锌离子荧光探针研究进展

doi:10.11944/j.issn.1000-0518.2017.12.170302

摘要/Abstract

摘要：

锌广泛存在于人体内,具有重要生理功能。因此,对游离锌离子的选择性识别和有效检测具有重要意义。荧光探针因其设计简单、易于操作、灵敏度高、可细胞成像等诸多优点而广泛应用于锌离子的识别研究。锌离子荧光探针常见的识别机理包括光致电子转移、分子内电荷转移、荧光共振能量转移、聚集诱导荧光增强、螯合荧光增强等。其中,基于螯合荧光增强机理的锌离子探针,其荧光团通常可同时作为识别基团,因此,相比于其它探针,具有设计较为简单、合成较为便捷的优点。本文综述了近年来文献中报道的基于以上各种识别机理的锌离子荧光探针,并着重介绍了螯合荧光增强机理在锌离子识别中的应用。

关键词: 锌离子, 荧光探针, 识别机理, 螯合荧光增强, 细胞成像

Abstract:

It is of great importance to selectively detect and effectively monitor zinc ion because of its wide distribution in human cells and vital roles in human metabolism. Fluorescent probes have been extensively applied in zinc sensing because of the advantages of simple-design, easy-operation, high sensitivity and cell imaging capability. Fluorescent zinc probes are generally constructed based on the mechanisms of photo-induced electron transfer, intra-molecular charge transfer, fluorescence resonance energy transfer, aggregation-induced emission and chelation-enhanced fluorescence. Among these mechanisms, zinc probes constructed on chelation-enhanced fluorescence have the advantages of easy design and synthesis because its fluorophore can simultaneously act as the receptor. In this review, fluorescent zinc probes based on the aforementioned mechanisms, especially, chelation-enhanced fluorescence, reported in recent years are briefly summarized.

Key words: zinc ion, fluorescent probes, sensing mechanism, chelation-enhanced fluorescence, cell imaging

卜露露,王晴,解永树. 锌离子荧光探针研究进展[J]. 应用化学, 2017, 34(12): 1355-1369.

BU Lulu,WANG Qing,XIE Yongshu. Research Progress of Fluorescent Zinc Probes[J]. Chinese Journal of Applied Chemistry, 2017, 34(12): 1355-1369.

参考文献

[1]	Frederickson C J,Koh J Y,Bush A I. The Neurobiology of Zinc in Health and Disease[J]. Nat Rev Neurosci,2005,6(6):449-462.
[2]	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.
[3]	Assaf S Y,Chung S H. Release of Endogenous Zn2+ from Brain Tissue During Activity[J]. Nature,1984,308(5961):734-736.
[4]	Choi D W,Koh J Y. Zinc and Brain Injury[J]. Annu Rev Neurosci,1998,21(21):347-375.
[5]	Wang L,Liu J H,Song Z M,et al.Interaction of Multi-Walled Carbon Nanotubes and Zinc Ions Enhances Cytotoxicity of Zinc Ions[J]. Sci China Chem,2016,59(7):910-917.
[6]	Maret W,Jacob C,Vallee B L,et al.Inhibitory Sites in Enzymes:Zinc Removal and Reactivation by Thionein[J]. Proc Natl Acad Sci USA,1999,96(5):1936-1940.
[7]	Falchuk K H. The Molecular Basis for the Role of Zinc in Developmental Biology[J]. Mol Cell Biochem,1998,188(1):41-48.
[8]	Cao M J,Chen H Y,Chen D,et al.Naphthalimide-Based Fluorescent Probe for Selectively and Specifically Detecting Glutathione in the Lysosomes of Living Cells[J]. Chem Commun,2016,52(4):721-724.
[9]	Maeda H,Bando Y,Shimomura K,et al.Chemical-Stimuli-Controllable Circularly Polarized Luminescence from Anion-Responsive π-Conjugated Molecules[J]. J Am Chem Soc,2011,133(24):9266-9269.
[10]	Akamatsu M,Komatsu H,Mori T,et al.Intracellular Imaging of Cesium Distribution in Arabidopsis Using Cesium Green[J]. ACS Appl Mater Interfaces,2014,6(11):8208-8211.
[11]	Mukherjee S,Salini P S,Srinivasan A,et al.AIEE Phenomenon:Tetraaryl vs. Triaryl Pyrazoles[J]. Chem Commun,2015,51(96):17148-17151.
[12]	Li J F,Yin C X,Huo F J. Development of Fluorescent Zinc Chemosensors Based on Various Fluorophores and Their Applications in Zinc Recognition[J]. Dyes Pigm,2016,131:100-133.
[13]	Maeda H,Kusunose Y. Dipyrrolyldiketone Difluoroboron Complexes: Novel Anion Sensors with C—H••••X Interactions[J]. Chem Eur J,2005,11(19):5661-5666.
[14]	Akamatsu M,Mori T,Okamoto K,et al.Detection of Ethanol in Alcoholic Beverages or Vapor Phase Using Fluorescent Molecules Embedded in a Nano Fibrous Polymer[J]. ACS Appl Mater Interfaces,2015,7(11):6189-6194.
[15]	Yin C X,Huo F J,Zhang J J,et al.Thiol-Addition Reactions and Their Applications in Thiol Recognition[J]. Chem Soc Rev,2013,42(14):6032-6059.
[16]	Zhang Y F,Chen H Y,Chen D,et al.A Colorimetric and Ratiometric Fluorescent Probe for Mercury(Ⅱ) in Lysosome[J]. Sens Actuators,B,2016,224:907-914.
[17]	Sreedevi K C G,Thomas A P,Aparna K H,et al. Photoenolization via Excited State Double Proton Transfer Induces “Turn On” Fluorescence in Diformyl Diaryl Dipyrromethane[J]. Chem Commun,2014,50(63):8667-8669.
[18]	Liu Y,Yu D H,Ding S S,et al.Rapid and Ratiometric Fluorescent Detection of Cysteine with High Selectivity and Sensitivity by a Simple and Readily Available Probe[J]. ACS Appl Mater Interfaces,2014,6(20):17543-17550.
[19]	Kumar K,Verma T,Mukherjee R,et al.Raman and Infra-Red Microspectroscopy:Towards Quantitative Evaluation for Clinical Research by Ratiometric Analysis[J]. Chem Soc Rev,2016,45:1879-1900.
[20]	Yu H O,Xiao Y,Qian X H,et al.Convenient and Efficient FRET Platform Featuring a Rigid Biophenyl Spacer Between Rhodamine and BODIPY:Transformation of “Turn-On” Sensors into Ratiometric Ones with Dual Emission[J]. Chem Eur J,2011,17(11):3179-3191.
[21]	Yu M X,Shi M,Chen Z G,et al.Highly Sensitive and Fast Responsive Fluorescence Turn-On Chemodosimeter for Cu2+ and Its Application in Live Cell Imaging[J]. Chem Eur J,2008,14(23):6892-6900.
[22]	Wu Y K,Peng X J,Guo B C,et al, Boron Dipyrromethene Fluorophore Based Fluorescence Sensor for the Selective Imaging of Zn(Ⅱ) in Living Cells[J]. Org Biomol Chem,2005,3(8):1387-1392.
[23]	Nan Q,Rong P,Jiang Y B,et al.New Highly Selective Turn-On Fluorescence Receptor for the Detection of Copper(Ⅱ)[J]. Spectrochim Acta A,2017,174(5):307-315.
[24]	Xu Z C,Yoon J,Spring D R. Fluorescent Chemosensors for Zn2+[J]. Chem Soc Rev,2010,39(6):1996-2006.
[25]	Chen Y C,Bai Y,Han Z,et al.Photoluminescence Imaging of Zn2+ in Living Systems[J]. Chem Soc Rev,2015,44(14):4517-4546.
[26]	Ding Y B,Tamg Y Y,Zhu W H,et al.Fluorescent and Colorimetric Ion Probes Based on Conjugated Oligopyrroles[J]. Chem Soc Rev,2015,44(5):1101-1112.
[27]	Li J,Yim D,Jang W D,et al.Recent Progress in the Design and Applications of Fluorescence Probes Containing Crown Ethers[J]. Chem Soc Rev,2016,46(9):2437-2650.
[28]	Ding Y B,Zhu W H,Xie Y S. Development of Ion Chemosensors Based on Porphyrin Analogues[J]. Chem Rev,2017,177(4):2203-2256.
[29]	Jiang P J,Guo Z J. Fluorescent Detection of Zinc in Biological Systems: Recent Development on the Design of Chemosensors and Biosensors[J]. Coord Chem Rev,2004,248(1/2):205-229.
[30]	Koike T,Watanabe T,Aoki S,et al.A Novel Biomimetic Zinc(Ⅱ)-Fluorophore, Dansylamidoethyl-Pendant Macrocyclic Tetraamine 1,4,7,10-Tetraazacyclododecane (Cyclen)[J]. J Am Chem Soc,1996,118(50):12696-12703.
[31]	WANG Zuohui,WANG Shumin. Research Advance on the Fluorescent Probe of Zn2+[J]. Guangzhou Chem Ind,2013,41(22)(in Chinese). 王作辉,王淑敏. 锌离子荧光探针研究进展[J]. 广州化工,2013,41(22).
[32]	de Silva P,de Silva S A. Fluorescent Signalling Crown Ethers; ‘Switching On’ of Fluorescence by Alkali Metal Ion Recognition and Binding in Situ[J]. J Chem Soc,Chem Commun,1986,1709(23):1709-1710.
[33]	Tomat E,Nolan E M,Jaworski J,et al.Organelle-Specific Zinc Detection Using Zinpyr-Labeled Fusion Proteins in Live Cells[J]. J Am Chem Soc,2008,130(47):15776-15777.
[34]	Zhang X A,Hayes D,Smith S J,et al.New Strategy for Quantifying Biological Zinc by a Modified Zinpyr Fluorescence Sensor[J]. J Am Chem Soc,2008,130(47):15788-15789.
[35]	Wong B A,Friedle S,Lippard S J. Solution and Fluorescence Properties of Symmetric Dipicolylamine-Containing Dichlorofluorescein-Based Zn2+ Sensors[J]. J Am Chem Soc,2009,131(20):7142-7152.
[36]	Tomat E,Lippard S J. Ratiometric and Intensity-Based Zinc Sensors Built on Rhodol and Rhodamine Platforms[J]. Inorg Chem,2010,49(20):9113-9115.
[37]	You Y M,Lee S,Kim T,et al.Phosphorescent Sensor for Biological Mobile Zinc[J]. J Am Chem Soc,2011,133(45):18328-18342.
[38]	Lin W,Buccella D,Lippard S J. Visualization of Peroxynitrite-Induced Changes of Labile Zn2+ in the Endoplasmic Reticulum with Benzoresorufin-Based Fluorescent Probes[J]. J Am Chem Soc,2013,135(36):13512-13520.
[39]	Rivera-Fuentes P,Lippard S J. SpiroZin 1:A Reversible and pH-Insensitive, Reaction-Based, Red-Fluorescent Probe for Imaging Biological Mobile Zinc[J]. Chem Med Chem,2014,9(6):1238-1243.
[40]	Radford R J,Chyan W,Lippard S J. Peptide Targeting of Fluorescein-Based Sensors to Discrete Intracellular Locales[J]. Chem Sci,2014,5(11):4512-4516.
[41]	Zastrow M L,Radford R J,Chyan W,et al.Reaction-Based Probes for Imaging Mobile Zinc in Live Cells and Tissues[J]. ACS Sens,2016,1(1):32-39.
[42]	Walkup G K,Burdette S C,Lippard S J,et al.A New Cell-Permeable Fluorescent Probe for Zn2+[J]. J Am Chem Soc,2000,122(23):5644-5645.
[43]	Burdette S C,Frederickson C J,Bu W M,et al.ZP4, an Improved Nuronal Zn2+ Sensor of The Zinpyr Family[J]. J Am Chem Soc,2003,125(7):1778-1787.
[44]	Nolan E M,Ryu J W,Jaworski J,et al.Zinspy Sensors with Enhanced Dynamic Range for Imaging Neuronal Cell Zinc Uptake and Mobilization[J]. J Am Chem Soc,2006,128(48):15517-15528.
[45]	Buccella D,Horowitz J A,Lippard S J. Understanding Zinc Quantification with Existing and Advanced Ditopic Fluorescent Zinpyr Sensors[J]. J Am Chem Soc,2011,133(11):4101-4114.
[46]	Xu Z C,Baek K H,Kim H N,et al.Zn2+-Triggered Amide Tautomerization Produces a Highly Zn2+-Selective, Cell-Permeable, and Ratiometric Fluorescent Sensor[J]. J Am Chem Soc,2010,132(2):601-610.
[47]	Hanaoka K,Kikuchi K,Kojima H,et al.Development of a Zinc Ion-Selective Luminescent Lanthanide Chemosensor for Biological Applications[J]. J Am Chem Soc,2004,126(39):12470-12476.
[48]	Shyamal M,Mazumdar P,Maity S,et al.Highly Selective Turn-On Fluorogenic Chemosensor for Robust Quantification of Zn(Ⅱ) Based on Aggregation Induced Emission Enhancement Feature[J]. ACS Sens,2016,1(6):739-747.
[49]	Xue L,Liu C,Jiang H. A Ratiometric Fluorescent Sensor with a Large Stokes Shift for Imaging Zinc Ions in Living Cells[J]. Chem Commun,2009,9(9):1061-1063.
[50]	Atilgan S,Ozdemir T,Akkaya E U. A Sensitive and Selective Ratiometric Near IR Fluorescent Probe for Zinc Ions Based on the Dstyryl-Bodipy Fluorophore[J]. Org Lett,2008,10(18):4065-4067.
[51]	Lu X Y,Zhu W H,Xie Y S,et al.Near-IR Core-Substituted Naphthalenediimide Fluorescent Chemosensors for Zinc Ions:Ligand Effects on PET and ICT Channels[J]. Chem Eur J,2010,16(28):8355-8364.
[52]	Sreenath K,Allen J R,Davidson M W,et al.A FRET-Based Indicator for Imaging Mitochondrial Zinc Ions[J]. Chem Commun,2011,47(42):11730-11732.
[53]	Woo H,You Y,Kim T,et al.Fluorescence Ratiometric Zinc Sensors Based on Controlled Energy Transfer[J]. J Mater Chem,2012,22(33):17100-17112.
[54]	Han Z X,Zhang X B,Li Z,et al.Efficient Fluorescence Resonance Energy Transfer-Based Ratiometric Fluorescent Cellular Imaging Probe for Zn2+ Using a Rhodamine Spirolactam as a Trigger[J]. Anal Chem,2010,82(8):3108-3113.
[55]	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(18):1740-1741.
[56]	Hong Y N,Chen S J, Leung C W T, et al. Fluorogenic Zn(Ⅱ) and Chromogenic Fe(Ⅱ) Sensors Based on Terpyridine-Substituted Tetraphenylethenes with Aggregation-Induced Emission Characteristics[J]. ACS Appl Mater Interfaces,2011,3(9):3411-3418.
[57]	Gabr M T,Pigge F C. A Selective Fluorescent Sensor for Zn2+ Based on Aggregation-Induced Emission(AIE) Activity and Metal Chelating Ability of Bis(2-pyridyl)-Diphenylethylene[J]. Dalton Trans,2016,45:14039-14043.
[58]	Sun F,Zhang G X,Zhang D Q,et al.Aqueous Fluorescence Turn-On Sensor for Zn2+ with a Tetraphenylethylene Compound[J]. Org Lett,2011,13(24):6378-6381.
[59]	Akkaya E U,Huston M E,Czarnik A W. Chelation-Enhanced Fluorescence of Anthrylazamacrocycle Conjugate Probes in Aqueous Solution[J]. J Am Chem Soc,1990,112:3590-3593.
[60]	Cockrell G M,Zhang G, VanDerveer D G, et al. Enhanced Metal Ion Selectivity of 2,9-Di-(pyrid-2-yl)-1,10-phenanthroline and Its Use as a Fluorescent Sensor for Cadmium(Ⅱ)[J]. J Am Chem Soc,2008,130(4):1420-1430.
[61]	Ding Y B,Xie Y S,Li X,et al.Selective and Sensitive “Turn-On” Fluorescent Zn2+ Sensors Basedon Di- and Tripyrrins with Readily Modulated Emission Wavelengths[J]. Chem Commun,2011,47(19):5431-5433.
[62]	Ding Y,Li X,Li T,et al.α'-Monoacylated and α,α'- and α,β'-Diacylated Dipyrrins as Highly Sensitive Fluorescence “Turn-on” Zn2+ Probes[J]. J Org Chem,2013,78(11):53285338.
[63]	Ding Y B,Li T,Zhu W H,et al.Highly Selective Colorimetric Sensing of Cyanide Based on Formation of Dipyrrin Adducts[J]. Org Biomol Chem,2012,10(21):4201-4207.
[64]	Xie Y S,Wei P C,Li X,et al.Macrocycle Contraction and Expansion of a Dihydrosapphyrin Isomer[J]. J Am Chem Soc,2013,135(51):19119-19122.
[65]	Lu C L,Xu Z C,Cui J N,et al.Ratiometric and Highly Selective Fluorescent Sensor for Cadmium under Physiological pH Range:A New Strategy to Discriminate Cadmium from Zinc[J]. J Org Chem,2007,72(9):3554-3557.
[66]	Taki M,Wolford J L, O'Halloran T V. Emission Ratiometric Imaging of Intracellular Zinc:Design of a Benzoxazole Fluorescent Sensor and Its Application in Two-Photon Microscopy[J]. J Am Chem Soc,2004,126(3):712-713.
[67]	Nolan E M,Jaworski J,Okamoto K I,et al.QZ1 and QZ2:Rapid, Reversible Quinoline-Derivatized Fluoresceins for Sensing Biological Zn(Ⅱ)[J]. J Am Chem Soc,2005,127(48):16812-16823.
[68]	Dennis A E,Smith R C. “Turn-On” Fluorescent Sensor for the Selective Detection of Zinc Ion by a Sterically-Encumbered Bipyridyl-Based Receptor[J]. Chem Commun,2007:4641-4643.
[69]	Wei X D,Wang Q,Tang W Q,et al.Combination of Pyrrole and Pyridine for Constructing Selective and Sensitive Zn2+ Probes[J]. Dyes Pigm,2017,140:320-327.
[70]	Manandhar E,Cragg P J,Wallace K J. Detection of Zn(Ⅱ) Ions by Fluorescent Pyrene-Derived Molecular Probes[J]. Supramol Chem,2014,26:141-150.
[71]	Henary M M,Wu Y G,Fahrni C J. Zinc(Ⅱ)-Selective Ratiometric Fluorescent Sensors Based on Inhibition of Excited-State Intramolecular Proton Transfer[J]. Chem Eur J,2004,10(12):3015-3025.
[72]	Chen W H,Xing Y,Pang Y. A Highly Selective Pyrophosphate Sensor Based on ESIPT Turn-On in Water[J]. Org Lett,2011,13(6):1362-1365.
[73]	An M,Kim B Y,Seo H,et al.Fluorescence Sensor for Sequential Detection of Zinc and Phosphate Ions[J]. Spectrochim Acta,Part A,2016,169:87-94.
[74]	Li X,Li J,Dong X W,et al.A Novel 3-Hydroxychromone Fluorescence Sensor for Intracellular Zn2+ and Its Application in the Recognition of Prostate Cancer Cells[J]. Sens Actuators,B,2017,245:129-136.
[75]	Wu J S,Liu W M,Zhang X Q,et al.Fluorescence Turn On of Coumarin Derivatives by Metal Cations:A New Signaling Mechanism Based on C=N Isomerization[J]. Org Lett,2007,9(1):33-36.
[76]	Bhattacharyya A,Ghosh S,Makhal S C,et al.Hydrazine Bridged Coumarin-Pyrimidine Conjugate as a Highly Selectiveand Sensitive Zn2+ Sensor:Spectroscopic Unraveling of Sensing Mechanism with Practical Application[J]. Spectrochim Acta,Part A,2017,183:306-311.
[77]	Guo Z Q,Kim G H,Shin I,et al.A Cyanine-Based Fluorescent Probe for Detecting Endogenous Zinc Ions in Live Cells and Organisms[J]. Biomaterials,2012,33(31):7818-7827.
[78]	Zhu H,Fan J L,Peng X J,et al.Ratiometric Fluorescence Imaging of Lysosomal Zn2+ Release Under Oxidative Stress in Neural Stem Cells[J]. Biomater Sci,2014,2(1):89-97.