Citation: Shupeng Han, Caiting Deng, Meichen Zheng, Linwei Yang, Hancun Kong, Yongchao He, Yinuo Zheng, Guowei Deng, Yu Ren, Feifei An. A GSH-responsive NIR-BODIPY fluorophore with large Stokes-shift for tumor specific fluorescence imaging and surgical guidance[J]. Chinese Chemical Letters, ;2025, 36(7): 110459. doi: 10.1016/j.cclet.2024.110459 shu

A GSH-responsive NIR-BODIPY fluorophore with large Stokes-shift for tumor specific fluorescence imaging and surgical guidance

Shupeng Han ^{a, b} ,
Caiting Deng ^{b, c} ,
Meichen Zheng ^b ,
Linwei Yang ^b ,
Hancun Kong ^b ,
Yongchao He ^b ,
Yinuo Zheng ^b ,
Guowei Deng ^d ,
Yu Ren ^{a, *,} ,
Feifei An ^{b, d, *,}

a.
Department of Breast Surgery, the First Affiliated Hospital of Xi'an Jiaotong University, Xi'an 710061, China
b.
School of Public Health, Health Science Center, Xi'an Jiaotong University, Xi'an 710061, China
c.
Institute of Medical Engineering, Department of Biophysics, School of Basic Medical Science, Health Science Center, Xi'an Jiaotong University, Xi'an 710061, China
d.
College of Chemistry and Life Science, Sichuan Provincial Key Laboratory for Structural Optimization and Application of Functional Molecules, Chengdu Normal University, Chengdu 611130, China

renyyyyy@xjtufh.edu.cn

anfeifei@xjtu.edu.cn

Received Date: 30 June 2024
Revised Date: 11 September 2024
Accepted Date: 13 September 2024
Available Online: 14 September 2024

Figures(4)

The tumor microenvironment (TME)-activatable probes have proven effective in enhancing the signal-to-background ratio (SBR) for precise fluorescence imaging in tumor diagnosis. However, many fluorophores have suboptimal emission spectra and a short Stokes shift, which may lead to overlap with bio-autofluorescence, excitation, and emission spectra, limiting their use in intraoperative guidance. Herein, a γ-glutathione (GSH) responsive near-infrared (NIR) BODIPY probe, named "Pro-Dye" was synthesized with a large Stokes shift of 91 nm. The Pro-Dye can be rapidly and specifically activated by high concentrations of GSH both in solution and inside cancer cells, while remaining inactive in normal cells (Human umbilical vein endothelial cells, HUVECs). The Pro-Dye was further encapsulated by 1, 2-distearoyl-sn‑glycero-3-phosphoethanolamine-N-(polyethylene glycol)-5000 (DSPE-PEG₅₀₀₀) to form Pro-Dye nanoparticles (NPs), making it water-dispersible for in vivo application. In vivo fluorescence imaging demonstrated that Pro-Dye NPs can accumulate at the tumor and exhibit an improved SBR compared to the "always-on" probe (Dye NPs). Moreover, the tumor can be precisely resected under the real-time guidance of fluorescence imaging of Pro-Dye NPs, showing a well-defined tumor margin.
- Tumor diagnosis,
- Intraoperative guidance,
- Large Stokes-shift,
- Near-infrared,
- GSH responsive
1. [1]
  K. Wang, Y. Du, Z. Zhang, et al., Nat. Rev. Bioeng. 1 (2023) 161–179. doi: 10.1038/s44222-022-00017-1
2. [2]
  L.J. Lauwerends, P. van Driel, R.J.B. de Jong, et al., Lancet Oncol. 22 (2021) 186–195.
3. [3]
  S. Hernot, L. van Manen, P. Debie, et al., Lancet Oncol. 20 (2019) 354–367.
4. [4]
  F.F. Faucher, K.J. Liu, E.D. Cosco, et al., ACS Cent. Sci. 9 (2023) 1059–1069. doi: 10.1021/acscentsci.3c00261
5. [5]
  A. Godard, G. Kalot, M. Privat, et al., J. Med. Chem. 66 (2023) 5185–5195. doi: 10.1021/acs.jmedchem.3c00100
6. [6]
  S. Zheng, W. Huang, N. Li, et al., Chin. Chem. Lett. 34 (2023) 107764.
7. [7]
  A.L. Vahrmeijer, M. Hutteman, J.R. van der Vorst, et al., Nat. Rev. Clin. Oncol. 10 (2013) 507–518. doi: 10.1038/nrclinonc.2013.123
8. [8]
  B. Huang, T. Tang, F. Liu, et al., Chin. Chem. Lett. 35 (2024) 109694. doi: 10.1016/j.cclet.2024.109694
9. [9]
  W.T. Huang, V. Rajendran, M. -H. Chan, et al., Adv. Opt. Mater. 11 (2023) 2202061.
10. [10]
  D.H. Li, R.S. Gamage, A.G. Oliver, et al., Angew. Chem. Int. Ed. 62 (2023) 202305062.
11. [11]
  C.W. Barth, S.Z.H. Rizvi, A.M. Masillati, et al., Small 20 (2024) 2300011. doi: 10.1002/smll.202300011
12. [12]
  I. Srivastava, B. Lew, Y. Wang, et al., ACS Nano 17 (2023) 8465–8482. doi: 10.1021/acsnano.3c00578
13. [13]
  H. Li, J. Wang, H. Kim, et al., Angew. Chem. Int. Ed. 63 (2024) e202311764. doi: 10.1002/anie.202311764
14. [14]
  H.B. Cheng, X. Cao, S. Zhang, et al., Adv. Mater. 35 (2023) 2207546.
15. [15]
  Xing, E. Pang, S. Zhao, et al., Chin. Chem. Lett. 35 (2024) 108467.
16. [16]
  M.L. Agazzi, M.B. Ballatore, A.M. Durantini, et al., J. Photoch. Photobio. C 40 (2019) 21–48.
17. [17]
  X. Guo, B. Tang, Q. Wu, et al., J. Mater. Chem. B 10 (2022) 5612–5623. doi: 10.1039/d2tb00921h
18. [18]
  W. Zhang, A. Ahmed, H. Cong, et al., Dyes Pigm. 185 (2021) 108937.
19. [19]
  Y.N. Li, T. Mei, S.P. Han, et al., Chin. Chem. Lett. 31 (2020) 3027–3040.
20. [20]
  S. Zeng, X. Liu, Y.S. Kafuti, et al., Chem. Soc. Rev. 52 (2023) 5607–5651. doi: 10.1039/d2cs00799a
21. [21]
  C. Deng, M. Zheng, S. Han, et al., Adv. Funct. Mater. 33 (2023) 2300348.
22. [22]
  T.X. Fang, X.A. Cao, L. Wang, et al., Bioact. Mater. 32 (2024) 530–542.
23. [23]
  W. Liu, J. Chen, Q. Qiao, et al., Chin. Chem. Lett. 33 (2022) 4943–4947.
24. [24]
  Z. Gao, X. Zheng, W. Liu, et al., Chin. Chem. Lett. 36 (2025) 109874.. doi: 10.1016/j.cclet.2024.109874
25. [25]
  C. Deng, J. Zhang, F. Hu, et al., Small 20 (2024) 2400667. doi: 10.1002/smll.202400667
26. [26]
  J. Zhang, N. Wang, X. Ji, et al., Chem. Eur. J. 26 (2020) 4172–4192. doi: 10.1002/chem.201904470
27. [27]
  J. Gao, R. Wang, K. Yin, et al., Chem. Eng. J. 466 (2023) 143102.
28. [28]
  Y.Y. Quan, L. Fan, H. Shen, et al., Dyes Pigm. 197 (2022) 109897.
29. [29]
  L.K.B. Tam, L. Yu, R.C.H. Wong, et al., J. Med. Chem. 64 (2021) 17455–17467. doi: 10.1021/acs.jmedchem.1c01634
30. [30]
  J. Xin, S. Han, M. Zheng, et al., Chin. Chem. Lett. 35 (2024) 109165.
31. [31]
  J.S. Armstrong, K.K. Steinauer, B. Hornung, et al., Cell Death Differ. 9 (2002) 252–263. doi: 10.1038/sj.cdd.4400959
32. [32]
  H. Chen, S. Yan, L. Zhang, et al., Sens. Actuators B: Chem. 405 (2024) 135346.
33. [33]
  Y. Zhang, H. Zhao, J. Tang, et al., Bioorg. Chem. 140 (2023) 106800.
34. [34]
  B. Chen, S. Mao, Y. Sun, et al., Chem. Commun. 57 (2021) 4376–4379. doi: 10.1039/d1cc01104a
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]
  Wenping Dong , Mo Ma , Jingkang Li , Lanlan Xu , Dejiang Gao , Pinyi Ma , Daqian Song . Near-infrared fluorescent probe with large Stokes shift and long emission wavelength for rapid diagnosis of lung cancer via aerosol inhalation delivery. Chinese Chemical Letters, 2025, 36(5): 110147-. doi: 10.1016/j.cclet.2024.110147
3. [3]
  Keliang Li , Guoqiang Dong , Shanchao Wu , Chunquan Sheng . Discovery of an activatable near-infrared fluorescent and theranostic PROTAC for tumor-targeted detecting and degrading of BRD4. Chinese Chemical Letters, 2025, 36(6): 110280-. doi: 10.1016/j.cclet.2024.110280
4. [4]
  Xianzhu Luo , Feifei Yu , Rui Wang , Tian Su , Pan Luo , Pengfei Wen , Fabiao Yu . A near-infrared two-photon fluorescent probe for the detection of HClO in inflammatory and tumor-bearing mice. Chinese Chemical Letters, 2025, 36(7): 110531-. doi: 10.1016/j.cclet.2024.110531
5. [5]
  Yupeng Liu , Hui Wang , Songnan Qu . Review on near-infrared absorbing/emissive carbon dots: From preparation to multi-functional application. Chinese Chemical Letters, 2025, 36(5): 110618-. doi: 10.1016/j.cclet.2024.110618
6. [6]
  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
7. [7]
  Wenxiang Ma , Xinyu He , Tianyi Chen , De-Li Ma , Hongzheng Chen , Chang-Zhi Li . Near-infrared non-fused electron acceptors for efficient organic photovoltaics. Chinese Chemical Letters, 2024, 35(4): 109099-. doi: 10.1016/j.cclet.2023.109099
8. [8]
  Dandan Tang , Ningge Xu , Yuyang Fu , Wei Peng , Jinsheng Wu , Heng Liu , Fabiao Yu . Rationally designed an innovative proximity labeling near-infrared fluorogenic probe for imaging of peroxynitrite in acute lung injury. Chinese Chemical Letters, 2025, 36(5): 110082-. doi: 10.1016/j.cclet.2024.110082
9. [9]
  Meiling Zhao , Yao Lu , Yutao Zhang , Haoyun Xue , Zhiqian Guo . Ultra-high signal-to-noise ratio near-infrared chemiluminescent probe for in vivo sensing singlet oxygen. Chinese Chemical Letters, 2025, 36(5): 110105-. doi: 10.1016/j.cclet.2024.110105
10. [10]
  Meng Gao , Jiqiu Yin , XianChao Jia , Ye Gao , Yang Jiao . On-target site enriching fluorescent bioprobe for imaging of receptor tyrosine kinase in tumor. Chinese Chemical Letters, 2025, 36(6): 110297-. doi: 10.1016/j.cclet.2024.110297
11. [11]
  Ziqin Li , Kai Hao , Longwei Xiang , Huayu Tian . Cationic covalent organic framework nanocarriers integrating both efficient gene silencing and real-time gene detection. Chinese Chemical Letters, 2025, 36(4): 109943-. doi: 10.1016/j.cclet.2024.109943
12. [12]
  Boran Cheng , Lei Cao , Chen Li , Fang-Yi Huo , Qian-Fang Meng , Ganglin Tong , Xuan Wu , Lin-Lin Bu , Lang Rao , Shubin Wang . Fluorine-doped carbon quantum dots with deep-red emission for hypochlorite determination and cancer cell imaging. Chinese Chemical Letters, 2024, 35(6): 108969-. doi: 10.1016/j.cclet.2023.108969
13. [13]
  Zihong Li , Jie Cheng , Ping Huang , Guoliang Wu , Weiying Lin . Activatable photoacoustic bioprobe for visual detection of aging in vivo. Chinese Chemical Letters, 2024, 35(4): 109153-. doi: 10.1016/j.cclet.2023.109153
14. [14]
  Gongcheng Ma , Qihang Ding , Yuding Zhang , Yue Wang , Jingjing Xiang , Mingle Li , Qi Zhao , Saipeng Huang , Ping Gong , Jong Seung Kim . Palladium-free chemoselective probe for in vivo fluorescence imaging of carbon monoxide. Chinese Chemical Letters, 2024, 35(9): 109293-. doi: 10.1016/j.cclet.2023.109293
15. [15]
  Yang Liu , Leilei Zhang , Kaixuan Liu , Ling-Ling Wu , Hai-Yu Hu . Penicillin G acylase-responsive near-infrared fluorescent probe: Unravelling biofilm regulation and combating bacterial infections. Chinese Chemical Letters, 2024, 35(11): 109759-. doi: 10.1016/j.cclet.2024.109759
16. [16]
  Yuqing Liu , Shiling Zhang , Kai Jiang , Shiyue Ding , Limei Xu , Yingqi Liu , Ting Wang , Fenfen Zheng , Weiwei Xiong , Jun-Jie Zhu . Near-infrared light responsive upconversion-DNA nanocapsules for remote-controlled CRISPR-Cas9 genome editing. Chinese Chemical Letters, 2025, 36(5): 110282-. doi: 10.1016/j.cclet.2024.110282
17. [17]
  Ying Zhang , Chuang Shen , Jiaxu Zhang , Qi Shen , Fei Xu , Shengheng Wang , Jiuyi Hu , Faisal Saleem , Feng Huang , Zhimin Luo . Ultrasmall PtCu nanosheets as a broadband phototheranostic agent in near-infrared biowindow. Chinese Chemical Letters, 2025, 36(6): 111059-. doi: 10.1016/j.cclet.2025.111059
18. [18]
  Yong-Dan Zhao , Yidan Wang , Rongrong Wang , Lina Chen , Hengtong Zuo , Xi Wang , Jihong Qiang , Geng Wang , Qingxia Li , Canqi Ping , Shuqiu Zhang , Hao Wang . Reversing artemisinin resistance by leveraging thermo-responsive nanoplatform to downregulating GSH. Chinese Chemical Letters, 2024, 35(6): 108929-. doi: 10.1016/j.cclet.2023.108929
19. [19]
  Di ZHANG , Tianxiang XIE , Xu HE , Wanyu WEI , Qi FAN , Jie QIAO , Gang JIN , Ningbo LI . Construction and antitumor activity of pH/GSH dual-responsive magnetic nanodrug. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 786-796. doi: 10.11862/CJIC.20240329
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(5)
HTML views(1)

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