Chinese Journal of Organic Chemistry >
Research Progress of Fluorescent Probes for Cysteine Targeting Cellular Organelles
Received date: 2022-09-05
Revised date: 2022-12-01
Online published: 2023-01-05
Supported by
National Natural Science Foundation of China(22174008); National Natural Science Foundation of China(22177013); National Natural Science Foundation of China(21974009); National Natural Science Foundation of China(22274010)
As an important endogenous biothiol, cysteine is involved in various physiological processes. Besides, cysteine also plays an important role in the regulation of intracellular redox levels and the synthesis of bioactive substances. Cellular organelles all act an essential role in the life process, but different cellular organelles have their own unique functions, which makes the mechanism of cysteine in different organelles may be different. The high sensitivity and in situ analyze ability of fluorescent probes provide a method to monitor cysteine in different organelles, which is helpful to understand the mechanism of cysteine in physiological process more comprehensively. In this review, the recent reports on cysteine specific fluorescent probes are classified according to their targeted organelles. Besides, the property of those probes, including their structure, response mechanism, spectral properties and biological applications, is summarized.
Key words: cysteine; cellular organelles; targetable localization; fluorescent probe
Feiran Liu , Jing Jing , Xiaoling Zhang . Research Progress of Fluorescent Probes for Cysteine Targeting Cellular Organelles[J]. Chinese Journal of Organic Chemistry, 2023 , 43(6) : 2053 -2067 . DOI: 10.6023/cjoc202209005
| [1] | Paul, B. D.; Sbodio, J. I.; Snyder, S. H. Trends Pharmacol. Sci. 2018, 39, 513. |
| [2] | Shahrokhian, S. Anal. Chem. 2001, 73, 5972. |
| [3] | Jung, H. S.; Chen, X.; Kim, J. S.; Yoon, J. Chem. Soc. Rev. 2013, 42, 6019. |
| [4] | Yin, C.; Huo, F.; Zhang, J.; Martínez-Má?ez, R.; Yang, Y.; Lv, H.; Li, S. Chem. Soc. Rev. 2013, 42, 6032. |
| [5] | Janáky, R.; Varga, V.; Hermann, A.; Saransaari, P.; Oja, S. S. Neurochem. Res. 2000, 25, 1397. |
| [6] | Anderson, C. L.; Iyer, S. S.; Ziegler, T. R.; Jones, D. P. Am. J. Physiol.: Regul., Integr. Comp. Physiol. 2007, 293, R1069. |
| [7] | Jones, D. P.; Go, Y.-M.; Anderson, C. L.; Ziegler, T. R.; Kinkade Jr, J. M.; Kirlin, W. G. FASEB J. 2004, 18, 1246. |
| [8] | Banjac, A.; Perisic, T.; Sato, H.; Seiler, A.; Bannai, S.; Weiss, N.; K?lle, P.; Tschoep, K.; Issels, R. D.; Daniel, P. T.; Conrad, M.; Bornkamm, G. W. Oncogene 2008, 27, 1618. |
| [9] | Zhang, R.; Yong, J.; Yuan, J.; Ping Xu, Z. Coord. Chem. Rev. 2020, 408, 213182. |
| [10] | Tcherkas, Y. V.; Denisenko, A. D. J. Chromatogr. A 2001, 913, 309. |
| [11] | Jia, D.; Li, F.; Sheng, L.; Ren, Q.; Dong, S.; Xu, S.; Mu, Y.; Miao, Y. Electrochem. Commun. 2011, 13, 1119. |
| [12] | Burford, N.; Eelman, M. D.; Mahony, D. E.; Morash, M. Chem. Commun. 2003, 146. |
| [13] | Tang, Y.; Ma, Y.; Yin, J.; Lin, W. Chem. Soc. Rev. 2019, 48, 4036. |
| [14] | Zhu, H.; Fan, J.; Du, J.; Peng, X. Acc. Chem. Res. 2016, 49, 2115. |
| [15] | Yin, J.; Huang, L.; Wu, L.; Li, J.; James, T. D.; Lin, W. Chem. Soc. Rev. 2021, 50, 12098. |
| [16] | Qi, Y.-L.; Wang, H.-R.; Chen, L.-L.; Duan, Y.-T.; Yang, S.-Y.; Zhu, H.-L. Chem. Soc. Rev. 2022, 51, 7752. |
| [17] | He, D.; Zhang, L.; Sun, Y. Coord. Chem. Rev. 2022, 461, 214507. |
| [18] | Dong, J.; Lu, G.; Tu, Y.; Fan, C. New J. Chem. 2022, 46, 10995. |
| [19] | Liu, W.; Chen, J.; Xu, Z. Coord. Chem. Rev. 2021, 429, 213638. |
| [20] | Yang, Q.; Lan, T.; He, W. Dyes Pigm. 2021, 186, 108997. |
| [21] | Dai, J.; Ma, C.; Zhang, P.; Fu, Y.; Shen, B. Dyes Pigm. 2020, 177, 108321. |
| [22] | Bock, F. J.; Tait, S. W. G. Nat. Rev. Mol. Cell Biol. 2020, 21, 85. |
| [23] | Pfanner, N.; Warscheid, B.; Wiedemann, N. Nat. Rev. Mol. Cell Biol. 2019, 20, 267. |
| [24] | Chan, D. C. Annu. Rev. Pathol.: Mech. Dis. 2020, 15, 235. |
| [25] | Bindoli, A.; Fukuto, J. M.; Forman, H. J. Antioxid. Redox Signaling 2008, 10, 1549. |
| [26] | Bak, D. W.; Weerapana, E. Mol. BioSyst. 2015, 11, 678. |
| [27] | Badgley, M. A.; Kremer, D. M.; Maurer, H. C.; DelGiorno, K. E.; Lee, H.-J.; Purohit, V.; Sagalovskiy, I. R.; Ma, A.; Kapilian, J.; Firl, C. E. M.; Decker, A. R.; Sastra, S. A.; Palermo, C. F.; Andrade, L. R.; Sajjakulnukit, P.; Zhang, L.; Tolstyka, Z. P.; Hirschhorn, T.; Lamb, C.; Liu, T.; Gu, W.; Seeley, E. S.; Stone, E.; Georgiou, G.; Manor, U.; Iuga, A.; Wahl, G. M.; Stockwell, B. R.; Lyssiotis, C. A.; Olive, K. P. Science 2020, 368, 85. |
| [28] | Gao, M.; Yi, J.; Zhu, J.; Minikes, A. M.; Monian, P.; Thompson, C. B.; Jiang, X. Mol. Cell 2019, 73, 354. |
| [29] | Wang, H.; Fang, B.; Peng, B.; Wang, L.; Xue, Y.; Bai, H.; Lu, S.; Voelcker, N. H.; Li, L.; Fu, L.; Huang, W. Front. Chem. 2021, 9, 683220. |
| [30] | Sun, C.; Du, W.; Wang, B.; Dong, B.; Wang, B. BMC Chem. 2020, 14, 21. |
| [31] | Zielonka, J.; Joseph, J.; Sikora, A.; Hardy, M.; Ouari, O.; Vasquez- Vivar, J.; Cheng, G.; Lopez, M.; Kalyanaraman, B. Chem. Rev. 2017, 117, 10043. |
| [32] | Shindy, H. A. Dyes Pigm. 2017, 145, 505. |
| [33] | Wang, R.; Yu, F.; Chen, L.; Chen, H.; Wang, L.; Zhang, W. Chem. Commun. 2012, 48, 11757. |
| [34] | Narayanan, N.; Patonay, G. J. Org. Chem. 1995, 60, 2391. |
| [35] | Yin, K.; Yu, F.; Zhang, W.; Chen, L. Biosens. Bioelectron. 2015, 74, 156. |
| [36] | Zhang, X.; He, N.; Huang, Y.; Yu, F.; Li, B.; Lv, C.; Chen, L. Sens. Actuators, B 2019, 282, 69. |
| [37] | Guo, T.; Chen, X.; Qu, W.; Yang, B.; Tian, R.; Geng, Z.; Wang, Z. Anal. Chem. 2022, 94, 5006. |
| [38] | Niu, L.; Luo, Y.; Gan, Y.; Cao, Q.; Zhu, C.; Wang, M.; Wang, J.; Zhang, W.; Wang, J. Talanta 2020, 219, 121291. |
| [39] | Zhang, H.; Yan, C.; Li, H.; Shi, L.; Wang, R.; Guo, Z.; Zhu, W.-H. ACS Appl. Bio Mater. 2021, 4, 2001. |
| [40] | Yue, L.; Huang, H.; Song, W.; Lin, W. Chem. Eng. J. 2022, 441, 135981. |
| [41] | Zhang, X.; Zhang, L.; Wang, X.; Han, X.; Huang, Y.; Li, B.; Chen, L. J. Hazard. Mater. 2021, 419, 126476. |
| [42] | Zhang, X.; Huang, Y.; Han, X.; Wang, Y.; Zhang, L.; Chen, L. Anal. Chem. 2019, 91, 14728. |
| [43] | Li, H.; Kim, H.; Xu, F.; Han, J.; Yao, Q.; Wang, J.; Pu, K.; Peng, X.; Yoon, J. Chem. Soc. Rev. 2022, 51, 1795. |
| [44] | Han, C.; Yang, H.; Chen, M.; Su, Q.; Feng, W.; Li, F. ACS Appl. Mater. Interfaces 2015, 7, 27968. |
| [45] | Kim, C. Y.; Kang, H. J.; Chung, S. J.; Kim, H.-K.; Na, S.-Y.; Kim, H.-J. Anal. Chem. 2016, 88, 7178. |
| [46] | Zhu, X.; Yuan, L.; Hu, X.; Zhang, L.; Liang, Y.; He, S.; Zhang, X.-B.; Tan, W. Sens. Actuators, B 2018, 259, 219. |
| [47] | Wei, Y.; Cheng, D.; Ren, T.; Li, Y.; Zeng, Z.; Yuan, L. Anal. Chem. 2016, 88, 1842. |
| [48] | Zhao, L.; He, X.; Li, D.; Xu, S.; Huang, Y.; Li, X.; Wang, X.; Sun, Y.; Ma, P.; Song, D. J. Mater. Chem. B 2020, 8, 7652. |
| [49] | Wang, X.; Zha, J.; Zhang, W.; Zhang, W.; Tang, B. Analyst 2020, 145, 6119. |
| [50] | Wang, H.; Wang, H.; Zhang, X.; Dong, M.; Huang, F.; Li, P.; Tang, B. Sens. Actuators, B 2021, 338, 129749. |
| [51] | Niu, L.; Luo, Y.; Zhao, H.; Cao, Q.; Wang, J.; Wang, J. Anal. Lett. 2021, 54, 2666. |
| [52] | Cai, S.; Liu, Q.; Liu, C.; He, S.; Zhao, L.; Zeng, X.; Gong, J. J. Mater. Chem. B 2022, 10, 1265. |
| [53] | Niu, W.; Guo, L.; Li, Y.; Shuang, S.; Dong, C.; Wong, M. S. Anal. Chem. 2016, 88, 1908. |
| [54] | Tang, L.; Xu, D.; Tian, M.; Yan, X. J. Lumin. 2019, 208, 502. |
| [55] | Fan, L.; Zhang, W.; Wang, X.; Dong, W.; Tong, Y.; Dong, C.; Shuang, S. Analyst 2019, 144, 439. |
| [56] | Ji, X.; Wang, N.; Zhang, J.; Xu, S.; Si, Y.; Zhao, W. Dyes Pigm. 2021, 187, 109089. |
| [57] | Liu, J.; Sun, Y.-Q.; Zhang, H.; Huo, Y.; Shi, Y.; Shi, H.; Guo, W. RSC Adv. 2014, 4, 64542. |
| [58] | Wei, Y.-N.; Lin, B.; Shu, Y.; Wang, J.-H. Analyst 2021, 146, 4642. |
| [59] | Ren, T.-B.; Zhang, Q.-L.; Su, D.; Zhang, X.-X.; Yuan, L.; Zhang, X.-B. Chem. Sci. 2018, 9, 5461. |
| [60] | Yuan, L.; Lin, W.; Zhao, S.; Gao, W.; Chen, B.; He, L.; Zhu, S. J. Am. Chem. Soc. 2012, 134, 13510. |
| [61] | Xia, S.; Zhang, Y.; Fang, M.; Mikesell, L.; Steenwinkel, T. E.; Wan, S.; Phillips, T.; Luck, R. L.; Werner, T.; Liu, H. ChemBioChem 2019, 20, 1986. |
| [62] | Yang, X.-Z.; Wei, X.-R.; Sun, R.; Xu, Y.-J.; Ge, J.-F. Talanta 2020, 209, 120580. |
| [63] | Chen, Y.; Zhong, X.; Yang, X.; Zhu, S.; Jiang, Y.; Jin, C. Chem. Commun. 2021, 57, 8198. |
| [64] | Zhang, P.; Guo, Z.-Q.; Yan, C.-X.; Zhu, W.-H. Chin. Chem. Lett. 2017, 28, 1952. |
| [65] | Huang, Y.; Zhou, Q.; Feng, Y.; Zhang, W.; Fang, G.; Fang, M.; Chen, M.; Xu, C.; Meng, X. Chem. Commun. 2018, 54, 10495. |
| [66] | Yue, Y.; Huo, F.; Pei, X.; Wang, Y.; Yin, C. Anal. Chem. 2020, 92, 6598. |
| [67] | Li, H.; Shi, W.; Li, X.; Hu, Y.; Fang, Y.; Ma, H. J. Am. Chem. Soc. 2019, 141, 18301. |
| [68] | Zhang, J.; Hao, X.; Sang, W.; Yan, Q. Small 2017, 13, 1701601. |
| [69] | Zhao, X.; Ji, H.; Hasrat, K.; Misal, S.; He, F.; Dai, Y.; Ma, F.; Qi, Z. Anal. Chim. Acta 2020, 1107, 172. |
| [70] | Luzio, J. P.; Pryor, P. R.; Bright, N. A. Nat. Rev. Mol. Cell Biol. 2007, 8, 622. |
| [71] | Lawrence, R. E.; Zoncu, R. Nat. Cell Biol. 2019, 21, 133. |
| [72] | Lie, P. P. Y.; Nixon, R. A. Neurobiol. Dis. 2019, 122, 94. |
| [73] | Yim, W. W.-Y.; Mizushima, N. Cell Discovery 2020, 6, 6. |
| [74] | Mego, J. L. Biochem. J. 1984, 218, 775. |
| [75] | Lloyd, J. B. Biochem. J. 1986, 237, 271. |
| [76] | Pisoni, R. L.; Acker, T. L.; Lisowski, K. M.; Lemons, R. M.; Thoene, J. G. J. Cell Biol. 1990, 110, 327. |
| [77] | Sulzer, D.; Zecca, L. Neurotox. Res. 1999, 1, 181. |
| [78] | Gahl, W. A.; Balog, J. Z.; Kleta, R. Ann. Intern. Med. 2007, 147, 242. |
| [79] | Lim, J.; Pellois, J.-P.; Simanek, E. E. Biorg. Med. Chem. Lett. 2010, 20, 6321. |
| [80] | Chen, C.; Zhou, L.; Liu, W.; Liu, W. Anal. Chem. 2018, 90, 6138. |
| [81] | Tasior, M.; Poronik, Y. M.; Vakuliuk, O.; Sadowski, B.; Karczewski, M.; Gryko, D. T. J. Org. Chem. 2014, 79, 8723. |
| [82] | Zhang, Y.; Zhang, Y.; Yue, Y.; Chao, J.; Huo, F.; Yin, C. Sens. Actuators, B 2020, 320, 128348. |
| [83] | Lu, G.; Dong, J.; Fan, C.; Tu, Y.; Pu, S. Bioorg. Chem. 2022, 119, 105558. |
| [84] | Zhang, H.; Li, K.; Li, L.-L.; Yu, K.-K.; Liu, X.-Y.; Li, M.-Y.; Wang, N.; Liu, Y.-H.; Yu, X.-Q. Chin. Chem. Lett. 2019, 30, 1063. |
| [85] | Jing, X.; Yu, F.; Lin, W. Anal. Chim. Acta 2021, 1174, 338738. |
| [86] | 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. |
| [87] | Cai, S.; Liu, C.; Jiao, X.; Zhao, L.; Zeng, X. J. Mater. Chem. B 2020, 8, 2269. |
| [88] | Liu, Q.; Liu, C.; Jiao, X.; Cai, S.; He, S.; Zhao, L.; Zeng, X.; Wang, T. Dyes Pigm. 2021, 190, 109293. |
| [89] | Yue, Y.; Huo, F.; Yue, P.; Meng, X.; Salamanca, J. C.; Escobedo, J. O.; Strongin, R. M.; Yin, C. Anal. Chem. 2018, 90, 7018. |
| [90] | Long, Z.; Chen, L.; Dang, Y.; Chen, D.; Lou, X.; Xia, F. Talanta 2019, 204, 762. |
| [91] | Wang, X.-D.; Fan, L.; Ge, J.-Y.; Li, F.; Zhang, C.-H.; Wang, J.-J.; Shuang, S.-M.; Dong, C. Spectrochim. Acta, Part A 2019, 221, 117175. |
| [92] | Jiang, C.; Huang, H.; Kang, X.; Yang, L.; Xi, Z.; Sun, H.; Pluth, M. D.; Yi, L. Chem. Soc. Rev. 2021, 50, 7436. |
| [93] | Jing, X.; Yu, F.; Lin, W. Spectrochim. Acta, Part A 2020, 240, 118555. |
| [94] | Gao, J.; Tao, Y.; Zhang, J.; Wang, N.; Ji, X.; He, J.; Si, Y.; Zhao, W. Chem.-Eur. J. 2019, 25, 11246. |
| [95] | Huang, Y.; Ren, Q.; Li, S.; Feng, Y.; Zhang, W.; Fang, G.; Li, L.; Sun, C.; Wang, X.; Meng, X. Sens. Actuators, B 2019, 293, 247. |
| [96] | Tamima, U.; Song, C. W.; Santra, M.; Reo, Y. J.; Banna, H.; Islam, M. R.; Ahn, K. H. Sens. Actuators, B 2020, 322, 128588. |
| [97] | Kosuge, Y. Exp. Ther. Med. 2020, 19, 1565. |
| [98] | Bechtel, T. J.; Li, C.; Kisty, E. A.; Maurais, A. J.; Weerapana, E. ACS Chem. Biol. 2020, 15, 543. |
| [99] | Carelli, S.; Ceriotti, A.; Cabibbo, A.; Fassina, G.; Ruvo, M.; Sitia, R. Science 1997, 277, 1681. |
| [100] | Ashraf, N. U.; Sheikh, T. A. Free Radical Res. 2015, 49, 1405. |
| [101] | Ji, Y.; Wu, Z.; Dai, Z.; Sun, K.; Zhang, Q.; Wu, G. Amino Acids 2016, 48, 149. |
| [102] | Singh, V. K.; Rahman, M. N.; Munro, K.; Uversky, V. N.; Smith, S. P.; Jia, Z. PLoS One 2012, 7, e34680. |
| [103] | Kabil, O.; Yadav, V.; Banerjee, R. J. Biol. Chem. 2016, 291, 16418. |
| [104] | Liu, S.; Xin, D.; Wang, L.; Zhang, T.; Bai, X.; Li, T.; Xie, Y.; Xue, H.; Bo, S.; Liu, D.; Wang, Z. Redox Biol. 2017, 13, 528. |
| [105] | Ali, F.; H. A, A.; Taye, N.; Gonnade, R. G.; Chattopadhyay, S.; Das, A. Chem. Commun. 2015, 51, 16932. |
| [106] | Meng, Q.; Jia, H.; Succar, P.; Zhao, L.; Zhang, R.; Duan, C.; Zhang, Z. Biosens. Bioelectron. 2015, 74, 461. |
| [107] | Dong, B.; Lu, Y.; Zhang, N.; Song, W.; Lin, W. Anal. Chem. 2019, 91, 5513. |
| [108] | Zhou, L.; Li, Y.; Zhou, A.; Zhang, G.; Cheng, Z.-Q.; Ge, Y.-X.; Liu, S.-K.; Azevedo, R. B.; Zhang, J.; Jiang, S.; Jiang, C.-S. J. Fluoresc. 2020, 30, 1357. |
| [109] | Lowe, M. Curr. Opin. Cell Biol. 2011, 23, 85. |
| [110] | Potelle, S.; Klein, A.; Foulquier, F. J. Inherit. Metab. Dis. 2015, 38, 741. |
| [111] | Sasaki, K.; Yoshida, H. J. Biochem. 2015, 157, 185. |
| [112] | Lange, P. S.; Chavez, J. C.; Pinto, J. T.; Coppola, G.; Sun, C.-W.; Townes, T. M.; Geschwind, D. H.; Ratan, R. R. J. Exp. Med. 2008, 205, 1227. |
| [113] | Sbodio, J. I.; Snyder, S. H.; Paul, B. D. Proc. Natl. Acad. Sci. U. S. A. 2018, 115, 780. |
| [114] | Paul, B. D. Antioxidants 2021, 10, 1468. |
| [115] | Chen, J.; Liu, H.; Yang, L.; Jiang, J.; Bi, G.; Zhang, G.; Li, G.; Chen, X. ACS Med. Chem. Lett. 2019, 10, 954. |
| [116] | Zhang, X.; Liu, C.; Chen, Y.; Cai, X.; Sheng, W.; Zhu, H.; Jia, P.; Li, Z.; Huang, S.; Zhu, B. Chem. Commun. 2020, 56, 1807. |
| [117] | Zhang, X.; Liu, C.; Cai, X.; Tian, B.; Zhu, H.; Chen, Y.; Sheng, W.; Jia, P.; Li, Z.; Yu, Y.; Huang, S.; Zhu, B. Sens. Actuators, B 2020, 310, 127820. |
| [118] | Zhu, H.; Liu, C.; Rong, X.; Zhang, Y.; Su, M.; Wang, X.; Liu, M.; Zhang, X.; Sheng, W.; Zhu, B. Bioorg. Chem. 2022, 122, 105741. |
| [119] | Ducharme, N. A.; Bickel, P. E. Endocrinology 2008, 149, 942. |
| [120] | Olzmann, J. A.; Carvalho, P. Nat. Rev. Mol. Cell Biol. 2019, 20, 137. |
| [121] | Mashek, D. G.; Khan, S. A.; Sathyanarayan, A.; Ploeger, J. M.; Franklin, M. P. Hepatology 2015, 62, 964. |
| [122] | Dai, J.; Liang, K.; Zhao, S.; Jia, W.; Liu, Y.; Wu, H.; Lv, J.; Cao, C.; Chen, T.; Zhuang, S.; Hou, X.; Zhou, S.; Zhang, X.; Chen, X.-W.; Huang, Y.; Xiao, R.-P.; Wang, Y.-L.; Luo, T.; Xiao, J.; Wang, C. Proc. Natl. Acad. Sci. U. S. A. 2018, 115, E5896. |
| [123] | Mok, W. J.; Hatanaka, Y.; Seoka, M.; Itoh, T.; Tsukamasa, Y.; Ando, M. Food Chem. 2014, 147, 340. |
| [124] | Yue, F.; Oprescu, S. N.; Qiu, J.; Gu, L.; Zhang, L.; Chen, J.; Narayanan, N.; Deng, M.; Kuang, S. Cell Rep. 2022, 38, 110267. |
| [125] | Cheng, W.; Xue, X.; Zhang, F.; Zhang, B.; Li, T.; Peng, L.; Cho, D.-H.; Chen, H.; Fang, J.; Chen, X. Anal. Chim. Acta 2020, 1127, 20. |
| [126] | Wang, Z.; Gui, C.; Zhao, E.; Wang, J.; Li, X.; Qin, A.; Zhao, Z.; Yu, Z.; Tang, B. Z. ACS Appl. Mater. Interfaces 2016, 8, 10193. |
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