Citation: Hanming Dai, Zijin Cheng, Tian Zhang, Weili Wang, Jinjun Shao, Wenjun Wang, Yongxiang Zhao, Xiaochen Dong, Liping Zhong. Boron difluoride formazanate dye for high-efficiency NIR-Ⅱ fluorescence imaging-guided cancer photothermal therapy[J]. Chinese Chemical Letters, ;2022, 33(5): 2501-2506. doi: 10.1016/j.cclet.2021.11.079 shu

Boron difluoride formazanate dye for high-efficiency NIR-Ⅱ fluorescence imaging-guided cancer photothermal therapy

Hanming Dai ^{a, 1} ,
Zijin Cheng ^{a, 1} ,
Tian Zhang ^a ,
Weili Wang ^a ,
Jinjun Shao ^{a, *,} ,
Wenjun Wang ^b ,
Yongxiang Zhao ^c ,
Xiaochen Dong ^{a, *,} ,
Liping Zhong ^{c, *,}

a.
Key Laboratory of Flexible Electronics (KLOFE) & Institute of Advanced Materials (IAM), Nanjing Tech University (NanjingTech), Nanjing 211800, China
b.
School of Physical Science and Information Technology, Liaocheng University, Liaocheng 252059, China
c.
National Center for International Biotargeting Theranostics, Guangxi Key Laboratory of Biotargeting Theranostics, Collaborative Innovation Center for Targeting Tumor Theranostics, Guangxi Medical University, Nanning 530021, China

iamjjshao@njtech.edu.cn

iamxcdong@njtech.edu.cn

zhong_liping@163.com

Received Date: 4 October 2021
Revised Date: 23 November 2021
Accepted Date: 26 November 2021
Available Online: 1 December 2021

Figures(6)

The small molecular second near-infrared (NIR-Ⅱ, 1000-1700 nm) dye-based nanotheranostics can concurrently combine deep-tissue photodiagnosis with in situ phototherapy, which occupies a vital position in the early detection and precise treatment of tumors. However, the development of small molecular NIR-Ⅱ dyes is still challenging due to the limited electron acceptors and cumbersome synthetic routes. Herein, we report a novel molecular electron acceptor, boron difluoride formazanate (BDF). Based on BDF, a new small molecular NIR-Ⅱ dye BDF1005 is designed and synthesized with strong NIR-Ⅰ absorption at 768 nm and bright NIR-Ⅱ peak emission at 1034 nm. In vitro and in vivo experiments demonstrate that BDF1005-based nanotheranostics can be applied for NIR-Ⅱ fluorescence imaging-guided photothermal therapy of 4T1 tumor-bearing mice. Under 808 nm laser irradiation, tumor growth can be effectively inhibited. This work opens up a new road for the exploitation of NIR-Ⅱ small molecular dyes for cancer phototheranostics.
- NIR-Ⅱ nanotheranostics,
- Boron difluoride formazanate,
- Fluorescence imaging,
- Photothermal therapy,
- Phototheranostics
1. [1]
  H. Sung, J. Ferlay, R. Siegel, et al., CA Cancer J. Clin. 71 (2021) 209-249. doi: 10.3322/caac.21660
2. [2]
  Y. Su, B. Yu, S. Wang, H. Cong, Y. Shen, Biomaterials 271 (2021) 120717. doi: 10.1016/j.biomaterials.2021.120717
3. [3]
  J. Chen, H. Pan, Z. Wang, et al., Chem. Commun. 56 (2020) 2731-2734. doi: 10.1039/C9CC09158K
4. [4]
  Z. Cao, L. Feng, G. Zhang, et al., Biomaterials 155 (2018) 103-111. doi: 10.1016/j.biomaterials.2017.11.016
5. [5]
  D. Voshart, J. Wiedemann, P. van Luijk, L. Barazzuol, Cancers 13 (2021) 367. doi: 10.3390/cancers13030367
6. [6]
  Y. Chen, L. Li, W. Chen, H. Chen, J. Yin, Chin. Chem. Lett. 30 (2019) 1353-1360. doi: 10.1016/j.cclet.2019.02.003
7. [7]
  Y. Cai, Z. Wei, C. Song, et al., Chem. Soc. Rev. 48 (2019) 22-37. doi: 10.1039/C8CS00494C
8. [8]
  L. Lu, B. Li, S. Ding, et al., Nat. Commun. 11 (2020) 4192. doi: 10.1038/s41467-020-18051-1
9. [9]
  S. Wang, B. Li, F. Zhang, ACS. Cent. Sci. 6 (2020) 1302-1316. doi: 10.1021/acscentsci.0c00544
10. [10]
  J. Li, Y. Liu, Y. Xu, et al., Coord. Chem. Rev. 415 (2020) 213318. doi: 10.1016/j.ccr.2020.213318
11. [11]
  Z. Hu, C. Fang, B. Li, et al., Nat. Biomed. Eng. 4 (2020) 259-271. doi: 10.1038/s41551-019-0494-0
12. [12]
  F. An, Z. Yang, M. Zheng, et al., J. Nanobiotechnol. 18 (2020) 49. doi: 10.1186/s12951-020-00603-8
13. [13]
  Y. Xiao, F. An, J. Chen, et al., Small 15 (2019) 1903121.
14. [14]
  G. Feng, G. Zhang, D. Ding, Chem. Soc. Rev. 49 (2020) 8179-8234. doi: 10.1039/D0CS00671H
15. [15]
  S. Li, Q. Deng, Y. Zhang, et al., Adv. Mater. 32 (2020) e2001146. doi: 10.1002/adma.202001146
16. [16]
  S. Liu, Y. Li, R. Kwok, J. Lam, B. Tang, Chem. Sci. 12 (2021) 3427-3436. doi: 10.1039/D0SC02911D
17. [17]
  H. Jung, P. Verwilst, A. Sharma, et al., Chem. Soc. Rev. 47 (2018) 2280-2297. doi: 10.1039/C7CS00522A
18. [18]
  D. Xi, M. Xiao, J. Cao, et al., Adv. Mater. 32 (2020) e1907855. doi: 10.1002/adma.201907855
19. [19]
  H. Sun, Q. Zhang, J. Li, et al., Nano Today 37 (2021) 101073. doi: 10.1016/j.nantod.2020.101073
20. [20]
  P. Zhao, H. Jiang, D. Su, et al., Mol. Med. Rep. 11 (2015) 327-332. doi: 10.3892/mmr.2014.2655
21. [21]
  Y. Cai, W. Si, W. Huang, et al., Small 14 (2018) e1704247. doi: 10.1002/smll.201704247
22. [22]
  J. Zhou, L. Rao, G. Yu, et al., Chem. Soc. Rev. 50 (2021) 2839-2891. doi: 10.1039/D0CS00011F
23. [23]
  S. Ling, X. Yang, C. Li, et al., Angew. Chem. Int. Ed. 59 (2020) 7219-7223. doi: 10.1002/anie.202000947
24. [24]
  H. Dai, X. Wang, J. Shao, et al., Small 17 (2021) e2102646. doi: 10.1002/smll.202102646
25. [25]
  Y. Yang, X. Fan, L. Li, et al., ACS Nano 14 (2020) 2509-2521. doi: 10.1021/acsnano.0c00043
26. [26]
  D. Zhao, X. Yang, X. Hou, et al., J. Mater. Chem. B 7 (2019) 2484-2492. doi: 10.1039/C8TB03043J
27. [27]
  Y. Zhang, T. Song, T. Feng, et al., Nano Today 35 (2020) 100987. doi: 10.1016/j.nantod.2020.100987
28. [28]
  L. Li, C. Shao, T. Liu, et al., Adv. Mater. 32 (2020) e2003471. doi: 10.1002/adma.202003471
29. [29]
  A.L. Antaris, H. Chen, K. Cheng, et al., Nat. Mater. 15 (2016) 235-242. doi: 10.1038/nmat4476
30. [30]
  L. Li, X. Dong, J. Li, J. Wei, Dye. Pigment. 183 (2020) 108756. doi: 10.1016/j.dyepig.2020.108756
31. [31]
  X. Zhen, K. Pu, X. Jiang, Small 17 (2021) e2004723. doi: 10.1002/smll.202004723
32. [32]
  H. Xu, D. Zhang, J. Li, J. Bioresour. Bioprod. 4 (2019) 177-182.
33. [33]
  H. Huang, L. Mao, Z. Li, et al., J. Bioresour. Bioprod. 4 (2019) 231-241.
34. [34]
  S. Zhu, R. Tian, A. Antaris, X. Chen, H. Dai, Adv. Mater. 31 (2019) e1900321.
35. [35]
  Q. Wang, X. Niu, L. Yang, et al., Mater. Chem. Front. 5 (2021) 5689-5697. doi: 10.1039/D1QM00472G
36. [36]
  Q. Yu, X. Huang, T. Zhang, et al., Chem. Res. Chin. Univ. 37 (2021) 951-959. doi: 10.1007/s40242-021-1190-7
37. [37]
  H. Dai, Q. Shen, J. Shao, et al., Innov. 2 (2021) 100082.
38. [38]
  Q. Zhang, Q. Wang, X. Xu, et al., Dye. Pigment. 193 (2021) 109480.
39. [39]
  H. Ma, C. Liu, Z. Hu, et al., Chem. Mater. 32 (2020) 2061-2069. doi: 10.1021/acs.chemmater.9b05159
40. [40]
  L. Bai, P. Sun, Y. Liu, et al., Chem. Commun. 55 (2019) 10920-10923. doi: 10.1039/C9CC03378E
41. [41]
  Z. Cheng, T. Zhang, W. Wang, et al., Chin. Chem. Lett. 32 (2021) 1580-1585. doi: 10.1016/j.cclet.2021.02.017
42. [42]
  G. He, J. Shao, Y. Li, et al., Phys. Chem. Chem. Phys. 18 (2016) 6789-6798. doi: 10.1039/C5CP07563G
43. [43]
  J. Qi, X. Duan, W. Liu, et al., Biomaterials 248 (2020) 120036. doi: 10.1016/j.biomaterials.2020.120036
44. [44]
  H. Wan, J. Yue, S. Zhu, et al., Nat. Commun. 9 (2018) 1171. doi: 10.1038/s41467-018-03505-4
45. [45]
  Q. Wang, Y. Dai, J. Xu, et al., Adv. Funct. Mater. 29 (2019) 1901480. doi: 10.1002/adfm.201901480
46. [46]
  X. Zeng, Y. Xiao, J. Lin, et al., Adv. Healthc. Mater. 7 (2018) e1800589. doi: 10.1002/adhm.201800589
47. [47]
  N. Alifu, A. Zebibula, J. Qi, et al., ACS Nano 12 (2018) 11282-11293. doi: 10.1021/acsnano.8b05937
48. [48]
  S. Gao, G. Wei, S. Zhang, et al., Nat. Commun. 10 (2019) 2206. doi: 10.1038/s41467-019-10056-9
49. [49]
  P. Sun, Q. Wu, X. Sun, et al., Chem. Commun. 54 (2018) 13395-13398. doi: 10.1039/C8CC08096H
50. [50]
  L. Tu, Y. Xu, Q. Ouyang, X. Li, Y. Sun, Chin. Chem. Lett. 30 (2019) 1731-1737. doi: 10.1016/j.cclet.2019.05.022
1. [1]
  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
2. [2]
  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
3. [3]
  Yiqiao Chen , Ao Liu , Biwen Yang , Zhenzhen Li , Binggang Ye , Zhouyi Guo , Zhiming Liu , Haolin Chen . Photoluminescence and photothermal conversion in boric acid derived carbon dots for targeted microbial theranostics. Chinese Chemical Letters, 2024, 35(9): 109295-. doi: 10.1016/j.cclet.2023.109295
4. [4]
  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
5. [5]
  Xiao-Fang Lv , Xiao-Yun Ran , Yu Zhao , Rui-Rui Zhang , Li-Na Zhang , Jing Shi , Ji-Xuan Xu , Qing-Quan Kong , Xiao-Qi Yu , Kun Li . Combing NIR-Ⅱ molecular dye with magnetic nanoparticles for enhanced photothermal theranostics with a 95.6% photothermal conversion efficiency. Chinese Chemical Letters, 2025, 36(4): 110027-. doi: 10.1016/j.cclet.2024.110027
6. [6]
  Songtao Cai , Liuying Wu , Yuan Li , Soham Samanta , Jinying Wang , Bing Liu , Feihu Wu , Kaitao Lai , Yingchao Liu , Junle Qu , Zhigang Yang . Intermolecular hydrogen-bonding as a robust tool toward significantly improving the photothermal conversion efficiency of a NIR-II squaraine dye. Chinese Chemical Letters, 2024, 35(4): 108599-. doi: 10.1016/j.cclet.2023.108599
7. [7]
  Gongcheng Ma , Qihang Ding , Yuding Zhang , Yue Wang , Jingjing Xiang , Mingle Li , Qi Zhao , Saipeng Huang , Ping Gong , Jong Seung Kim . Palladium-free chemoselective probe for in vivo fluorescence imaging of carbon monoxide. Chinese Chemical Letters, 2024, 35(9): 109293-. doi: 10.1016/j.cclet.2023.109293
8. [8]
  Jiao Chen , Zihan Zhang , Guojin Sun , Yudi Cheng , Aihua Wu , Zefan Wang , Wenwen Jiang , Fulin Chen , Xiuying Xie , Jianli Li . Benzo[4,5]imidazo[1,2-a]pyrimidine-based structure-inherent targeting fluorescent sensor for imaging lysosomal viscosity and diagnosis of lysosomal storage disorders. Chinese Chemical Letters, 2024, 35(11): 110050-. doi: 10.1016/j.cclet.2024.110050
9. [9]
  Qiuye Wang , Yabing Sun , Liangxue Lai , Haijing Cui , Yonglong Ye , Ming Yang , Weihao Zhu , Bo Yuan , Quanliang Mao , Wenzhi Ren , Aiguo Wu . MMP-9-responsive probe for fluorescence-magnetic resonance dual-mode imaging of hepatocellular carcinoma models with different metastatic capacities. Chinese Chemical Letters, 2025, 36(4): 110212-. doi: 10.1016/j.cclet.2024.110212
10. [10]
  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
11. [11]
  Lijia Xu , Tong Zhong , Wei Zhao , Bing Yao , Lin Ding , Huangxian Ju . Chemoselective labeling-based spermatozoa glycan imaging reveals abnormal glycosylation in oligoasthenotspermia. Chinese Chemical Letters, 2024, 35(4): 108760-. doi: 10.1016/j.cclet.2023.108760
12. [12]
  Xiangqian Cao , Chenkai Yang , Xiaodong Zhu , Mengxin Zhao , Yilin Yan , Zhengnan Huang , Jinming Cai , Jingming Zhuang , Shengzhou Li , Wei Li , Bing Shen . Synergistic enhancement of chemotherapy for bladder cancer by photothermal dual-sensitive nanosystem with gold nanoparticles and PNIPAM. Chinese Chemical Letters, 2024, 35(8): 109199-. doi: 10.1016/j.cclet.2023.109199
13. [13]
  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
14. [14]
  Tingting Hu , Chao Shen , Xueyan Wang , Fengbo Wu , Zhiyao He . Tumor microenvironment-sensitive polymeric nanoparticles for synergetic chemo-photo therapy. Chinese Chemical Letters, 2024, 35(11): 109562-. doi: 10.1016/j.cclet.2024.109562
15. [15]
  Yupeng Liu , Hui Wang , Songnan Qu . Review on near-infrared absorbing/emissive carbon dots: From preparation to multi-functional application. Chinese Chemical Letters, 2025, 36(5): 110618-. doi: 10.1016/j.cclet.2024.110618
16. [16]
  Jiajia Lv , Jie Gao , Hongyu Li , Zeli Yuan , Nan Dong . Rational design of hydroxytricyanopyrrole-based probes with high affinity and rapid visualization for amyloid-β aggregates in vitro and in vivo. Chinese Chemical Letters, 2024, 35(5): 108940-. doi: 10.1016/j.cclet.2023.108940
17. [17]
  Fengkai Zou , Borui Su , Han Leng , Nini Xin , Shichao Jiang , Dan Wei , Mei Yang , Youhua Wang , Hongsong Fan . Red-emissive carbon quantum dots minimize phototoxicity for rapid and long-term lipid droplet monitoring. Chinese Chemical Letters, 2024, 35(10): 109523-. doi: 10.1016/j.cclet.2024.109523
18. [18]
  Zhipeng Li , Qincong Feng , Jianliang Shen . A β-lactamase-activatable photosensitizer for the treatment of resistant bacterial infections. Chinese Chemical Letters, 2024, 35(11): 109602-. doi: 10.1016/j.cclet.2024.109602
19. [19]
  Sixin Ai , Wenxiu Li , Huayong Zhu , Yang Wan , Weiying Lin . Viscosity-responsive signal amplification dual-modal probe triggered by cysteine/homocysteine for monitoring diabetic liver damages and repair processes. Chinese Chemical Letters, 2025, 36(3): 109904-. doi: 10.1016/j.cclet.2024.109904
20. [20]
  Tianze Wang , Junyi Ren , Dongxiang Zhang , Huan Wang , Jianjun Du , Xin-Dong Jiang , Guiling Wang . Development of functional dye with redshifted absorption based on Knoevenagel condensation at 1-site in phenyl[b]-fused BODIPY. Chinese Chemical Letters, 2024, 35(6): 108862-. doi: 10.1016/j.cclet.2023.108862

Get Citation

PDF

XML

Metrics

PDF Downloads(16)
Abstract views(1089)
HTML views(263)

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