Chinese Journal of Organic Chemistry >
Recent Advances in Fluorescent Probes for Biothiols
Received date: 2020-06-23
Revised date: 2020-07-27
Online published: 2020-08-19
Supported by
the National Natural Science Foundation of China(51703171); and the Graduate Innovative Fund of Wuhan Institute of Technology(CX2019003)
Biothiols, including cysteine (Cys), homocysteine (Hcy) and glutathione (GSH), play an important role in life activities, and the fluctuation of their concentrations is closely related to many diseases. Therefore, it is of great importance to detect the content of biothiols. Among all varieties of techniques, the fluorescent probe demonstrates tremendous advantages ascribed to its good sensitivity, high temporal-spatial resolution, noninvasiveness and visualization. Taking advantage of the commonality and differences among the three thiols, namely, the similar reactive groups of sulfhydryl group and amino group, and the different molecular size, nucleophilicity, steric hindrance and intracellular contents, various recognition mechanisms, such as Michael addition, aromatic nucleophilic reaction and concerted addition and cyclization reaction, are all implemented to realize the specific detection of biothiols. The research progress of thiol fluorescent probes in recent three years is reviewed. The fluorescent probes that can selectively respond to biothiols as well as to Cys, Hcy and GSH are systemically analyzed and summarized. The molecular design, recognition mechanism, fluorescence properties and imaging applications are emphasized,, and the application of biothiol fluorescent probe on monitoring life activities is preliminary introduced. In addition, a perspective of future development in this area is also presented.
Key words： biothiol; fluorescent probe; cysteine; homocysteine; glutathione; advance
Li Chen , Junbo Li , Dugang Chen . Recent Advances in Fluorescent Probes for Biothiols[J]. Chinese Journal of Organic Chemistry, 2021 , 41(2) : 611 -623 . DOI: 10.6023/cjoc202006046
| [1] | Zhang W.; Liu J.; Yu Y.; Han Q.; Cheng T.; Shen J.; Wang B.; Jiang Y. Talanta 2018, 185, 477. |
| [2] | Abbasi-Moayed S.; Golmohammadi H.; Bigdeli A.; Hormozi- Nezhad, M.R.Analyst 2018, 143, 3415. |
| [3] | Chen D.; Yang J.; Dai J.; Lou X.; Zhong C.; Yu X.; Xia F. J. Mater. Chem. B 2018, 6, 5248. |
| [4] | Alberti G.; Nurchi V.M.; Magnaghi L.R.; Biesuz R. Anal. Methods 2019, 11, 4464. |
| [5] | Yang Y.; Wang Y.; Feng Y.; Cao C.; Song X.; Zhang G.; Liu W. J. Mater. Chem. B 2019, 7, 7723. |
| [6] | Zhan C.; Zhang G.; Zhang D. ACS Appl. Mater. Interfaces 2017, 10, 12141. |
| [7] | Jiao S.; He X.; Xu L.; Ma P.; Liu C.; Huang Y.; Sun Y.; Wang X.; Song D. Sens. Actuators, B 2019, 290, 47. |
| [8] | Li M.; Kang N.; Zhang C.; Liang W.; Zhang G.; Jia J.; Yao Q.; Shuang S.; Dong C. Spectrochim. Acta, Part A 2019, 222, 117262. |
| [9] | Wu Q.; Mao M.; Liang W.; Stadler F.J. Talanta 2018, 186, 110. |
| [10] | Yin C.X.; Xiong K.M.; Huo F.J.; Salamanca J.C.; Strongin R.M. Angew. Chem. Int. Ed. 2017, 56, 13188. |
| [11] | Niu H.; Ni B.; Chen K.; Yang X.; Cao W.; Ye Y.; Zhao Y. Talanta 2019, 196, 145. |
| [12] | Kim C.Y.; Kang H.J.; Chung S.J.; Kim H.K.; Na S.Y.; Kim H.J. Anal. Chem 2016, 88, 7178. |
| [13] | Wang H.; Zhang Y.; Yang Y.; He Z.; Wu C.; Zhang W.; Zhang W.; Liu J.; Li P.; Tang B. Chem. Commun. 2019, 55, 9685. |
| [14] | Bai Z.; Yan F.; Xu J.; Zhang J.; Wei J.; Luo Y.; Chen L. Spectrochim. Acta, Part A 2018, 205, 29. |
| [15] | Yue Y.; Huo F.; Ning P.; Zhang Y.; Chao J.; Meng X.; Yin C. J. Am. Chem. Soc. 2017, 139, 3181. |
| [16] | Yang M.W.; Fan J.L.; Sun W.; Du J.J.; Peng X.J. Anal. Chem. 2019, 19, 12531. |
| [17] | Li M.; Zheng K.; Chen H.; Liu X.; Xiao S.; Yan J.; Tan X.; Zhang N. Spectrochim. Acta, Part A 2019, 217, 1. |
| [18] | Meng X.; Ye W.; Wang S.; Feng Y.; Chen M.; Zhu M.; Guo Q. Sens. Actuators, B 2014, 201, 520. |
| [19] | Zhang Q.; Cui Z.; Wang Q.; Zheng G. Sens. Actuators, B 2019, 295, 79. |
| [20] | Guo Z.B.; Zheng X.Y.; Li X.Y.; Jia Q.F.; Zhang P.Z.; Wei C.; Li X.L. Chin. J. Org. Chem. 2020, 40, 1239. (in Chinese) |
| [20] | 郭振波, 郑雪阳, 李雪艳, 贾清菲, 张平竹, 魏超, 李小六, 有机化学, 2020, 40, 1239.). |
| [21] | Chen D.; Zhong C.; Zhao Y.; Nan L.; Liu Y.; Qin J. J. Mater. Chem. C 2017, 5, 5199. |
| [22] | Li D.-P.; Zhang J.-F.; Cui J.; Ma X.-F.; Liu J.-T.; Miao J.-Y.; Zhao B.-X. Sens. Actuators, B 2016, 234, 231. |
| [23] | Zhang Y.; Wang X.; Bai X.; Li P.; Su D.; Zhang W.; Zhang W.; Tang B. Anal. Chem. 2019, 91, 8591. |
| [24] | Dang Y.; Chen L.; Yuan L.; Li J.; Chen D. ChemistrySelect 2020, 5, 584. |
| [25] | Yan P.P.; Wang T.; Zhang D.; Ma X.X. Chin. J. Org. Chem. 2019, 39, 916. (in Chinese) |
| [25] | 闫沛沛, 王婷, 张丹, 马晓雪, 有机化学, 2019, 39, 916.). |
| [26] | Chen H.; Tang Y.; Lin W. Trends Anal. Chem. 2016, 76, 166. |
| [27] | Chao J.; Li M.; Liu Y.; Zhang Y.; Huo F.; Yin C. Sens. Actuators, B 2019, 298, 126844. |
| [28] | Huang Y.; Mei J.; Ma X. Dyes Pigm. 2019, 165, 499. |
| [29] | Liu Z.; Zhou X.; Miao Y.; Hu Y.; Kwon N.; Wu X.; Yoon J. Angew. Chem. Int. Ed. 2017, 56, 5812. |
| [30] | Yang T.; Niu D.; Chen J.; He J.; Yang S.; Jia X.; Hao J.; Zhao W.; Li Y. Biomater. Sci. 2019, 7, 2951. |
| [31] | Wang L.; Wu S.; Tang H.; Meier H.; Cao D. Sens. Actuators, B 2018, 273, 1085. |
| [32] | Long Z.; Chen L.; Dang Y.; Chen D.; Lou X.; Xia F. Talanta 2019, 204, 762. |
| [33] | Zhou T.T.; Yang Y.T.; Zhou K.Y.; Xu W.Z.; Li W. Chin. J. Org. Chem. 2019, 39, 3498. (in Chinese) |
| [33] | 周婷婷, 杨瑜涛, 周柯岩, 胥稳智, 李玮, 有机化学, 2019, 39, 3498.). |
| [34] | Nia N.N.; Hadjmohammadi M.R. Anal. Methods 2019, 11, 5134. |
| [35] | Cao L.; Liang Q.; Wei T.; Shi Y.; Deng T.; Meng J. J. Chromatogr. A 2018, 1577, 47. |
| [36] | Zhang Y.; Zhang Y.; Zhu L.; He P.; Wang Q. Anal. Methods 2019, 11, 1558. |
| [37] | Otto P.; Bergmann S.; Sandmeyer A.; Dirksen M.; Wrede O.; Hellweg T.; Huser T. Nanoscale Adv. 2020. |
| [38] | Zhang Y.N.; Niu Q.; Gu X.; Yang N.; Zhao G. Nanoscale 2019, 11, 11992. |
| [39] | Hagemann L.T.; McCartney M.M.; Fung A.G.; Peirano D.J.; Davis C.E.; Mizaikoff B. Analyst 2018, 143, 5683. |
| [40] | Jiang T.; Wang X.; Wang G.; Wang Y.F.; Wang K.; Xuan X.P.; Chen C.P.; Jiang K.; Zhang H. Chem. Commun. 2019, 55, 5279. |
| [41] | Li R.; Huang X.; Lu G.; Feng C. RSC Adv. 2018, 8, 24346. |
| [42] | Dai X.; Zhang T.; Miao J.-Y.; Zhao B.-X. Sens. Actuators, B 2016, 223, 274. |
| [43] | Ramachandran R.; Chen T.-W.; Chen S.-M.; Baskar T.; Kannan R.; Elumalai P.; Raja P.; Jeyapragasam T.; Dinakaran K.; Gnana kumar, G.p.Inorg. Chem. Front. 2019, 6, 3418. |
| [44] | Chen K.; Han B.C.; Ji S.X.; Sun J.; Gao Z.Z.; Hou X.F. Acta Chim. Sinica 2019, 77, 365. (in Chinese) |
| [44] | 陈凯, 韩百川, 嵇思鑫, 孙瑾, 高振忠, 侯贤锋, 化学学报, 2019, 77, 365.). |
| [45] | Xie C.; Ma C.; Jia X.; Zhang X.Q.; Wei C.; Zhang P.Z.; Li X.L. Chin. J. Org. Chem. 2019, 39, 3277. (in Chinese) |
| [45] | 解畅, 马趁, 贾旭, 张学琪, 魏超, 张平竹, 李小六, 有机化学, 2019, 39, 3277.). |
| [46] | Liu H.; Zhu L.; Lou X.; Yuan L.; Zhang X. Acta Chim. Sinica 2020, 78, 1240. (in Chinese) |
| [46] | 刘红文, 朱隆民, 娄霄峰, 袁林, 张晓兵, 化学学报, 2020, 78, 1240.). |
| [47] | Zhang J.D.; Liu A.C.; Chen J.; Yuan G.H.; Jin H.F. Prog. Chem. 2020, 32, 594. (in Chinese) |
| [47] | 张继东, 刘阿晨, 陈娇, 袁光辉, 金华峰, 化学进展, 2020, 32, 594.). |
| [48] | Liu Y.; Niu L.-Y.; Chen Y.-Z.; Yang Q.-Z. J. Photochem. Photobiol. A, Chem. 2018, 355, 311. |
| [49] | Wang Y.; Huang C.S.; Jia N.Q. Prog. Chem. 2019, 32, 204. (in Chinese) |
| [49] | 王阳, 黄楚森, 贾能勤, 化学进展, 2019, 32, 204.). |
| [50] | Zhu D.; Yan X.; Ren A.; Xie W.; Duan Z. Anal. Chim. Acta 2019, 1058, 136. |
| [51] | Chen D.; Long Z.; Sun Y.; Luo Z.; Lou X. J. Photochem. Photobiol. A, Chem. 2019, 368, 90. |
| [52] | Yang L.; Xiong H.; Su Y.; Tian H.; Liu X.; Song X. Chin. Chem. Lett. 2019, 30, 563. |
| [53] | Du W.; Liu R.; Fang J.; Gao H.; Wang Y.; Peng Y. Tetrahedron 2019, 75, 130477. |
| [54] | Huang Y.; Zhang Y.; Huo F.; Liu Y.; Yin C. Sens. Actuators, B 2019, 301, 127123. |
| [55] | Luo J.; Xie Z.; Lam J. W. Y.; Cheng L.; Chen H.; Qiu C.; Kwok H.S.; Zhan X.; Liu Y.; Zhu D.; Tang B.Z. Chem. Commun. 2001, 18, 1740. |
| [56] | Mei J.; Leung N. L. C.; Kwok R. T. K.; Lam J. W. Y.; Tang B.Z. Chem. Rev. 2015, 115, 11718. |
| [57] | Dong F.; Lai H.; Liu Y.; Li Q.; Chen H.; Ji S.; Zhang J.; Huo Y. Talanta 2020, 206, 120177. |
| [58] | Das S.; Ghosh A.; Kundu S.; Saha S.; Sarkar H.S.; Sahoo P. Anal. Bioanal. Chem. 2019, 411, 6203. |
| [59] | Huang Z.; Wu C.; Li Y.; Zhou Z.; Xie R.; Pang X.; Xu H.; Li H.; Zhang Y. Anal. Methods 2019, 11, 3280. |
| [60] | Wang B.J.; Liu R.J.; Fang J.G.; Wang Y.W.; Peng Y. Chem. Commun. 2019, 55, 11762. |
| [61] | Ning Z.W.; Wu S.Z.; Liu G.J.; Ji Y.M.; Jia L.Y.; Niu X.X.; Ma R.F.; Zhang Y.; Xing G.W. Chem. Asian J. 2019, 14, 2220. |
| [62] | Khatik G.L.; Kumar R.; Chakraborti A.K. Org. Lett. 2006, 8, 2433. |
| [63] | Lin W.; Yuan L.; Cao Z.; Feng Y.; Long L. Chem.- Eur. J. 2009, 15, 5096. |
| [64] | Zhou X.; Jin X.; Sun G.; Li D.; Wu X. Chem. Commun. 2012, 48, 8793. |
| [65] | Zhao N.; Wu Y.H.; Shi L.X.; Lin Q.P.; Chen Z.N. Dalton Trans. 2010, 39, 8288. |
| [66] | Li Y.; Shi N.; Li M. New J. Chem. 2019, 43, 18517. |
| [67] | Chen X.; Xu H.; Ma S.; Tong H.; Lou K.; Wang W. RSC Adv. 2018, 8, 13388. |
| [68] | Zhu M.; Wu X.; Sang L.; Fan F.; Wang L.; Wu X.; Hua R.; Wang Y.; Li Q.X. New J. Chem. 2019, 43, 13463. |
| [69] | Zhang P.; Xiao Y.; Zhang Q.; Zhang Z.; Yu H.; Ding C. New J. Chem. 2019, 43, 7620. |
| [70] | Han C.; Song B.; Liang X.; Pan H.; Dong W. Anal. Methods 2019, 11, 2513. |
| [71] | Wu Y.; Shi A.; Zeng H.; Li Y.; Li H.; Chen X.; Wong W.-Y.; Fan X. Dyes Pigm. 2019, 170, 107563. |
| [72] | Lu Z.; Lu Y.; Fan C.; Sun X.; Shao W.; Jiang N.; Gong X.; Lu Y.; Sun G.; Jiang X. Sens. Actuators, B 2019, 290, 581. |
| [73] | Zhang S.; Wu D.; Wu J.; Xia Q.; Jia X.; Song X.; Zeng L.; Yuan Y. Talanta 2019, 204, 747. |
| [74] | Yu Y.; Xu H.; Zhang W.; Han Q.; Wang B.; Jiang Y. J. Photochem. Photobiol. A, Chem 2017, 346, 215. |
| [75] | Dai Y.; Xue T.; Zhang X.; Misal S.; Ji H.; Qi Z. Spectrochim. Acta, Part A 2019, 216, 365. |
| [76] | Liu D.; Lv Y.; Chen M.; Cheng D.; Song Z.; Yuan L.; Zhang X. J. Mater. Chem. B 2019, 7, 3970. |
| [77] | Chen D.; Long Z.; Dang Y.; Chen L. Dyes Pigm. 2019, 166, 266. |
| [78] | Liang B.; Wang B.; Ma Q.; Xie C.; Li X.; Wang S. Spectrochim. Acta, Part A 2018, 192, 67. |
| [79] | Bai Y.; Wu M.-X.; Ma Q.-J.; Wang C.-Y.; Sun J.-G.; Tian M.-J.; Li J.-S. New J. Chem. 2019, 43, 14763. |
| [80] | Kang Y.-F.; Niu L.-Y.; Yang Q.-Z. Chin. Chem. Lett. 2019, 30, 1791. |
| [81] | Yang Y.; Wang H.; Wei Y.-L.; Zhou J.; Zhang J.-F.; Zhou Y. Chin. Chem. Lett. 2017, 28, 2023. |
| [82] | Liu J.; Liu M.; Zhang H.; Wei X.; Wang J.; Xian M.; Guo W. Chem. Sci. 2019, 10, 10065. |
| [83] | Chen X.; Wang F.; Hyun J.Y.; Wei T.; Qiang J.; Ren X.; Shin I.; Yoon J. Chem. Soc. Rev. 2016, 45, 2976. |
| [84] | Wang K.; Xu S.; Lei Y.; Zheng W.; Zhang Q.; Chen S.; Hu H.; Hu Z. Talanta 2019, 196, 243. |
| [85] | Wang Y.W.; Liu S.B.; Ling W.J.; Peng Y. Chem. Commun. 2016, 52, 827. |
| [86] | Chu Y.; Xie Z.; Zhuang D.; Yue Y.; Yue Y.; Shi W.; Feng S. Chin. J. Chem. 2019, 37, 1216. |
| [87] | Wang C.; Xia X.; Luo J.; Qian Y. Dyes Pigm. 2018, 152, 85. |
| [88] | Jiang X.; Chen J.; Bajic A.; Zhang C.; Song X.; Carroll S.L.; Cai Z.L.; Tang M.; Xue M.; Cheng N.; Schaaf C.P.; Li F.; MacKenzie K.R.; Ferreon A. C. M.; Xia F.; Wang M.C.; Maletic-Savatic M.; Wang J. Nat. Commun. 2017, 8, 16087. |
| [89] | Ren M.; Wang L.; Lv X.; Sun Y.; Chen H.; Zhang K.; Wu Q.; Bai Y.; Guo W. Analyst 2019, 144, 7457. |
| [90] | Xu Y.; Li R.; Zhou X.; Li W.; Ernest U.; Wan H.; Li L.; Chen H.; Yuan Z. Talanta 2019, 205, 120125. |
| [91] | Xu Z.; Huang X.; Han X.; Wu D.; Zhang B.; Tan Y.; Cao M.; Liu S.H.; Yin J.; Yoon J. Chem. 2018, 4, 1609. |
| [92] | Xu Z.; Zhang M.-X.; Xu Y.; Liu S.H.; Zeng L.; Chen H.; Yin J. Sens. Actuators, B 2019, 290, 676. |
| [93] | Gong D.; Ru J.; Cao T.; Qian J.; Liu W.; Iqbal A.; Liu W.; Qin W.; Guo H. Sens. Actuators, B 2018, 258, 72. |
| [94] | Gu Y.; Zhao Z.; Niu G.; Zhang R.; Zhang H.; Shan G.-G.; Feng H.-T.; Kwok R. T. K.; Lam J. W. Y.; Yu X.; Tang B.Z. ACS Appl. Bio Mater. 2019, 2, 3120. |
/
| 〈 |
|
〉 |
