Citation: 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[J]. Chinese Chemical Letters, ;2025, 36(2): 109910. doi: 10.1016/j.cclet.2024.109910 shu

Three-in-one erlotinib-modified NIR photosensitizer for fluorescence imaging and synergistic chemo-photodynamic therapy

College of Chemistry & Chemical Engineering, Central South University, Changsha 410083, China

benhuawang@csu.edu.cn

chaoyiyao@csu.edu.cn

xzsong@csu.edu.cn

Received Date: 29 February 2024
Revised Date: 16 April 2024
Accepted Date: 18 April 2024
Available Online: 21 April 2024

Figures(5)

Photodynamic therapy (PDT) presents a promising avenue in cancer treatment. Erlotinib, an FDA-approved anticancer drug targeting epidermal growth factor receptor (EGFR), has shown effectiveness in normalizing tumor vasculature across various tumors, thereby promoting tumor oxygenation and facilitating PDT. In this work, erlotinib was conjugated with a near-infrared (NIR) photosensitizer, benzo[a]phenoselenazinium, yielding three EGFR-targeted PDT agents (NBSe-nC-Er). These newly synthesized photosensitizers demonstrate specificity in binding to EGFR, thereby enhancing their accumulation in cancer cells and tumors, and consequently improving the efficiency of both PDT and chemotherapy. Additionally, the NIR fluorescence emitted by the photosensitizer allows for imaging-guided therapy, offering a non-invasive means of monitoring treatment progress. The distinctive properties of the three-in-one photosensitizer render it an ideal candidate for precise tumor treatment, overcoming the limitations of conventional therapies.
- Photosensitizer,
- Benzo[a]phenoselenazinium,
- Fluorescence imaging,
- Photodynamic therapy,
- Chemotherapy
1. [1]
  J. Chen, F. Zeng, S.J. Forrester, et al., Physiol. Rev. 96 (2016) 1025–1069. doi: 10.1152/physrev.00030.2015
2. [2]
  T. Yamaoka, M. Ohba, T. Ohmori, Int. J. Mol. Sci. 18 (2017) 2420. doi: 10.3390/ijms18112420
3. [3]
  M.K. Mayekar, T.G. Bivona, Clin. Pharmacol. Ther. 102 (2017) 757–764. doi: 10.1002/cpt.810
4. [4]
  Q. He, M. Qu, H. Bao, et al., Cytokine Growth Factor Rev. 70 (2023) 41–53. doi: 10.1016/j.cytogfr.2023.03.003
5. [5]
  Q. Guo, L. Liu, Z. Chen, et al., Front. Oncol. 12 (2022) 945102. doi: 10.3389/fonc.2022.945102
6. [6]
  K.H. Dragnev, W.J. Petty, S. Shah, et al., J. Clin. Oncol. 23 (2005) 8757–8764. doi: 10.1200/JCO.2005.01.9521
7. [7]
  M.H. Cohen, J.R. Johnson, Y.F. Chen, et al., Oncologist 10 (2005) 461–466. doi: 10.1634/theoncologist.10-7-461
8. [8]
  M. Bersanelli, R. Minari, P. Bordi, et al., J. Thorac. Oncol. 11 (2016) e121–e123. doi: 10.1016/j.jtho.2016.05.019
9. [9]
  A. Ramos, S. Sadeghi, H. Tabatabaeian, Int. J. Mol. Sci. 22 (2021) 9451. doi: 10.3390/ijms22179451
10. [10]
  H.A. Yu, S.K. Tian, A.E. Drilon, et al., JAMA Oncol. 1 (2015) 982–984. doi: 10.1001/jamaoncol.2015.1066
11. [11]
  A.N. Hata, M.J. Niederst, H.L. Archibald, et al., Nat. Med. 22 (2016) 262–269. doi: 10.1038/nm.4040
12. [12]
  X. Zhao, J. Liu, J. Fan, et al., Chem. Soc. Rev. 50 (2021) 4185–4219. doi: 10.1039/d0cs00173b
13. [13]
  G. Feng, G.Q. Zhang, D. Ding, Chem. Soc. Rev. 49 (2020) 8179–8234. doi: 10.1039/d0cs00671h
14. [14]
  T.C. Pham, V.N. Nguyen, Y. Choi, et al., Chem. Rev. 121 (2021) 13454–13619. doi: 10.1021/acs.chemrev.1c00381
15. [15]
  T. Hu, C. Shen, X. Wang, et al., Chin. Chem. Lett. 35 (2024) 109562. doi: 10.1016/j.cclet.2024.109562
16. [16]
  W. Liu, Y. Hou, W. Liu, et al., Chin. Chem. Lett. 35 (2024) 109631. doi: 10.1016/j.cclet.2024.109631
17. [17]
  D. Zhang, K.X. Teng, L. Zhao, et al., Adv. Mater. 35 (2023) 2209789. doi: 10.1002/adma.202209789
18. [18]
  S. Su, X. Li, Q. An, et al., Chem. Commun. 60 (2024) 3910–3913. doi: 10.1039/d3cc06019e
19. [19]
  S.Y. Wang, Y.H. Pan, Y.C. Qu, et al., Smart Mol. 2 (2024) e20230024. doi: 10.1002/smo.20230024
20. [20]
  L. Huang, S. Zhao, J. Wu, et al., Coord. Chem. Rev. 438 (2021) 213888. doi: 10.1016/j.ccr.2021.213888
21. [21]
  J.H. Correia, J.A. Rodrigues, S. Pimenta, et al., Pharmaceutics 13 (2021) 1332. doi: 10.3390/pharmaceutics13091332
22. [22]
  Q. Zhao, G. Qing, J. Yu, et al., Chin. Chem. Lett. 35 (2024) 108535. doi: 10.1016/j.cclet.2023.108535
23. [23]
  W. Su, X. Luo, P. Li, et al., Chin. Chem. Lett. 35 (2024) 109522. doi: 10.1016/j.cclet.2024.109522
24. [24]
  K.X. Teng, D. Zhang, B.K. Liu, et al., Angew. Chem. Int. Ed. 63 (2024) e202318783. doi: 10.1002/anie.202318783
25. [25]
  P.V. Nguyen, K. Hervé-Aubert, I. Chourpa, et al., Int. J. Pharm. 609 (2021) 121134. doi: 10.1016/j.ijpharm.2021.121134
26. [26]
  S.M. Gallagher-Colombo, J. Miller, K.A. Cengel, et al., Cancer Res. 75 (2015) 3118–3126.
27. [27]
  L. Ulfo, P.E. Costantini, M. Di Giosia, et al., Pharmaceutics 14 (2022) 241–285. doi: 10.3390/pharmaceutics14020241
28. [28]
  L. Yan, J. Miller, M. Yuan, et al., Biomacromolecules 18 (2017) 1836–1844. doi: 10.1021/acs.biomac.7b00274
29. [29]
  Q. Chen, L. Xu, J. Chen, et al., Biomaterials 148 (2017) 69–80. doi: 10.1016/j.biomaterials.2017.09.021
30. [30]
  Y. Liu, X. Ma, Y. Zhu, et al., Chem. Eng. J. 437 (2022) 135305. doi: 10.1016/j.cej.2022.135305
31. [31]
  M.R. Younis, G. He, J. Qu, et al., Adv. Sci. 8 (2021) 2102587. doi: 10.1002/advs.202102587
32. [32]
  F.L. Zhang, Q. Huang, K. Zheng, et al., Chem. Commun. 49 (2013) 9570–9572. doi: 10.1039/c3cc45487h
33. [33]
  E.Y. Gül, E.A. Karataş, H.A. Doğan, et al., ChemMedChem 18 (2023) e202200439. doi: 10.1002/cmdc.202200439
34. [34]
  B.G. Ongarora, K.R. Fontenot, X. Hu, et al., J. Med. Chem. 55 (2012) 3725–3738. doi: 10.1021/jm201544y
35. [35]
  R.R. Cheruku, J. Cacaccio, F.A. Durrani, et al., J. Med. Chem. 62 (2019) 2598–2617. doi: 10.1021/acs.jmedchem.8b01927
36. [36]
  J. Shi, P.W. Kantoff, R. Wooster, et al., Nat. Rev. Cancer 17 (2017) 20–37. doi: 10.1038/nrc.2016.108
37. [37]
  M. Xu, Y. Qi, G. Liu, et al., ACS Nano 17 (2023) 20825–20849. doi: 10.1021/acsnano.3c05853
38. [38]
  M. Li, T. Xiong, J. Du, et al., J. Am. Chem. Soc. 141 (2019) 2695–2702. doi: 10.1021/jacs.8b13141
39. [39]
  C. Shi, X. Zhou, Q. Zhao, et al., CCS Chem. 4 (2022) 2662–2673. doi: 10.31635/ccschem.021.202101222
40. [40]
  X. Yue, B. Wang, M. Lan, et al., Chem. Commun. 59 (2023) 4676–4679. doi: 10.1039/d3cc00214d
41. [41]
  X. Yue, T. Guo, H. Zhang, et al., Chem. Commun. 59 (2023) 7060–7063. doi: 10.1039/d3cc00063j
42. [42]
  Y. Li, Z. Gao, X. Yue, et al., Chin. Chem. Lett. 35 (2024) 109133. doi: 10.1016/j.cclet.2023.109133
43. [43]
  K.H. Gebremedhin, M. Li, F. Gao, et al., Dyes Pigm. 170 (2019) 107617. doi: 10.1016/j.dyepig.2019.107617
44. [44]
  J.W. Foley, X. Song, T.N. Demidova, et al., J. Med. Chem. 49 (2006) 5291–5299. doi: 10.1021/jm060153i
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沈阳化工大学材料科学与工程学院沈阳 110142