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

doi:10.6023/cjoc201812016

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (7): 1891-1912.DOI: 10.6023/cjoc201812016 Previous Articles Next Articles

Special Issue: 荧光探针-生物传感合辑；有机超分子化学合辑

Reviews

氟硼类荧光染料及其衍生物在肿瘤诊疗一体化中的应用

冯彤, 薛中博, 尹娟娟, 蒋旭, 冯亚青, 孟舒献

天津大学化工学院天津 300350

收稿日期:2018-12-10 修回日期:2019-01-06 发布日期:2019-02-19
通讯作者: 孟舒献 E-mail:msxmail@tju.edu.cn
基金资助:
国家自然科学基金（No.21676187）、中国国际科技计划（Nos.2012DFG41980，2016YFE0114900）资助项目.

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

Feng Tong, Xue Zhongbo, Yin Juanjuan, Jiang Xu, Feng Yaqing, Meng Shuxian

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

Received:2018-12-10 Revised:2019-01-06 Published:2019-02-19
Contact: 10.6023/cjoc201812016 E-mail:msxmail@tju.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21676187), and the China International Science and Technology Project (Nos. 2012DFG41980, 2016YFE0114900).

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.

Key words: tumor, BODIPY, photodynamic therapy, photothermal therapy, photoacoustic imaging, synergistic theranostics

Cite this article

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]. Chin. J. Org. Chem., 2019, 39(7): 1891-1912.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Ranji-Burachaloo, H.; Gurr, P. A.; Dunstan, D. E.; Qiao, G. G. ACS Nano 2018.
[2] Matsui, H.; Hazama, S.; Shindo, Y.; Nagano, H. Expert Rev. Anticancer Ther. 2018, 18, 1205.
[3] Bertrand, B.; Passador, K.; Goze, C.; Denat, F.; Bodio, E.; Salmain, M. Coord. Chem. Rev. 2018, 358, 108.
[4] Kamkaew, A.; Lim, S. H.; Lee, H. B.; Kiew, L. V.; Chung, L. Y.; Burgess, K. Chem. Soc. Rev. 2013, 42, 77.
[5] Yao, L.; Xiao, S.; Dan, F. J. Chem. 2013, 2013, 10.
[6] Zhao, J.; Xu, K.; Yang, W.; Wang, Z.; Zhong, F. Chem. Soc. Rev. 2015, 44, 8904.
[7] Awuah, S. G.; You, Y. RSC Adv. 2012, 2, 11169.
[8] Durantini, A. M.; Heredia, D. A.; Durantini, J. E.; Durantini, E. N. Eur. J. Med. Chem. 2018, 144, 651.
[9] Zhang, J.; Jiang, C.; Figureueiro Longo, J. P.; Azevedo, R. B.; Zhang, H.; Muehlmann, L. A. Acta Pharm. Sin. B 2018, 8, 137.
[10] Zou, J.; Yin, Z.; Wang, P.; Chen, D.; Shao, J.; Zhang, Q.; Sun, L.; Huang, W.; Dong, X. Chem. Sci. 2018, 9, 2188.
[11] Raza, M. K.; Gautam, S.; Howlader, P.; Bhattacharyya, A.; Kondaiah, P.; Chakravarty, A. R. Inorg. Chem. 2018, 57, 14374.
[12] Wang, Q.; Ng, D. K.; Lo, P.-C. J. Mater. Chem. B 2018, 6, 3285.
[13] Ruan, Z.; Miao, W.; Yuan, P.; Le, L.; Jiao, L.; Hao, E.; Yan, L. Bioconjugate Chem. 2018, 29, 3441.
[14] Yuan, P.; Ruan, Z.; Jiang, W.; Liu, L.; Dou, J.; Li, T.; Yan, L. J. Mater. Chem. B 2018, 6, 2323.
[15] Yuan, P.; Ruan, Z.; Li, T.; Tian, Y.; Cheng, Q.; Yan, L. Nanomedicine 2018, 15, 198.
[16] Ruan, Z.; Zhao, Y.; Yuan, P.; Liu, L.; Wang, Y.; Yan, L. J. Mater. Chem. B 2018, 6, 753.
[17] Liu, L.; Li, T.; Ruan, Z.; Yan, L. J. Mater. Sci. 2018, 53, 9368.
[18] Chen, H.; Bi, Q.; Yao, Y.; Tan, N. J. Mater. Chem. B 2018, 6, 4351.
[19] Wang, W.; Wang, L.; Li, Z.; Xie, Z. Chem. Commun. 2016, 52, 5402.
[20] Guan, Q.; Zhou, L. L.; Li, Y. A.; Dong, Y. B. Inorg. Chem. 2018, 57, 10137.
[21] Liu, Y.; Bhattarai, P.; Dai, Z.; Chen, X. Chem. Soc. Rev. 2019.
[22] Kim, S. H.; Lee, J. E.; Sharker, S. M.; Jeong, J. H.; In, I.; Park, S. Y. Biomacromolecules 2015, 16, 3519.
[23] Liu, Y.; Song, N.; Chen, L.; Liu, S.; Xie, Z. Chem. Asian J. 2018, 13, 989.
[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.
[25] Zhu, Y.; Lin, W.; Wang, X.; Zhang, W.; Chen, L.; Xie, Z. Chem. Commun. 2018, 54, 11921.
[26] Lin, W.; Sun, T.; Xie, Z.; Gu, J.; Jing, X. Chem. Sci. 2016, 7, 1846.
[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] Kang, E. B.; Lee, J. E.; Jeong, J. H.; Lee, G.; In, I.; Park, S. Y. J. Ind. Eng. Chem. 2016, 33, 336.
[29] Li, J.; Rao, J.; Pu, K. Biomaterials 2018, 155, 217.
[30] Lyu, Y.; Zeng, J.; Jiang, Y.; Zhen, X.; Wang, T.; Qiu, S.; Lou, X.; Gao, M.; Pu, K. ACS Nano 2018, 12, 1801.
[31] Zhou, E. Y.; Knox, H. J.; Reinhardt, C. J.; Partipilo, G.; Nilges, M. J.; Chan, J. J. Am. Chem. Soc. 2018, 140, 11686.
[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.
[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] Ni, Y.; Kannadorai, R. K.; Peng, J.; Yu, S. W.; Chang, Y. T.; Wu, J. Chem. Commun. 2016, 52, 11504.
[35] Ni, Y.; Kannadorai, R. K.; Yu, S. W.; Chang, Y. T.; Wu, J. Org. Biomol. Chem. 2017, 15, 4531.
[36] Chen, Q.; Liu, X.; Chen, J.; Zeng, J.; Cheng, Z.; Liu, Z. Adv. Mater. 2015, 27, 6820.
[37] Liu, X.; Zhao, M.; Chen, P.; Fan, Q.; Wang, W.; Huang, W. J. Mater. Chem. B 2018, 6, 4531.
[38] Miki, K.; Enomoto, A.; Inoue, T.; Nabeshima, T.; Saino, S.; Shimizu, S.; Matsuoka, H.; Ohe, K. Biomacromolecules 2017, 18, 249.
[39] Zhao, M.; Xu, Y.; Xie, M.; Zou, L.; Wang, Z.; Liu, S.; Zhao, Q. Adv. Healthcare Mater. 2018, 7, 1800606.
[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.
[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.
[42] Liu, Y.; Song, N.; Li, Z.; Chen, L.; Xie, Z. Dyes Pigm. 2019, 160, 71.
[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.
[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] 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] Gawale, Y.; Adarsh, N.; Kalva, S. K.; Joseph, J.; Pramanik, M.; Ramaiah, D.; Sekar, N. Chemistry 2017, 23, 6570.
[47] Tang, Q.; Si, W.; Huang, C.; Ding, K.; Huang, W.; Chen, P.; Zhang, Q.; Dong, X. J. Mater. Chem. B 2017, 5, 1566.
[48] Tang, Q.; Xiao, W.; Huang, C.; Si, W.; Shao, J.; Huang, W.; Chen, P.; Zhang, Q.; Dong, X. Chem. Mater. 2017, 29, 5216.
[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.
[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.
[51] Chen, D.; Tang, Q.; Zou, J.; Yang, X.; Huang, W.; Zhang, Q.; Shao, J.; Dong, X. Adv. Healthcare Mater. 2018, 7, 1701272.
[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] Ramu, V.; Gautam, S.; Garai, A.; Kondaiah, P.; Chakravarty, A. R. Inorg. Chem. 2018, 57, 1717.
[54] Wang, X.; Lin, W.; Zhang, W.; Li, C.; Sun, T.; Chen, G.; Xie, Z. J. Colloid Interface Sci. 2018, 536, 208.
[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.
[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.

氟硼类荧光染料及其衍生物在肿瘤诊疗一体化中的应用

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

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Cuiyun Ma, Hailan Luo, Fuhua Zhang, Dan Guo, Shuxing Chen, Fei Wang. Green Biosynthesis, Photophysical Properties and Application of 3-Pyrrolyl BODIPY [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 216-223.
[2]	Bozhen Wang, Jie Zhang, Chunhui Nian, Mingming Jin, Miaomiao Kong, Wulan Li, Wenfei He, Jianzhang Wu. Synthesis and Antitumor Activity of 3,4-Dichlorophenyl Amides [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 232-241.
[3]	Xiaolong Zhao, Liangwu Guo, Yuqing Li, Qiyuan Ran, Huihui Wu, Zhen Zhang, Yingpeng Su, Pengxin Zhou, Na Yan. Near-Infrared Visualization Fluoroboron Dipyrrole (BODIPY) Fluore-scent Probe with Large Stokes Shift for Detecting Na₂S₂O₄ in vivo [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2484-2491.
[4]	Panxing Pang, Rong Ning, Chuang Zhu, Wenjie Huang, Xianli Ma, Caina Jiang, Fangyao Li, Xiaoqun Zhou. Synthesis and in Vitro Antitumor Activity of Matrine Semicarbazide Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2126-2135.
[5]	Kanghui Duan, Junlong Tang, Wanqing Wu. Recent Advances in the Synthesis of Fused Heterocyclic Compounds and Their Antitumor Activities [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 826-854.
[6]	Chujie Liao, Hongyao Ruan, Junfeng Jiang, Lun Luo, Yanggen Hu. Synthesis and Activity Evaluation of 3-Aryl-2-imino-benzo[e][1,3]-oxazin-4-ol Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 763-770.
[7]	Zhangyang Shen, Yujie Li, Yimeng Zhao, Yayuan Deng, Yawen Guo, Yu Wang, Yanping Liu, Yanhui Fu. A New Prenylated Isoflavone from the Stems of Harrisonia perforata [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 771-776.
[8]	Bingwen Zhang, Yuqi Lin, Yanqing Xue, Jing Wang, Wenchao Yang, Xiaofeng Wang, Wen Liu. Study on Secondary Metabolites from Fusarium graminearum [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 4003-4007.
[9]	Weiqin Liu, Lihui Shao, Chengpeng Li, Yayu Zou, Haitao Long, Yan Li, Qiangsheng Ge, Zhenchao Wang, Guiping Ouyang. Synthesis and Antitumor Activity of 3-Hydrazone Quinazolinone Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 214-222.
[10]	Guangping Liang, Wei Wang, Xuxiu Zhu, Guangyan Liang, Jun Yang, Daoping Wang. Synthesis and in Vitro Anti-tumor Activity of Novel Spliced Compounds of Zidovudine and 4-Anilinoquinazolines [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2793-2805.
[11]	Dongyan Hu, Guangtian Han, Xi'an Li, Huazhong Ren, Lirong Yue, Li Guo, Jiafu Feng. Synthesis and Evaluation in vitro of Novel Harmine Derivatives as Anticancer Activity Agents [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1863-1871.
[12]	Bin-Kai Liu, Kun-Xu Teng, Li-Ya Niu, Qing-Zheng Yang. Progress in the Synthesis of Boron Dipyrromethene (BODIPY) Fluorescent Dyes [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1265-1285.
[13]	Lu Xue, Lihua Zhang, Chengyu Zhang, Xin Zhao, Weifan Dang, Zhaoxin Wang, Chunhua Wang, Tongchuan Suo, Xiaohui Yan. Discovery of Tiancimycin Congeners from Streptomyces sp. CB03234-S [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1241-1247.
[14]	Siyu Zhu, Xinyu Huo, Qin Ma, Wei Chen, Jie Zhang, Liang Guo. Design, Synthesis, and Antitumor Activity of β-Carboline-Benzimidazole Hybrids [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1129-1135.
[15]	Honglin Dai, Xiaojie Si, Lingling Chi, Hao Wang, Chao Gao, Zhengjie Wang, Limin Liu, Jiajie Ma, Fuqiang Yu, Hongmin Liu, Yu Ke, Qiurong Zhang. Synthesis and Antitumor Activity Evaluation of 2,4,6-Trisubstituted Quinazoline Derivatives Containing Thiazole Structure [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3853-3862.