Rapid-responsive Fluorescent Probes Based on Coumarin Dye for Sensitive Detection of Hypochlorite

CHENG Xiao-hong; RUAN Zhi-jun; ZHONG Zhi-cheng; LI Wang-nan

doi:10.3788/fgxb20183908.1182

您当前的位置：

首页 >

文章列表页 >

Rapid-responsive Fluorescent Probes Based on Coumarin Dye for Sensitive Detection of Hypochlorite

更新时间：2020-08-12

- Rapid-responsive Fluorescent Probes Based on Coumarin Dye for Sensitive Detection of Hypochlorite
- Chinese Journal of Luminescence Vol. 39, Issue 8, Pages: 1182-1191(2018)
- 作者机构：
  
  1. 湖北文理学院低维光电材料与器件湖北省重点实验室,湖北襄阳,441053
  2. 黄冈师范学院化学化工学院催化材料制备及应用湖北省重点实验室, 湖北黄冈 438000
- 作者简介：
- 基金信息：
  
  Supported by National Natural Science Foundation of China(21502047);Natural Scienc
- DOI：10.3788/fgxb20183908.1182
  CLC： O622.4
- Received：16 November 2017，
  
  Revised：04 March 2018，
  
  Published Online：08 April 2018，
  
  Published：05 August 2018
- 稿件说明：
移动端阅览
程晓红, 阮志军, 钟志成等. 基于香豆素的荧光传感器及其对次氯酸根的快速检测[J]. 发光学报, 2018,39(8): 1182-1191

CHENG Xiao-hong, RUAN Zhi-jun, ZHONG Zhi-cheng etc. Rapid-responsive Fluorescent Probes Based on Coumarin Dye for Sensitive Detection of Hypochlorite[J]. Chinese Journal of Luminescence, 2018,39(8): 1182-1191
程晓红, 阮志军, 钟志成等. 基于香豆素的荧光传感器及其对次氯酸根的快速检测[J]. 发光学报, 2018,39(8): 1182-1191 DOI： 10.3788/fgxb20183908.1182.

CHENG Xiao-hong, RUAN Zhi-jun, ZHONG Zhi-cheng etc. Rapid-responsive Fluorescent Probes Based on Coumarin Dye for Sensitive Detection of Hypochlorite[J]. Chinese Journal of Luminescence, 2018,39(8): 1182-1191 DOI： 10.3788/fgxb20183908.1182.

摘要

本文报道了两个基于香豆素染料的次氯酸根荧光传感器（化合物C2和C4），可在不同条件下实现对次氯酸根的快速响应。利用次氯酸独特的氧化性，传感器C2和C4均可实现对次氯酸根的高选择性检测。在化合物C2的溶液中加入次氯酸根之后，溶液的荧光光谱表现出极大的荧光猝灭，这有利于在检测过程中产生明显的荧光信号输出。不同的是，化合物C4则对次氯酸根表现出明显的荧光增强响应。

Abstract

Taking advantage of the special oxidation property of hypochlorite

two novel coumarin-type fluorescent probes (compound C2 and C4) were synthesized for the rapid detection of ClO

. By virtue of its special oxidation property

both probes displayed high selectivity for ClO

over other anions. Upon the addition of ClO

anion

probe C2 displays extraordinary fluorescence quenching

which is beneficial to the production of a high signal output during detection process. Differently

probe C4 displays apparent enhancement in fluorescence emission spectra.

关键词

Keywords

references

XU Z, KIM S K, YOON J. Revisit to imidazolium receptors for the recognition of anions:highlighted research during 2006-2009[J]. Chem. Soc. Rev., 2010, 39:1457-1466.

THOMAS S W, JOLY G D, SWAGER T M. Chemical sensors based on amplifying fluorescent conjugated polymers[J]. Chem. Rev., 2007, 107:1339-1386.

YOON J, KIM S K, SINGH N J, et al.. Imidazolium receptors for the recognition of anions[J]. Chem. Soc. Rev., 2006, 35:355-360.

SUGIYAMA S, KUGIYAMA K, AIKAWA M, et al.. Hypochlorous acid, a macrophage product, induces endothelial apoptosis and tissue factor expression:involvement of myeloperoxidase-mediated oxidant in plaque erosion and thrombogenesis[J]. Atrerioscler. Thromb. Vasc. Biol., 2004, 24:1309-1314.

PATTISON D I, DAVIES M J. Absolute rate constants for the reaction of hypochlorous acid with protein side-chains and peptide bonds[J]. Chem. Res. Toxicol., 2001, 14:1453-1464.

STEINBECK M J, NESTI L J, SHARKEY P F, et al.. Myeloperoxidase and chlorinated peptides in osteoarthritis:potential biomarkers of the disease[J]. J. Orthop. Res., 2007, 25:1128-1135.

AOKL T, MUNEMORL M. Continuous flow determination of free chlorine in water[J]. Anal. Chem., 1983, 55:209-212.

WANG B H, CHEN D, KAMBAM S, et al.. A highly specific fluorescent probe for hypochlorite based on fluorescein derivative and its endogenous imaging in living cells[J]. Dyes Pigments, 2015, 120:22-29.

CUI K, ZHANG D Q, ZHANG G X, et al.. A highly selective naked-eye probe for hypochlorite with the p-methoxyphenol-substituted aniline compound[J]. Tetrahedron Lett., 2010, 51:6052-6055.

HWANG J, CHOI M G, BAE J, et al.. Signaling of hypochlorous acid by selective deprotection of dithiolane[J]. Org. Biomol. Chem., 2011, 9:7011-7015.

KIM T-Ⅱ, PARK S, CHOI Y, et al.. A BODIPY-based probe for the selective detection of hypochlorous acid in living cells[J]. Chem.-Asian J., 2011, 6:1358-1361.

KIM H N, LEE M H, KIM H J, et al.. A new trend in rhodamine-based chemosensors:application of spirolactam ring-opening to sensing ions[J]. Chem. Soc. Rev., 2008, 37:1465-1472.

QUANG D T, KIM J S. Fluoro-and chromogenic chemodosimeters for heavy metal ion detection in solution and biospecimens[J]. Chem. Rev., 2010, 110:6280-6301.

SHEPHERD J, HILDERBRAND S A, WATERMAN P, et al.. A fluorescent probe for the detection of myeloperoxidase activity in atherosclerosis-associated macrophages[J]. Chem. Biol., 2007, 14:1221-1231.

SUN Z N, LIU F Q, CHEN Y, et al.. A highly specific BODIPY-based fluorescent probe for the detection of hypochlorous acid[J]. Org. Lett., 2008, 10:2171-2174.

YUAN L, LIN W Y, SONG J Z, et al.. Development of an ICT-based ratiometric fluorescent hypochlorite probe suitable for living cell imaging[J]. Chem. Commun., 2011, 47:12691-12693.

YANG Y K, CHO H J, LEE J, et al.. A rhodamine-hydroxamic acid-based fluorescent probe for hypochlorous acid and its applications to biological imagings[J]. Org. Lett., 2009, 11:859-861.

CHEN X Q, WANG X C, WANG S J, et al.. Selective and sensitive fluorescence probe for the hypochlorite anion[J]. Chem. Eur. J., 2008, 14:4719-4724.

CHEN X Q, LEE K A, HA E M, et al.. A specific and sensitive method for detection of hypochlorous acid for the imaging of microbe-induced HOCl production[J]. Chem. Commun., 2011, 47:4373-4375.

WANG Y, XIA J C, HAN J, et al.. A fast-responsive fluorescent probe based on BODIPY dye for sensitive detection of hypochlorite and its application in real water samples[J]. Talanta, 2016, 161:847-853.

WANG B H, CHEN D, KAMBAM S, et al.. A highly specific fluorescent probe for hypochlorite based on fluorescein derivative and its endogenous imaging in living cells[J]. Dyes Pigments, 2015, 120:22-29.

LIA D X, FENG Y, LIN J Z, et al.. A mitochondria-targeted two-photon fluorescent probe for highly selective and rapid detection of hypochlorite and its bio-imaging in living cells[J]. Sens. Actuator B:Chem., 2016, 222:483-491.

MAITY D, GOVINDARAJU T. Conformationally constrained(coumarin-triazolyl-bipyridyl) click fluoroionophore as a selective Al3+ sensor[J]. Inorg. Chem.. 2010, 49:7229-7231.

WANG L, LI Y F, LI G P, et al.. Electrochemical characters ofhymecromone at the graphene modified electrode and its analytical application[J]. Anal. Methods, 2015, 7:3000-3005.

SARKAR D, PRAMANIK A, BISWAS S, et al.. Al3+ selective coumarin based reversible chemosensor:application in living cell imaging and as integrated molecular logic gate[J]. RSC Adv., 2014, 4:30666-30672.

ZHANG Y, GUO X, TIAN X, et al.. Carboxamidoquinoline-coumarin derivative:a ratiometric fluorescent sensor for Cu(Ⅱ) in a dual fluorophore hybrid[J]. Sens. Actuators B:Chem., 2015, 218:37-41.

VASYLEVSKA A S, KARASYOV A A, BORISOV S M, et al.. Novel coumarin-based fluorescent pH indicators, probes and membranes covering a broad pH range[J]. Anal. Bioanal. Chem., 2007, 387:2131-2141.

LIU X D, XU Y, SUN R, et al.. A coumarin-indole-based near-infrared ratiometric pH probe for intracellular fluorescence imaging[J]. Analyst, 2013, 138:6542-6550.

YUAN L, LIN W, XIE Y, et al.. Development of a ratiometric fluorescent sensor for ratiometric imaging of endogenously produced nitricoxide in macrophage cells[J]. Chem. Commun., 2011, 47:9372-9374.

ZHANG K M, DOU W, LI P X, et al.. A coumarin-based two-photon probe for hydrogen peroxide[J]. Biosens. Bioelectron., 2015, 64:542-546.

DEROSA M C, HODGSON D J, ENRIGHT G D, et al.. Iridium luminophore complexes for unimolecular oxygen sensors[J]. J. Am. Chem. Soc., 2004, 126:7619-7626.

JUNG H S, KWON P S, LEE J W, et al.. Coumarin-derived Cu2+-selective fluorescence sensor:synthesis, mechanisms, and applications in living cells[J]. J. Am. Chem. Soc., 2009, 131:2008-2012.

SARKAR D, PRAMANIK A K, MONDAL T K. A novel coumarin based molecular switch for dual sensing of Zn(Ⅱ) and Cu(Ⅱ)[J]. RSC Adv., 2015, 5:7647-7653.

HATAI J, BANDYOPADHYAY S. Altered selectivity of a dipicolylamine based metalion receptor[J]. Chem. Commun. 2014, 50:64-66.

ZHANG H, RUDKEVICH D M. A FRET approach to phosgene detection[J]. Chem. Commun., 2007, 43:1238-1239.

CHO D G, SESSLER J L. Modern reaction-based indicator systems[J]. Chem. Soc. Rev., 2009, 38:1647-1662.

KIM S Y, HONG J I. Chromogenic and fluorescent chemodosimeter for detection of fluoride in aqueous solution[J]. Org. Lett., 2007, 9:3109-3112.

ZHANG M, YU M, LI F, et al.. A highly selective fluorescence turn-on sensor for cysteine/homocysteine and its application in bioimaging[J]. J. Am. Chem. Soc., 2007, 129:10322-10323.

LIN W Y, LONG L L, CHEN B B, et al.. A ratiometric fluorescent probe for hypochlorite based on a deoximation reaction[J]. Chem. Eur. J., 2009, 15:2305-2309.

YUAN L, LIN W Y, XIE Y N, et al.. Fluorescent detection of hypochlorous acid from turn-on to fret-based ratiometry by a HOCl-mediated cyclization reaction[J]. Chem. Eur. J., 2012, 18:2700-2706.

SHI J, LI Q Q, ZHANG X, et al.. Simple triphenylamine-based luminophore as a hypochlorite chemosensor[J]. Sens. Actuators B:Chem., 2010, 145:583-587.

ZHANG D Q. Highly selective and sensitive colorimetric probes for hypochlorite anion based on azo derivatives[J]. Spectrochim. Acta Part A, 2010, 77:397-401.

ZHAO N, WU Y H, WANG R M, et al.. An iridium(Ⅲ) complex of oximated 2,2-bipyridine as a sensitive phosphorescent sensor for hypochlorite[J]. Analyst, 2011, 136:2277-2282.

KIM J H, KIM H J, KIM S H, et al.. Fluorescent coumarinyldithiane as a selective chemodosimeter for mercury(Ⅱ) ion in aqueous solution[J]. Tetrahedron Lett., 2009, 50:5958-5961.

WILLIAMS A T R, WINFIELD S A, MILLER J N. Relative fluorescence quantum yields using a computer-controlled luminescence spectrometer[J]. Analyst, 1983, 108:1067-1071.

BIRKS J B. Photophysics of Aromatic Molecules[M]. New York:Wiley, 1970.

TURRO N J, RAMAMURTHY V, SCAIANO J C. Modern Molecular Photochemistry of Organic Molecules[M]. Sausalito:University Science Books, 2010.

LEE K S, KIM H J, KIM G H, et al.. Fluorescent chemodosimeter for selective detection of cyanide in water[J]. Org. Lett., 2008, 10:49-51.

WU J S, LIU W M, GE J, et al.. New sensing mechanisms for design of fluorescent chemosensors emerging in recent years[J]. Chem. Soc. Rev., 2011, 40:3483-3495.

LUO J, XIE Z, LAM J W Y, et al.. Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole[J]. Chem. Commun., 2001, 37:1740-1741.

WU J S, LIU W M, ZHUANG X Q, et al.. Fluorescence turn on of coumarin derivatives by metal cations:a new signaling mechanism based on C[FY=,1] N isomerization[J]. Org. Lett., 2007, 9:33-36.

WANG P, LIU J, LV X, et al.. A naphthalimide-based glyoxal hydrazone for selective fluorescence turn-on sensing of cys and hcy[J]. Org. Lett., 2012, 14:520-523.

LI D X, FENG Y, LIN J Z, et al.. A mitochondria-targeted two-photon fluorescent probe for highly selective and rapid detection of hypochlorite and its bio-imaging in living cells[J]. Sens. Actuators B:Chem., 2016, 222:483-491.

SHORTREED M, KOPELMAN R, KUHN M, et al.. Fluorescent fiber-optic calcium sensor for physiological measurements[J]. Anal. Chem., 1996, 68:1414-1418.

Views

117

下载量

CSCD

Alert me when the article has been cited

提交

Tools

Publicity Resources

Research Progress of Circulating Tumor Cell Detection Based on Fluorescence Method

Rapid Detection of Neonicotinoids by Metal Halide CH₃NH₃PbBr₃ Perovskite Quantum Dots

Crosslinking Agents Enhancing Fluorescence Performance of Carboxylate Graphene Quantum Dots

Preparation of Copper/Silver Bimetallic Nanoclusters Stabilized by Penicillamine and Their Application in Silver Ion Detection

Fluorescence Interaction Between Folate Molecules and CdTe and CdTe/CdS Quantum Dots

Related Author

YANG Rui

LI Ziyue

SHEN Yi

GUO Lihua

ZHOU Bingshuai

LI Jiawei

LIU Haipeng

DONG Biao

Related Institution

State Key Laboratory of Integrated Optoelectronics， College of Electronic Science and Engineering， Jilin University

Department of Plastic and Aesthetic Surgery， The First Hospital of Jilin University

Hubei Key Laboratory of Nutritional Quality and Safety of Agro Products， Institute of Agricultural Quality Standards and Testing Technology Research， Hubei Academy of Agricultural Science

College of Life Science， Yangtze University

Nanophotonics and Biophotonics Key Laboratory of Jilin Province， School of Physics， Changchun University of Science and Technology

AI问答

Address：No.3888 Dong Nanhu Road, Changchun, Jilin, China Postal code：130033
Tel：0431-86176862 Email：fgxbt@126.com
Technical support is provided by Beijing Founder electronics co., LTD 吉ICP备11002662号-17 京公网安备11010802024621
It is recommended to read the content of this site in Chrome&IE9+. Please switch to extreme mode in browser 360.
Cookies We use cookies to help provide and enhance our service and tailor content. By continuing, you agree to the use of cookies.

⁰