Citation: Xingxing Zhang, Feiyu Yang, Tianbing Ren, Yingxin Zheng, Xiao-Bing Zhang, Lin Yuan. Evolving a novel red-emitting two-photon dye with optically tunable amino group for monitoring the degree of hypoxia during liver fibrosis[J]. Chinese Chemical Letters, ;2023, 34(5): 107835. doi: 10.1016/j.cclet.2022.107835 shu

Evolving a novel red-emitting two-photon dye with optically tunable amino group for monitoring the degree of hypoxia during liver fibrosis

State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China

rentianbing@hnu.edu.cn

lyuan@hnu.edu.cn

Received Date: 26 May 2022
Revised Date: 14 September 2022
Accepted Date: 14 September 2022
Available Online: 17 September 2022

Figures(5)

Two-photon imaging has attracted increasing attention owing to its deep tissue imaging capabilities. Therefore, many fluorophores have been developed to satisfy its requirements. However, long-wavelength emission fluorophores with an optically tunable group are rarely developed. In this study, two long-wavelength emission fluorophores with an optically tunable amino group were successfully developed by introducing strong electron acceptor and large conjugated group to the TPQL dye. TPCO2 displayed a bright red emission (λ_em = 638 nm, Φ = 0.15) together with high two-photon action cross section and good water solubility, which enabled higher signal-to-background ratios and deep tissue imaging. The proof-of-concept probe (TPCONO₂) was successfully applied to the high signal-to-background ratio imaging of nitroreductase in liver fibrosis, further realizing diagnosis of the degree of hypoxia during liver fibrosis.
- Fluorescent probes,
- Two-photon imaging,
- Fluorophores,
- Nitroreductase,
- Hypoxia
1. [1]
  T.B. Ren, W. Xu, W. Zhang, et al., J. Am. Chem. Soc. 140 (2018) 7716–7722. doi: 10.1021/jacs.8b04404
2. [2]
  X. Fan, T. Ren, W. Yang, X. Zhang, L. Yuan, Chem. Commun. 57 (2021) 8644–8647. doi: 10.1039/d1cc02999a
3. [3]
  G. Jiang, T.B. Ren, E. D'Este, et al., Nat. Commun. 13 (2022) 2264. doi: 10.1038/s41467-022-29547-3
4. [4]
  W. Xu, Z. Zeng, J.H. Jiang, Y.T. Chang, L. Yuan, Angew. Chem. Int. Ed. 55 (2016) 13658–13699. doi: 10.1002/anie.201510721
5. [5]
  X. Chen, F. Wang, J.Y. Hyun, et al., Chem. Soc. Rev. 45 (2016) 2976–3016. doi: 10.1039/C6CS00192K
6. [6]
  D. Cao, Z. Liu, P. Verwilst, et al., Chem. Rev. 119 (2019) 10403–10519. doi: 10.1021/acs.chemrev.9b00145
7. [7]
  J. Bai, J. Zhou, X. Ji, W. Zhao, et al., Chin. Chem. Lett. 33 (2022) 4175–4178. doi: 10.1016/j.cclet.2022.02.017
8. [8]
  G. Hu, H. Jia, L. Zhao, D. Cho, J. Fang, Chin. Chem. Lett. 30 (2019) 1704–1716. doi: 10.1016/j.cclet.2019.06.039
9. [9]
  X. Zhang, C. Wang, L. Jin, Z. Han, Y. Xiao, ACS Appl. Mater. Interfaces 6 (2014) 12372–12379. doi: 10.1021/am503849c
10. [10]
  S. Pascal, S. David, C. Andraud, O. Maury, Chem. Soc. Rev. 50 (2021) 6613–6658. doi: 10.1039/d0cs01221a
11. [11]
  L. Wu, J. Liu, P. Li, B. Tang, T.D. James, Chem. Soc. Rev. 50 (2021) 702–734. doi: 10.1039/d0cs00861c
12. [12]
  L. Yuan, W. Lin, H. Chen, S. Zhu, L. He, Angew. Chem. Int. Ed. 52 (2013) 10018–10022. doi: 10.1002/anie.201303179
13. [13]
  X. Zhang, T. Ren, Q. Zhang, et al., Cell Rep. Phys. Sci. 2 (2021) 100471. doi: 10.1016/j.xcrp.2021.100471
14. [14]
  T.B. Ren, W. Xu, Q.L. Zhang, et al., Angew. Chem. Int. Ed. 57 (2018) 7473–7477. doi: 10.1002/anie.201800293
15. [15]
  Y. Zheng, X.X. Zhang, L. Shi, et al., Chem. Asian J. 17 (2022) e202101197.
16. [16]
  X. Zhang, T. Ren, L. Yuan, et al., Chin. Chem. Lett. 32 (2021) 3890–3894. doi: 10.1016/j.cclet.2021.06.038
17. [17]
  H.M. Kim, C. Jung, B.R. Kim, et al., Angew. Chem. Int. Ed. 46 (2007) 3460–3463. doi: 10.1002/anie.200700169
18. [18]
  C. Zhang, P. Wang, X. Yin, et al., Anal. Chem. 91 (2019) 6371–6377. doi: 10.1021/acs.analchem.9b01455
19. [19]
  J. Ning, Z. Tian, J. Wang, et al., Angew. Chem. Int. Ed. 61 (2022) e202113191.
20. [20]
  H. Fang, R. Shi, D. Chen, et al., Chem. Commun. 57 (2021) 11260–11263. doi: 10.1039/d1cc04744b
21. [21]
  R. Zipfel Warren, M. Williams Rebecca, R. Christie, et al., Proc. Natl. Acad. Sci. U. S. A. 100 (2003) 7075–7080. doi: 10.1073/pnas.0832308100
22. [22]
  S. Huang, A.A. Heikal, W.W. Webb, Biophys. J. 82 (2002) 2811–2825. doi: 10.1016/S0006-3495(02)75621-X
23. [23]
  A.J. Radosevich, M.B. Bouchard, S.A. Burgess, B.R. Chen, E.M.C. Hillman, Opt. Lett. 33 (2008) 2164–2166. doi: 10.1364/OL.33.002164
24. [24]
  C.H. Heo, K.H. Kim, H.J. Kim, et al., Chem. Commun. 49 (2013) 1303–1305. doi: 10.1039/c2cc38570h
25. [25]
  G. Niu, X. Zheng, Z. Zhao, et al., J. Am. Chem. Soc. 141 (2019) 15111–15120. doi: 10.1021/jacs.9b06196
26. [26]
  X. Zhang, Kevin D. Belfield, Y. Xiao, J. Qi, J. Qu, et al., J. Org. Chem. 78(2013) 9153–9160. doi: 10.1021/jo401379g
27. [27]
  D. Kim, H. Moon, S.H. Baik, et al., J. Am. Chem. Soc. 137 (2015) 6781–6789. doi: 10.1021/jacs.5b03548
28. [28]
  M. Li, X. Wu, Y. Wang, et al., Chem. Commun. 50 (2014) 1751–1753. doi: 10.1039/c3cc48128j
29. [29]
  S. Singha, Y.W. Jun, S. Sarkar, K.H. Ahn, Acc. Chem. Res. 52 (2019) 2571–2581. doi: 10.1021/acs.accounts.9b00314
30. [30]
  K. Gu, Y. Xu, H. Li, et al., J. Am. Chem. Soc. 138 (2016) 5334–5340. doi: 10.1021/jacs.6b01705
31. [31]
  T. Liu, M. Zhang, L. Feng, et al., Sens. Actuators B: Chem. 337 (2021) 129764. doi: 10.1016/j.snb.2021.129764
32. [32]
  L. He, H. Xiong, B. Wang, et al., Anal. Chem. 92 (2020) 11029–11034. doi: 10.1021/acs.analchem.0c00030
33. [33]
  A. Gandioso, S. Contreras, I. Melnyk, et al., J. Org. Chem. 82 (2017) 5398–5408. doi: 10.1021/acs.joc.7b00788
34. [34]
  S.S. Matikonda, J. Ivanic, M. Gomez, G. Hammersley, M.J. Schnermann, Chem. Sci. 11 (2020) 7302–7307. doi: 10.1039/d0sc02566f
35. [35]
  Brown, J., Wilson, W., Nat. Rev. Cancer 4 (2004) 437–447. doi: 10.1038/nrc1367
36. [36]
  E. Seki, D.A. Brenner, J. Hepato-Bil-Pan Sci. 22 (2015) 512–518. doi: 10.1002/jhbp.245
37. [37]
  M. Fernandez, D. Semela, J. Hepatol. 50 (2009) 604–620. doi: 10.1016/j.jhep.2008.12.011
38. [38]
  T. Kietzmann, E.Y. Dimova, D. Flügel, J.G. Scharf, Z. Gastroenterol. 44 (2006) 67–76. doi: 10.1055/s-2005-858987
39. [39]
  R. Kumari, D. Sunil, R.S. Ningthoujam, Bioorg. Chem. 88 (2019) 102979. doi: 10.1016/j.bioorg.2019.102979
40. [40]
  D.J. Manalo, A. Rowan, T. Lavoie, et al., Blood 105 (2005) 659–669. doi: 10.1182/blood-2004-07-2958
41. [41]
  E. Novo, S. Cannito, E. Zamara, et al., Am. J. Pathol. 170 (2007) 1942–1953. doi: 10.2353/ajpath.2007.060887
42. [42]
  J. Cai, M. Hu, Z. Chen, Z. Ling, J. Transl. Med. 19 (2021) 186. doi: 10.1186/s12967-021-02854-x
1. [1]
  Jingqi Xin , Shupeng Han , Meichen Zheng , Chenfeng Xu , Zhongxi Huang , Bin Wang , Changmin Yu , Feifei An , Yu Ren . A nitroreductase-responsive nanoprobe with homogeneous composition and high loading for preoperative non-invasive tumor imaging and intraoperative guidance. Chinese Chemical Letters, 2024, 35(7): 109165-. doi: 10.1016/j.cclet.2023.109165
2. [2]
  Linfang Wang , Jing Liu , Minghao Ren , Wei Guo . A highly sensitive fluorescent HClO probe for discrimination between cancerous and normal cells/tissues. Chinese Chemical Letters, 2024, 35(6): 108945-. doi: 10.1016/j.cclet.2023.108945
3. [3]
  Ling-Ling Wu , Xiangchuan Meng , Qingyang Zhang , Xiaowan Han , Feiya Yang , Qinghua Wang , Hai-Yu Hu , Nianzeng Xing . Heavy-atom engineered hypoxia-responsive probes for precisive photoacoustic imaging and cancer therapy. Chinese Chemical Letters, 2024, 35(4): 108663-. doi: 10.1016/j.cclet.2023.108663
4. [4]
  Yiling Li , Zekun Gao , Xiuxiu Yue , Minhuan Lan , Xiuli Zheng , Benhua Wang , Shuang Zhao , Xiangzhi Song . FRET-based two-photon benzo[a] phenothiazinium photosensitizer for fluorescence imaging-guided photodynamic therapy. Chinese Chemical Letters, 2024, 35(7): 109133-. doi: 10.1016/j.cclet.2023.109133
5. [5]
  Lixian Fu , Yiyun Tan , Yue Ding , Weixia Qing , Yong Wang . Water–soluble and polarity–sensitive near–infrared fluorescent probe for long–time specific cancer cell membranes imaging and C. Elegans label. Chinese Chemical Letters, 2024, 35(4): 108886-. doi: 10.1016/j.cclet.2023.108886
6. [6]
  Xuejian Xing , Pan Zhu , E Pang , Shaojing Zhao , Yu Tang , Zheyu Hu , Quchang Ouyang , Minhuan Lan . D-A-D-structured boron-dipyrromethene with aggregation-induced enhanced phototherapeutic efficiency for near-infrared fluorescent and photoacoustic imaging-guided synergistic photodynamic and photothermal cancer therapy. Chinese Chemical Letters, 2024, 35(10): 109452-. doi: 10.1016/j.cclet.2023.109452
7. [7]
  Jiajia Lv , Jie Gao , Hongyu Li , Zeli Yuan , Nan Dong . Rational design of hydroxytricyanopyrrole-based probes with high affinity and rapid visualization for amyloid-β aggregates in vitro and in vivo. Chinese Chemical Letters, 2024, 35(5): 108940-. doi: 10.1016/j.cclet.2023.108940
8. [8]
  Kun Zou , Yihang Xiao , Jinyu Yang , Mingxuan Wu . Facile semisynthesis of histone H3 enables nucleosome probes for investigation of histone H3K79 modifications. Chinese Chemical Letters, 2024, 35(10): 109497-. doi: 10.1016/j.cclet.2024.109497
9. [9]
  Wenyi Mei , Lijuan Xie , Xiaodong Zhang , Cunjian Shi , Fengzhi Wang , Qiqi Fu , Zhenjiang Zhao , Honglin Li , Yufang Xu , Zhuo Chen . Design, synthesis and biological evaluation of fluorescent derivatives of ursolic acid in living cells. Chinese Chemical Letters, 2024, 35(5): 108825-. doi: 10.1016/j.cclet.2023.108825
10. [10]
  Chuan-Zhi Ni , Ruo-Ming Li , Fang-Qi Zhang , Qu-Ao-Wei Li , Yuan-Yuan Zhu , Jie Zeng , Shuang-Xi Gu . A chiral fluorescent probe for molecular recognition of basic amino acids in solutions and cells. Chinese Chemical Letters, 2024, 35(10): 109862-. doi: 10.1016/j.cclet.2024.109862
11. [11]
  Xing Tian , Di Wu , Wanheng Wei , Guifu Dai , Zhanxian Li , Benhua Wang , Mingming Yu . A lipid droplets-targetable fluorescent probe for polarity detection in cells of iron death, inflammation and fatty liver tissue. Chinese Chemical Letters, 2024, 35(6): 108912-. doi: 10.1016/j.cclet.2023.108912
12. [12]
  Liangji Chen , Zhen Yuan , Fudong Feng , Xin Zhou , Zhile Xiong , Wuji Wei , Hao Zhang , Banglin Chen , Shengchang Xiang , Zhangjing Zhang . A hydrogen-bonded organic framework containing fluorescent carbazole and responsive pyridyl units for sensing organic acids. Chinese Chemical Letters, 2024, 35(9): 109344-. doi: 10.1016/j.cclet.2023.109344
13. [13]
  Shuangying Li , Qingxiang Zhou , Zhi Li , Menghua Liu , Yanhui Li . Sensitive measurement of silver ions in environmental water samples integrating magnetic ion-imprinted solid phase extraction and carbon dot fluorescent sensor. Chinese Chemical Letters, 2024, 35(5): 108693-. doi: 10.1016/j.cclet.2023.108693
14. [14]
  Yudi Cheng , Xiao Wang , Jiao Chen , Zihan Zhang , Jiadong Ou , Mengyao She , Fulin Chen , Jianli Li . A near-infrared fluorescent probe for visualizing transformation pathway of Cys/Hcy and H₂S and its applications in living system. Chinese Chemical Letters, 2024, 35(5): 109156-. doi: 10.1016/j.cclet.2023.109156
15. [15]
  Xiaofei NIU , Ke WANG , Fengyan SONG , Shuyan YU . Self-assembly of [Pd₆(L)₄]⁸⁺-type macrocyclic complexes for fluorescent sensing of HSO₃^-. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1233-1242. doi: 10.11862/CJIC.20240057
16. [16]
  Chuanfeng Fan , Jian Gao , Yingkai Gao , Xintong Yang , Gaoning Li , Xiaochun Wang , Fei Li , Jin Zhou , Haifeng Yu , Yi Huang , Jin Chen , Yingying Shan , Li Chen . A non-peptide-based chymotrypsin-targeted long-wavelength emission fluorescent probe with large Stokes shift and its application in bioimaging. Chinese Chemical Letters, 2024, 35(10): 109838-. doi: 10.1016/j.cclet.2024.109838
17. [17]
  Lei Shen , Hongmei Liu , Ming Jin , Jinchao Zhang , Caixia Yin , Shuxiang Wang , Yutao Yang . “Three-in-one” strategy of trifluoromethyl regulated blood-brain barrier permeable fluorescent probe for peroxynitrite and antiepileptic evaluation of edaravone. Chinese Chemical Letters, 2024, 35(10): 109572-. doi: 10.1016/j.cclet.2024.109572
18. [18]
  Jing-Jing Zhang , Lujun Lou , Rui Lv , Jiahui Chen , Yinlong Li , Guangwei Wu , Lingchao Cai , Steven H. Liang , Zhen Chen . Recent advances in photochemistry for positron emission tomography imaging. Chinese Chemical Letters, 2024, 35(8): 109342-. doi: 10.1016/j.cclet.2023.109342
19. [19]
  Shihong Wu , Ronghui Zhou , Hang Zhao , Peng Wu . Sonoafterglow luminescence for in vivo deep-tissue imaging. Chinese Chemical Letters, 2024, 35(10): 110026-. doi: 10.1016/j.cclet.2024.110026
20. [20]
  Bo Yu , Pengchen Du , Jianwen Guo , Hanshen Xin , Jianhua Zhang . Nonalternant isomer of pentacene fusing two azulene units. Chinese Chemical Letters, 2024, 35(5): 109321-. doi: 10.1016/j.cclet.2023.109321

Get Citation

PDF

XML

Metrics

PDF Downloads(14)
Abstract views(475)
HTML views(39)

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