Citation: Wang Lingyun, Xin Shuqi, Tang Hao, Cao Derong. Research Progress in Cancer Treatment by Diketopyrrolopyrrole-Based Photosensitizers and Photothermal Agents[J]. Chinese Journal of Organic Chemistry, ;2020, 40(12): 4155-4167. doi: 10.6023/cjoc202005041 shu

Research Progress in Cancer Treatment by Diketopyrrolopyrrole-Based Photosensitizers and Photothermal Agents

School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640

Corresponding author: Wang Lingyun, lingyun@scut.edu.cn
Received Date: 18 May 2020
Revised Date: 17 June 2020
Available Online: 8 July 2020
Fund Project: the China Scholarship Council 201906155012the National Natural Science Foundation of China 22071065the Natural Science Foundation of Guangdong Province 2018B030311008Project supported by the National Natural Science Foundation of China (Nos. 21772045, 22071065), the Natural Science Foundation of Guangdong Province (No. 2018B030311008), the China Scholarship Council (No. 201906155012) and the Technology Program of Guangzhou City (No. 201904010414)the Technology Program of Guangzhou City 201904010414the National Natural Science Foundation of China 21772045

Figures(17)

Cancer has become one of the major threats to human health in modern society. Phototherapy including photodynamic therapy (PDT) and photothermal therapy (PTT), as a new type of tumor treatment, has received more and more attentions due to its high spatiotemporal precision, noninvasive nature, controllability, low toxicity and repeatable treatment without initial resistance. It is important to obtain a highly efficient and ideal photosensitizer for reactive oxygen species (ROS) generation for PDT. Photothermal agents with high photothermal conversion efficiency are also in urgent need for PTT. Diketopyrrolopyrrole (DPP) is an excellent type of photosensitizer and photothermal reagent because of its good structural planarity, strong electron affinity, simple synthesis, easy structure modification and high molar absorption coefficient. The research progress of DPP-based photosensitizers and photothermal agents in recent year, including structural modification of DPP, the structure-activity relationship, the mechanism of phototherapy and some representative examples is summarized. Finally, a perspective on the future development of phototherapy based on DPP is presented.
- diketopyrrolopyrrole,
- photodynamic therapy,
- photothermal therapy,
- combined therapy
1. [1]
  Wilson, B.; Weersink, R. Photochem. Photobiol. 2020, 96, 219. doi: 10.1111/php.13184
2. [2]
  Liu, Y.; Bhattarai, P.; Dai, Z.; Chen, X. Chem. Soc. Rev. 2019, 48, 2053. doi: 10.1039/C8CS00618K
3. [3]
  Wang, P.; Sun, S.; Ma, H.; Sun, S.; Zhao, D.; Wang, S.; Liang, X. Mater. Sci. Eng., C 2020, 108, 11019.
4. [4]
  Rejinold, N.; Choi, Choy, G. Coord. Chem. Rev. 2020, 411, 213252. doi: 10.1016/j.ccr.2020.213252
5. [5]
  Fan, W.; Huang, P.; Chen, X. Chem. Soc. Rev. 2016, 45, 6488. doi: 10.1039/C6CS00616G
6. [6]
  Yano, S.; Hirohara, S.; Obata, M.; Hagiya, Y.; Ogura, S. I.; Ikeda, A.; Kataoka, H.; Tanaka, M.; Joh, T. J. Photochem. Photobiol., C 2011, 12, 46. doi: 10.1016/j.jphotochemrev.2011.06.001
7. [7]
  Allison, R. R; Sibata, C. H. Photodiagn. Photodyn. Ther. 2010, 7, 61. doi: 10.1016/j.pdpdt.2010.02.001
8. [8]
  Cai, Y.; Tang, Q.; Wu, X.; Si, W.; Zhang, Q.; Huang, W.; Dong, X. ACS Appl. Mater. Inter. 2016, 8, 10737. doi: 10.1021/acsami.6b01533
9. [9]
  Liang, P.; Shao, J.; Tang, Q.; Si, W.; Wang, Q.; Zhang, Q.; Dong, X. RSC Adv. 2017, 7, 37369. doi: 10.1039/C7RA06551E
10. [10]
  Zou, J.; Yin, Z.; Wang, P.; Chen, D.; Shao, J.; Zhang, Q.; Sun, L.; Huang, W.; Dong, X. Chem. Sci. 2018, 9, 2188. doi: 10.1039/C7SC04694D
11. [11]
  He, H.; Zheng, X.; Liu, S.; Zheng, M.; Xie, Z.; Wang, Y.; Yu, M.; Shuai, X. Nanoscale 2018, 10, 10991. doi: 10.1039/C8NR02643B
12. [12]
  Schmitt, J.; Heitz, V.; Sour, A.; Bolze, F.; Ftouni, H.; Nicoud, J.; Flamigni, L.; Ventura, B. Angew. Chem., Int. Ed. 2015, 54, 169. doi: 10.1002/anie.201407537
13. [13]
  Schmitt, J.; Heitz, V.; Sour, A.; Bolze, F.; Kessler, P.; Flamigni, L.; Ventura, B.; Bonnet, C. S.; Tóth, É. Chem.-Eur. J 2016, 22, 2775. doi: 10.1002/chem.201503433
14. [14]
  Fisher, J. W.; Sarkar, S.; Buchanan, C. F.; Szot, C. S.; Whitney, J.; Hatcher, H. C.; Torti, S. V.; Rylander, C. G.; Rylander, M. N. Cancer Res. 2010, 70, 9855. doi: 10.1158/0008-5472.CAN-10-0250
15. [15]
  Gaca, S.; Reichert, S.; Multhoff, G.; Wacker, M.; Hehlgans, S.; Botzler, C.; Gehrmann, M.; Rodel, C.; Kreuter, J.; Rodel, F. J. Controlled Release 2013, 172, 201. doi: 10.1016/j.jconrel.2013.08.020
16. [16]
  Liang, P.; Tang, Q.; Cai, Y.; Liu, G.; Si, W.; Shao, J.; Huang, W.; Zhang, Q.; Dong, X. Chem. Sci. 2017, 8, 7457. doi: 10.1039/C7SC03351F
17. [17]
  Zong, S.; Wang, X.; Lin, W.; Liu, S.; Zhang, W. Bioconjugate Chem. 2018, 29, 2619. doi: 10.1021/acs.bioconjchem.8b00333
18. [18]
  Wu, F.; Chen, L.; Yue, L.; Wang, K.; Cheng, K.; Chen, J.; Luo, X.; Zhang, T. ACS Appl. Mater. Interfaces 2019, 11, 21408. doi: 10.1021/acsami.9b06866
19. [19]
  Cai, Y.; Si, W.; Tang, Q.; Liang, P.; Zhang, C.; Chen, P.; Zhang, Q.; Huang, W.; Dong, X. Nano Res. 2017, 10, 794. doi: 10.1007/s12274-016-1332-2
20. [20]
  Chen, H.; Zhang, J.; Chang, K.; Men, X.; Fang, X.; Zhou, L.; Li, D.; Gao, D.; Yin, S.; Zhang, X.; Yuan, Z.; Wu, C. Biomaterials 2017, 144, 42. doi: 10.1016/j.biomaterials.2017.08.007
21. [21]
  Li, S.; Deng, Q.; Li, X.; Huang, Y.; Li, X.; Liu, F.; Wang, H.; Qing, W.; Liu, Z.; Lee, C. Biomaterials 2019, 216, 119252. doi: 10.1016/j.biomaterials.2019.119252
22. [22]
  Guo, L.; Liu, W.; Niu, G.; Zhang, P.; Zheng, X.; Jia, Q.; Zhang, H.; Ge, J.; Wang, P. J. Mater. Chem. B 2017, 5, 2832. doi: 10.1039/C7TB00498B
23. [23]
  Wei, Z.; Wu, M.; Lan, S.; Li, J.; Zhang, X.; Zhang, D.; Liu, X.; Liu, J. Chem. Commun. 2018, 54, 13599. doi: 10.1039/C8CC07583B
24. [24]
  Lu, X.; Yuan, P.; Zhang, W.; Wu, Q.; Wang, X.; Zhao, M.; Sun, P.; Huang, W.; Fan, Q. Polym. Chem. 2018, 9, 3118. doi: 10.1039/C8PY00215K
25. [25]
  Zhang, W.; Lin, W.; Li, C.; Liu, S.; Hu, X.; Xie, Z. ACS Appl. Mater. Interfaces 2019, 11, 32720. doi: 10.1021/acsami.9b10713
26. [26]
  Liu, H.; Wang, K.; Yang, C.; Huang, S.; Wang, M. Colloids Surf., B 2017, 157, 398. doi: 10.1016/j.colsurfb.2017.05.080
27. [27]
  Cao, Y.; Yi, J.; Yang, X.; Liu, L.; Yu, C.; Huang, Y.; Sun, L.; Bao, Y.; Li, Y. Biomacromolecules 2017, 18, 2306. doi: 10.1021/acs.biomac.7b00464
28. [28]
  Cao, Y.; Wu, Y.; Wang, G.; Yi, J.; Yu, C.; Huang, Y.; Sun, L.; Bao, Y.; Li, Y. J. Mater. Chem. B 2017, 5, 5479. doi: 10.1039/C7TB01264K
29. [29]
  Wu, Y.; Wang, K.; Huang, S.; Yang, C.; Wang, M. ACS Appl. Mater. Interfaces 2017, 9, 13602. doi: 10.1021/acsami.7b01016
30. [30]
  Xu, Y.; Chen, J.; Tong, L.; Su, P.; Liu, Y.; Gu, B.; Bao, B.; Wang, L. J. Controlled Release 2019, 293, 94. doi: 10.1016/j.jconrel.2018.11.016
31. [31]
  Guo, W.; Guo, C.; Zheng, N.; Sun, T.; Liu, S. Adv. Mater. 2017, 29, 1604157. doi: 10.1002/adma.201604157
32. [32]
  Liang, P.; Wang, Y.; Wang, P.; Zou, J.; Xu, H.; Zhang, Y.; Si, W.; Dong, X. Nanoscale 2017, 9, 18890. doi: 10.1039/C7NR07204J
33. [33]
  Cai, Y.; Liang, P.; Tang, Q; Yang, X.; Si, W.; Huang, W.; Zhang, Q.; Dong, X. ACS Nano 2017, 11, 1054. doi: 10.1021/acsnano.6b07927
34. [34]
  Cai, Y.; Liang, P.; Si, W.; Zhao, B.; Shao, J.; Huang, W.; Zhang, Y.; Zhang, Q.; Dong, X. Org. Chem. Front. 2018, 5, 98. doi: 10.1039/C7QO00755H
35. [35]
  Wang, Q.; Xia, B.; Xu, J.; Niu, X.; Cai, J.; Shen, Q.; Wang, W.; Huang, W.; Fan, Q. Mater. Chem. Front. 2019, 3, 650. doi: 10.1039/C9QM00036D
36. [36]
  Yang, J.; Cai, Y.; Zhou, Y.; Zhang, C.; Liang, P.; Zhao, B.; Shao, J.; Fu, N.; Huang, W.; Dong, X. Dyes Pigm. 2017, 147, 270. doi: 10.1016/j.dyepig.2017.08.023
37. [37]
  Yang, X.; Yu, Q.; Yang, N.; Xue, L.; Shao, J.; Li, B.; Shao, J.; Dong, X. J. Mater. Chem. B 2019, 7, 2454. doi: 10.1039/C8TB03185A
38. [38]
  Huang, X.; Gu, R.; Li, J.; Yang, N.; Cheng, Z.; Si, W.; Chen, P.; Huang, W.; Dong, X. Sci. China:Chem. 2020, 63, 55. doi: 10.1007/s11426-019-9531-4
39. [39]
  Wang, P.; Wu, W.; Gao, R.; Zhu, H.; Wang, J.; Du, R.; Li, X.; Zhang, C.; Cao, S.; Xiang, R. ACS Appl. Mater. Interfaces 2019, 11, 13935. doi: 10.1021/acsami.9b00022
40. [40]
  Deng, W.; Wu, Q.; Sun, P.; Yuan, P.; Lu, X.; Fan, Q.; Huang, W. Polym. Chem. 2018, 9, 2805. doi: 10.1039/C8PY00244D
41. [41]
  Shi, H.; Wang, Y.; Huang, X.; Liang, P.; Tang, Y.; Zhang, Y.; Fu, N., Huang, W.; Dong, X. J. Mater. Chem. B 2018, 6, 7402. doi: 10.1039/C8TB02349B
42. [42]
  Zhou, S.; Yang, C.; Guo, L.; Wang, Y.; Zhang, G.; Feng, L. Chem. Commun. 2019, 55, 8615. doi: 10.1039/C9CC03744F
43. [43]
  Gong, H.; Cheng, L.; Xiang, J.; Xu, H.; Feng, L.; Shi, X.; Liu, Z. Funct. Mater. 2013, 23, 6059. doi: 10.1002/adfm.201301555
44. [44]
  Wang, H.; Agarwal, P.; Zhao, S.; Yu, J.; Lu, X.; He, X. Biomaterials 2016, 97, 62. doi: 10.1016/j.biomaterials.2016.04.030
45. [45]
  Cai, Y.; Liang, P.; Tang, Q.; Si, W.; Chen, P.; Zhang, Q.; Dong, X. ACS Appl. Mater. Interfaces 2017, 9, 30398. doi: 10.1021/acsami.7b09025
46. [46]
  Wang, Q.; Dai, Y.; Xu, J.; Cai, J.; Niu, X.; Zhang, L.; Chen, R.; Shen, Q.; Huang, W.; Fan, Q. Adv. Funct. Mater. 2019, 29, 1901480. doi: 10.1002/adfm.201901480
47. [47]
  Liang, P.; Huang, H.; Wang, Y.; Chen, D.; Ou, C.; Zhang, Q.; Shao, J.; Huang, W.; Dong, X. ACS Nano 2018, 12, 11446. doi: 10.1021/acsnano.8b06478
1. [1]
  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
2. [2]
  Peng GENG , Guangcan XIANG , Wen ZHANG , Haichuang LAN , Shuzhang XIAO . Hollow copper sulfide loaded protoporphyrin for photothermal-sonodynamic therapy of cancer cells. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1903-1910. doi: 10.11862/CJIC.20240155
3. [3]
  Di WU , Ruimeng SHI , Zhaoyang WANG , Yuehua SHI , Fan YANG , Leyong ZENG . Construction of pH/photothermal dual-responsive delivery nanosystem for combination therapy of drug-resistant bladder cancer cell. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1679-1688. doi: 10.11862/CJIC.20240135
4. [4]
  Aiai WANG , Lu ZHAO , Yunfeng BAI , Feng FENG . Research progress of bimetallic organic framework in tumor diagnosis and treatment. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1825-1839. doi: 10.11862/CJIC.20240225
5. [5]
  Tingting Yu , Si Chen , Lianglong Sun , Tongtong Shi , Kai Sun , Xin Wang . Comprehensive Experimental Design for the Photochemical Synthesis, Analysis, and Characterization of Difluoropyrroles. University Chemistry, 2024, 39(11): 196-203. doi: 10.3866/PKU.DXHX202401022
6. [6]
  Lijuan Wang , Yuping Ning , Jian Li , Sha Luo , Xiongfei Luo , Ruiwen Wang . Enhancing the Advanced Nature of Natural Product Chemistry Laboratory Courses with New Research Findings: A Case Study of the Application of Berberine Hydrochloride in Photodynamic Antimicrobial Films. University Chemistry, 2024, 39(11): 241-250. doi: 10.12461/PKU.DXHX202403017
7. [7]
  Liangzhen Hu , Li Ni , Ziyi Liu , Xiaohui Zhang , Bo Qin , Yan Xiong . A Green Chemistry Experiment on Electrochemical Synthesis of Benzophenone. University Chemistry, 2024, 39(6): 350-356. doi: 10.3866/PKU.DXHX202312001
8. [8]
  Baohua LÜ , Yuzhen LI . Anisotropic photoresponse of two-dimensional layered α-In₂Se₃(2H) ferroelectric materials. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1911-1918. doi: 10.11862/CJIC.20240105
9. [9]
  Chengqian Mao , Yanghan Chen , Haotong Bai , Junru Huang , Junpeng Zhuang . Photodimerization of Styrylpyridinium Salt and Its Application in Silk Screen Printing. University Chemistry, 2024, 39(5): 354-362. doi: 10.3866/PKU.DXHX202312014
10. [10]
  Jiaxin Su , Jiaqi Zhang , Shuming Chai , Yankun Wang , Sibo Wang , Yuanxing Fang . Optimizing Poly(heptazine imide) Photoanodes Using Binary Molten Salt Synthesis for Water Oxidation Reaction. Acta Physico-Chimica Sinica, 2024, 40(12): 2408012-. doi: 10.3866/PKU.WHXB202408012
11. [11]
  Wenlong LI , Xinyu JIA , Jie LING , Mengdan MA , Anning ZHOU . Photothermal catalytic CO₂ hydrogenation over a Mg-doped In₂O_3-x catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 919-929. doi: 10.11862/CJIC.20230421
12. [12]
  Xinxin JING , Weiduo WANG , Hesu MO , Peng TAN , Zhigang CHEN , Zhengying WU , Linbing SUN . Research progress on photothermal materials and their application in solar desalination. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1033-1064. doi: 10.11862/CJIC.20230371
13. [13]
  Caixia Lin , Zhaojiang Shi , Yi Yu , Jianfeng Yan , Keyin Ye , Yaofeng Yuan . Ideological and Political Design for the Electrochemical Synthesis of Benzoxathiazine Dioxide Experiment. University Chemistry, 2024, 39(2): 61-66. doi: 10.3866/PKU.DXHX202309005
14. [14]
  Zhuoming Liang , Ming Chen , Zhiwen Zheng , Kai Chen . Multidimensional Studies on Ketone-Enol Tautomerism of 1,3-Diketones By ¹H NMR. University Chemistry, 2024, 39(7): 361-367. doi: 10.3866/PKU.DXHX202311029
15. [15]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
16. [16]
  Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
17. [17]
  Shule Liu . Application of SPC/E Water Model in Molecular Dynamics Teaching Experiments. University Chemistry, 2024, 39(4): 338-342. doi: 10.3866/PKU.DXHX202310029
18. [18]
  Yaling Chen . Basic Theory and Competitive Exam Analysis of Dynamic Isotope Effect. University Chemistry, 2024, 39(8): 403-410. doi: 10.3866/PKU.DXHX202311093
19. [19]
  Lihui Jiang , Wanrong Dong , Hua Yang , Yongqing Xia , Hongjian Peng , Jun Yuan , Xiaoqian Hu , Zihan Zeng , Yingping Zou , Yiming Luo . Study on Extraction of p-Hydroxyacetophenone. University Chemistry, 2024, 39(11): 259-268. doi: 10.12461/PKU.DXHX202402056
20. [20]
  Zizheng LU , Wanyi SU , Qin SHI , Honghui PAN , Chuanqi ZHAO , Chengfeng HUANG , Jinguo PENG . Surface state behavior of W doped BiVO₄ photoanode for ciprofloxacin degradation. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 591-600. doi: 10.11862/CJIC.20230225

Get Citation

PDF

XML

Metrics

PDF Downloads(124)
Abstract views(5299)
HTML views(1556)

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