Citation: Feng Tong, Xue Zhongbo, Yin Juanjuan, Jiang Xu, Feng Yaqing, Meng Shuxian. Application of Fluoroboron Fluoresceins (BODIPYS) and Their Derivatives in the Synergistic Diagnosis and Treatment of Tumor[J]. Chinese Journal of Organic Chemistry, ;2019, 39(7): 1891-1912. doi: 10.6023/cjoc201812016 shu

Application of Fluoroboron Fluoresceins (BODIPYS) and Their Derivatives in the Synergistic Diagnosis and Treatment of Tumor

School of Chemical Engineering and Technology, Tianjin University, Tianjin 300350

Corresponding author: Meng Shuxian, msxmail@tju.edu.cn
Received Date: 10 December 2018
Revised Date: 6 January 2019
Available Online: 19 July 2019
Fund Project: the China International Science and Technology Project 2012DFG41980the China International Science and Technology Project 2016YFE0114900Project supported by the National Natural Science Foundation of China (No. 21676187), and the China International Science and Technology Project (Nos. 2012DFG41980, 2016YFE0114900)the National Natural Science Foundation of China 21676187

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Tumor is one of the diseases with the highest mortality rate in the world. In view of the high risk and high mortality of tumor, researchers around the world are committed to develop more accurate and rapid diagnostic strategies and more effective treatments to fight tumor. Gradually, integrated optical diagnosis and treatment technologies for tumors have emerged. Fluoroboron fluorescein (BODIPY) has been widely used in tumor phototherapy because of its excellent optical properties. In this paper, BODIPY and its derivatives are introduced in detail as photosensitizers, photothermal transformants, and contrast agents in the diagnosis and treatment of tumors (photodynamic therapy, photothermal therapy, photoacoustic imaging) and integration of diagnosis and treatment. The effects of different BODIPY structures and their derivatives in tumor diagnosis and treatment were evaluated systematically. This is of great significance for the rational design of near-infrared BODIPY materials with high singlet oxygen quantum yield, high photothermal conversion, and good light stability and solubility.
- tumor,
- BODIPY,
- photodynamic therapy,
- photothermal therapy,
- photoacoustic imaging,
- synergistic theranostics
1. [1]
  Ranji-Burachaloo, H.; Gurr, P. A.; Dunstan, D. E.; Qiao, G. G. ACS Nano 2018.
2. [2]
  Matsui, H.; Hazama, S.; Shindo, Y.; Nagano, H. Expert Rev. Anticancer Ther. 2018, 18, 1205. doi: 10.1080/14737140.2018.1531707
3. [3]
  Bertrand, B.; Passador, K.; Goze, C.; Denat, F.; Bodio, E.; Salmain, M. Coord. Chem. Rev. 2018, 358, 108. doi: 10.1016/j.ccr.2017.12.007
4. [4]
  Kamkaew, A.; Lim, S. H.; Lee, H. B.; Kiew, L. V.; Chung, L. Y.; Burgess, K. Chem. Soc. Rev. 2013, 42, 77. doi: 10.1039/C2CS35216H
5. [5]
  Yao, L.; Xiao, S.; Dan, F. J. Chem. 2013, 2013, 10.
6. [6]
  Zhao, J.; Xu, K.; Yang, W.; Wang, Z.; Zhong, F. Chem. Soc. Rev. 2015, 44, 8904. doi: 10.1039/C5CS00364D
7. [7]
  Awuah, S. G.; You, Y. RSC Adv. 2012, 2, 11169. doi: 10.1039/c2ra21404k
8. [8]
  Durantini, A. M.; Heredia, D. A.; Durantini, J. E.; Durantini, E. N. Eur. J. Med. Chem. 2018, 144, 651. doi: 10.1016/j.ejmech.2017.12.068
9. [9]
  Zhang, J.; Jiang, C.; Figureueiro Longo, J. P.; Azevedo, R. B.; Zhang, H.; Muehlmann, L. A. Acta Pharm. Sin. B 2018, 8, 137. doi: 10.1016/j.apsb.2017.09.003
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]
  Raza, M. K.; Gautam, S.; Howlader, P.; Bhattacharyya, A.; Kondaiah, P.; Chakravarty, A. R. Inorg. Chem. 2018, 57, 14374. doi: 10.1021/acs.inorgchem.8b02546
12. [12]
  Wang, Q.; Ng, D. K.; Lo, P.-C. J. Mater. Chem. B 2018, 6, 3285. doi: 10.1039/C8TB00593A
13. [13]
  Ruan, Z.; Miao, W.; Yuan, P.; Le, L.; Jiao, L.; Hao, E.; Yan, L. Bioconjugate Chem. 2018, 29, 3441. doi: 10.1021/acs.bioconjchem.8b00576
14. [14]
  Yuan, P.; Ruan, Z.; Jiang, W.; Liu, L.; Dou, J.; Li, T.; Yan, L. J. Mater. Chem. B 2018, 6, 2323. doi: 10.1039/C8TB00493E
15. [15]
  Yuan, P.; Ruan, Z.; Li, T.; Tian, Y.; Cheng, Q.; Yan, L. Nanomedicine 2018, 15, 198.
16. [16]
  Ruan, Z.; Zhao, Y.; Yuan, P.; Liu, L.; Wang, Y.; Yan, L. J. Mater. Chem. B 2018, 6, 753. doi: 10.1039/C7TB02924A
17. [17]
  Liu, L.; Li, T.; Ruan, Z.; Yan, L. J. Mater. Sci. 2018, 53, 9368. doi: 10.1007/s10853-018-2276-6
18. [18]
  Chen, H.; Bi, Q.; Yao, Y.; Tan, N. J. Mater. Chem. B 2018, 6, 4351. doi: 10.1039/C8TB00665B
19. [19]
  Wang, W.; Wang, L.; Li, Z.; Xie, Z. Chem. Commun. 2016, 52, 5402. doi: 10.1039/C6CC01048B
20. [20]
  Guan, Q.; Zhou, L. L.; Li, Y. A.; Dong, Y. B. Inorg. Chem. 2018, 57, 10137. doi: 10.1021/acs.inorgchem.8b01316
21. [21]
  Liu, Y.; Bhattarai, P.; Dai, Z.; Chen, X. Chem. Soc. Rev. 2019.
22. [22]
  Kim, S. H.; Lee, J. E.; Sharker, S. M.; Jeong, J. H.; In, I.; Park, S. Y. Biomacromolecules 2015, 16, 3519. doi: 10.1021/acs.biomac.5b00944
23. [23]
  Liu, Y.; Song, N.; Chen, L.; Liu, S.; Xie, Z. Chem. Asian J. 2018, 13, 989. doi: 10.1002/asia.201701727
24. [24]
  Xu, Y.; Feng, T.; Yang, T.; Wei, H.; Yang, H.; Li, G.; Zhao, M.; Liu, S.; Huang, W.; Zhao, Q. ACS Appl. Mater. Interfaces 2018, 10, 16299. doi: 10.1021/acsami.8b03568
25. [25]
  Zhu, Y.; Lin, W.; Wang, X.; Zhang, W.; Chen, L.; Xie, Z. Chem. Commun. 2018, 54, 11921. doi: 10.1039/C8CC07106C
26. [26]
  Lin, W.; Sun, T.; Xie, Z.; Gu, J.; Jing, X. Chem. Sci. 2016, 7, 1846. doi: 10.1039/C5SC03707G
27. [27]
  Sharker, S. M.; Kang, E. B.; Shin, C. I.; Kim, S. H.; Lee, G.; Park, S. Y. J. Appl. Polym. Sci. 2016, 133.
28. [28]
  Kang, E. B.; Lee, J. E.; Jeong, J. H.; Lee, G.; In, I.; Park, S. Y. J. Ind. Eng. Chem. 2016, 33, 336. doi: 10.1016/j.jiec.2015.10.026
29. [29]
  Li, J.; Rao, J.; Pu, K. Biomaterials 2018, 155, 217. doi: 10.1016/j.biomaterials.2017.11.025
30. [30]
  Lyu, Y.; Zeng, J.; Jiang, Y.; Zhen, X.; Wang, T.; Qiu, S.; Lou, X.; Gao, M.; Pu, K. ACS Nano 2018, 12, 1801. doi: 10.1021/acsnano.7b08616
31. [31]
  Zhou, E. Y.; Knox, H. J.; Reinhardt, C. J.; Partipilo, G.; Nilges, M. J.; Chan, J. J. Am. Chem. Soc. 2018, 140, 11686. doi: 10.1021/jacs.8b05514
32. [32]
  Frenette, M.; Hatamimoslehabadi, M.; Bellinger-Buckley, S.; Laoui, S.; La, J.; Bag, S.; Mallidi, S.; Hasan, T.; Bouma, B.; Yelleswarapu, C. J. Am. Chem. Soc. 2014, 136, 15853. doi: 10.1021/ja508600x
33. [33]
  Laoui, S.; Bag, S.; Dantiste, O.; Frenette, M.; Hatamimoslehabadi, M.; Bellinger-Buckley, S.; Tseng, J. C.; Rochford, J.; Yelleswarapu, C. Inter. Soc. Opt. 2014, 89, 5609.
34. [34]
  Ni, Y.; Kannadorai, R. K.; Peng, J.; Yu, S. W.; Chang, Y. T.; Wu, J. Chem. Commun. 2016, 52, 11504. doi: 10.1039/C6CC05126J
35. [35]
  Ni, Y.; Kannadorai, R. K.; Yu, S. W.; Chang, Y. T.; Wu, J. Org. Biomol. Chem. 2017, 15, 4531. doi: 10.1039/C7OB00965H
36. [36]
  Chen, Q.; Liu, X.; Chen, J.; Zeng, J.; Cheng, Z.; Liu, Z. Adv. Mater. 2015, 27, 6820. doi: 10.1002/adma.201503194
37. [37]
  Liu, X.; Zhao, M.; Chen, P.; Fan, Q.; Wang, W.; Huang, W. J. Mater. Chem. B 2018, 6, 4531. doi: 10.1039/C8TB01158C
38. [38]
  Miki, K.; Enomoto, A.; Inoue, T.; Nabeshima, T.; Saino, S.; Shimizu, S.; Matsuoka, H.; Ohe, K. Biomacromolecules 2017, 18, 249. doi: 10.1021/acs.biomac.6b01568
39. [39]
  Zhao, M.; Xu, Y.; Xie, M.; Zou, L.; Wang, Z.; Liu, S.; Zhao, Q. Adv. Healthcare Mater. 2018, 7, 1800606. doi: 10.1002/adhm.201800606
40. [40]
  Wang, Q.; Tian, L.; Xu, J.; Xia, B.; Li, J.; Lu, F.; Lu, X.; Wang, W.; Huang, W.; Fan, Q. Chem. Commun. 2018, 54, 10328. doi: 10.1039/C8CC05560B
41. [41]
  Chen, D.; Zhang, J.; Tang, Y.; Huang, X.; Shao, J.; Si, W.; Ji, J.; Zhang, Q.; Huang, W.; Dong, X. J. Mater. Chem. B 2018, 6, 4522. doi: 10.1039/C8TB01347K
42. [42]
  Liu, Y.; Song, N.; Li, Z.; Chen, L.; Xie, Z. Dyes Pigm. 2019, 160, 71. doi: 10.1016/j.dyepig.2018.07.034
43. [43]
  Lu, W. L.; Lan, Y. Q.; Xiao, K. J.; Xu, Q. M.; Qu, L. L.; Chen, Q. Y.; Huang, T.; Gao, J.; Zhao, Y. J. Mater. Chem. B 2017, 5, 1275. doi: 10.1039/C6TB02575G
44. [44]
  Zou, J.; Wang, P.; Wang, Y.; Liu, G.; Zhang, Y.; Zhang, Q.; Shao, J.; Si, W.; Huang, W.; Dong, X. Chem. Sci. 2018.
45. [45]
  Ye, S.; Rao, J.; Qiu, S.; Zhao, J.; He, H.; Yan, Z.; Yang, T.; Deng, Y.; Ke, H.; Yang, H.; Zhao, Y.; Guo, Z.; Chen, H. Adv. Mater. 2018, 1801216.
46. [46]
  Gawale, Y.; Adarsh, N.; Kalva, S. K.; Joseph, J.; Pramanik, M.; Ramaiah, D.; Sekar, N. Chemistry 2017, 23, 6570. doi: 10.1002/chem.201605702
47. [47]
  Tang, Q.; Si, W.; Huang, C.; Ding, K.; Huang, W.; Chen, P.; Zhang, Q.; Dong, X. J. Mater. Chem. B 2017, 5, 1566. doi: 10.1039/C6TB02979E
48. [48]
  Tang, Q.; Xiao, W.; Huang, C.; Si, W.; Shao, J.; Huang, W.; Chen, P.; Zhang, Q.; Dong, X. Chem. Mater. 2017, 29, 5216. doi: 10.1021/acs.chemmater.7b01075
49. [49]
  Xiao, W.; Wang, P.; Ou, C.; Huang, X.; Tang, Y.; Wu, M.; Si, W.; Shao, J.; Huang, W.; Dong, X. Biomaterials 2018, 183, 1. doi: 10.1016/j.biomaterials.2018.08.034
50. [50]
  Hu, W.; Ma, H.; Hou, B.; Zhao, H.; Ji, Y.; Jiang, R.; Hu, X.; Lu, X.; Zhang, L.; Tang, Y.; Fan, Q.; Huang, W. ACS Appl. Mater. Interfaces 2016, 8, 12039. doi: 10.1021/acsami.6b02721
51. [51]
  Chen, D.; Tang, Q.; Zou, J.; Yang, X.; Huang, W.; Zhang, Q.; Shao, J.; Dong, X. Adv. Healthcare Mater. 2018, 7, 1701272. doi: 10.1002/adhm.201701272
52. [52]
  He, H.; Ji, S.; He, Y.; Zhu, A.; Zou, Y.; Deng, Y.; Ke, H.; Yang, H.; Zhao, Y.; Guo, Z.; Chen, H. Adv. Mater. 2017, 29.
53. [53]
  Ramu, V.; Gautam, S.; Garai, A.; Kondaiah, P.; Chakravarty, A. R. Inorg. Chem. 2018, 57, 1717. doi: 10.1021/acs.inorgchem.7b02249
54. [54]
  Wang, X.; Lin, W.; Zhang, W.; Li, C.; Sun, T.; Chen, G.; Xie, Z. J. Colloid Interface Sci. 2018, 536, 208.
55. [55]
  Guo, Z.; Zou, Y.; He, H.; Rao, J.; Ji, S.; Cui, X.; Ke, H.; Deng, Y.; Yang, H.; Chen, C.; Zhao, Y.; Chen, H. Adv. Mater. 2016, 28, 10155. doi: 10.1002/adma.201602738
56. [56]
  Zhou, J.; Zhang, Y.; Yu, G.; Crawley, M. R.; Fulong, C. R. P.; Friedman, A. E.; Sengupta, S.; Sun, J.; Li, Q.; Huang, F.; Cook, T. R. J. Am. Chem. Soc. 2018, 140, 7730. doi: 10.1021/jacs.8b04929
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