Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

A Red-Emissive AIE Probe for Targeting Mitochondria in Living Cells

Lufei Xiao https://orcid.org/0000-0002-1053-9216 A D , Rui Xiao C , Bingsong Xu B , Hao Chen B and Hui Wang B D
+ Author Affiliations
- Author Affiliations

A School of Food and Environmental Engineering, Chuzhou Polytechnic, Chuzhou 239000, China.

B Department of Chemistry, Wannan Medical College, Wuhu 241002, China.

C School of Mechanical Engineering, Taiyuan University of Science and Technology, Taiyuan 030024, China.

D Corresponding authors. Email: xiaolufei@chzc.edu.cn; wanghias@126.com

Australian Journal of Chemistry 74(2) 151-156 https://doi.org/10.1071/CH20122
Submitted: 16 April 2020  Accepted: 21 June 2020   Published: 10 July 2020

Abstract

A novel compound has been synthesised and characterised by various spectroscopic techniques. Analysing the crystal structures of the compound shows that multiple molecular interactions exist. The compound exhibits distinct aggregation-induced emission activity in EtOH/H2O accompanying a 2-fold enhancement of fluorescence intensity at ~609 nm. In addition, the cytotoxicity assay and confocal microscopy imaging show that the compound is hypotoxic and can be used as a fluorescent labelling dye in the near-infrared region to track mitochondria in living cells.


References

[1]  J. M. Jiao, J. X. Kang, Y. N. Ma, Q. Y. Zhao, H. Z. Li, J. Zhang, X. N. Chen, Front Chem. 2019, 7, 768.
         | Crossref | GoogleScholarGoogle Scholar |

[2]  M. G. Lin, J. Huang, F. Zeng, S. Z. Wu, Chem. Asian J. 2019, 14, 802.
         | Crossref | GoogleScholarGoogle Scholar |

[3]  S. M. Feng, S. Y. Gong, G. Q. Feng, Chem. Commun. 2020, 56, 2511.
         | Crossref | GoogleScholarGoogle Scholar |

[4]  Y. L. Zhang, M. J. Jiang, T. Han, X. T. Xiao, W. L. Chen, L. Wang, K. S. Wong, R. Wang, K. Wang, B. Z. Tang, K. S. Wu, ACS Appl. Mater. Interfaces 2018, 10, 34418.
         | Crossref | GoogleScholarGoogle Scholar |

[5]  J. Dai, C. Duan, Y. Huang, X. D. Lou, F. Xia, S. X. Wang, J. Mater. Chem. B Mater. Biol. Med. 2020, 8, 3357.
         | Crossref | GoogleScholarGoogle Scholar | 31951233PubMed |

[6]  L. Biesen, N. Nirmalananthan-Budau, K. Hoffmann, U. Resch-Genger, T. J. J. Müller, Angew. Chem. Int. Ed. 2020, 59, 10037.
         | Crossref | GoogleScholarGoogle Scholar |

[7]  S. Li, M. Wu, Y. Kang, H. W. Zheng, X. J. Zheng, D. C. Fang, L. P. Jin, Inorg. Chem. 2019, 58, 4626.
         | Crossref | GoogleScholarGoogle Scholar | 30869518PubMed |

[8]  G. X. Feng, R. T. K. Kwok, B. Z. Tang, B. Lin, Appl. Phys. Rev. 2017, 4, 021307.
         | Crossref | GoogleScholarGoogle Scholar |

[9]  E. R. Jimenez, H. Rodríguez, J. Mater. Sci. 2020, 55, 1366.
         | Crossref | GoogleScholarGoogle Scholar |

[10]  A. Gupta, ChemistrySelect 2019, 4, 12848.
         | Crossref | GoogleScholarGoogle Scholar |

[11]  U. S. Schubert, A. Winter, G. R. Newkome, Terpyridine-Based Materials 2011 (Wiley-VCH Verlag & Co. KGaA: Weinheim).

[12]  X. H. Tian, S. Hussain, H. Wang, Q. Zhang, M. Zhao, J. Y. Chen, H. Zhang, H. P. Zhou, Y. Chen, Y. P. Tian, Dyes Pigm. 2017, 147, 90.
         | Crossref | GoogleScholarGoogle Scholar |

[13]  S. Hussain, W. Du, M. Z. Zhang, B. Fang, G. C. Zhang, R. Su, K. Q. Nan, Q. Zhang, X. H. Tian, Y. P. Tian, Y. Chen, J. Mater. Chem. B Mater. Biol. Med. 2018, 6, 1943.
         | Crossref | GoogleScholarGoogle Scholar | 32254360PubMed |

[14]  J. Liu, Q. Zhang, H. J. Ding, J. Zhang, J. Y. Tan, C. K. Wang, J. Y. Wu, S. L. Li, H. P. Zhou, J. X. Yang, Sci. China Chem. 2013, 56, 1315.
         | Crossref | GoogleScholarGoogle Scholar |

[15]  J. J. Guo, X. L. Li, H. Nie, W. W. Luo, S. F. Gan, S. M. Hu, R. R. Hu, A. J. Qin, Z. J. Zhao, S. J. Su, B. Z. Tang, Adv. Funct. Mater. 2017, 27, 1606458.
         | Crossref | GoogleScholarGoogle Scholar |

[16]  S. D. Xu, T. T. Liu, Y. X. Mu, Y. F. Wang, Z. G. Chi, C. C. Lo, S. W. Liu, Y. Zhang, A. Lien, J. R. Xu, Angew. Chem. Int. Ed. 2015, 54, 874.
         | Crossref | GoogleScholarGoogle Scholar |

[17]  L. F. Xiao, H. J. Sun, L. Zhou, H. Wang, Chem. Pap. 2018, 72, 2813.
         | Crossref | GoogleScholarGoogle Scholar |

[18]  Y. Ren, X. Q. Yu, D. J. Zhang, D. Wang, M. L. Zhang, G. B. Xu, X. Zhao, Y. P. Tian, M. H. Jiang, J. Mater. Chem. 2002, 12, 3431.
         | Crossref | GoogleScholarGoogle Scholar |

[19]  C. Tang, Q. Zhang, D. D. Li, J. Zhang, P. F. Shi, S. L. Li, J. Y. Wu, Y. P. Tian, Dyes. Pigm. 2013, 99, 20.

[20]  L. Kong, Y. P. Tian, Q. Y. Chen, Q. Zhang, H. Wang, D. Q. Tan, Z. M. Xue, J. Y. Wu, H. P. Zhou, J. X. Yang, J. Mater. Chem. C Mater. Opt. Electron. Devices 2015, 3, 570.
         | Crossref | GoogleScholarGoogle Scholar |

[21]  Z. Zheng, Z. Yu, M. D. Yang, F. Jin, H. P. Zhou, J. Y. Wu, Y. P. Tian, J. Org. Chem. 2013, 78, 3222.
         | Crossref | GoogleScholarGoogle Scholar | 23506080PubMed |

[22]  T. F. Zhang, Y. Y. Li, Z. Zheng, R. Q. Ye, Y. R. Zhang, R. T. K. Kwok, J. W. Y. Lam, B. Z. Tang, J. Am. Chem. Soc. 2019, 141, 5612.
         | Crossref | GoogleScholarGoogle Scholar |

[23]  F. Ren, P. Liu, Y. Gao, J. B. Shi, B. Tong, Z. X. Cai, Y. P. Dong, Mater. Chem. Front. 2019, 3, 57.
         | Crossref | GoogleScholarGoogle Scholar |

[24]  M. J. Jiang, R. T. K. Kwok, X. S. Li, C. Gui, J. W. Y. Lam, J. N. Qu, B. Z. Tang, J. Mater. Chem. B Mater. Biol. Med. 2018, 6, 2557.
         | Crossref | GoogleScholarGoogle Scholar |

[25]  N. Zhao, S. J. Chen, Y. N. Hong, B. Z. Tang, Chem. Commun. 2015, 51, 13599.
         | Crossref | GoogleScholarGoogle Scholar |