Citation: Yu Zhang, Shan Lei, Yuantao Pan, Chao Zhao, Qiang Liu, Yumeng Wu, Yurong Liu, Meng Li, Peng Huang, Jing Lin. In vivo second near-infrared fluorescence and ratiometric photoacoustic dual-modality imaging of glutathione[J]. Chinese Chemical Letters, ;2026, 37(2): 110977. doi: 10.1016/j.cclet.2025.110977 shu

In vivo second near-infrared fluorescence and ratiometric photoacoustic dual-modality imaging of glutathione

Marshall Laboratory of Biomedical Engineering, International Cancer Center, Laboratory of Evolutionary Theranostics (LET), School of Biomedical Engineering, Shenzhen University Medical School, Shenzhen University, Shenzhen 518055, China

jingl@szu.edu.cn

Received Date: 25 November 2024
Revised Date: 15 February 2025
Accepted Date: 19 February 2025
Available Online: 19 February 2025

Figures(6)

The level of glutathione (GSH) is significantly associated with numerous pathological processes, thus, real-time detection of the GSH level is of significance for early diagnosis of GSH-related diseases. Herein, we developed in vivo second near-infrared (NIR-Ⅱ) window fluorescence (FL) and ratiometric photoacoustic (RPA) dual-modality imaging of GSH using a GSH-activatable probe (LET-14). LET-14 was synthesized based on a rhodamine hybrid xanthene skeleton with a FL shielding 2,4-dinitrobenzene sulfonyl group that can be specifically cleaved by GSH, thus resulting in a markedly bathochromic-shift absorption, a 6.5-fold increase in NIR-Ⅱ FL intensity (FL₉₂₀) and a 13-fold increase in RPA signal (PA₈₈₀/PA₇₀₅) in vitro. Intriguingly, LET-14 exhibits good selectivity and sensitivity for NIR-Ⅱ FL and RPA dual-modality imaging of GSH in 4T1 tumor-bearing mouse model. Our findings develop an in vivo detection tool of GSH, which has great potential in the field of cancer diagnosis.
- Glutathione,
- In vivo,
- Second near-infrared dye,
- Fluorescence imaging,
- Ratiometric photoacoustic imaging
1. [1]
  K. Umezawa, M. Yoshida, M. Kamiya, T. Yamasoba, Y. Urano, Nat. Chem. 9 (2017) 279–286. doi: 10.1038/nchem.2648
2. [2]
  J. Zhou, P. Jangili, S. Son, et al., Adv. Mater. 32 (2020) 2001945. doi: 10.1002/adma.202001945
3. [3]
  Y. Xiong, C. Xiao, Z. Li, X. Yang, Chem. Soc. Rev. 50 (2021) 6013–6041. doi: 10.1039/d0cs00718h
4. [4]
  B.D. Paul, Front. Aging Neurosci. 13 (2021) 659402. doi: 10.3389/fnagi.2021.659402
5. [5]
  Y. Wang, H. Yan, Y. Yue, et al., Chem. Eng. J. 464 (2023) 142496. doi: 10.1016/j.cej.2023.142496
6. [6]
  H. Fan, Z. Guo, Coordin. Chem. Rev. 480 (2023) 215027. doi: 10.1016/j.ccr.2023.215027
7. [7]
  G.K. Balendiran, R. Dabur, D. Fraser, Cell Biochem. Funct. 22 (2004) 343–352. doi: 10.1002/cbf.1149
8. [8]
  M.P. Gamcsik, M.S. Kasibhatla, S.D. Teeter, O.M. Colvin, Biomarkers 17 (2012) 671–691. doi: 10.3109/1354750X.2012.715672
9. [9]
  B. Niu, K. Liao, Y. Zhou, et al., Biomaterials 277 (2021) 671–691. doi: 10.1080/10410236.2020.1712034
10. [10]
  X. Jiang, J. Chen, A. Bajic, et al., Nat. Chem. 8 (2017) 16163.
11. [11]
  S. Lee, J. Li, X. Zhou, J. Yin, J. Yoon, Coordin. Chem. Rev. 366 (2018) 29–68. doi: 10.1016/j.ccr.2018.03.021
12. [12]
  S. Mo, X. Zhang, S. Hameed, Y. Zhou, Z. Dai, Theranostics 10 (2020) 2130–2140. doi: 10.7150/thno.39673
13. [13]
  Q. Wu, W. Li, J. Zhao, et al., Biomed. Pharmacother. 137 (2021) 111308. doi: 10.1016/j.biopha.2021.111308
14. [14]
  Y. Hu, Y. Wang, X. Wen, et al., Research 2020 (2020) 4087069.
15. [15]
  N. Li, T. Wang, N. Wang, M. Fan, X. Cui, Angew. Chem. Int. Ed. 62 (2023) e202217326. doi: 10.1002/anie.202217326
16. [16]
  Y. Zhang, Y. Zhang, Y. Yue, et al., Chin. Chem. Lett. 32 (2021) 2873–2876. doi: 10.1016/j.cclet.2021.05.016
17. [17]
  W. Liu, J. Chen, Q. Qiao, X. Liu, Z. Xu, Chin. Chem. Lett. 33 (2022) 4943–4947. doi: 10.1016/j.cclet.2022.03.121
18. [18]
  F. Wang, Y. Liu, B. Wang, et al., Dyes Pigm. 152 (2018) 29–35. doi: 10.1016/j.dyepig.2018.01.023
19. [19]
  M. Tian, X. Liu, H. He, et al., Anal. Chem. 92 (2020) 10068–10075. doi: 10.1021/acs.analchem.0c01881
20. [20]
  M. Tian, Y. Liu, F. Jiang, Anal. Chem. 92 (2020) 14285–14291. doi: 10.1021/acs.analchem.0c03418
21. [21]
  Y. Su, B. Yu, S. Wang, H. Cong, Y. Shen, Biomaterials 271 (2021) 120717. doi: 10.1016/j.biomaterials.2021.120717
22. [22]
  Y. Pan, S. Lei, J. Zhang, et al., Anal. Chem. 93 (2021) 17103–17109. doi: 10.1021/acs.analchem.1c04504
23. [23]
  Y. Zhang, J. Fang, S. Ye, et al., Nat. Commun. 13 (2022) 1685. doi: 10.1007/s42765-022-00213-z
24. [24]
  S. Lei, F. Zhao, J. Zhang, et al., Anal. Chem. 94 (2022) 8399–8408. doi: 10.1021/acs.analchem.2c00929
25. [25]
  F. Zhao, X. Zhang, F. Bai, et al., Adv. Mater. 35 (2023) 2208097. doi: 10.1002/adma.202208097
26. [26]
  Y. Guo, Z. Li, B. Guo, B. Wang, Y. Tu, Nano Biomed. Eng. 16 (2024) 135–151. doi: 10.26599/nbe.2024.9290061
27. [27]
  Q. Lan, P. Yu, K. Yan, et al., J. Am. Chem. Soc. 144 (2022) 21010–21015. doi: 10.1021/jacs.2c10041
28. [28]
  X. Zhang, Y. Chen, H. He, et al., Angew. Chem. Int. Ed. 60 (2021) 26337–26341. doi: 10.1002/anie.202109728
29. [29]
  S. Bi, X. Wen, G. Sun, S. Zeng, Nano Today 53 (2023) 102027. doi: 10.1016/j.nantod.2023.102027
30. [30]
  L. Nie, X. Chen, Chem. Soc. Rev. 43 (2014) 7132–7170. doi: 10.1039/C4CS00086B
31. [31]
  X. Li, J. Kim, J. Yoon, X. Chen, Adv. Mater. 29 (2017) 1606854.
32. [32]
  Y. Liu, L. Teng, B. Yin, et al., Chem. Rev. 122 (2022) 6850–6918. doi: 10.1021/acs.chemrev.1c00875
33. [33]
  E.Y. Zhou, H.J. Knox, C.J. Reinhardt, et al., J. Am. Chem. Soc. 140 (2018) 11686–11697. doi: 10.1021/jacs.8b05514
34. [34]
  Y. Cui, X. Wang, Z. Jiang, et al., Angew. Chem. Int. Ed. 135 (2023) e202214505. doi: 10.1002/ange.202214505
35. [35]
  C. Moore, Y. Cheng, N. Tjokro, et al., Angew. Chem. Int. Ed. 61 (2022) e202201843. doi: 10.1002/anie.202201843
36. [36]
  Q. Fu, R. Zhu, J. Song, H. Yang, X. Chen, Adv. Mater. 31 (2019) 1805875. doi: 10.1002/adma.201805875
37. [37]
  X. Gao, G. Ma, C. Jiang, et al., Anal. Chem. 91 (2019) 7112–7117. doi: 10.1021/acs.analchem.9b00109
38. [38]
  L. Yin, H. Sun, H. Zhang, et al., J. Am. Chem. Soc. 141 (2019) 3265–3273. doi: 10.1021/jacs.8b13628
39. [39]
  L. Wu, Y. Ishigaki, W. Zeng, et al., Nat. Commun. 12 (2021) 6145. doi: 10.1038/s41467-021-26380-y
40. [40]
  Z. Zeng, S.S. Liew, X. Wei, K. Pu, Angew. Chem. Int. Ed. 60 (2021) 26454–26475. doi: 10.1002/anie.202107877
41. [41]
  Y. Ma, L. Xu, B. Yin, et al., Nano Lett. 21 (2021) 4484–4493. doi: 10.1021/acs.nanolett.1c01359
42. [42]
  X. Zhang, K. Jiang, S. Jiang, et al., Anal. Chem. 94 (2022) 13770–13776. doi: 10.1021/acs.analchem.2c02153
43. [43]
  Y. Zhang, S. He, C. Xu, et al., Angew. Chem. Int. Ed. 61 (2022) e202203184. doi: 10.1002/anie.202203184
1. [1]
  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
2. [2]
  Ru Ding , Chunfei Wang , E Lv , Jingjing Zhao , Xucong Zhou , Yuanyi Li , Ying Wang , Bingxue Li , Lixia Zhang , Jin Zhou . A near-infrared fluorescent probe based on Au³⁺/Pd²⁺ complexes for glutathione sensing: Applications in acute liver injury, hepatocellular carcinoma, and ferroptosis exploration. Chinese Chemical Letters, 2025, 36(11): 111497-. doi: 10.1016/j.cclet.2025.111497
3. [3]
  Jiao Chen , Zihan Zhang , Guojin Sun , Yudi Cheng , Aihua Wu , Zefan Wang , Wenwen Jiang , Fulin Chen , Xiuying Xie , Jianli Li . Benzo[4,5]imidazo[1,2-a]pyrimidine-based structure-inherent targeting fluorescent sensor for imaging lysosomal viscosity and diagnosis of lysosomal storage disorders. Chinese Chemical Letters, 2024, 35(11): 110050-. doi: 10.1016/j.cclet.2024.110050
4. [4]
  Du Liu , Yuyan Li , Hankun Zhang , Benhua Wang , Chaoyi Yao , Minhuan Lan , Zhanhong Yang , Xiangzhi Song . Three-in-one erlotinib-modified NIR photosensitizer for fluorescence imaging and synergistic chemo-photodynamic therapy. Chinese Chemical Letters, 2025, 36(2): 109910-. doi: 10.1016/j.cclet.2024.109910
5. [5]
  Qiuye Wang , Yabing Sun , Liangxue Lai , Haijing Cui , Yonglong Ye , Ming Yang , Weihao Zhu , Bo Yuan , Quanliang Mao , Wenzhi Ren , Aiguo Wu . MMP-9-responsive probe for fluorescence-magnetic resonance dual-mode imaging of hepatocellular carcinoma models with different metastatic capacities. Chinese Chemical Letters, 2025, 36(4): 110212-. doi: 10.1016/j.cclet.2024.110212
6. [6]
  Lijia Xu , Tong Zhong , Wei Zhao , Bing Yao , Lin Ding , Huangxian Ju . Chemoselective labeling-based spermatozoa glycan imaging reveals abnormal glycosylation in oligoasthenotspermia. Chinese Chemical Letters, 2024, 35(4): 108760-. doi: 10.1016/j.cclet.2023.108760
7. [7]
  Qingyuan Guo , Aojie Liu , Yinghui Huang , Jiayu Ding , Junjie Ding , Limin Wang , Yang Ding , Bo Peng , Lin Li , Bin Fang , Shan Jiang , Hua Bai . Small-molecule fluorescent probes for imaging and diagnosing ischemia-reperfusion injury. Chinese Chemical Letters, 2025, 36(12): 110943-. doi: 10.1016/j.cclet.2025.110943
8. [8]
  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
9. [9]
  Tiancong Shi , Xi Chen , Xiao Zhou , Hongyi Zhang , Fuping Han , Lihan Cai , Wen Sun , Jianjun Du , Jiangli Fan , Xiaojun Peng . Azaindole-based asymmetric pentamethine cyanine dye for mitochondrial pH detection and near-infrared ratiometric fluorescence imaging of mitophagy. Chinese Chemical Letters, 2025, 36(6): 110408-. doi: 10.1016/j.cclet.2024.110408
10. [10]
  Xianghan Zhang , Yuan Qin , Huaicong Zhang , Yutian Cao , Haixing Zhu , Yingdi Tang , Zimeng Ma , Zehua Li , Jialin Zhou , Qunyan Dong , Peng Yang , Yuqiong Xia , Zhongliang Wang . An aggregation-independent and rotor-specific TPE-cyanine probe for in vivo near-infrared fluorescent imaging. Chinese Chemical Letters, 2025, 36(9): 110715-. doi: 10.1016/j.cclet.2024.110715
11. [11]
  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
12. [12]
  Yiqiao Chen , Ao Liu , Biwen Yang , Zhenzhen Li , Binggang Ye , Zhouyi Guo , Zhiming Liu , Haolin Chen . Photoluminescence and photothermal conversion in boric acid derived carbon dots for targeted microbial theranostics. Chinese Chemical Letters, 2024, 35(9): 109295-. doi: 10.1016/j.cclet.2023.109295
13. [13]
  Fengkai Zou , Borui Su , Han Leng , Nini Xin , Shichao Jiang , Dan Wei , Mei Yang , Youhua Wang , Hongsong Fan . Red-emissive carbon quantum dots minimize phototoxicity for rapid and long-term lipid droplet monitoring. Chinese Chemical Letters, 2024, 35(10): 109523-. doi: 10.1016/j.cclet.2024.109523
14. [14]
  Zhipeng Li , Qincong Feng , Jianliang Shen . A β-lactamase-activatable photosensitizer for the treatment of resistant bacterial infections. Chinese Chemical Letters, 2024, 35(11): 109602-. doi: 10.1016/j.cclet.2024.109602
15. [15]
  Sixin Ai , Wenxiu Li , Huayong Zhu , Yang Wan , Weiying Lin . Viscosity-responsive signal amplification dual-modal probe triggered by cysteine/homocysteine for monitoring diabetic liver damages and repair processes. Chinese Chemical Letters, 2025, 36(3): 109904-. doi: 10.1016/j.cclet.2024.109904
16. [16]
  Yaojun Li , Yun Li , Shenglong Liao , Yang Li , Shouchun Yin . Revolutionizing cancer therapies with organic photovoltaic non-fullerene acceptors: A deep dive into molecular engineering for advanced phototheranostics. Chinese Chemical Letters, 2025, 36(8): 110832-. doi: 10.1016/j.cclet.2025.110832
17. [17]
  Mingrui Zhang , Lingyu Jin , Yuda Zhu , Junfeng Kou , Bo Liu , Jing Chen , Xiaolin Zhong , Xianghua Wu , Junfeng Zhang , Wenxiu Ren . A near-infrared Ⅱ fluorescent dye based on oxanthracene: Real-time imaging of drug-induced acute liver injury and photothermal therapy for tumor. Chinese Chemical Letters, 2025, 36(10): 110772-. doi: 10.1016/j.cclet.2024.110772
18. [18]
  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
19. [19]
  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
20. [20]
  Linfang ZHANG , Wenzhu YIN , Gui YIN . A 2-dicyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran-based near-infrared fluorescence probe for the detection of hydrogen sulfide and imaging of living cells. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 540-548. doi: 10.11862/CJIC.20240405

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(10)
HTML views(0)

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