Citation: Li Yangjie, Lü Ziqi, Liu Min, Xing Guowen. Recent Progresses on Mitochondria-Targetable Fluorescent Probes[J]. Chinese Journal of Organic Chemistry, ;2016, 36(5): 962-975. doi: 10.6023/cjoc201510012 shu

Recent Progresses on Mitochondria-Targetable Fluorescent Probes

  • Corresponding author: Xing Guowen, gwxing@bnu.edu.cn
  • Received Date: 12 October 2015
    Revised Date: 28 December 2015

    Fund Project: Project supported by the National Natural Science Foundation of China No. 21272027

Figures(9)

  • Over the past few years, many bifunctional fluorescent probes based on small organic molecules, which can be located on the mitochondria to detect specific reactive small molecules (RSMs), including reactive oxygen species, reducing species, metal ions, proton and small anions, have been reported to be successful in achieving visual imaging in mitochondria. For further detection and imaging of the reactive small molecules in tissue, the design and synthesis of two-photon fluorescent probes and near-infrared fluorescent probes bearing good optical properties become increasingly popular. The recently reported mitochondrial fluorescent probes are classified, summarized and reviewed. The bright prospects of these probes in the application of preliminary diagnosis and therapy of some diseases are also discussed.
  • 加载中
    1. [1]

      Cui, Y.; Long, J. G. In Mitochondrial Medicine and Health, Eds.: Liu, J. K.; Wang, X. M., Science Press, Beijing, 2012, Chapter 1.

    2. [2]

      Pak, Y. L.; Swamy, K. M. K.; Yoon, J. Sensors 2015, 15, 24374.

    3. [3]

      Carvalho, P. H. P. R.; Correa, J. R.; Guido, B. C.; Gatto, C. C.; Oliveira, H. C. B. D.; Soares, T. A.; Neto, B. A. D. Chem. Eur. J. 2014, 20, 15360. 

    4. [4]

      Liu, X. L.; Du, X. J.; Dai, C. G.; Song, Q. H. J. Org.Chem. 2014, 79, 9481. 

    5. [5]

      Wei, L.; Yi, L.; Song, F. B.; Wei, C.; Wang, B. F.; Xi, Z. Sci.Rep. 2014, 4, 4521.

    6. [6]

      Hirosawa, S.; Arai, S.; Takeoka, S. Chem.Commun. 2012, 48, 4845.

    7. [7]

      Chen, J. H.; Liu, W. M.; Zhou, B. J.; Niu, G. L.; Zhang, H. Y.; Wu, J. S.; Wang, Y.; Ju, W. G.; Wang, P. F. J. Org. Chem.2013, 78, 6121. 

    8. [8]

      Zhang, S. L.; Fan, J. L.; Zhang, S. Z.; Wang, X. W.; Du, J. J.; Peng, X. J. Chem.Commun.2014, 50, 14021. 

    9. [9]

      Chan, J.; Dodani, S. C.; Chang, C. J. Nat. Chem. 2012, 4, 973 

    10. [10]

      Ding, Y.; Tang, Y.; Zhu, W.; Xie, Y. Chem. Soc. Rev. 2015, 44, 1101. (b) Xie, Y.; Wei, P.; Li, X.; Hong T.; Zhang, K.; Furuta, H. J. Am. Chem. Soc., 2013, 135, 19119. (c) Xie, Y.; Ding, Y.; Li, X.; Wang, C.; Hill, J. P.; Ariga, K.; Zhang, W.; Zhu, W. Chem. Commun. 2012, 48, 11513. (d) Ding, Y.; Li, X.; Li, T.; Zhu, W.; Xie, Y. J. Org. Chem. 2013, 78, 5328. (e) Chen, B.; Ding, Y.; Li, X.; Zhu, W.; Hill, J. P.; Ariga, K.; Xie, Y. Chem. Commun.2013, 49, 10136. 

    11. [11]

      Neto, B. A. D.; Correa, J. R.; Silva, R. G. RSC Adv. 2013, 3, 5291. 

    12. [12]

      Leung, C. W. T.; Hong, Y. N.; Chen, S. J.; Zhao, E. G.; Lam, J. W. Y.; Tang, B. Z. J. Am. Chem. Soc.2013, 135, 62. 

    13. [13]

      Zhao, N.; Li, M.; Yan, Y. L.; Lam, J. W. Y.; Zhang, Y. L.; Zhao, Y. S.; Wong, K. S.; Tang, B. Z. J. Mater. Chem. C 2013, 1, 4640. 

    14. [14]

      Zhao, N.; Chen, S.; Hong, Y.; Tang, B. Z. Chem. Commun. 2015, 51, 13599 

    15. [15]

      Zhang, S.; Wu, T.; Fan, J. L.; Li, Z. Y.; Jiang, N.; Wang, J. Y.; Dou, B. R.; Sun, S. G.; Song, F. L.; Peng, X. J. Org. Biomol. Chem. 2013, 11, 555. 

    16. [16]

      Jiang, N.; Fan, J. L.; Liu, T.; Cao, J. F.; Qiao, B.; Wang, J. Y.; Gao, P.; Peng, X. J. Chem. Commun. 2013, 49, 10620. 

    17. [17]

      Yang, W. G.; Chan, P. S.; Chan, M. S.; Li, K. F.; Lo, P. K.; Mak, N. K.; Cheah, K. W.; Wong, M. S. Chem. Commun. 2013, 49, 3428. 

    18. [18]

      Liu, X.; Sun, Y. M.; Zhang, Y. H.; Zhao, N.; Zhao, H. S.; Wang, G. C.; Yu, X. Q.; Liu, H. J. Fluoresc.2011, 21, 497. 

    19. [19]

      Sarkar, A. R.; Heo, C. H.; Lee, H. W.; Park, K. H.; Suh, Y. H.; Kim, H. M. Anal. Chem. 2014, 86, 5638. 

    20. [20]

      Wu, S.; Cao, Q. Z.; Wang, X. L.; Cheng, K.; Cheng, Z. Chem. Commun. 2014, 50, 8919.

    21. [21]

      Yuan, H(s).; Cho, H. O.; Chen, H. H.; Panagia, M.; Sosnovik, D. E.; Josephson, L. Chem. Commun. 2013, 49, 10361.

    22. [22]

      Zhang, X. T.; Gu, Z. Y.; Liu, L. B.; Wang, S.; Xing, G. W. Chem Commun. 2015, 51, 8606. 

    23. [23]

      Liu, F.; Wu, J. F.; Cao, J. F.; Zhang, H.; Hu, M. M.; Sun, S. G.; Song, F. L.; Fan, J. L.; Wang, J. Y.; Peng, X. J. Analyst 2013, 138, 775. 

    24. [24]

      Xiao, H.; Xin, K.; Dou, H.; Yin, G.; Quan, Y.; Wang, R. Chem. Commun.2015, 51, 1442

    25. [25]

      Cheng, G. H.; Fan, J. L.; Sun, W.; Sui K.; Jin, X.; Wang, J. Y.; Peng, X. J. Analyst 2013, 138, 6091. 

    26. [26]

      Cheng, G. H.; Fan, J. L.; Sun, W.; Cao, J. F.; Hu, C.; Peng, X. J. Chem. Commun. 2014, 50, 1018. 

    27. [27]

      Hou, J. T.; Wu, M. Y.; Li, K.; Yang, J.; Yu, K. K.; Xie, Y. M.; Yu, X. Q. Chem. Commun. 2014, 50, 8640 

    28. [28]

      Dickinson, B. C.; Chang, C. J. J. Am. Chem. Soc. 2008, 130, 9638. 

    29. [29]

      Dickinson, B. C.; Lin, V. S.; Chang, C. J. Nat. Protoc. 2013, 8, 1249. 

    30. [30]

      Masanta, G.; Heo, C. H.; Lim, C. S.; Bae, S. K.; Cho, B. R.; Kim, H. M. Chem.Commun. 2012, 48, 3518. 

    31. [31]

      Xu, J.; Li, Q.; Guo, Y.; Yue, Y.; Shao, S. J. Biosens.Bioelectron.2014, 56, 58. 

    32. [32]

      Yu, H. B.; Zhang, X. F.; Xiao, Y.; Zou, W.; Wang, L. P.; Jin, L. J. Anal. Chem. 2013, 85, 7076. 

    33. [33]

      Sun, Y. Q.; Liu, J.; Zhang, H. X.; Huo, Y. Y.; Lv, X.; Shi, Y. W.; Guo, W. J. Am. Chem. Soc. 2014, 136, 12520. 

    34. [34]

      Li, P.; Zhang, W.; Li, K. X.; Liu, X.; Xiao, H. B.; Zhang, W.; Tang, B. Anal.Chem.2013, 85, 9877.

    35. [35]

      Xu, K. H.; Qiang M. M.; Gao, W.; Su, R. X.; Li, N.; Gao, Y.; Xie, Y. X.; Kong, F. P.; Tang, B. Chem. Sci. 2013, 4, 1079.

    36. [36]

      Lim, C. S.; Masanta, G.; Kim, H. J.; Han, J. H.; Kim, H. M.; Cho, B. R. J. Am.Chem. Soc.2011, 133, 11132. 

    37. [37]

      Lim, S. Y.; Hong, K. H.; Kim, D. I.; Kwon, H.; Kim, H. J. J. Am.Chem. Soc. 2014, 136, 7018. 

    38. [38]

      Liu, J.; Sun, Y. Q.; Zhang, H. X.; Huo, Y. Y.; Shi, Y. W.; Shi, H. P.; Guo, W. RSC Adv. 2014, 4, 64542. 

    39. [39]

      Han, C.; Yang, H.; Chen, M. ; Su, Q.; Feng, W.; Li, F. ACS Appl. Mater. Interfaces 2015, 7, 27968. 

    40. [40]

      Lee, M. H.; Han, J. H.; Lee, J. H.; Choi, H. G.; Kang, C.; Kim, J. S. J. Am.Chem. Soc. 2012, 134, 17314. 

    41. [41]

      Chen, Y. C.; Zhu, C. C.; Yang, Z. H.; Chen, J. J.; He, Y. F.; Jiao, Y.; He, W. J.; Qiu, L.; Cen, J. J.; Guo, Z. J. Angew. Chem., Int. Ed. 2013, 52, 1688. 

    42. [42]

      Bae, S. K.; Heo, C. H.; Choi, D. J.; Sen, D.; Joe, E. H.; Cho, B. R.; Kim, H. M. J. Am. Chem. Soc.2013, 135, 9915. 

    43. [43]

      Yuan, L.; Zuo, Q. -P. Chem.Asian J. 2014, 9, 1544.

    44. [44]

      Wang, X.; Sun, J.; Zhang, W. H.; Ma, X. X.; Lv, J. Z.; Tang, B. Chem. Sci. 2013, 4, 2551.

    45. [45]

      Xue, L.; Li, G. P.; Yu, C. L.; Jiang, H. Chem. Eur. J.2012, 18, 1050. 

    46. [46]

      Chyan, W.; Zhang, D. Y.; Lippard, S. J.; Radford, R. J. Proc. Natl. Acad. Sci. U. S. A. 2014, 111, 143. 

    47. [47]

      Masanta, G.; Lim, C. S.; Kim, H. J.; Han, J. H.; Kim, H. M.; Cho, B. R. J. Am.Chem. Soc.2011, 133, 5698. 

    48. [48]

      Dodani, S. C.; Leary, S. C.; Cobine, P. A.; Winge D. R.; Chang, C. J. J. Am. Chem. Soc.2011, 133, 8606. 

    49. [49]

      Taki, M.; Akaoka, K.; Mitsui, K.; Yamamoto, Y. Org.Biomol. Chem. 2014, 12, 4999. 

    50. [50]

      Lee, M. H.; Park, N.; Yi, C.; Han, J. H.; Hong, J. H.; Kim, K. P.; Kang, D. H.; Sessler. J. L.; Kang, C.; Kim, J. S. J. Am. Chem. Soc. 2014, 136, 14136. 

    51. [51]

      Denisov, S. S.; Kotova, E. A.; Plotnikov, E. Y.; Tikhonov, A. A.; Zorov, D. B.; Korshunova, G. A.; Antonenko, Y. N. Chem.Commun. 2014, 50, 15366. 

    52. [52]

      Li, P.; Xiao, H. B.; Cheng, Y. F.; Zhang, W.; Huang, F.; Zhang, W.; Wang, H.; Tang, B. Chem.Commun. 2014, 50, 7184.

  • 加载中
    1. [1]

      Jinlong YANWeina WUYuan 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

    2. [2]

      Yanxi LIUMengjia XUHaonan CHENQuan LIUYuming 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

    3. [3]

      Jun LUOBaoshu LIUYunchang ZHANGBingkai WANGBeibei GUOLan SHETianheng 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

    4. [4]

      Yu SUXinlian FANYao YINLin WANG . From synthesis to application: Development and prospects of InP quantum dots. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2105-2123. doi: 10.11862/CJIC.20240126

    5. [5]

      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

    6. [6]

      Zhifang SUZongjie GUANYu FANG . Process of electrocatalytic synthesis of small molecule substances by porous framework materials. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2373-2395. doi: 10.11862/CJIC.20240290

    7. [7]

      Zheqi Wang Yawen Lin Shunliu Deng Huijun Zhang Jinmei Zhou . Antiviral Strategies: A Brief Review of the Development History of Small Molecule Antiviral Drugs. University Chemistry, 2024, 39(9): 85-93. doi: 10.12461/PKU.DXHX202403108

    8. [8]

      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

    9. [9]

      Dan Liu . 可见光-有机小分子协同催化的不对称自由基反应研究进展. University Chemistry, 2025, 40(6): 118-128. doi: 10.12461/PKU.DXHX202408101

    10. [10]

      Meirong HANXiaoyang WEISisi FENGYuting BAI . A zinc-based metal-organic framework for fluorescence detection of trace Cu2+. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1603-1614. doi: 10.11862/CJIC.20240150

    11. [11]

      Yuan ZHUXiaoda ZHANGShasha WANGPeng WEITao YI . Conditionally restricted fluorescent probe for Fe3+ and Cu2+ based on the naphthalimide structure. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 183-192. doi: 10.11862/CJIC.20240232

    12. [12]

      Shuwen SUNGaofeng WANG . Design and synthesis of a Zn(Ⅱ)-based coordination polymer as a fluorescent probe for trace monitoring 2, 4, 6-trinitrophenol. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 753-760. doi: 10.11862/CJIC.20240399

    13. [13]

      Zhifeng CAIYing WUYanan LIGuiyu MENGTianyu MIAOYihao ZHANG . Effective detection of malachite green by folic acid stabilized silver nanoclusters. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 983-993. doi: 10.11862/CJIC.20240394

    14. [14]

      Wei GAOMeiqi SONGXuan RENJianliang BAIJing SUJianlong MAZhijun WANG . A self-calibrating fluorescent probe for the selective detection and bioimaging of HClO. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1173-1182. doi: 10.11862/CJIC.20250112

    15. [15]

      Lei ZHANGCheng HEYang JIAO . An azo-based fluorescent probe for the detection of hypoxic tumor cells. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1162-1172. doi: 10.11862/CJIC.20250081

    16. [16]

      Siyi ZHONGXiaowen LINJiaxin LIURuyi WANGTao LIANGZhengfeng DENGAo ZHONGCuiping 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

    17. [17]

      Jiakun BAITing XULu ZHANGJiang PENGYuqiang LIJunhui 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

    18. [18]

      Jin Tong Shuyan Yu . Crystal Engineering for Supramolecular Chirality. University Chemistry, 2024, 39(3): 86-93. doi: 10.3866/PKU.DXHX202308113

    19. [19]

      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

    20. [20]

      Wen-Bing Hu . Systematic Introduction of Polymer Chain Structures. University Chemistry, 2025, 40(4): 15-19. doi: 10.3866/PKU.DXHX202401014

Metrics
  • PDF Downloads(0)
  • Abstract views(7630)
  • HTML views(1557)

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

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return