chemistry*; D057230:Limit of Detection; D051379:Mice; D008856:Microscopy, Fluorescence / Q000379:methods*; D008958:Models, Molecular; D009569:Nitric Oxide / Q000032:analysis*; D011725:Pyridines / Q000737:chemistry; D000067996:RAW 264.7 Cells; D012995:Solubility; D013050:Spectrometry, Fluorescence / Q000379:methods; D014867:Water / Q000737:chemistry
D003374:Coumarins; D004952:Esters; D005456:Fluorescent Dyes; D011725:Pyridines; D014867:Water; D009569:Nitric Oxide; C030123:coumarin; C023666:pyridine
Cell-imaging; Fluorescent probe; Hantzsch ester; Nitric oxide