Citation: Lü Hui, Xu Xuetao, Huang Danying, Wu Panpan, Sheng Zhaojun, Liu Wenfeng, Li Dongli, Alharbi Njud S., Zhang Kun, Wang Shaohua. Recent Progress on Endoplasmic Reticulum-Targetable Fluorescence Probe[J]. Chinese Journal of Organic Chemistry, ;2018, 38(12): 3165-3175. doi: 10.6023/cjoc201806043 shu

Recent Progress on Endoplasmic Reticulum-Targetable Fluorescence Probe

Lü Hui ^a,b ,
Xu Xuetao ^a,b,, ,
Huang Danying ^a,b ,
Wu Panpan ^a,b ,
Sheng Zhaojun ^a,b ,
Liu Wenfeng ^a,b ,
Li Dongli ^a,b ,
Alharbi Njud S. ^c ,
Zhang Kun ^a,b ,
Wang Shaohua ^a,b,d,,

a.
School of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020
b.
International Healthcare Innovation Institute, Jiangmen 529000
c.
Faculty of Science, King Abdulaziz University, Jeddah 999088
d.
School of Pharmacy, Lanzhou University, Lanzhou 730000

Corresponding author: Xu Xuetao, wyuchemxxt@126.com Wang Shaohua, wangshh@lzu.edu.cn
Received Date: 28 June 2018
Revised Date: 26 July 2018
Available Online: 22 December 2018
Fund Project: Project supported by the Department of Education of Guangdong Province (Nos. 2017KTSCX185, 2017KSYS010, 2016KCXTD005), the Youth Team Fund of Wuyi University, and the National Natural Science Foundation of China (Nos. 21472077, 21772071)

The endoplasmic reticulum, a subcellular organelle, plays an important role in the life activities of mammalian cells. Therefore, visualizing the endoplasmic reticulum, and further examining its active substances, microenvironments and physiological processes have important guiding value for the diagnosis and treatment of related diseases. In recent years, the design and synthesis of endoplasmic reticulum-targetable fluorescent probes have received more and more attentions. Currently, reported endoplasmic reticulum-targetable fluorescent probes mainly include simple endoplasmic reticulum imaging, metal ions, small molecule material, big molecule material, microenvironments, etc. This article summarizes and describes the design and synthesis of the reported endoplasmic reticulum-targetable fluorescent probes, analyzes the application of endoplasmic reticulum fluorescent probes in the study of cellular physiological processes, and prospects the development trend of endoplasmic reticulum-targetable fluorescent probes.
- endoplasmic reticulum,
- fluorescence,
- imaging,
- probe,
- active small molecule
1. [1]
  Vance, J. E. Traffic 2015, 16, 1. doi: 10.1111/tra.2015.16.issue-1
2. [2]
  Sovolyova, N.; Healy, S.; Samali, A.; Logue, S. E. Biol. Chem. 2014, 395, 1. doi: 10.1515/hsz-2013-0174
3. [3]
  Zhang, H.; Hu, J. Trends Cell Biol. 2016, 26, 934. doi: 10.1016/j.tcb.2016.06.002
4. [4]
  Brodsky, J. L.; Skach, W. R. Curr. Opin. Cell Biol. 2011, 23, 464. doi: 10.1016/j.ceb.2011.05.004
5. [5]
  Borgese, N.; Francolini, M.; Snapp, E. Curr. Opin. Cell Biol. 2006, 18, 358. doi: 10.1016/j.ceb.2006.06.008
6. [6]
  Westrate, L. M.; Lee, J. E.; Prinz, W. A.; Voeltz, G. K. Annu. Rev. Biochem. 2015, 84, 791. doi: 10.1146/annurev-biochem-072711-163501
7. [7]
  Li, M.; Fan, J. L.; Li, H. D.; Du, J. J.; Long, S. R.; Peng, X. J. Biomaterials 2018, 164, 98. doi: 10.1016/j.biomaterials.2018.02.044
8. [8]
  Liu, S. Y.; Ge, G. B.; Dong, W. B.; Peng, X. J.; Liu, F. Y.; Chen, S. S.; Sun, S. G. Sens. Actuators, A 2017, 253, 1145.
9. [9]
  Li, H. D.; Yao, Q. C.; Fan, J. L.; Du, J. J.; Wang, J. Y.; Peng, X. J. Biosens. Bioelecton. 2017, 94, 536. doi: 10.1016/j.bios.2017.03.039
10. [10]
  Xu, G.; Yan, Q. L.; Lv, X. G.; Zhu, Y.; Xin, K.; Shi, B.; Wang, R. C.; Chen, J.; Gao, W.; Shi, P.; Fan, C. H.; Zhao, C. C.; Tian, H. Angew. Chem., Int. Ed. 2018, 57, 3626. doi: 10.1002/anie.201712528
11. [11]
  Han, H. H.; Qiu, Y. J.; Shi, Y. Y.; Wen, W.; He, X. P.; Dong, L. W.; Tan, Y. X.; Long, Y. T.; Tian, H.; Wang, H. Y. Theranostics 2017, 8, 3268.
12. [12]
  Zhang, J. J.; Fu, Y. X.; Han, H. H.; Zang, Y.; Li, J.; He, X. P.; Feringa, B. L.; Tian, H. Nat. Commun. 2017, 8, 987. doi: 10.1038/s41467-017-01137-8
13. [13]
  Wu, H. J.; Jia, J. H.; Xu, Y. F.; Qian, X. H.; Zhu, W. P. Sens. Actuator, B 2018, 265, 59.
14. [14]
  Ti, Y. Z.; Yu, L.; Tang, Y. Jin, T. X.; Yang, M.; Wang, R.; Xu, Y. F.; Zhu, W. P. Sens. Actuator, B 2018, 265, 582.
15. [15]
  Li, D. D.; Xu, Y. Q.; Zhou, N. N.; Liu, J. X.; Wang, R.; Cheng, T.; Tang, Y.; Zhu, W. P.; Xu, Y. F.; Qian, X. H. Dyes Pigm. 2017, 136, 627. doi: 10.1016/j.dyepig.2016.09.014
16. [16]
  Li, J.; Chen, Y. H.; Chen, T. T.; Qiang, J.; Zhang, Z. J.; Wei, T. W.; Zhang, W.; Wang, F.; Chen, X. Q. Sens. Actuator, B 2018, 268, 446.
17. [17]
  Lee, D.; Jeong, K.; Luo, X.; Kim, G.; Yang, Y. J.; Chen, X. Q.; Kim, S.; Yoon, J. J. Mater. Chem. B 2018, 6, 2541. doi: 10.1039/C7TB01560G
18. [18]
  Zhang, Z. J.; Wei, T. W.; Chen, Y. H.; Chen, T. T.; Chi, B.; Wang, F.; Chen, X. Q. Sens. Actuator, B 2018, 255, 2211.
19. [19]
  Wu, X. F.; Shi, W.; Li, X. H.; Ma, H. M. Angew. Chem., Int. Ed. 2017, 56, 15319. doi: 10.1002/anie.201708428
20. [20]
  Xu, Y. H.; Shi, W.; He, X. Y.; Wu, X. F.; Li, X. H.; Ma, H. M. Anal. Chem. 2017, 89, 10980. doi: 10.1021/acs.analchem.7b02815
21. [21]
  Fang, Y.; Chen, W.; Shi, W.; Li, H. Y.; Xian, M.; Ma, H. M. Chem. Commun. 2017, 53, 8759. doi: 10.1039/C7CC04093H
22. [22]
  Wang, H.; Xue, K.; Li, P.; Yang, Y. Y.; He, Z. X.; Zhang, W.; Zhang, W.; Tang, B. Anal. Chem. 2018, 90, 6020. doi: 10.1021/acs.analchem.7b04885
23. [23]
  Yang, L. M.; Li, J.; Pan, W.; Wang, H. Y.; Li, N.; Tang, B. Chem. Commun. 2018, 54, 3656. doi: 10.1039/C8CC01335G
24. [24]
  Gao, X. N.; Jiang, L. L.; Hu, B.; Kong, F. P.; Liu, X. J.; Xu, K. H.; Tang, B. Anal. Chem. 2018, 90, 4719. doi: 10.1021/acs.analchem.7b05343
25. [25]
  Jones, V. C.; McKeown, L.; Verkhratsky, A.; Jones, O. T. BMC Neurosci. 2008, 9, 10. doi: 10.1186/1471-2202-9-10
26. [26]
  Diniz, J. R.; Correa, J. R.; Moreira, D.; Fontenele, R. S.; Oliveira, A. L.; Abdelnur, P. V.; Dutra, J. D. L.; Freire, R. O.; Rodrigues, M. O.; Neto, B. A. D. Inorg. Chem. 2013, 52, 10199. doi: 10.1021/ic4017678
27. [27]
  Zhang, H; Fan, J. L.; Dong, H. J.; Zhang, S. Z.; Xu, W. Y.; Wang, J. Y.; Gao, P.; Peng, X. J. J. Mater. Chem. B 2013, 1, 5450. doi: 10.1039/c3tb20646g
28. [28]
  D'Amore, C.; Orso, G.; Fusi, F.; Pagano, M. A.; Miotto, G.; Forgiarini, A.; Martin, S. D.; Castellani, G.; Ribaudo, G.; Rennison, D.; Brimble, M. A.; Hopkins, B.; Ferrarese, A.; Bova, S. Front Pharmacol. 2016, 7, 315.
29. [29]
  Collot, M.; Kreder, R.; Tatarets, A. L., Patsenker, L. D.; Mely, Y.; Klymchenko, A. Chem. Commun. 2015, 51, 17136. doi: 10.1039/C5CC06094J
30. [30]
  Kamkaew, A.; Thavornpradit, S.; Puangsamlee, T.; Xin, D.; Wanichachev, N.; Burgess, K. Org. Biomol. Chem. 2015, 13, 8271. doi: 10.1039/C5OB01104C
31. [31]
  Phaniraj, S.; Gao, Z.; Rane, D.; Peterson, B. R. Dyes Pigm. 2016, 135, 127. doi: 10.1016/j.dyepig.2016.05.007
32. [32]
  Zheng, S.; Huang, C.; Zhao, X.; Zhang, Y.; Liu, S.; Zhu, Q. Spectrochem. Acta A 2017, 189, 231.
33. [33]
  Meinig, J. M.; Fu, L.; Peterson, B. R. Angew. Chem., Int. Ed. 2015, 54, 9696. doi: 10.1002/anie.v54.33
34. [34]
  Lew, R. L.; Briskin, D. P.; Wyse, R. E. Plant Physiol. 1986, 82, 47. doi: 10.1104/pp.82.1.47
35. [35]
  Giannini, J. L.; Gildensoph, L. H.; Reynolds-niesman, I.; Briskin, D. P. Plant Physiol. 1987, 85, 1129-1136. doi: 10.1104/pp.85.4.1129
36. [36]
  Lee, Y. H.; Park, N.; Park, Y. B.; Hwang, Y. J.; kang, C.; Kim, J. S. Chem. Commun. 2014, 50, 3197. doi: 10.1039/C4CC00091A
37. [37]
  Park, S. Y.; Kim, W.; Park, S. H.; Han, J. Y.; Lee, J.; Kang, C.; Lee, M. H. Chem. Commun. 2017, 53, 32.
38. [38]
  Lin, W.; Buccella, D.; Lippard, S. J. J. Am. Chem. Soc. 2013, 135, 13512. doi: 10.1021/ja4059487
39. [39]
  Gan, X.; Sun, P.; Li, H.; Tian, X.; Zhang, B.; Wu, J.; Tian, Y.; Zhou, H. Biosens. Bioelectron. 2016, 86, 393. doi: 10.1016/j.bios.2016.06.087
40. [40]
  Lee, M. H.; Lee, H.; Chang, M. J.; Kim, H. S.; Kang, C.; Kim, J. S. Dyes Pigm. 2016, 130, 245. doi: 10.1016/j.dyepig.2016.03.032
41. [41]
  Xiao, H.; Li, P.; Hu, X.; Shi, X.; Zhang, W.; Tang, B. Chem. Sci. 2016, 7, 6153. doi: 10.1039/C6SC01793B
42. [42]
  Gao, C.; Tian, Y.; Zhang, R. B.; Jing, J.; Zhang, X. Anal. Chem. 2017, 89, 12945. doi: 10.1021/acs.analchem.7b03809
43. [43]
  Xiao, H.; Liu, X.; Wu, C.; Wu, Y.; Li, P.; Guo, X.; Tang, B. Biosens. Bioelectron. 2017, 91, 449. doi: 10.1016/j.bios.2016.12.068
44. [44]
  Li, J. P.; Xia, S.; Zhang, H.; Qu, G. R.; Guo, H. M. Sens Actuator, B 2018, 255, 622.
45. [45]
  Liu, P.; Han, X. Y.; Yu, F. B.; Chen, L. X. Chin. J. Anal. Chem. 2015, 43, 1829. doi: 10.1016/S1872-2040(15)60883-0
46. [46]
  Ali, F.; Sreedharan, S.; Ashoka, A. H.; Saeed, H. K.; Smythe, C. G. W.; Thomas, J. A.; Das, A. Anal. Chem. 2017, 89, 12087. doi: 10.1021/acs.analchem.7b02567
47. [47]
  Tang, Y.; Ma, Y.; Xu, A.; Xu G.; Lin, W. Methods Appl. Fluoresc. 2017, 5, 024005. doi: 10.1088/2050-6120/aa6773
48. [48]
  Tang, Y.; Xu, A.; Ma, Y.; Xu, G.; Gao, S.; Lin, W. Sci. Rep. 2017, 7, 12944. doi: 10.1038/s41598-017-13325-z
49. [49]
  Meng, Q.; Jia, H.; Succar, P.; Zhao, L.; Zhang, R.; Duan, C.; Zhang, Z. Biosens. Bioelectron. 2015, 74, 461. doi: 10.1016/j.bios.2015.06.077
50. [50]
  Hakamata, W.; Tamura, S.; Hirano, T.; Nishio, T. ACS Med. Chem. Lett. 2014, 5, 321. doi: 10.1021/ml400398t
51. [51]
  Shaulov-Rotem, Y.; Merquiol, E.; Weiss-Sadan, T.; Moshel, O.; Salpeter, S.; Shabat, D.; Kaschani, F.; Kaiser, M.; Blum, G. Chem. Sci. 2016, 7, 1322. doi: 10.1039/C5SC03207E
52. [52]
  Xu, S.; Liu, H. W.; Hu, X. X.; Huan, S. Y.; Zhang, Y.; Liu, Y.; Yuan, L.; Qu, F. L.; Zhang, X. B.; Tan, W. Anal. Chem. 2017, 89, 7641. doi: 10.1021/acs.analchem.7b01561
53. [53]
  McMahon, B. K.; Pal, R.; Parker, D. Chem. Commun. 2013, 49, 5363. doi: 10.1039/c3cc42308e
54. [54]
  Ghule, N. V.; Bhosale, R. S.; Kharat, K.; Puyad, A. L.; Bhosale, S. V.; Bhosale, S. V. ChemPlusChem 2015, 80, 485. doi: 10.1002/cplu.201402307
55. [55]
  Upendar, R. G.; Anila, H. A.; Firoj, A.; Nandaraj, T.; Samit, C.; Amitava, D. Org. Lett. 2015, 17, 5532. doi: 10.1021/acs.orglett.5b02568
56. [56]
  Arai, S.; Lee, S. C.; Zhai, D.; Suzuki, M.; Chang, Y. T. Sci. Rep. 2014, 4, 6701.
57. [57]
  Yang, Z.; He, Y.; Lee, J. H.; Chae, W. S.; Ren, W. X.; Lee, J. H.; Kang, C.; Kim, J. S. Chem. Commun. 2014, 50, 11672. doi: 10.1039/C4CC04915B
58. [58]
  Lee, H.; Yang, Z.; Wi, Y.; Kim, T. W.; Verwilst, P.; Lee, Y. H.; Han, G.; Kang, C.; Kim, J. S. Bioconjugate Chem. 2015, 26, 2474. doi: 10.1021/acs.bioconjchem.5b00508
59. [59]
  Xiao, H.; Wu, C.; Li, P.; Gao, W.; Zhang, W.; Zhang, W.; Tong, L.; Tang, B. Chem. Sci. 2017, 8, 7025. doi: 10.1039/C7SC02330H
60. [60]
  Takakura, H.; Zhang, Y.; Erdmann, R. S.; Thompson, A. D.; Lin, Y.; McNellis, B.; Rivera-Molina, F.; Uno, S.; Kamiya, M.; Urano, Y.; Rothman, J. E.; Bewersdorf, J.; Schepartz, A.; Toomre, D. Nat. Biotechnol. 2017, 35, 773. doi: 10.1038/nbt.3876
61. [61]
  Kaplfán, P.; Račay, P.; Lehotský, J.; Mézešová, V. Neurochem. Res. 1995, 20, 815. doi: 10.1007/BF00969693
62. [62]
  Yang, Z.; Wi, Y.; Yoon, Y. M.; Verwilst, P.; Jang, J. H.; Kim, T. H.; Kang, C.; Kim, J. S. Chem. Asian J. 2016, 11, 527. doi: 10.1002/asia.v11.4
1. [1]
  Yang Wang , Yunpeng Fu , Xiaoji Liu , Guotao Zhang , Guobin Li , Wanqiang Liu , Jinglun Wang . Structural Analysis of Nitrile Solutions Based on Infrared Spectroscopy Probes. University Chemistry, 2025, 40(4): 367-374. doi: 10.12461/PKU.DXHX202406113
2. [2]
  Zehua Zhang , Haitao Yu , Yanyu Qi . 多重共振TADF分子的设计策略. Acta Physico-Chimica Sinica, 2025, 41(1): 2309042-. doi: 10.3866/PKU.WHXB202309042
3. [3]
  Xiao SANG , Qi LIU , Jianping LANG . Synthesis, structure, and fluorescence properties of Zn(Ⅱ) coordination polymers containing tetra-alkenylpyridine ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2124-2132. doi: 10.11862/CJIC.20240158
4. [4]
  Feng Lu , Tao Wang , Qi Wang . Preparation and Characterization of Water-Soluble Silver Nanoclusters: A New Design and Teaching Practice in Materials Chemistry Experiment. University Chemistry, 2025, 40(4): 375-381. doi: 10.12461/PKU.DXHX202406005
5. [5]
  YanYuan Jia , Rong Rong , Jie Liu , Jing Guo , GuoYu Jiang , Shuo Guo . Unity is Strength, and Independence Shines: A Science Popularization Experiment on AIE and ACQ Effects. University Chemistry, 2024, 39(9): 349-358. doi: 10.12461/PKU.DXHX202402035
6. [6]
  Qin Li , Kexin Yang , Qinglin Yang , Xiangjin Zhu , Xiaole Han , Tao Huang . Illuminating Chlorophyll: Innovative Chemistry Popularization Experiment. University Chemistry, 2024, 39(9): 359-368. doi: 10.3866/PKU.DXHX202309059
7. [7]
  Chen LU , Qinlong HONG , Haixia ZHANG , Jian ZHANG . Syntheses, structures, and properties of copper-iodine cluster-based boron imidazolate framework materials. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 149-154. doi: 10.11862/CJIC.20240407
8. [8]
  Jinlong YAN , Weina WU , Yuan WANG . A simple Schiff base probe for the fluorescent turn-on detection of hypochlorite and its biological imaging application. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1653-1660. doi: 10.11862/CJIC.20240154
9. [9]
  Yanxi LIU , Mengjia XU , Haonan CHEN , Quan LIU , Yuming ZHANG . A fluorescent-colorimetric probe for peroxynitrite-anion-imaging in living cells. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1112-1122. doi: 10.11862/CJIC.20240423
10. [10]
  Siyi ZHONG , Xiaowen LIN , Jiaxin LIU , Ruyi WANG , Tao LIANG , Zhengfeng DENG , Ao ZHONG , Cuiping HAN . Targeting imaging and detection of ovarian cancer cells based on fluorescent magnetic carbon dots. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1483-1490. doi: 10.11862/CJIC.20240093
11. [11]
  Jiakun BAI , Ting XU , Lu ZHANG , Jiang PENG , Yuqiang LI , Junhui JIA . A red-emitting fluorescent probe with a large Stokes shift for selective detection of hypochlorous acid. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1095-1104. doi: 10.11862/CJIC.20240002
12. [12]
  Jun LUO , Baoshu LIU , Yunchang ZHANG , Bingkai WANG , Beibei GUO , Lan SHE , Tianheng CHEN . Europium(Ⅲ) metal-organic framework as a fluorescent probe for selectively and sensitively sensing Pb²⁺ in aqueous solution. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2438-2444. doi: 10.11862/CJIC.20240240
13. [13]
  Benhua Wang , Chaoyi Yao , Yiming Li , Qing Liu , Minhuan Lan , Guipeng Yu , Yiming Luo , Xiangzhi Song . 一种基于香豆素氟离子荧光探针的合成、表征及性能测试——“科研反哺教学”在有机化学综合实验教学中的探索与实践. University Chemistry, 2025, 40(6): 201-209. doi: 10.12461/PKU.DXHX202408070
14. [14]
  Shuwen SUN , Gaofeng WANG . Two cadmium coordination polymers constructed by varying Ⅴ-shaped co-ligands: Syntheses, structures, and fluorescence properties. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 613-620. doi: 10.11862/CJIC.20230368
15. [15]
  Dongdong YANG , Jianhua XUE , Yuanyu YANG , Meixia WU , Yujia BAI , Zongxuan WANG , Qi MA . Design and synthesis of two coordination polymers for the rapid detection of ciprofloxacin based on triphenylpolycarboxylic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2466-2474. doi: 10.11862/CJIC.20240266
16. [16]
  Jiming XI , Yukang TENG , Rui ZHANG , Zhenzhong LU . Fluorescent coordination polymers based on anthracene-and pyrene-derivative ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 847-854. doi: 10.11862/CJIC.20240367
17. [17]
  Yuanyu YANG , Jianhua XUE , Yujia BAI , Lulu CUI , Dongdong YANG , Qi MA . Design, synthesis, and detection of Al³⁺ of two zinc complexes based on Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1207-1216. doi: 10.11862/CJIC.20250005
18. [18]
  Qi Wang , Yicong Gao , Feng Lu , Quli Fan . Preparation and Performance Characterization of the Second Near-Infrared Phototheranostic Probe: A New Design and Teaching Practice of Polymer Chemistry Comprehensive Experiment. University Chemistry, 2024, 39(11): 342-349. doi: 10.12461/PKU.DXHX202404141
19. [19]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
20. [20]
  Wenyan Dan , Weijie Li , Xiaogang Wang . The Technical Analysis of Visual Software ShelXle for Refinement of Small Molecular Crystal Structure. University Chemistry, 2024, 39(3): 63-69. doi: 10.3866/PKU.DXHX202302060

Get Citation

PDF

XML

Metrics

PDF Downloads(16)
Abstract views(1405)
HTML views(252)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142