四苯乙烯类聚集诱导发光探针在生物分子检测领域的应用

杨学琴; 来守军; 丁媛媛; 马丽丽; 王晶凤; 关晓琳

doi:10.37188/CJL.20220080

您当前的位置：

首页 >

文章列表页 >

四苯乙烯类聚集诱导发光探针在生物分子检测领域的应用

发光学应用及交叉前沿 | 更新时间：2022-10-19

- 四苯乙烯类聚集诱导发光探针在生物分子检测领域的应用
  增强出版
- Application of Tetraphenylene Aggregation-induced Emission Probes in Field of Biomolecular Detection
- 发光学报 2022年43卷第6期页码：961-985
- 作者机构：
  
  1.西北师范大学化学化工学院，甘肃兰州　730070
  2.兰州文理学院化工学院，甘肃兰州　730000
- 作者简介：
  
  [ "杨学琴（1996-），女，甘肃会宁人，硕士研究生，2019年于兰州文理学院获得学士学位，主要从事AIE荧光探针及其在生物成像方面应用的研究。Email: 2410121332@qq.com" ]
  [ "关晓琳（1979-），女，甘肃兰州人，博士，副教授，硕士生导师，2007 年于兰州大学获得博士学位，主要从事生物荧光成像探针和药物释放领域的各类量子点材料及功能AIE 聚合物的研究。Email: guanxiaolin@nwnu.edu.cn" ]
- 基金信息：
  
  国家自然科学基金(21761032;21965032;51302222;1363021);甘肃省自然科学研究基金(20JR5RA525;20JR10RA143);兰州文理学院博士专项计划基金(2020BSZX08)
- DOI：10.37188/CJL.20220080
  中图分类号： O657.3
- 纸质出版日期：2022-06-05，
  
  收稿日期：2022-03-10，
  
  修回日期：2022-03-20，
- 稿件说明：
移动端阅览
杨学琴,来守军,丁媛媛等.四苯乙烯类聚集诱导发光探针在生物分子检测领域的应用[J].发光学报,2022,43(06):961-985.

YANG Xue-qin,LAI Shou-jun,DING Yuan-yuan,et al.Application of Tetraphenylene Aggregation-induced Emission Probes in Field of Biomolecular Detection[J].Chinese Journal of Luminescence,2022,43(06):961-985.
杨学琴,来守军,丁媛媛等.四苯乙烯类聚集诱导发光探针在生物分子检测领域的应用[J].发光学报,2022,43(06):961-985. DOI： 10.37188/CJL.20220080.

YANG Xue-qin,LAI Shou-jun,DING Yuan-yuan,et al.Application of Tetraphenylene Aggregation-induced Emission Probes in Field of Biomolecular Detection[J].Chinese Journal of Luminescence,2022,43(06):961-985. DOI： 10.37188/CJL.20220080.

摘要

生物体内存在各类生物离子和分子，其含量变化可以反映生物体的健康情况。因此，开发用于监测生物系统中离子或分子含量的方法是非常重要的。近年来，具有聚集诱导发光（Aggregation⁃induced emission，AIE）性质的荧光材料由于其独特的光电性能及生物活性，在光电材料、化学传感、生物成像等领域展现出广泛的应用前景。目前，在具有较高荧光量子产率的聚集诱导发光分子（AIEgens）中，四苯乙烯（TPE）成为最具有代表性和常用的分子之一，具有合成简便、易功能化以及优异的AIE效应等优点。本文综述了近年来基于TPE的荧光材料在生物金属离子、生物小分子和生物大分子检测方面的研究进展，分析了基于TPE的荧光探针所面临的挑战，并对其应用前景进行了展望，以期为制备合成简单、生物相容性好、检出限低的AIE荧光探针提供参考。

Abstract

There are various types of biometal ions and biomolecules in the organism and their content changes can reflect the health of living body. Therefore， it is very important to develop a detection method for monitoring the content of biometal ions or biomolecules in biological systems. In recent years， fluorescent materials with enhanced properties of aggregation-induced emission（AIE） have shown wide application prospects in the fields of optoelectronic materials， chemical sensing， and bio-imaging due to their unique optoelectronic properties and biological activities. At present， tetraphenylethylene（TPE） has become one of the most representative and commonly used molecules among aggregation-induced luminescent molecules（AIEgens） with high fluorescence quantum yield， which has the advantages of simple synthesis， easy to functionalize， and excellent AIE effect. This paper reviews the research progress of tetraphenylethylene-based fluorescent materials in the detection of biometal ions， small biomolecules and biomacromolecules in recent years. The challenges faced of fluorescent probes are analyzed and the development prospects are expected. It is expected to provide a reference for preparing and synthesizing fluorescent probes with good biocompatibility and low detection limit.

关键词

聚集诱导发光四苯乙烯生物金属离子生物小分子生物大分子

Keywords

aggregation-induced emissiontetraphenylethylenebiometal ionssmall biomoleculebiomacromolecule

references

DING D，LI K，LIU B，et al. Bioprobes based on AIE fluorogens ［J］. Acc. Chem. Res.， 2013，46（11）：2441-2453. doi: 10.1021/ar3003464http://dx.doi.org/10.1021/ar3003464

XIE H F，YU C J，HUANG Y L，et al. A turn-off fluorescent probe for the detection of Cu2+ based on a tetraphenylethylene-functionalized salicylaldehyde Schiff-base ［J］. Mater. Chem. Front.， 2020，4（5）：1500-1506. doi: 10.1039/c9qm00759hhttp://dx.doi.org/10.1039/c9qm00759h

NIU G L，ZHANG R Y，SHI X J，et al. AIE luminogens as fluorescent bioprobes ［J］. Trends Analyt. Chem.， 2020，123：115769-1-28. doi: 10.1016/j.trac.2019.115769http://dx.doi.org/10.1016/j.trac.2019.115769

ZHAO M C，WANG M，LIU H J，et al. Continuous on-site label-free ATP fluorometric assay based on aggregation-induced emission of silole ［J］. Langmuir， 2009，25（2）：676-678. doi: 10.1021/la803762bhttp://dx.doi.org/10.1021/la803762b

HU F，LIU B. Organelle-specific bioprobes based on fluorogens with aggregation-induced emission（AIE） characteristics ［J］. Org. Biomol. Chem.， 2016，14（42）：9931-9944. doi: 10.1039/C6OB01414Chttp://dx.doi.org/10.1039/C6OB01414C

LI H Y，LIN H Y，LV W X，et al. Equipment-free and visual detection of multiple biomarkers via an aggregation induced emission luminogen-based paper biosensor ［J］. Biosens. Bioelectron.， 2020，165：112336. doi: 10.1016/j.bios.2020.112336http://dx.doi.org/10.1016/j.bios.2020.112336

吕妍婷，王琪，朱为宏. 聚集诱导发光材料在食品安全检测中的应用［J］. 发光学报， 2021，42（3）：319-335. doi: 10.37188/CJL.20200382http://dx.doi.org/10.37188/CJL.20200382

LYU Y T，WANG Q，ZHU W H. Food safety detection using aggregation-induced emission materials ［J］. Chin. J. Lumin.， 2021，42（3）：319-335. （in Chinese）. doi: 10.37188/CJL.20200382http://dx.doi.org/10.37188/CJL.20200382

LUO J D，XIE Z L，LAM J W Y，et al. Aggregation-induced emission of 1-methyl-1，2，3，4，5-pentaphenylsilole ［J］. Chem. Commun.， 2001，（18）：1740-1741. doi: 10.1039/b105159hhttp://dx.doi.org/10.1039/b105159h

王嘉慧，曾晓璇，吴玥，等. 具有pH响应性能的聚集诱导发光材料制备与表征［J］. 发光学报， 2021，42（3）：311-318. doi: 10.37188/CJL.20210020http://dx.doi.org/10.37188/CJL.20210020

WANG J H，ZENG X X，WU Y，et al. Synthesis and characterization of pH-responsive material with aggregation-induced emission property ［J］. Chin. J. Lumin.， 2021，42（3）：311-318. （in Chinese）. doi: 10.37188/CJL.20210020http://dx.doi.org/10.37188/CJL.20210020

MEI J，LEUNG N L C，KWOK R T K，et al. Aggregation-induced emission：together we shine，united we soar！［J］. Chem. Rev.， 2015，115（21）：11718-11940. doi: 10.1021/acs.chemrev.5b00263http://dx.doi.org/10.1021/acs.chemrev.5b00263

ZHAN C，YOU X，ZHANG G X，et al. Bio-/chemosensors and imaging with aggregation-induced emission luminogens ［J］. Chem. Rec.， 2016，16（4）：2142-2160. doi: 10.1002/tcr.201600045http://dx.doi.org/10.1002/tcr.201600045

赵思宇，张祥，卢伶，等. 具有聚集诱导发光性质的热活化延迟荧光材料综述［J］. 材料导报， 2020，34（17）：17155-17167. doi: 10.11896/cldb.20030026http://dx.doi.org/10.11896/cldb.20030026

ZHAO S Y，ZHANG X，LU L，et al. A review on thermally activated delayed fluorescent material with aggregation-induced emission property ［J］. Mater. Rep.， 2020，34（17）：17155-17167. （in Chinese）. doi: 10.11896/cldb.20030026http://dx.doi.org/10.11896/cldb.20030026

HUANG L，DAI L M. Aggregation-induced emission for highly selective and sensitive fluorescent biosensing and cell imaging ［J］. J. Polym. Sci. A Polym. Chem.， 2017，55（4）：653-659. doi: 10.1002/pola.28447http://dx.doi.org/10.1002/pola.28447

ZHANG P S，NIE X Z，GAO M，et al. A highly selective fluorescent nanoprobe based on AIE and ESIPT for imaging hydrogen sulfide in live cells and zebrafish ［J］. Mater. Chem. Front.， 2017，1（5）：838-845. doi: 10.1039/c6qm00223dhttp://dx.doi.org/10.1039/c6qm00223d

赵秋丽，卞洁鹏，杨庆浩，等. 聚集诱导发红光材料在生物成像领域的应用［J］. 材料导报， 2019，33（3）：522-535. doi: 10.11896/cldb.201903020http://dx.doi.org/10.11896/cldb.201903020

ZHAO Q L，BIAN J P，YANG Q H，et al. Application of aggregation-induced red emission materials in bioimaging ［J］. Mater. Rep.， 2019，33（3）：522-535. （in Chinese）. doi: 10.11896/cldb.201903020http://dx.doi.org/10.11896/cldb.201903020

GAO M，TANG B Z. AIE-based cancer theranostics ［J］. Coord. Chem. Rev.， 2020，402：213076-1-41. doi: 10.1016/j.ccr.2019.213076http://dx.doi.org/10.1016/j.ccr.2019.213076

张志军，康苗苗，王媛玮，等. 聚集诱导发光材料在光学诊疗中的研究进展［J］. 发光学报， 2021，42（3）：361-378. doi: 10.37188/CJL.20210029http://dx.doi.org/10.37188/CJL.20210029

ZHANG Z J，KANG M M，WANG Y W，et al. Recent advances of aggregation-induced emission materials in phototheranostics ［J］. Chin. J. Lumin.， 2021，42（3）：361-378. （in Chinese）. doi: 10.37188/CJL.20210029http://dx.doi.org/10.37188/CJL.20210029

KWOK R T K，LEUNG C W T，LAM J W Y，et al. Biosensing by luminogens with aggregation-induced emission characteristics ［J］. Chem. Soc. Rev.， 2015，44（13）：4228-4238. doi: 10.1039/c4cs00325jhttp://dx.doi.org/10.1039/c4cs00325j

SELVARAJ M，RAJALAKSHMI K，AHN D H，et al. Tetraphenylethene-based fluorescent probe with aggregation-induced emission behavior for Hg2+ detection and its application ［J］. Anal. Chim. Acta， 2021，1148：238178-1-12. doi: 10.1016/j.aca.2020.12.053http://dx.doi.org/10.1016/j.aca.2020.12.053

DONG X B，ZHANG G X，SHI J B，et al. A highly selective fluorescence turn-on detection of ClO- with 1-methyl-1，2-dihydropyridine-2-thione unit modified tetraphenylethylene ［J］. Chem. Commun.， 2017，53（85）：11654-11657. doi: 10.1039/c7cc07092fhttp://dx.doi.org/10.1039/c7cc07092f

WANG Y L，LIU H L，CHEN Z，et al. Aggregation-induced emission enhancement（AIEE）-active tetraphenylethene （TPE）-based chemosensor for CN- ［J］. Spectrochim. Acta A Mol. Biomol. Spectrosc.， 2021，245：118928. doi: 10.1016/j.saa.2020.118928http://dx.doi.org/10.1016/j.saa.2020.118928

HUANG X H，GU X G，ZHANG G X，et al. A highly selective fluorescence turn-on detection of cyanide based on the aggregation of tetraphenylethylene molecules induced by chemical reaction ［J］. Chem. Commun.， 2012，48（100）：12195-12197. doi: 10.1039/c2cc37094hhttp://dx.doi.org/10.1039/c2cc37094h

JIANG G Y，ZHU W P，CHEN Q Q，et al. A new tetraphenylethylene based AIE sensor with light-up and tunable measuring range for adenosine triphosphate in aqueous solution and in living cells ［J］. Analyst， 2017，142（23）：4388-4392. doi: 10.1039/c7an01336ahttp://dx.doi.org/10.1039/c7an01336a

TONG H，HONG Y N，DONG Y Q，et al. Protein detection and quantitation by tetraphenylethene-based fluorescent probes with aggregation-induced emission characteristics ［J］. J. Phys. Chem. B， 2007，111（40）：11817-11823. doi: 10.1021/jp073147mhttp://dx.doi.org/10.1021/jp073147m

TESKEY G，ABRAHEM R，CAO R Q，et al. Glutathione as a marker for human disease ［J］. Adv. Clin. Chem.， 2018，87：141-159. doi: 10.1016/bs.acc.2018.07.004http://dx.doi.org/10.1016/bs.acc.2018.07.004

LIAO C W，HSU Y C，CHU C C，et al. Aggregation-induced emission tetraphenylethene type derivatives for blue tandem organic light-emitting diodes ［J］. Org. Electron.， 2019，67：279-286. doi: 10.1016/j.orgel.2018.12.025http://dx.doi.org/10.1016/j.orgel.2018.12.025

FREDERICKSON C J. Neurobiology of zinc and zinc-containing neurons ［J］. Int. Rev. Neurobiol.，1989，31：145-238. doi: 10.1016/s0074-7742(08)60279-2http://dx.doi.org/10.1016/s0074-7742(08)60279-2

ASSAF S Y，CHUNG S H. Release of endogenous Zn2+ from brain tissue during activity ［J］. Nature，1984，308（5961）：734-736. doi: 10.1038/308734a0http://dx.doi.org/10.1038/308734a0

KUMAR V，KUMAR A，SINGH K，et al. Neurobiology of zinc and its role in neurogenesis ［J］. Eur. J. Nutr.， 2021，60（1）：55-64. doi: 10.1007/s00394-020-02454-3http://dx.doi.org/10.1007/s00394-020-02454-3

DOU M，GONG A J，LIANG H，et al. Improvement of symptoms in a rat model of depression through combined zinc and folic acid administration via up-regulation of the Trk B and NMDA ［J］. Neurosci. Lett.， 2018，683：196-201. doi: 10.1016/j.neulet.2018.07.036http://dx.doi.org/10.1016/j.neulet.2018.07.036

吴红梅，何成，王健，等. 基于水解活性的Zn2+荧光探针［J］. 发光学报， 2009，30（3）：275-284. doi: 10.1088/1674-1137/33/8/010http://dx.doi.org/10.1088/1674-1137/33/8/010

WU H M，HE C，WANG J，et al. Hydrolysis-activated fluorophore system as a molecular sensor for selective detection of Zn2+ ［J］. Chin. J. Lumin.， 2009，30（3）：275-284. （in English）. doi: 10.1088/1674-1137/33/8/010http://dx.doi.org/10.1088/1674-1137/33/8/010

QUE E L，DOMAILLE D W，CHANG C J. Metals in neurobiology：probing their chemistry and biology with molecular imaging ［J］. Chem. Rev.， 2008，108（5）：1517-1549. doi: 10.1021/cr078203uhttp://dx.doi.org/10.1021/cr078203u

XU J X，XIONG J W，QIN Y L，et al. A novel quinolinyl-tetraphenylethene-based fluorescence “turn-on” sensor for Zn2+ with a large Stokes shift and its applications for portable test strips and biological imaging ［J］. Mater. Chem. Front.， 2020，4（11）：3338-3348. doi: 10.1039/d0qm00446dhttp://dx.doi.org/10.1039/d0qm00446d

HE X X，WANG X M，ZHANG L，et al. Sensing and intracellular imaging of Zn2+ based on affinity peptide using an aggregation induced emission fluorescence “switch-on” probe ［J］. Sens. Actuators B Chem.， 2018，271：289-299. doi: 10.1016/j.snb.2018.05.082http://dx.doi.org/10.1016/j.snb.2018.05.082

MENG Q H，LIU H，SEN C，et al. A novel molecular probe sensing polynuclear hydrolyzed aluminum by chelation-enhanced fluorescence ［J］. Talanta， 2012，99：464-470. doi: 10.1016/j.talanta.2012.06.011http://dx.doi.org/10.1016/j.talanta.2012.06.011

DARBRE P D. Aluminium，antiperspirants and breast cancer ［J］. J. Inorg. Biochem.， 2005，99（9）：1912-1919. doi: 10.1016/j.jinorgbio.2005.06.001http://dx.doi.org/10.1016/j.jinorgbio.2005.06.001

LIAO Z C，YANG Z Y，LI Y，et al. A simple structure fluorescent chemosensor for high selectivity and sensitivity of aluminum ions ［J］. Dyes Pigm.， 2013，97（1）：124-128. doi: 10.1016/j.dyepig.2012.12.017http://dx.doi.org/10.1016/j.dyepig.2012.12.017

LI Y P，LIU X M，ZHANG Y H，et al. A fluorescent and colorimetric sensor for Al3+ based on a dibenzo-18-crown-6 derivative ［J］. Inorg. Chem. Commun.， 2013，33：6-9. doi: 10.1016/j.inoche.2013.03.020http://dx.doi.org/10.1016/j.inoche.2013.03.020

XIE H T，WU Y L，HUANG J，et al. A ratiometric fluorescent probe for aluminum ions based-on monomer/excimer conversion and its applications to real samples ［J］. Talanta， 2016，151：8-13. doi: 10.1016/j.talanta.2016.01.015http://dx.doi.org/10.1016/j.talanta.2016.01.015

GUPTA V K，SHOORA S K，KUMAWAT L K，et al. A highly selective colorimetric and turn-on fluorescent chemosensor based on 1-（2-pyridylazo）-2-naphthol for the detection of aluminium（Ⅲ） ions ［J］. Sens. Actuators B Chem.， 2015， 209：15-24. doi: 10.1016/j.snb.2014.10.143http://dx.doi.org/10.1016/j.snb.2014.10.143

XU Z J，LIU Y N，WANG R T，et al. AIEE based “turn-on” fluorescent sensor for Al3+ ions and induced tetraphenylethene self-assemblies ［J］. Org. Electron.， 2020，85：105820-1-6. doi: 10.1016/j.orgel.2020.105820http://dx.doi.org/10.1016/j.orgel.2020.105820

PURI P，KUMAR G，PAUL K，et al. Self-agglomerated crystalline needles harnessing ESIPT and AIEE features for the ‘turn-on’ fluorescence detection of Al3+ ions ［J］. New J. Chem.， 2018，42（23）：18550-18558. doi: 10.1039/c8nj03577fhttp://dx.doi.org/10.1039/c8nj03577f

GUI S L，HUANG Y Y，HU F，et al. Fluorescence turn-on chemosensor for highly selective and sensitive detection and bioimaging of Al3+ in living cells based on ion-induced aggregation ［J］. Anal. Chem.， 2015，87（3）：1470-1474. doi: 10.1021/ac504153chttp://dx.doi.org/10.1021/ac504153c

XU P F，BAO Z Y，YU C Y，et al. A water-soluble molecular probe with aggregation-induced emission for discriminative detection of Al3+ and Pb2+ and imaging in seedling root of Arabidopsis ［J］. Spectrochim. Acta A Mol. Biomol. Spectrosc.， 2019，223：117335-1-8. doi: 10.1016/j.saa.2019.117335http://dx.doi.org/10.1016/j.saa.2019.117335

PROHASKA J R，GYBINA A A. Intracellular copper transport in mammals ［J］. J. Nutr， 2004，134（5）：1003-1006. doi: 10.1093/jn/134.5.1003http://dx.doi.org/10.1093/jn/134.5.1003

JIANG N，GONG X，ZHONG T Y，et al. A highly selective and sensitive “turn-on” fluorescent probe for rapid recognition and detection of Cu2+ in aqueous solution and in living cells ［J］. J. Mol. Struct.， 2020，1219：128573. doi: 10.1016/j.molstruc.2020.128573http://dx.doi.org/10.1016/j.molstruc.2020.128573

NADIMETLA D N，BHOSALE S V. Tetraphenylethylene AIEgen bearing thiophenylbipyridine receptor for selective detection of copper（Ⅱ） ion ［J］. New J. Chem.， 2021，45（17）：7614-7621. doi: 10.1039/d1nj01001hhttp://dx.doi.org/10.1039/d1nj01001h

GENG L Y，ZHAO Y，KAMYA E，et al. Turn-off/on fluorescent sensors for Cu2+ and ATP in aqueous solution based on a tetraphenylethylene derivative ［J］. J. Mater. Chem. C， 2019，7（9）：2640-2645. doi: 10.1039/c8tc06075dhttp://dx.doi.org/10.1039/c8tc06075d

WANG D Q，ZHOU X，MA C，et al. An amphiphilic fluorogen with aggregation-induced emission characteristic for highly sensitive and selective detection of Cu2+ in aqueous solution and biological system ［J］. Arab. J. Chem.， 2021，14（10）：103351. doi: 10.1016/j.arabjc.2021.103351http://dx.doi.org/10.1016/j.arabjc.2021.103351

HUANG W H，REN J，YANG Y H，et al. Water-stable metal-organic frameworks with selective sensing on Fe3+ and nitroaromatic explosives，and stimuli-responsive luminescence on lanthanide encapsulation ［J］. Inorg. Chem.， 2019，58（2）：1481-1491. doi: 10.1021/acs.inorgchem.8b02994http://dx.doi.org/10.1021/acs.inorgchem.8b02994

PETRONEK M S，SPITZ D R，BUETTNER G R，et al. Linking cancer metabolic dysfunction and genetic instability through the lens of iron metabolism ［J］. Cancers， 2019，11（8）：1077-1-20. doi: 10.3390/cancers11081077http://dx.doi.org/10.3390/cancers11081077

ZHANG W，LUO Y，ZHAO J，et al. tQ［14］-based AIE supramolecular network polymers as potential bioimaging agents for the detection of Fe3+ in live HeLa cells ［J］. Sens. Actuators B Chem.， 2022，354，131189. doi: 10.1016/j.snb.2021.131189http://dx.doi.org/10.1016/j.snb.2021.131189

ZAHEER A，MURSHED M，DE GRAND A M，et al. Optical imaging of hydroxyapatite in the calcified vasculature of transgenic animals ［J］. Arterioscler. Thromb. Vasc. Biol.， 2006，26（5）：1132-1136. doi: 10.1161/01.atv.0000210016.89991.2ahttp://dx.doi.org/10.1161/01.atv.0000210016.89991.2a

SUI B L，LIU X L，WANG M Y，et al. A highly selective fluorescence turn-on sensor for extracellular calcium ion detection ［J］. Chem. Eur. J.， 2016，22（30）：10351-10354. doi: 10.1002/chem.201602162http://dx.doi.org/10.1002/chem.201602162

ZHANG J D，YAN Z，WANG S，et al. Water soluble chemosensor for Ca2+ based on aggregation-induced emission characteristics and its fluorescence imaging in living cells ［J］. Dyes Pigm.， 2018，150：112-120. doi: 10.1016/j.dyepig.2017.11.012http://dx.doi.org/10.1016/j.dyepig.2017.11.012

WANG D Q，MA C，ZHOU X，et al. Self-dispersible fluorescent probe with aggregation-induced emission feature for sequence detection of Fe3+ and Ca2+ ［J］. Colloid Interface Sci. Commun.， 2021，40：100358. doi: 10.1016/j.colcom.2020.100358http://dx.doi.org/10.1016/j.colcom.2020.100358

XUAN W M，PAN R，CAO Y T，et al. A fluorescent probe capable of detecting H2S at submicromolar concentrations in cells ［J］. Chem. Commun.， 2012，48（86）：10669-10671. doi: 10.1039/c2cc35602chttp://dx.doi.org/10.1039/c2cc35602c

PARK C M，ZHAO Y，ZHU Z H，et al. Synthesis and evaluation of phosphorodithioate-based hydrogen sulfide donors ［J］. Mol. Biosyst.， 2013，9（10）：2430-2434. doi: 10.1039/c3mb70145jhttp://dx.doi.org/10.1039/c3mb70145j

KIMURA H. Hydrogen sulfide：its production，release and functions ［J］. Amino Acids， 2011，41（1）：113-121. doi: 10.1007/s00726-010-0510-xhttp://dx.doi.org/10.1007/s00726-010-0510-x

WHITEMAN M，GOODING K M，WHATMORE J L，et al. Adiposity is a major determinant of plasma levels of the novel vasodilator hydrogen sulphide ［J］. Diabetologia， 2010，53（8）：1722-1726. doi: 10.1007/s00125-010-1761-5http://dx.doi.org/10.1007/s00125-010-1761-5

WANG X D，AN L，TIAN Q W，et al. Recent progress in H2S activated diagnosis and treatment agents ［J］. RSC Adv.， 2019，9（58）：33578-33588. doi: 10.1039/c9ra06698ehttp://dx.doi.org/10.1039/c9ra06698e

ZHANG Y，HUANG X H，LIU W W，et al. Organic nanoparticles formed by aggregation-induced fluorescent molecules for detection of hydrogen sulfide in living cells ［J］. Sci. China Chem.， 2016，59（1）：106-113. doi: 10.1007/s11426-015-5543-2http://dx.doi.org/10.1007/s11426-015-5543-2

REHMAN T，SHABBIR M A，INAM-UR-RAHEEM M，et al. Cysteine and homocysteine as biomarker of various diseases ［J］. Food Sci. Nutr.， 2020，8（9）：4696-4707. doi: 10.1002/fsn3.1818http://dx.doi.org/10.1002/fsn3.1818

TOWNSEND D M，TEW K D，TAPIERO H. The importance of glutathione in human disease ［J］. Biomed. Pharmacother.， 2003，57（3-4）：145-155. doi: 10.1016/s0753-3322(03)00043-xhttp://dx.doi.org/10.1016/s0753-3322(03)00043-x

LIN J，LEE I M，SONG Y Q，et al. Plasma homocysteine and cysteine and risk of breast cancer in women ［J］. Cancer Res.， 2010，70（6）：2397-2405. doi: 10.1158/0008-5472.can-09-3648http://dx.doi.org/10.1158/0008-5472.can-09-3648

HUANG C C，TSENG W L. Role of fluorosurfactant-modified gold nanoparticles in selective detection of homocysteine thiolactone：remover and sensor ［J］. Anal. Chem.， 2008，80（16）：6345-6350. doi: 10.1021/ac8006973http://dx.doi.org/10.1021/ac8006973

LI P，GE M H，YANG L B，et al. Metal coordination-functionalized Au-Ag bimetal SERS nanoprobe for sensitive detection of glutathione ［J］. Analyst， 2019，144（2）：421-425. doi: 10.1039/c8an02206bhttp://dx.doi.org/10.1039/c8an02206b

UMEZAWA K，YOSHIDA M，KAMIYA M，et al. Rational design of reversible fluorescent probes for live-cell imaging and quantification of fast glutathione dynamics ［J］. Nat. Chem.， 2017，9（3）：279-286. doi: 10.1038/nchem.2648http://dx.doi.org/10.1038/nchem.2648

NIU L Y，CHEN Y Z，ZHENG H R，et al. Design strategies of fluorescent probes for selective detection among biothiols ［J］. Chem. Soc. Rev.， 2015，44（17）：6143-6160. doi: 10.1039/c5cs00152hhttp://dx.doi.org/10.1039/c5cs00152h

LEE D，KIM G，YIN J，et al. An aryl-thioether substituted nitrobenzothiadiazole probe for the selective detection of cysteine and homocysteine ［J］. Chem. Commun.， 2015，51（30）：6518-6520. doi: 10.1039/c5cc01071chttp://dx.doi.org/10.1039/c5cc01071c

LI R R，HUANG X Y，LU G L，et al. A fluorescence and UV/vis absorption dual-signaling probe with aggregation-induced emission characteristics for specific detection of cysteine ［J］. RSC Adv.， 2018，8（43）：24346-24354. doi: 10.1039/c8ra03756fhttp://dx.doi.org/10.1039/c8ra03756f

WANG B，LI C，YANG L J，et al. Tetraphenylethene decorated with disulfide-functionalized hyperbranched poly（amido amine）s as metal/organic solvent-free turn-on AIE probes for biothiol determination ［J］. J. Mater. Chem. B， 2019，7（24）：3846-3855. doi: 10.1039/c9tb00214fhttp://dx.doi.org/10.1039/c9tb00214f

ZHENG D，SEFEROS D S，GILJOHANN D A，et al. Aptamer nano-flares for molecular detection in living cells ［J］. Nano Lett.， 2009，9（9）：3258-3261. doi: 10.1021/nl901517bhttp://dx.doi.org/10.1021/nl901517b

KOSCHINSKY T，HEINEMANN L. Sensors for glucose monitoring：technical and clinical aspects ［J］. Diabetes Metab. Res. Rev.， 2001，17（2）：113-123. doi: 10.1002/dmrr.188http://dx.doi.org/10.1002/dmrr.188

OLIVER N S，TOUMAZOU C，CASS A E G，et al. Glucose sensors：a review of current and emerging technology ［J］. Diabet. Med.， 2009，26（3）：197-210. doi: 10.1111/j.1464-5491.2008.02642.xhttp://dx.doi.org/10.1111/j.1464-5491.2008.02642.x

LI H H，ZHU L，ZHU X Y，et al. Glucose detection via glucose-induced disaggregation of ammonium-modified tetraphenylethylene from polyanion ［J］. Sens. Actuators B Chem.， 2017，246：819-825. doi: 10.1016/j.snb.2017.02.155http://dx.doi.org/10.1016/j.snb.2017.02.155

WANG X W，HUANG Y Z，LV W W，et al. A novel fluorescent probe based on ESIPT and AIE processes for the detection of hydrogen peroxide and glucose and its application in nasopharyngeal carcinoma imaging ［J］. Anal. Methods， 2017，9（12）：1872-1875. doi: 10.1039/c7ay00167chttp://dx.doi.org/10.1039/c7ay00167c

WU W T，ZHOU T，BERLINER A，et al. Glucose-mediated assembly of phenylboronic acid modified CdTe/ZnTe/ZnS quantum dots for intracellular glucose probing ［J］. Angew. Chem. Int. Ed.， 2010，49（37）：6554-6558. doi: 10.1002/anie.201001508http://dx.doi.org/10.1002/anie.201001508

LIU Y，DENG C M，TANG L，et al. Specific detection of D-Glucose by a tetraphenylethene-based fluorescent sensor ［J］. J. Am. Chem. Soc.， 2011，133（4）：660-663. doi: 10.1021/ja107086yhttp://dx.doi.org/10.1021/ja107086y

SPERGEL D J，KRÜTH U，SHIMSHEK D R，et al. Using reporter genes to label selected neuronal populations in transgenic mice for gene promoter，anatomical，and physiological studies ［J］. Prog. Neurobiol.， 2001，63（6）：673-686. doi: 10.1016/s0301-0082(00)00038-1http://dx.doi.org/10.1016/s0301-0082(00)00038-1

CHATTERJEE S K，BHATTACHARYA M，BARLOW J J. Glycosyltransferase and glycosidase activities in ovarian cancer patients ［J］. Cancer Res.，1979，39（6）：1943-1951.

NIU Y，WANG H P，WANG Y X，et al. A “turn-on” fluorescent probe for ultra-sensitive detection of β-galactosidase ［J］. Microchem. J.， 2021，166：106205. doi: 10.1016/j.microc.2021.106205http://dx.doi.org/10.1016/j.microc.2021.106205

JIANG G Y，ZENG G J，ZHU W P，et al. A selective and light-up fluorescent probe for β-galactosidase activity detection and imaging in living cells based on an AIE tetraphenylethylene derivative ［J］. Chem. Commun.， 2017，53（32）：4505-4508. doi: 10.1039/c7cc00249ahttp://dx.doi.org/10.1039/c7cc00249a

HOTCHKISS R S，CHANG K C，SWANSON P E，et al. Caspase inhibitors improve survival in sepsis：a critical role of the lymphocyte ［J］. Nat. Immunol.， 2000，1（6）：496-501. doi: 10.1038/82741http://dx.doi.org/10.1038/82741

ELMORE S. Apoptosis：a review of programmed cell death ［J］. Toxicol. Pathol.， 2007，35（4）：495-516. doi: 10.1080/01926230701320337http://dx.doi.org/10.1080/01926230701320337

SHAULOV-ROTEM Y，MERQUIOL E，WEISS-SADAN T，et al. A novel quenched fluorescent activity-based probe reveals caspase-3 activity in the endoplasmic reticulum during apoptosis ［J］. Chem. Sci.， 2016，7（2）：1322-1337. doi: 10.1039/c5sc03207ehttp://dx.doi.org/10.1039/c5sc03207e

YE D J，SHUHENDLER A J，CUI L N，et al. Bioorthogonal cyclization-mediated in situ self-assembly of small-molecule probes for imaging caspase activity in vivo ［J］. Nat. Chem.， 2014，6（6）：519-526. doi: 10.1038/nchem.1920http://dx.doi.org/10.1038/nchem.1920

HAN A T，WANG H M，KWOK R T K，et al. Peptide-induced AIEgen self-assembly：a new strategy to realize highly sensitive fluorescent light-up probes ［J］. Anal. Chem.， 2016，88（7）：3872-3878. doi: 10.1021/acs.analchem.6b00023http://dx.doi.org/10.1021/acs.analchem.6b00023

OOI K，SHIRAKI K，MORISHITA Y，et al. High-molecular intestinal alkaline phosphatase in chronic liver diseases ［J］. J. Clin. Lab. Anal.， 2007，21（3）：133-139. doi: 10.1002/jcla.20178http://dx.doi.org/10.1002/jcla.20178

SONG Z G，HONG Y N，KWOK R T K，et al. A dual-mode fluorescence “turn-on” biosensor based on an aggregation-induced emission luminogen ［J］. J. Mater. Chem. B， 2014，2（12）：1717-1723. doi: 10.1039/c3tb21576hhttp://dx.doi.org/10.1039/c3tb21576h

XU L B，HE X，HUANG Y B，et al. A novel near-infrared fluorescent probe for detecting intracellular alkaline phosphatase and imaging of liv ing cells ［J］. J. Mater. Chem. B， 2019，7（8）：1284-1291. doi: 10.1039/c8tb03230khttp://dx.doi.org/10.1039/c8tb03230k

ZHANG W J，YANG H X，LI N，et al. A sensitive fluorescent probe for alkaline phosphatase and an activity assay based on the aggregation-induced emission effect ［J］. RSC Adv.， 2018，8（27）：14995-15000. doi: 10.1039/c8ra01786ghttp://dx.doi.org/10.1039/c8ra01786g

CAO F Y，LONG Y，WANG S B，et al. Fluorescence light-up AIE probe for monitoring cellular alkaline phosphatase activity and detecting osteogenic differentiation ［J］. J. Mater. Chem. B， 2016，4（26）：4534-4541. doi: 10.1039/c6tb00828chttp://dx.doi.org/10.1039/c6tb00828c

GAO Y X，WEI K L，LI J Z，et al. A facile four-armed AIE fluorescent sensor for heparin and protamine ［J］. Sens. Actuators B Chem.， 2018，277：408-414. doi: 10.1016/j.snb.2018.09.054http://dx.doi.org/10.1016/j.snb.2018.09.054

MARCHETTI M，ZERMATTEN M G，CALDERARA D B，et al. Heparin-induced thrombocytopenia：a review of new concepts in pathogenesis，diagnosis，and management ［J］. J. Clin. Med.， 2021，10（4）：683-1-16.

LEE H，IN B，MEHTA P K，et al. Dual role of a fluorescent peptidyl probe based on self-assembly for the detection of heparin and for the inhibition of the heparin-digestive enzyme reaction ［J］. ACS Appl. Mater. Interfaces， 2018，10（3）：2282-2290. doi: 10.1021/acsami.7b15411http://dx.doi.org/10.1021/acsami.7b15411

CHEN L J，REN Y Y，WU N W，et al. Hierarchical self-assembly of discrete organoplatinum（Ⅱ） metallacycles with polysaccharide via electrostatic interactions and their application for heparin detection ［J］. J. Am. Chem. Soc.， 2015，137（36）：11725-11735. doi: 10.1021/jacs.5b06565http://dx.doi.org/10.1021/jacs.5b06565

ZHENG J，YE T，CHEN J Y，et al. Highly sensitive fluorescence detection of heparin based on aggregation-induced emission of a tetraphenylethene derivative ［J］. Biosens. Bioelectron.， 2017，90：245-250. doi: 10.1016/j.bios.2016.11.056http://dx.doi.org/10.1016/j.bios.2016.11.056

YANG Z Y，FAN X，CHENG W J，et al. AIE nanoassemblies for discrimination of glycosaminoglycans and heparin quality control ［J］. Anal. Chem.， 2019，91（15）：10295-10301. doi: 10.1021/acs.analchem.9b02516http://dx.doi.org/10.1021/acs.analchem.9b02516

CUI J，ZANG S P，SHU W，et al. Highly sensitive and selective detection of heparin in serum based on a long-wavelength tetraphenylethylene-cyanopyridine aggregation-induced emission luminogen ［J］. Anal. Chem.， 2020，92（10）：7106-7113. doi: 10.1021/acs.analchem.0c00496http://dx.doi.org/10.1021/acs.analchem.0c00496

PODE Z，PERI-NAOR R，GEORGESON J M，et al. Protein recognition by a pattern-generating fluorescent molecular probe ［J］. Nat. Nanotechnol.， 2017，12（12）：1161-1168. doi: 10.1038/nnano.2017.175http://dx.doi.org/10.1038/nnano.2017.175

TYAGI A，CHU K L，ABIDI I H，et al. Single-probe multistate detection of DNA via aggregation-induced emission on a graphene oxide platform ［J］. Acta Biomater.， 2017，50：334-343. doi: 10.1016/j.actbio.2016.12.003http://dx.doi.org/10.1016/j.actbio.2016.12.003

ZHANG R Y，KWOK R T K，TANG B Z，et al. Hybridization induced fluorescence turn-on of AIEgen-oligonucleotide conjugates for specific DNA detection ［J］. RSC Adv.， 2015，5（36）：28332-28337. doi: 10.1039/c5ra00322ahttp://dx.doi.org/10.1039/c5ra00322a

浏览量

308

下载量

CSCD

文章被引用时，请邮件提醒。

提交

工具集

关联资源

含苯甲酸乙酯结构的共轭材料对硝基芳烃爆炸物的荧光检测

用于全氟辛烷磺酸盐检测的“开启”式荧光探针

以二苯并吩嗪为核心的聚集诱导发红光材料制备及表征