A 2,5-diaryl-1,3,4-oxadiazole-based fluorescent probe for rapid and highly selective recognition of hydrogen sulfide with a large Stokes shift through switching on ESIPT

被引：32

作者：

Tang, Lijun ^{[1
]}

Zheng, Zhuxuan ^{[1
]}

Zhong, Keli ^{[1
]}

Bian, Yanjiang ^{[1
]}

机构：

[1] Bohai Univ, Dept Chem, Jinzhou 121013, Peoples R China

来源：

TETRAHEDRON LETTERS | 2016年 / 57卷 / 12期

基金：

中国国家自然科学基金;

关键词：

Hydrogen sulfide; Fluorescence probe; Ratiometric; ESIPT; 1,3,4-Oxadiazole; THICK-FILM RESISTORS; H2S; SENSOR; CHEMODOSIMETER; CHEMOSENSORS; CONSUMPTION; DERIVATIVES; COPPER; CELLS; ANION;

D O I：

10.1016/j.tetlet.2016.02.056

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new 2,5-diaryl-1,3,4-oxadiazole derived ratiometric fluorescent probe (OXDNP) for hydrogen sulfide recognition has been developed. Probe OXDNP displays highly selective and sensitive detection to HS- over other anions and thiol-containing amino acids in DMSO solution with fast response and a large Stokes shift. Through HS- induced thiolysis of the dinitrophenyl ether, the excited state intramolecular proton transfer (ESIPT) featured precursor was released, which led to dual fluorescence emission 'turn on' and ratiometric emission behavior of the sensing system. The pseudo-first-order reaction rate constant was calculated to be 1.234 s(-1). The HS- recognition mechanism was proved by HPLC-MS and H-1 NMR comparison investigations. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：1361 / 1364

页数：4

共 70 条

[21] Design, synthesis and biological evaluation of 1,3,4-oxadiazole derivatives [J].

Jha, Keshari Kishore ;

Samad, Abdul ;

Kumar, Yatendra ;

Shaharyar, Mohd. ;

Khosa, Ratan Lal ;

Jain, Jainendra ;

Kumar, Vikash ;

Singh, Priyanka .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (11) :4963-4967

[22] A new chromo-chemodosimeter selective for sulfide anion [J].

Jiménez, D ;

Martínez-Máñez, R ;

Sancenón, F ;

Ros-Lis, JV ;

Benito, A ;

Soto, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (30) :9000-9001

[23] Endogenous production of hydrogen sulfide in mammals [J].

Kamoun, P .

AMINO ACIDS, 2004, 26 (03) :243-254

[24] Endogenous hydrogen sulfide overproduction in Down syndrome [J].

Kamoun, P ;

Belardinelli, MC ;

Chabli, A ;

Lallouchi, K ;

Chadefaux-Vekemans, B .

AMERICAN JOURNAL OF MEDICAL GENETICS PART A, 2003, 116A (03) :310-311

[25] 1, 3, 4-Oxadiazoles from functionalized N-acylbenzotriazoles and acyl hydrazides [J].

Katritzky, Alan R. ;

Mohapatra, Prabhu P. ;

Huang, Longchuan .

ARKIVOC, 2008, :62-68

[26] Disodium Salt of 2-(5-phenyl-1, 3, 4-oxadiazol-2-yl) Phenyl Phosphate as a Fluorescent Probe for Determination of ALP [J].

Lei Yingjie ;

Ouyang Jie ;

Ding Mei .

APPLIED MECHANICS AND MECHANICAL ENGINEERING II, PTS 1 AND 2, 2012, 138-139 :1109-1114

[27] A fluorescent probe for H2S in vivo with fast response and high sensitivity [J].

Li, H. D. ;

Yao, Q. C. ;

Fan, J. L. ;

Jiang, N. ;

Wang, J. Y. ;

Xia, J. ;

Peng, X. J. .

CHEMICAL COMMUNICATIONS, 2015, 51 (90) :16225-16228

[28] Syntheses, photoluminescence and electroluminescence of four heteroleptic iridium complexes with 2-(5-phenyl-1,3,4-oxadiazol-2-yl)phenol derivatives as ancillary ligands [J].

Li, Hong-Yan ;

Li, Tian-Yi ;

Teng, Ming-Yu ;

Xu, Qiu-Lei ;

Zhang, Song ;

Jin, Yi-Ming ;

Liu, Xuan ;

Zheng, You-Xuan ;

Zuo, Jing-Lin .

JOURNAL OF MATERIALS CHEMISTRY C, 2014, 2 (06) :1116-1124

[29] Chromogenic and fluorogenic chemosensors for hydrogen sulfide: review of detection mechanisms since the year 2009 [J].

Li, Jianfang ;

Yin, Caixia ;

Huo, Fangjun .

RSC ADVANCES, 2015, 5 (03) :2191-2206

[30] Hydrogen Sulfide and Cell Signaling [J].

Li, Ling ;

Rose, Peter ;

Moore, Philip K. .

ANNUAL REVIEW OF PHARMACOLOGY AND TOXICOLOGY, VOL 51, 2011, 2011, 51 :169-187

← 1 2 3 4 5 6 7 →