基于指示剂置换法的大环荧光传感平台的构建及应用研究进展

doi:10.6023/cjoc202310017

摘要/Abstract

超分子荧光传感器可以解决与环境及人类健康相关的检测和成像问题. 指示剂置换法(IDA)是一种能够将分子识别所引起的化学变化转化为易于观察的荧光信号的超分子荧光传感方法, 为分析物的检测提供了独特且创新的传感策略. 近年来, 由于其灵敏度高、可调节、实时和无需复杂合成的优点, 基于非共价结合的IDA得到了快速的发展. 为了满足IDA发展的多样化需求, 超分子科学家们引入了各种超分子大环主体, 如杯[n]芳烃、葫芦[n]脲及柱[n]芳烃等.根据大环进行分类, 对近些年该领域的研究进展进行简要综述, 重点关注在生化传感方面的应用, 为今后基于IDA的新型荧光生化传感平台的构建及应用提供参考.

关键词: 指示剂置换法, 超分子化学, 主-客体相互作用, 大环主体

Supramolecular fluorescent sensors can address various detection and bioimaging issues related to the environment and human health. Indicator displacement assay (IDA) is a supramolecular fluorescence sensing method that can convert the chemical changes caused by molecular recognition into easily observed fluorescence signals. It provides a unique and innovative sensing method for the detection of analytes. In recent years, IDA based on non-covalent binding has been developed rapidly due to its advantages of high sensitivity, adjustability, real-time, and low synthesis effort. In order to meet the diverse needs of IDA development, a variety of supramolecular macrocyclic hosts have been involved in the construction of IDA sensors, such as calix[n]arenes, cucurbit[n]uril, pillar[n]arenes, etc. The recent research progress in this field based on different classes of macrocycles is briefly reviewed, focusing on the application in biochemical sensing, and providing a reference for the construction and application of novel fluorescent biochemical sensing platforms based on IDA in the future.

Key words: indicator displacement assay, supramolecular chemistry, host-guest interaction, macrocyclic host

引用此文

谌泽亚, 李诗瑶, 杨留攀, 王力立, 姚欢. 基于指示剂置换法的大环荧光传感平台的构建及应用研究进展[J]. 有机化学, 2024, 44(4): 1151-1159.

Zeya Shen, Shiyao Li, Liupan Yang, Lili Wang, Huan Yao. Research Progress on the Construction and Application of Macrocyclic Fluorescent Sensing Platform Based on Indicator Displacement Assay[J]. Chinese Journal of Organic Chemistry, 2024, 44(4): 1151-1159.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

图/表 11

图1. 基于三足阴离子主体-荧光团复合物的柠檬酸盐的荧光传感[1]

Figure 1. Fluorescent sensing for citrate based on atripodal anion host-fluorophore complex[1]

图2. 利用IDA监测活细胞中生物有机分析物的摄取和运输的示意图[20]

Figure 2. Schematic illustration of monitoring the uptake and transport of organic analytes in living cells by using IDA[20]

图3. 缺氧反应系统的构建策略[30]

Figure 3. Strategies for creating hypoxia-responsive systems[30]

图4. LPA和GC5A之间的键合以及LPA荧光传感的IDA原理示意图[21]

Figure 4. Schematic illustration of the binding between LPA and GC5A and the IDA principle of fluorescence sensing[21]

图5. 通过GC5A?Fl荧光主客体对对TMAO进行荧光传感的IDA操作原理示意图以及荧光主客体对的化学结构[22]

Figure 5. Schematic illustration for IDA operating principle of TMAO fluorescence sensing by the GC5A·Fl reporter pair and chemical structures of the tested reporter pairs[22]

图6. FRET辅助的IDA超分子生物成像策略[25]

Figure 6. FRET assisted IDA supramolecular bioimaging strategies[25]

图7. 用于监测酶活性的产物与底物选择性串联测定[36]

Figure 7. Product versus substrate-selective tandem assays for monitoring enzymatic activity[36]

图8. 利用超分子膜转运法检测肽转运的策略[40]

Figure 8. Strategy for supramolecular membrane transport assays to detect peptide transport[40]

图9. 基于单分子CB[n]的化学传感器的示意图[41]

Figure 9. Schematic representation of the unimolecular CB[n]- based chemosensor[41]

图10. 探针P1~P3和DCM探针P1~P3和DCM7-β-CD之间的顺序主-客体和第二阶段有序自组装的示意图[52]

Figure 10. Schematic iSchematic illustration of the sequential host-guest and second-stage ordered self-assembly between probes P1~P3 and DCM7-β-CD[52]

图11. 基于四内酰胺大环的指示剂置换法用于 UA 的双模式比色和荧光检测示意图[54]

Figure 11. Schematic illustration of the tetralactam macrocycle based dual-mode colorimetric and fluorescence indicator displacement assay for UA[54]

参考文献 58

[1]	Guo C.; Sedgwick A. C.; Hirao T.; Sessler J. L. Coord. Chem. Rev. 2021, 427, 213560. doi: 10.1016/j.ccr.2020.213560
[2]	Wu D.; Sedgwick A. C.; Gunnlaugsson T.; Akkaya E. U.; Yoon J.; James T. D. Chem. Soc. Rev. 2017, 46, 7105. doi: 10.1039/C7CS00240H
[3]	Mako T. L.; Racicot J. M.; Levine M. Chem. Rev. 2018, 119, 322. doi: 10.1021/acs.chemrev.8b00260
[4]	Brzechwa-Chodzyńska A.; Drożdż W.; Harrowfield J.; Stefankiewicz A. R. Coord. Chem. Rev. 2021, 434, 213820. doi: 10.1016/j.ccr.2021.213820
[5]	He Y.; Chen L.; He R.; Zhong K.; Tang L. Chin. J. Org. Chem. 2022, 42, 785. (in Chinese) doi: 10.6023/cjoc202108024
	(何雨晴, 陈琳, 贺瑞丽, 钟克利, 汤立军, 有机化学, 2022, 42, 785.) doi: 10.6023/cjoc202108024
[6]	Tian X.; Zuo M.; Niu P.; Wang K.; Hu X. Chin. J. Org. Chem., 2020, 40, 1823. (in Chinese) doi: 10.6023/cjoc202003066
	(田雪琪, 左旻瓒, 牛蓬勃, 王开亚, 胡晓玉, 有机化学, 2020, 40, 1823.) doi: 10.6023/cjoc202003066
[7]	Liu L.; Hao T.; Wu W.; Yang C. Chin. J. Org. Chem. 2023, 43, 2189. (in Chinese) doi: 10.6023/cjoc202210020
	(刘铃, 浩涛涛, 伍晚花, 杨成, 有机化学, 2023, 43, 2189.)
[8]	Cao X.; Gao A.; Hou J.; Yi T. Coord. Chem. Rev. 2021, 434, 213792. doi: 10.1016/j.ccr.2021.213792
[9]	Rather I. A.; Ali R. Org. Biomol. Chem. 2021, 19, 5926. doi: 10.1039/D1OB00518A
[10]	Sedgwick A. C.; Brewster J. T.; Wu T.; Feng X.; Bull S. D.; Qian X.; Sessler J. L.; James T. D.; Anslyn E. V.; Sun X. Chem. Soc. Rev. 2021, 50, 9. doi: 10.1039/c9cs00538b pmid: 33169731
[11]	Inouye M.; Hashimoto K.-I.; Isagawa K. J. Am. Chem. Soc. 1994, 116, 5517. doi: 10.1021/ja00091a085
[12]	Pilicer S. L.; Bakhshi P. R.; Bentley K. W.; Wolf C. J. Am. Chem. Soc. 2017, 139, 1758. doi: 10.1021/jacs.6b12056
[13]	Beatty M. A.; Borges-González J.; Sinclair N. J.; Pye A. T.; Hof F. J. Am. Chem. Soc. 2018, 140, 3500. doi: 10.1021/jacs.7b13298
[14]	Minami T.; Liu Y.; Akdeniz A.; Koutnik P.; Esipenko N. A.; Nishiyabu R.; Kubo Y.; Anzenbacher P. J. Am. Chem. Soc. 2014, 136, 11396. doi: 10.1021/ja504535q
[15]	Minaker S. A.; Daze K. D.; Ma M. C. F.; Hof F. J. Am. Chem. Soc. 2012, 134, 11674. doi: 10.1021/ja303465x pmid: 22703116
[16]	Liu Y.; Perez L.; Mettry M.; Easley C. J.; Hooley R. J.; Zhong W. J. Am. Chem. Soc. 2016, 138, 10746. doi: 10.1021/jacs.6b05897
[17]	Wiskur S.-L. H., H.; Lavigne, J.-J.; Anslyn, E.-V. Acc. Chem. Res. 2001, 34, 963. doi: 10.1021/ar9600796
[18]	Ghale G.; Nau W. M. Acc. Chem. Res. 2014, 47, 2150. doi: 10.1021/ar500116d
[19]	Dsouza R. N.; Pischel U.; Nau W. M. Chem. Rev. 2011, 111, 7941. doi: 10.1021/cr200213s pmid: 21981343
[20]	Norouzy A.; Azizi Z.; Nau W. M. Angew. Chem., Int. Ed. 2015, 54, 792. doi: 10.1002/anie.201407808 pmid: 25430503
[21]	Zheng Z.; Geng W.-C.; Gao J.; Wang Y.-Y.; Sun H.; Guo D.-S. Chem. Sci. 2018, 9, 2087. doi: 10.1039/c7sc04989g pmid: 29675249
[22]	Yu H.; Geng W.-C.; Zheng Z.; Gao J.; Guo D.-S.; Wang Y. Theranostics 2019, 9, 4624. doi: 10.7150/thno.33459
[23]	Zhang Y.; Yu H.; Chai S.; Chai X.; Wang L.; Geng W. C.; Li J. J.; Yue Y. X.; Guo D. S.; Wang Y. Adv. Sci. 2022, 9, 2104463. doi: 10.1002/advs.v9.18
[24]	Yu H.; Chai X.; Geng W.-C.; Zhang L.; Ding F.; Guo D.-S.; Wang Y. Biosens. Bioelectron. 2021, 192, 113488. doi: 10.1016/j.bios.2021.113488
[25]	Geng W. C.; Ye Z.; Zheng Z.; Gao J.; Li J. J.; Shah M. R.; Xiao L.; Guo D. S. Angew. Chem., Int. Ed. 2021, 60, 19614. doi: 10.1002/anie.v60.36
[26]	Tian J.-H.; Hu X.-Y.; Hu Z.-Y.; Tian H.-W.; Li J.-J.; Pan Y.-C.; Li H.-B.; Guo D.-S. Nat. Commun. 2022, 13, 4293. doi: 10.1038/s41467-022-31986-x
[27]	Gutsche C. D.; Muthukrishnan R. J. Org. Chem. 1978, 43, 4905. doi: 10.1021/jo00419a052
[28]	Bakirci H.; Nau W. M. Adv. Funct. Mater. 2006, 16, 237. doi: 10.1002/adfm.v16:2
[29]	Yang L.; Xie X.; Cai L.; Ran X.; Li Y.; Yin T.; Zhao H.; Li C.-P. Biosens. Bioelectron. 2016, 82, 146. doi: 10.1016/j.bios.2016.04.005
[30]	Geng W. C.; Jia S.; Zheng Z.; Li Z.; Ding D.; Guo D. S. Angew. Chem., Int. Ed. 2019, 58, 2377. doi: 10.1002/anie.v58.8
[31]	Duan Q.; Chen R.; Deng S.; Yang C.; Ji X.; Qi G.; Li H.; Li X.; Chen S.; Lou M.; Lu K. Front. Chem. 2023, 11, 1124705. doi: 10.3389/fchem.2023.1124705
[32]	Liu S. R., C.; Mukhopadhyay, P.; Chakrabarti, S.; Zavalij, P. Y.; Isaacs, L. J. Am. Chem. Soc. 2005, 217, 15959.
[33]	Liu M.; Zhou Y.; Chen L.; Bian B.; Xiao X.; Tao Z. Chin. Chem. Lett. 2021, 32, 375. doi: 10.1016/j.cclet.2020.03.042
[34]	Lin R.-L.; Liu J.-X.; Chen K.; Redshaw C. Inorg. Chem. Front. 2020, 7, 3217. doi: 10.1039/D0QI00529K
[35]	Hennig A.; Bakirci H.; Nau W. M. Nat. Methods 2007, 4, 629. doi: 10.1038/nmeth1064
[36]	Nau W. M. G., G.; Hennig, A.; Bakirci, H.; Bailey, D. M. J. Am. Chem. Soc. 2009, 131, 11558. doi: 10.1021/ja904165c
[37]	Yin T.; Zhang S.; Li M.; Redshaw C.; Ni X.-L. Sens. Actuators, B 2019, 281, 568. doi: 10.1016/j.snb.2018.10.136
[38]	Sinn S.; Spuling E.; Bräse S.; Biedermann F. Chem. Sci. 2019, 10, 6584. doi: 10.1039/C9SC00705A
[39]	Wang C.; Tang Q.; Xi Y.; Yang M.; Li T.; Huang Y.; Tao Z. Chin. J. Org. Chem., 2018, 38, 1394. (in Chinese) doi: 10.6023/cjoc201711018
	(王成会, 唐青, 席芸芸, 杨梅, 李涛, 黄英, 陶朱, 有机化学, 2018, 38, 1394.) doi: 10.6023/cjoc201711018
[40]	Barba-Bon A.; Pan Y.-C.; Biedermann F.; Guo D.-S.; Nau W. M.; Hennig A. J. Am. Chem. Soc. 2019, 141, 20137. doi: 10.1021/jacs.9b09563 pmid: 31739668
[41]	Hu C.; Jochmann T.; Chakraborty P.; Neumaier M.; Levkin P. A.; Kappes M. M.; Biedermann F. J. Am. Chem. Soc. 2022, 144, 13084. doi: 10.1021/jacs.2c01520
[42]	Ogoshi T. K., S.; Fujinami, S.; Yamagishi, T.; Nakamoto, Y. J. Am. Chem. Soc. 2008, 130, 5022. doi: 10.1021/ja711260m
[43]	Xu X.; Jerca V. V.; Hoogenboom R. Angew. Chem., Int. Ed. 2020, 59, 6314. doi: 10.1002/anie.v59.16
[44]	Murray J.; Kim K.; Ogoshi T.; Yao W.; Gibb B. C. Chem. Soc. Rev. 2017, 46, 2479. doi: 10.1039/c7cs00095b pmid: 28338130
[45]	Ogoshi T.; Yamagishi T.-a.; Nakamoto Y. Chem. Rev. 2016, 116, 7937. doi: 10.1021/acs.chemrev.5b00765
[46]	Strutt N. L.; Zhang H.; Schneebeli S. T.; Stoddart J. F. Acc. Chem. Res. 2014, 47, 2631. doi: 10.1021/ar500177d
[47]	Bojtár M.; Kozma J.; Szakács Z.; Hessz D.; Kubinyi M.; Bitter I. Sens. Actuators, B 2017, 248, 305. doi: 10.1016/j.snb.2017.03.163
[48]	Hua B.; Shao L.; Zhang Z.; Sun J.; Yang J. Sens. Actuators, B. 2018, 255, 1430. doi: 10.1016/j.snb.2017.08.141
[49]	Paudics A.; Hessz D.; Bojtár M.; Bitter I.; Horváth V.; Kállay M.; Kubinyi M. Sens. Actuators, B 2022, 369, 132364. doi: 10.1016/j.snb.2022.132364
[50]	Yang L.; Zhao H.; Li Y.; Zhang Y.; Ye H.; Zhao G.; Ran X.; Liu F.; Li C.-P. Biosens. Bioelectron. 2017, 87, 737. doi: 10.1016/j.bios.2016.09.044
[51]	Lee J. Y.; Root H. D.; Ali R.; An W.; Lynch V. M.; Bähring S.; Kim I. S.; Sessler J. L.; Park J. S. J. Am. Chem. Soc. 2020, 142, 19579. doi: 10.1021/jacs.0c08106
[52]	Jiao J.-B.; Wang G.-Z.; Hu X.-L.; Zang Y.; Maisonneuve S.; Sedgwick A. C.; Sessler J. L.; Xie J.; Li J.; He X.-P.; Tian H. J. Am. Chem. Soc. 2019, 142, 1925. doi: 10.1021/jacs.9b11207
[53]	Sierra A. F.; Hernández-Alonso D.; Romero M. A.; González-Delgado J. A.; Pischel U.; Ballester P. J. Am. Chem. Soc. 2020, 142, 4276. doi: 10.1021/jacs.9b12071
[54]	Yao H.; Li S.-Y.; Zhang H.; Pang X.-Y.; Lu J.-L.; Chen C.; Jiang W.; Yang L.-P.; Wang L.-L. Chem. Commun. 2023, 59, 5411. doi: 10.1039/D2CC06622J
[55]	Yao H.; Qin J.; Wang Y.-F.; Wang S.-M.; Yi L.-H.; Li S.-Y.; Du F.; Yang L.-P.; Wang L.-L. Chin. Chem. Lett. 2023, doi: 10.1016/j.cclet.2023.109154.
[56]	Hu C.; Grimm L.; Prabodh A.; Baksi A.; Siennicka A.; Levkin P. A.; Kappes M. M.; Biedermann F. Chem. Sci. 2020, 11, 11142. doi: 10.1039/D0SC03079A
[57]	Bockus A.-T. S., L.; Grice, A.-G.; Ali, O.-A.; Young, C.-C.; Mobley, W.; Leek, A.; Roberts, J.-L.; Vinciguerra, B.; Isaacs, L.; Urbach, A.-R. J. Am. Chem. Soc. 2016, 138, 16549. doi: 10.1021/jacs.6b11140
[58]	Das Saha N.; Pradhan S.; Sasmal R.; Sarkar A.; Berač C. M.; Kölsch J. C.; Pahwa M.; Show S.; Rozenholc Y.; Topçu Z.; Alessandrini V.; Guibourdenche J.; Tsatsaris V.; Gagey-Eilstein N.; Agasti S. S. J. Am. Chem. Soc. 2022, 144, 14363. doi: 10.1021/jacs.2c05969