Water-soluble Hantzsch ester as switch-on fluorescent probe for efficiently detecting nitric oxide

被引：26

作者：

Wang, Hui-Li ^{[1
]}

Liu, Fu-Tao ^{[2
]}

Ding, Ai-Xiang ^{[2
]}

Ma, Su-Fang ^{[2
]}

He, Lan ^{[1
]}

Lin, Lan ^{[1
]}

Lu, Zhong-Lin ^{[2
]}

机构：

[1] Natl Inst Food & Drug Control, Beijing 100050, Peoples R China

[2] Beijing Normal Univ, Coll Chem, Beijing 100875, Peoples R China

来源：

SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY | 2016年 / 169卷

关键词：

Nitric oxide; Hantzsch ester; Fluorescent probe; Cell-imaging; RATIONAL DESIGN; CELLS; CHROMOPHORE; INDICATORS; STRATEGY; COMPLEX;

D O I：

10.1016/j.saa.2016.06.014

中图分类号：

O433 [光谱学];

学科分类号：

0703 ; 070302 ;

摘要：

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 18 nM. 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. (C) 2016 Elsevier B.V. All rights reserved.

引用

页码：1 / 6

页数：6

共 48 条

[1] DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].

BECKE, AD .

JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652

[2] Nitric oxide and the immune response [J].

Bogdan, C .

NATURE IMMUNOLOGY, 2001, 2 (10) :907-916

[3]

Cannon RO, 1998, CLIN CHEM, V44, P1809

[4] Novel B,O-chelated fluorescent probe for nitric oxide imaging in Raw 264.7 macrophages and onion tissues [J].

Chen, Jian-Bo ;

Zhang, Hui-Xian ;

Guo, Xiao-Feng ;

Wang, Hong ;

Zhang, Hua-Shan .

ANALYTICA CHIMICA ACTA, 2013, 800 :77-86

[5] A fast and selective two-photon phosphorescent probe for the imaging of nitric oxide in mitochondria [J].

Chen, Xiang ;

Sun, Lingli ;

Chen, Yu ;

Cheng, Xiaolin ;

Wu, Weijun ;

Ji, Liangnian ;

Chao, Hui .

BIOMATERIALS, 2015, 58 :72-81

[6] Studies on the α-acetylation of δ-valerolactone and ε-caprolactone [J].

Christoffers, J ;

Oertling, H ;

Fischer, P ;

Frey, W .

TETRAHEDRON, 2003, 59 (21) :3769-3778

[7] Quinoline-Based Two-Photon Fluorescent Probe for Nitric Oxide in Live Cells and Tissues [J].

Dong, Xiaohu ;

Heo, Cheol Ho ;

Chen, Shiyu ;

Kim, Hwan Myung ;

Liu, Zhihong .

ANALYTICAL CHEMISTRY, 2014, 86 (01) :308-311

[8] Photoactivable Platforms for Nitric Oxide Delivery with Fluorescence Imaging [J].

Fraix, Aurore ;

Sortino, Salvatore .

CHEMISTRY-AN ASIAN JOURNAL, 2015, 10 (05) :1116-1125

[9]

Frisch M.J., 2016, Gaussian, V16

[10] Highly sensitive fluorescence probes for nitric oxide based on boron dipyrromethene chromophore-rational design of potentially useful bioimaging fluorescence probe [J].

Gabe, Y ;

Urano, Y ;

Kikuchi, K ;

Kojima, H ;

Nagano, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (10) :3357-3367

← 1 2 3 4 5 →