Citation: Wenkai Liu, Yanxian Hou, Weijian Liu, Ran Wang, Shan He, Xiang Xia, Chengyuan Lv, Hua Gu, Qichao Yao, Qingze Pan, Zehou Su, Danhong Zhou, Wen Sun, Jiangli Fan, Xiaojun Peng. Se-substituted pentamethine cyanine for anticancer photodynamic therapy mediated using the hot band absorption process[J]. Chinese Chemical Letters, ;2024, 35(12): 109631. doi: 10.1016/j.cclet.2024.109631 shu

Se-substituted pentamethine cyanine for anticancer photodynamic therapy mediated using the hot band absorption process

Wenkai Liu ^a ,
Yanxian Hou ^a ,
Weijian Liu ^b ,
Ran Wang ^a ,
Shan He ^c ,
Xiang Xia ^a ,
Chengyuan Lv ^a ,
Hua Gu ^a ,
Qichao Yao ^a ,
Qingze Pan ^a ,
Zehou Su ^a ,
Danhong Zhou ^a ,
Wen Sun ^{a, *,} ,
Jiangli Fan ^{a, *,} ,
Xiaojun Peng ^a

a.
State Key Laboratory of Fine Chemicals, Frontiers Science Center for Smart Materials Oriented Chemical Engineering, Dalian University of Technology, Dalian 116024, China
b.
Shandong Laboratory of Yantai Advanced Materials and Green Manufacturing, Yantai 264006, China
c.
Department of Chemistry, Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and Reconstruction and Institute for Advanced Study, The Hong Kong University of Science and Technology, Hong Kong 999077, China

sunwen@dlut.edu.cn

fanjl@dlut.edu.cn

Received Date: 18 December 2023
Revised Date: 2 February 2024
Accepted Date: 3 February 2024
Available Online: 13 February 2024

Figures(4)

Photodynamic therapy (PDT) is a promising cancer treatment modality owing to its high spatiotemporal selectivity and noninvasive nature. However, conventional photosensitizers (PSs) used in PDT are responsive only to visible light, which makes them unsuitable for tissue penetration. In this study, we propose a PS based on hot band absorption (HBA), which can be triggered by anti-Stokes light at 808 nm via a one-photon process. The introduction of selenium (Se) into pentamethine cyanine (Secy5) not only facilitates intersystem crossing for reactive oxygen species (ROS) production but also enhances HBA efficiency, thereby prolonging the excitation wavelength. In addition, Secy5 demonstrates excellent biocompatibility, unlike its I-substituted counterpart (Icy5), and produces not only ¹O₂ but also O₂^•−, making it a desirable candidate for treating hypoxic solid tumors. According to the results of in vivo and in vitro experiments, Secy5 can efficiently inhibit cancer cell growth via anti-Stokes activation processes, thereby providing a novel approach to design anti-Stokes excitation PSs for anticancer treatment.
- Cyanine dyes,
- Hot band absorption,
- Anti-Stokes,
- Photodynamic therapy,
- Anticancer treatment
1. [1]
  H.S. Jung, S. Koo, M. Won, et al., Chem. Sci. 14 (2023) 1808–1819. doi: 10.1039/D2SC03945A
2. [2]
  J. Xie, Y. Wang, W. Choi, et al., Chem. Soc. Rev. 50 (2021) 9152–9201. doi: 10.1039/D0CS01370F
3. [3]
  Q. Chen, V. Ramu, Y. Aydar, et al., Cancers 12 (2020) 587. doi: 10.3390/cancers12030587
4. [4]
  S. Flitsch, C. Duboc, S. Bonnet, JACS Au 2 (2022) 1018–1019. doi: 10.1021/jacsau.2c00249
5. [5]
  B. Sun, R. Chang, S. Cao, et al., Angew. Chem. Int. Ed. 59 (2020) 20582–20588. doi: 10.1002/anie.202008708
6. [6]
  S. Gao, Y. Jin, K. Ge, et al., Adv. Sci. 6 (2019) 1902137. doi: 10.1002/advs.201902137
7. [7]
  Q. Ma, X. Sun, W. Wang, et al., Chin. Chem. Lett. 33 (2022) 1681–1692. doi: 10.1016/j.cclet.2021.10.054
8. [8]
  S. Zhou, H. Tian, J. Yan, et al., Chin. Chem. Lett. 35 (2024) 108312. doi: 10.1016/j.cclet.2023.108312
9. [9]
  Z. Li, S. Li, Y. Guo, et al., ACS Nano 15 (2021) 4979–4988. doi: 10.1021/acsnano.0c09913
10. [10]
  Y. Cai, D. Ni, W. Cheng, et al., Angew. Chem. Int. Ed. 59 (2020) 14014–14018. doi: 10.1002/anie.202001107
11. [11]
  C. Ji, Q. Gao, X. Dong, et al., Angew. Chem. Int. Ed. 57 (2018) 11384–11388. doi: 10.1002/anie.201807602
12. [12]
  K.X. Teng, L.Y. Niu, N. Xie, Q.Z. Yang, Nat. Commun. 13 (2022) 6179. doi: 10.1038/s41467-022-33924-3
13. [13]
  K.X. Teng, L.Y. Niu, Q.Z. Yang, J. Am. Chem. Soc. 145 (2023) 4081–4087. doi: 10.1021/jacs.2c11868
14. [14]
  H. Chen, P. Timashev, Y. Zhang, X. Xue, X.J. Liang, RSC Adv. 12 (2022) 9725–9737. doi: 10.1039/D1RA09067D
15. [15]
  Z. Liu, J. Zhang, H. Liu, et al., Adv. Mater. 35 (2023) 2208692. doi: 10.1002/adma.202208692
16. [16]
  W. Fan, P. Huang, X. Chen, Chem. Soc. Rev. 45 (2016) 6488–6519. doi: 10.1039/C6CS00616G
17. [17]
  X. Miao, W. Hu, T. He, et al., Chem. Sci. 10 (2019) 3096–3102. doi: 10.1039/C8SC04840A
18. [18]
  M. Wang, M. Chang, C. Li, et al., Adv. Mater. 34 (2022) 2106010. doi: 10.1002/adma.202106010
19. [19]
  H. Chen, B. Ding, P. Ma, J. Lin, Adv. Drug Deliv. Rev. 188 (2022) 114414. doi: 10.1016/j.addr.2022.114414
20. [20]
  X. Wei, W.B. Cui, G.Y. Qin, et al., J. Med. Chem. 66 (2023) 4167–4178. doi: 10.1021/acs.jmedchem.3c00047
21. [21]
  J. Xu, L. Xu, C. Wang, et al., ACS Nano 11 (2017) 4463–4474. doi: 10.1021/acsnano.7b00715
22. [22]
  H. Liang, X. Liu, Li. Tang, et al., Chin. Chem. Lett. 34 (2023) 107515. doi: 10.1016/j.cclet.2022.05.029
23. [23]
  W. Zhao, Y. Zhao, Q. Wang, et al., Small 15 (2019) 1903060. doi: 10.1002/smll.201903060
24. [24]
  L. Wu, J. Liu, P. Li, B. Tang, T.D. James, Chem. Soc. Rev. 50 (2021) 702–734. doi: 10.1039/D0CS00861C
25. [25]
  Y. Liu, Q. Su, X. Zou, et al., Chem. Commun. 52 (2016) 7466–7469. doi: 10.1039/C6CC03401B
26. [26]
  X. Zhu, Q. Su, W. Feng, F. Li, Chem. Soc. Rev. 46 (2017) 1025–1039. doi: 10.1039/C6CS00415F
27. [27]
  E.M. Rodrigues, N.D. Calvert, J.C. Crawford, et al., Small 18 (2022) 2107130. doi: 10.1002/smll.202107130
28. [28]
  D. Ma, H. Bian, S. Long, et al., Sci. China Chem. 65 (2022) 563–573. doi: 10.1007/s11426-021-1179-7
29. [29]
  R. Tian, W. Sun, M. Li, et al., Chem. Sci. 10 (2019) 10106–10112. doi: 10.1039/C9SC04034J
30. [30]
  W. Sun, S. Guo, C. Hu, J. Fan, X. Peng, Chem. Rev. 116 (2016) 7768–7817. doi: 10.1021/acs.chemrev.6b00001
31. [31]
  E. Delaey, F. van Laar, D. De Vos, et al., J. Photochem. Photobiol. B Biol. 55 (2000) 27–36. doi: 10.1016/S1011-1344(00)00021-X
32. [32]
  H.J. Zhou, T.B. Ren, Chem. Asian J. 17 (2022) 202200147. doi: 10.1002/asia.202200147
33. [33]
  C. Zhang, L. Long, C. Shi, Adv. Therap. 1 (2018) 1800069. doi: 10.1002/adtp.201800069
34. [34]
  C. Zhang, T. Liu, Y. Su, et al., Biomaterials 31 (2010) 6612–6617. doi: 10.1016/j.biomaterials.2010.05.007
35. [35]
  J.A. Carr, D. Franke, J.R. Caram, et al., Proc. Natl. Acad. Sci. U. S. A. 115 (2018) 4465–4470. doi: 10.1073/pnas.1718917115
36. [36]
  Y. Xu, J. Yu, J. Hu, et al., Adv. Healthc. Mater. 12 (2023) 2203080. doi: 10.1002/adhm.202203080
37. [37]
  S. Qi, Y. Wang, Y. Zhu, et al., Nano Today 49 (2023) 101795. doi: 10.1016/j.nantod.2023.101795
38. [38]
  X. Zhao, Q. Yao, S. Long, et al., J. Am. Chem. Soc. 143 (2021) 12345–12354. doi: 10.1021/jacs.1c06275
39. [39]
  W. Liu, H. Gu, B. Ran, et al., Sci. China Mater. 65 (2022) 845–854. doi: 10.1007/s40843-021-1770-0
40. [40]
  D. Chen, Q. Xu, W. Wang, et al., Small 17 (2021) 2006742. doi: 10.1002/smll.202006742
41. [41]
  H. Ma, Y. Lu, Z. Huang, et al., J. Am. Chem. Soc. 144 (2022) 3477–3486. doi: 10.1021/jacs.1c11886
42. [42]
  Z. Wang, A. Toffoletti, Y. Hou, et al., Chem. Sci. 12 (2020) 2829–2840.
43. [43]
  J. An, S. Tang, G. Hong, et al., Nat. Commun. 13 (2022) 2225. doi: 10.1038/s41467-022-29862-9
44. [44]
  K.X. Teng, W.K. Chen, L.Y. Niu, et al., Angew. Chem. Int. Ed. 60 (2021) 19912–19920. doi: 10.1002/anie.202106748
45. [45]
  A.V. Kachynski, A.N. Kuzmin, H.E. Pudavar, P.N. Prasad, Appl. Phy. Lett. 87 (2005) 023901. doi: 10.1063/1.1993761
46. [46]
  X. Zhao, S. He, W. Chi, et al., Adv. Sci. 9 (2022) 2202885. doi: 10.1002/advs.202202885
47. [47]
  J.L. Clark, P.F. Miller, G. Rumbles, J. Phys. Chem. A 102 (1998) 4428–4437. doi: 10.1021/jp980589c
48. [48]
  R.K. Jain, C. Hu, T.K. Gustafson, S.S. Elliot, M.S. Chang, J. Appl. Phys. 44 (1973) 3157–3161. doi: 10.1063/1.1662724
49. [49]
  H. Xiao, X. Li, B. Li, et al., Small 19 (2023) 2300280. doi: 10.1002/smll.202300280
1. [1]
  Qihang Wu , Hui Wen , Wenhai Lin , Tingting Sun , Zhigang Xie . Alkyl chain engineering of boron dipyrromethenes for efficient photodynamic antibacterial treatment. Chinese Chemical Letters, 2024, 35(12): 109692-. doi: 10.1016/j.cclet.2024.109692
2. [2]
  Yongkang Yue , Zhou Xu , Kaiqing Ma , Fangjun Huo , Xuemei Qin , Kuanshou Zhang , Caixia Yin . HSA shrinkage optimizes the photostability of embedded dyes fundamentally to amplify their efficiency as photothermal materials. Chinese Chemical Letters, 2024, 35(8): 109223-. doi: 10.1016/j.cclet.2023.109223
3. [3]
  Wei Su , Xiaoyan Luo , Peiyuan Li , Ying Zhang , Chenxiang Lin , Kang Wang , Jianzhuang Jiang . Phthalocyanine self-assembled nanoparticles for type Ⅰ photodynamic antibacterial therapy. Chinese Chemical Letters, 2024, 35(12): 109522-. doi: 10.1016/j.cclet.2024.109522
4. [4]
  Di An , Mingdong She , Ziyang Zhang , Ting Zhang , Miaomiao Xu , Jinjun Shao , Qian Shen , Xuna Tang . Light-responsive nanomaterials for biofilm removal in root canal treatment. Chinese Chemical Letters, 2025, 36(2): 109841-. doi: 10.1016/j.cclet.2024.109841
5. [5]
  Yihao Zhang , Yang Jiao , Xianchao Jia , Qiaojia Guo , Chunying Duan . Highly effective self-assembled porphyrin MOCs nanomaterials for enhanced photodynamic therapy in tumor. Chinese Chemical Letters, 2024, 35(5): 108748-. doi: 10.1016/j.cclet.2023.108748
6. [6]
  Yu Qin , Mingyang Huang , Chenlu Huang , Hannah L. Perry , Linhua Zhang , Dunwan Zhu . O₂-generating multifunctional polymeric micelles for highly efficient and selective photodynamic-photothermal therapy in melanoma. Chinese Chemical Letters, 2024, 35(7): 109171-. doi: 10.1016/j.cclet.2023.109171
7. [7]
  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
8. [8]
  Hao Cai , Xiaoyan Wu , Lei Jiang , Feng Yu , Yuxiang Yang , Yan Li , Xian Zhang , Jian Liu , Zijian Li , Hong Bi . Lysosome-targeted carbon dots with a light-controlled nitric oxide releasing property for enhanced photodynamic therapy. Chinese Chemical Letters, 2024, 35(4): 108946-. doi: 10.1016/j.cclet.2023.108946
9. [9]
  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
10. [10]
  Liangliang Jia , Ye Hong , Xinyu He , Ying Zhou , Liujiao Ren , Hongjun Du , Bin Zhao , Bin Qin , Zhe Yang , Di Gao . Fighting hypoxia to improve photodynamic therapy-driven immunotherapy: Alleviating, exploiting and disregarding. Chinese Chemical Letters, 2025, 36(2): 109957-. doi: 10.1016/j.cclet.2024.109957
11. [11]
  Leichen Wang , Anqing Mei , Na Li , Xiaohong Ruan , Xu Sun , Yu Cai , Jinjun Shao , Xiaochen Dong . Aza-BODIPY dye with unexpected bromination and high singlet oxygen quantum yield for photoacoustic imaging-guided synergetic photodynamic/photothermal therapy. Chinese Chemical Letters, 2024, 35(6): 108974-. doi: 10.1016/j.cclet.2023.108974
12. [12]
  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
13. [13]
  Yuequan Wang , Congtian Wu , Chengcheng Feng , Qin Chen , Zhonggui He , Shenwu Zhang , Cong Luo , Jin Sun . Spatiotemporally-controlled supramolecular hybrid nanoassembly enabling ferroptosis-augmented photodynamic immunotherapy of cancer. Chinese Chemical Letters, 2025, 36(3): 109902-. doi: 10.1016/j.cclet.2024.109902
14. [14]
  Kun-Heng Li , Hong-Yang Zhao , Dan-Dan Wang , Ming-Hui Qi , Zi-Jian Xu , Jia-Mi Li , Zhi-Li Zhang , Shi-Wen Huang . Mitochondria-targeted nano-AIEgens as a powerful inducer for evoking immunogenic cell death. Chinese Chemical Letters, 2024, 35(5): 108882-. doi: 10.1016/j.cclet.2023.108882
15. [15]
  Xinyue Lan , Junguang Liang , Churan Wen , Xiaolong Quan , Huimin Lin , Qinqin Xu , Peixian Chen , Guangyu Yao , Dan Zhou , Meng Yu . Photo-manipulated polyunsaturated fatty acid-doped liposomal hydrogel for flexible photoimmunotherapy. Chinese Chemical Letters, 2024, 35(4): 108616-. doi: 10.1016/j.cclet.2023.108616
16. [16]
  Zhongyu Wang , Lijun Wang , Huaixin Zhao . DNA-based nanosystems to generate reactive oxygen species for nanomedicine. Chinese Chemical Letters, 2024, 35(11): 109637-. doi: 10.1016/j.cclet.2024.109637
17. [17]
  Yunkang Tong , Haiqiao Huang , Haolan Li , Mingle Li , Wen Sun , Jianjun Du , Jiangli Fan , Lei Wang , Bin Liu , Xiaoqiang Chen , Xiaojun Peng . Cooperative bond scission by HRP/H₂O₂ for targeted prodrug activation. Chinese Chemical Letters, 2024, 35(12): 109663-. doi: 10.1016/j.cclet.2024.109663
18. [18]
  Yueying Wang , Jianming Xiong , Linwei Xin , Yuanyuan Li , He Huang , Wenjun Miao . Photosensitizer-synergized g-carbon nitride nanosheets with enhanced photocatalytic activity for eradicating drug-resistant bacteria and promoting wound healing. Chinese Chemical Letters, 2025, 36(4): 110003-. doi: 10.1016/j.cclet.2024.110003
19. [19]
  Tong Tong , Lezong Chen , Siying Wu , Zhong Cao , Yuanbin Song , Jun Wu . Establishment of a leucine-based poly(ester amide)s library with self-anticancer effect as nano-drug carrier for colorectal cancer treatment. Chinese Chemical Letters, 2024, 35(12): 109689-. doi: 10.1016/j.cclet.2024.109689
20. [20]
  Xin Lv , Hongxing Zhang , Kaibo Duan , Wenhui Dai , Zhihui Wen , Wei Guo , Junsheng Hao . Lighting the Way Against Cancer: Photodynamic Therapy. University Chemistry, 2024, 39(5): 70-79. doi: 10.3866/PKU.DXHX202309090

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(278)
HTML views(8)

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