Citation: 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[J]. Chinese Chemical Letters, ;2024, 35(6): 108862. doi: 10.1016/j.cclet.2023.108862 shu

Development of functional dye with redshifted absorption based on Knoevenagel condensation at 1-site in phenyl[b]-fused BODIPY

Tianze Wang ^{a, 1} ,
Junyi Ren ^{b, 1} ,
Dongxiang Zhang ^{a, 1} ,
Huan Wang ^b ,
Jianjun Du ^{c, *,} ,
Xin-Dong Jiang ^{a, *,} ,
Guiling Wang ^{b, *,}

a.
Liaoning & Shenyang Key Laboratory of Functional Dye and Pigment, Shenyang University of Chemical Technology, Shenyang 110142, China
b.
Department of Cell Biology, China Medical University, Shenyang 110122, China
c.
State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, China

dujj@dlut.edu.cn

xdjiang@syuct.edu.cn

glingwang@cmu.edu.cn

Received Date: 10 April 2023
Revised Date: 24 July 2023
Accepted Date: 26 July 2023
Available Online: 28 July 2023

Figures(6)

Integrating ring-fused modification with π-conjugated extension is an effective approach for designing, synthesizing, and application for novel borondipyrromethene (BODIPY) structures. In this work, based on phenyl[b]-fused BODIPY, we made reasonable modification of the methyl group at 1-site to generate dye NBDP. NBDP possessed near-infrared region (NIR) absorption and emission properties, and the intramolecular charge transfer (ICT) resulted in low fluorescence. Whereas, heat energy is evidently released in the presence of light, which can be exploited for intracellular photothermal therapy via the cell apoptosis process, reducing the inflammatory side-effects induced by necrosis. This research provides a crucial foundation for the novel molecule via BODIPY multi-directional alteration and its potential application in anti-tumor phototherapy.
- NIR dyes,
- [b]-Fused BODIPY,
- Knoevenagel condensation,
- Photothermal therapy,
- Cell apoptosis
1. [1]
  J. Wang, C. Yu, E. Hao, et al., Coord. Chem. Rev. 470 (2022) 214709. doi: 10.1016/j.ccr.2022.214709
2. [2]
  Y. Wang, D. Zhang, K. Xiong, et al., Chin. Chem. Lett. 33 (2022) 115–122. doi: 10.1016/j.cclet.2021.06.083
3. [3]
  J. Wang, N. Boens, L. Jiao, et al., Org. Biomol. Chem. 18 (2020) 4135–4156. doi: 10.1039/D0OB00790K
4. [4]
  A. Loudet, K. Burgess, Chem. Rev. 107 (2007) 4891–4932. doi: 10.1021/cr078381n
5. [5]
  H. Lu, J. Mack, Z. Shen, et al., Chem. Soc. Rev. 43 (2014) 4778–4823. doi: 10.1039/C4CS00030G
6. [6]
  Q. Gong, Y. Xiao, E. Hao, et al., J. Am. Chem. Soc. 144 (2022) 21992–21999. doi: 10.1021/jacs.2c08947
7. [7]
  W. Miao, E. Hao, L. Jiao, et al., Chem. Eur. J. 29 (2023) e202203832. doi: 10.1002/chem.202203832
8. [8]
  W. Sheng, Z. Wang, E. Hao, L. Jiao, Chin. Chem. Lett. 32 (2021) 1249–1252. doi: 10.1016/j.cclet.2020.08.047
9. [9]
  R. Wang, J. Chen, C. Zhao, et al., Chem. Sci. 10 (2019) 7222–7227. doi: 10.1039/C9SC02093D
10. [10]
  H. Zhang, J. Liu, W. Guo, et al., J. Am. Chem. Soc. 142 (2020) 17069–17078. doi: 10.1021/jacs.0c06916
11. [11]
  L. Gai, Y. Liu, H. Lu, et al., Coord. Chem. Rev. 481 (2023) 215041. doi: 10.1016/j.ccr.2023.215041
12. [12]
  A. Aguiar, J. Farinhas, W. Silva, et al., Dyes Pigment. 172 (2020) 107842. doi: 10.1016/j.dyepig.2019.107842
13. [13]
  A. Aguiar, J. Farinhas, W. Silv, et al., Dyes Pigment. 193 (2021) 109517. doi: 10.1016/j.dyepig.2021.109517
14. [14]
  D. Tungulin, J. Leier, A.B. Carter, et al., Chem. Eur. J. 25 (2019) 3816–3827. doi: 10.1002/chem.201806330
15. [15]
  M. Chapran, E. Angioni, N.J. Findlay, et al., ACS Appl. Mater. Interfaces 9 (2017) 4750–4757. doi: 10.1021/acsami.6b13689
16. [16]
  J. Zou, L. Li, X. Chen, et al., Adv. Mater. 33 (2021) 2103627. doi: 10.1002/adma.202103627
17. [17]
  Z. Wang, L. Huang, Y. Yan, et al., Angew. Chem. Int. Ed. 59 (2020) 16114–16121. doi: 10.1002/anie.202005269
18. [18]
  D. Chen, Q. Yu, X. Dong, et al., Small 16 (2020) 2001059. doi: 10.1002/smll.202001059
19. [19]
  K.X. Teng, L.Y. Niu, Q.Z. Yang, J. Am. Chem. Soc. 145 (2023) 4081–4087. doi: 10.1021/jacs.2c11868
20. [20]
  D. Xi, M. Xiao, X. Peng, et al., Adv. Mater. 32 (2020) 1907855. doi: 10.1002/adma.201907855
21. [21]
  H. Dang, D. Yin, Y. Tian, et al., J. Mater. Chem. B 10 (2022) 5279–5290. doi: 10.1039/D2TB00705C
22. [22]
  C. Ma, T. Zhang, Z. Xie, J. Mater. Chem. B 9 (2021) 7318–7327. doi: 10.1039/D1TB00855B
23. [23]
  T. Zhang, X. Ma, H. Tian, Chem. Sci. 11 (2020) 482–487. doi: 10.1039/C9SC05502A
24. [24]
  P. Rana, N. Singh, P. Majumdar, et al., Coord. Chem. Rev. 470 (2022) 214698. doi: 10.1016/j.ccr.2022.214698
25. [25]
  J. Zhao, K. Xu, W. Yang, et al., Chem. Soc. Rev. 44 (2015) 8904–8939. doi: 10.1039/C5CS00364D
26. [26]
  T. Yu, D. Zhang, X.D. Jiang, et al., J. Mater. Chem. B 10 (2022) 3048–3054. doi: 10.1039/D2TB00012A
27. [27]
  D. Zhang, N. Xu, X. Peng, et al., Chin. J. Chem. 36 (2018) 119–123. doi: 10.1002/cjoc.201700598
28. [28]
  L. Gai, J. Mack, H. Yamada, et al., Chem. Eur. J. 20 (2014) 1091–1102. doi: 10.1002/chem.201303291
29. [29]
  R. Hu, M. Hassan, L. Liu, S. Zhang, W. Gong, Chin. Chem. Lett. 34 (2023) 107541. doi: 10.1016/j.cclet.2022.05.055
30. [30]
  X. Jiang, S. Yue, K. Chen, et al., Chin. Chem. Lett. 30 (2019) 2271–2273. doi: 10.1016/j.cclet.2019.07.027
31. [31]
  J. Li, Y. Dong, Y. Yang, et al., J. Am. Chem. Soc. 144 (2022) 14351–14562. doi: 10.1021/jacs.2c05826
32. [32]
  Z. Ye, C. Xiong, J. Pan, et al., Dyes Pigment. 155 (2018) 30–35. doi: 10.1016/j.dyepig.2018.03.015
33. [33]
  X. Zhang, L. Chen, Y. Xiao, et al., Chem. Eur. J. 27 (2021) 3688–3693. doi: 10.1002/chem.202005296
34. [34]
  P. Xiao, Z. Shen, B.Z. Tang, et al., Adv. Sci. 9 (2022) 2104079. doi: 10.1002/advs.202104079
35. [35]
  M. Tian, D. Guo, W. Lin, Dyes Pigm. 197 (2022) 109951. doi: 10.1016/j.dyepig.2021.109951
36. [36]
  K. Li, X. Duan, Z. Jiang, et al., Nat. Commun. 12 (2021) 2376. doi: 10.1038/s41467-021-22686-z
37. [37]
  L. Zeng, T. Chen, J.S. Kim, et al., Chem. Sci. 13 (2022) 4523–4532. doi: 10.1039/D2SC00299J
38. [38]
  Z. Ye, M. Ji, D. Liu, et al., Angew. Chem. Int. Ed. 61 (2022) e202204518. doi: 10.1002/anie.202204518
39. [39]
  Y. Liu, P. Bhattarai, X. Chen, et al., Chem. Soc. Rev. 48 (2019) 2053–2108. doi: 10.1039/C8CS00618K
40. [40]
  Q. Yu, L. Tu, Q. Zhao, et al., ACS Appl. Mater. Interfaces 14 (2022) 50637–50648. doi: 10.1021/acsami.2c15844
41. [41]
  J.R. Melamed, R.S. Edelstein, E.S. Day, ACS Nano 9 (2015) 6–11. doi: 10.1021/acsnano.5b00021
42. [42]
  M.P. Hernandez, P.D. Pino, S.G. Mitchell, et al., ACS Nano 9 (2015) 52–61. doi: 10.1021/nn505468v
1. [1]
  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
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]
  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
4. [4]
  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
5. [5]
  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
6. [6]
  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
7. [7]
  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
8. [8]
  Tao LIU , Yuting TIAN , Ke GAO , Xuwei HAN , Ru'nan MIN , Wenjing ZHAO , Xueyi SUN , Caixia YIN . A photothermal agent with high photothermal conversion efficiency and high stability for tumor therapy. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1622-1632. doi: 10.11862/CJIC.20240107
9. [9]
  Jianqiu Li , Yi Zhang , Songen Liu , Jie Niu , Rong Zhang , Yong Chen , Yu Liu . Cucurbit[8]uril-based non-covalent heterodimer realized NIR cell imaging through topological transformation from nanowire to nanorod. Chinese Chemical Letters, 2024, 35(10): 109645-. doi: 10.1016/j.cclet.2024.109645
10. [10]
  Ji Liu , Dongsheng He , Tianjiao Hao , Yumin Hu , Yan Zhao , Zhen Li , Chang Liu , Daquan Chen , Qiyue Wang , Xiaofei Xin , Yan Shen . Gold mineralized "hybrid nanozyme bomb" for NIR-II triggered tumor effective permeation and cocktail therapy. Chinese Chemical Letters, 2024, 35(9): 109296-. doi: 10.1016/j.cclet.2023.109296
11. [11]
  Jieqiong Xu , Wenbin Chen , Shengkai Li , Qian Chen , Tao Wang , Yadong Shi , Shengyong Deng , Mingde Li , Peifa Wei , Zhuo Chen . Organic stoichiometric cocrystals with a subtle balance of charge-transfer degree and molecular stacking towards high-efficiency NIR photothermal conversion. Chinese Chemical Letters, 2024, 35(10): 109808-. doi: 10.1016/j.cclet.2024.109808
12. [12]
  Rakesh Kumar Gupta , Zhi Wang , Di Sun . Shining bright: Revolutionary near-unity NIR phosphorescent metal nanoclusters. Chinese Journal of Structural Chemistry, 2024, 43(11): 100417-100417. doi: 10.1016/j.cjsc.2024.100417
13. [13]
  Yuqing Wang , Zhemin Li , Qingjun Lu , Qizhao Li , Jiaxin Luo , Chengjie Li , Yongshu Xie . Solar cells based on doubly concerted companion dyes with the efficiencies modulated by inserting an ethynyl group at different positions. Chinese Chemical Letters, 2024, 35(5): 109093-. doi: 10.1016/j.cclet.2023.109093
14. [14]
  Supphachok Chanmungkalakul , Syed Ali Abbas Abedi , Federico J. Hernández , Jianwei Xu , Xiaogang Liu . The dark side of cyclooctatetraene (COT): Photophysics in the singlet states of “self-healing” dyes. Chinese Chemical Letters, 2024, 35(8): 109227-. doi: 10.1016/j.cclet.2023.109227
15. [15]
  Yunan Yuan , Zhimin Luo , Jie Chen , Chaoliang He , Kai Hao , Huayu Tian . Constructing thermoresponsive PNIPAM-based microcarriers for cell culture and enzyme-free cell harvesting. Chinese Chemical Letters, 2024, 35(7): 109549-. doi: 10.1016/j.cclet.2024.109549
16. [16]
  Hui-Juan Wang , Wen-Wen Xing , Zhen-Hai Yu , Yong-Xue Li , Heng-Yi Zhang , Qilin Yu , Hongjie Zhu , Yao-Yao Wang , Yu Liu . Cucurbit[7]uril confined phenothiazine bridged bis(bromophenyl pyridine) activated NIR luminescence for lysosome imaging. Chinese Chemical Letters, 2024, 35(6): 109183-. doi: 10.1016/j.cclet.2023.109183
17. [17]
  Yu Pang , Min Wang , Ning-Hua Yang , Min Xue , Yong Yang . One-pot synthesis of a giant twisted double-layer chiral macrocycle via [4 + 8] imine condensation and its X-ray structure. Chinese Chemical Letters, 2024, 35(10): 109575-. doi: 10.1016/j.cclet.2024.109575
18. [18]
  Zikang Hu , Hengjie Zhang , Zhengqiu Li , Tianbao Zhao , Zhipeng Gu , Qijuan Yuan , Baoshu Chen . Multifunctional photothermal hydrogels: Design principles, various functions, and promising biological applications. Chinese Chemical Letters, 2024, 35(10): 109527-. doi: 10.1016/j.cclet.2024.109527
19. [19]
  Junchuan Sun , Lu Wang . Carbon exchange enabled supra-photothermal methane dry reforming. Chinese Journal of Structural Chemistry, 2024, 43(10): 100330-100330. doi: 10.1016/j.cjsc.2024.100330
20. [20]
  Zhenhao Wang , Yuliang Tang , Ruyu Li , Shuai Tian , Yu Tang , Dehai Li . Bioinspired synthesis of cochlearol B and ganocin A. Chinese Chemical Letters, 2024, 35(7): 109247-. doi: 10.1016/j.cclet.2023.109247

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(139)
HTML views(6)

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