Citation: Junping Bai, Junliang Zhou, Xin Ji, Nannan Wang, Xiaochun Dong, Wei Wu, Weili Zhao. Development of environment-insensitive and highly emissive BODIPYs via installation of N, N'-dialkylsubstituted amide at meso position[J]. Chinese Chemical Letters, ;2022, 33(9): 4175-4178. doi: 10.1016/j.cclet.2022.02.017 shu

Development of environment-insensitive and highly emissive BODIPYs via installation of N, N'-dialkylsubstituted amide at meso position

Junping Bai ^a ,
Junliang Zhou ^a ,
Xin Ji ^a ,
Nannan Wang ^b ,
Xiaochun Dong ^{a, *,} ,
Wei Wu ^{a, *,} ,
Weili Zhao ^{a, b, *,}

a.
School of Pharmacy, Institutes of Integrative Medicine, Fudan University, Shanghai 201203, China
b.
Key Laboratory for Special Functional Materials of Ministry of Education, School of Materials Science and Engineering, Henan University, Kaifeng 475004, China

xcdong@fudan.edu.cn

wuwei@shmu.edu.cn

zhaoweili@fudan.edu.cn

Received Date: 31 July 2021
Revised Date: 29 January 2022
Accepted Date: 9 February 2022
Available Online: 14 February 2022

Figures(4)

Fluorescent dyes play a crucial role in fluorescence imaging and sensing technology. However, there is a dilemma that they are usually intrinsically hydrophobic which lacks of emission in water and modification with ionic groups to access water solubility may result in poor membrane permeability. Fluorescent dyes with strong fluorescence emission in both nonpolar and polar solvents are highly desirable. In this manuscript, we reported a strategy to develop fluorescent BODIPY dyes via installation of amide moiety at meso position of 1, 3, 5, 7-tetramethyl-BODIPY and discovered that N, N'-dialkylsubstituted BODIPY amides possessed highly fluorescent emission with favorable environment-insensitive properties.
- Fluorescent dyes,
- BODIPY,
- Environment-insensitive,
- Bioimaging
1. [1]
  Y. Wang, K. Zhou, G. Huang, et al., Nat. Mater. 13 (2014) 204-212. doi: 10.1038/nmat3819
2. [2]
  H. Li, J.C. Vaughan, Chem. Rev. 118 (2018) 9412-9454. doi: 10.1021/acs.chemrev.7b00767
3. [3]
  X. Li, J. Zheng, W. Liu, et al., Chin. Chem. Lett. 31 (2020) 2937-2940. doi: 10.1016/j.cclet.2020.05.043
4. [4]
  L. Wang, M.S. Frei, A. Salim, et al., J. Am. Chem. Soc. 141 (2019) 2770-2781. doi: 10.1021/jacs.8b11134
5. [5]
  D. Yue, M. Wang, F. Deng, et al., Chin. Chem. Lett. 29 (2018) 648-656. doi: 10.1016/j.cclet.2018.01.046
6. [6]
  J. Chan, S.C. Dodani, C.J. Chang, Nat. Chem. 4 (2012) 973-984. doi: 10.1038/nchem.1500
7. [7]
  H.W. Liu, L. Chen, C. Xu, et al., Chem. Soc. Rev. 47 (2018) 7140-7180. doi: 10.1039/C7CS00862G
8. [8]
  G.M. van Dam, G. Themelis, L.M. Crane, et al., Nat. Med. 17 (2011) 1315-1319. doi: 10.1038/nm.2472
9. [9]
  H. Chen, Z. Liu, O. Jiang, et al., Giant 8 (2021) 100073. doi: 10.1016/j.giant.2021.100073
10. [10]
  H. Chen, Z. Liu, B. Wei, et al., Bioact. Mater. 6 (2021) 655-665. doi: 10.1016/j.bioactmat.2020.08.034
11. [11]
  J. Qi, X. Hu, X. Dong, et al., Adv. Drug Deliv. Rev. 143 (2019) 206-225. doi: 10.1016/j.addr.2019.05.009
12. [12]
  X. Li, X. Gao, W. Shi, et al., Chem. Rev. 114 (2014) 590-659. doi: 10.1021/cr300508p
13. [13]
  T. Kowada, H. Maeda, K. Kikuchi, Chem. Soc. Rev. 44 (2015) 4953-4972. doi: 10.1039/C5CS00030K
14. [14]
  M. Liu, S. Ma, M. She, et al., Chin. Chem. Lett. 30 (2019) 1815-1824. doi: 10.1016/j.cclet.2019.08.028
15. [15]
  B. Barut, C.O. Yalcin, S. Sari, et al., Eur. J. Med. Chem. 183 (2019) 111685. doi: 10.1016/j.ejmech.2019.111685
16. [16]
  J. Pliquett, A. Dubois, C. Racoeur, et al., Bioconjugate Chem. 30 (2019) 1061-1066. doi: 10.1021/acs.bioconjchem.8b00795
17. [17]
  L. Li, J. Han, B. Nguyen, et al., J. Org. Chem. 73 (2008) 1963-1970.
18. [18]
  J.M. Franke, B.K. Raliski, S.C. Boggess, et al., J. Am. Chem. Soc. 141 (2019) 12824-12831. doi: 10.1021/jacs.9b05912
19. [19]
  D. Kand, P. Liu, M.X. Navarro, et al., J. Am. Chem. Soc. 142 (2020) 4970-4974. doi: 10.1021/jacs.9b13219
20. [20]
  M. Kamiya, K. Johnsson, Anal. Chem. 82 (2010) 6472-6479. doi: 10.1021/ac100741t
21. [21]
  Z.A. Mazrad Khoerunnisa, I. In, et al., Biosens. Bioelectron. 90 (2017) 394-402. doi: 10.1016/j.bios.2016.12.013
22. [22]
  H. Chen, X. He, M. Su, et al., J. Am. Chem. Soc. 139 (2017) 10157-10163. doi: 10.1021/jacs.7b05920
23. [23]
  Y. Zhu, W. Lin, W. Zhang, et al., Chin. Chem. Lett. 28 (2017) 1875-1877.
24. [24]
  M.N. Belzile, R. Godin, A.M. Durantini, et al., J. Am. Chem. Soc. 138 (2016) 16388-16397. doi: 10.1021/jacs.6b09735
25. [25]
  S. Kim, H. Kim, Y. Choi, et al., Chemistry 21 (2015) 9645-9649. doi: 10.1002/chem.201501127
26. [26]
  S. Kim, J. Bouffard, Y. Kim, Chem. Eur. J. 21 (2015) 17459-17465. doi: 10.1002/chem.201503040
27. [27]
  Y. Jang, T.I. Kim, H. Kim, et al., ACS Appl. Bio. Mater. 2 (2019) 2567-2572. doi: 10.1021/acsabm.9b00259
28. [28]
  T.I. Kim, H. Kim, Y. Choi, et al., Sens. Actuators B 249 (2017) 229-234. doi: 10.1016/j.snb.2017.04.093
29. [29]
  M. Su, S. Li, H. Zhang, et al., J. Am. Chem. Soc. 141 (2019) 402-413. doi: 10.1021/jacs.8b10396
30. [30]
  S. Jeon, T.I. Kim, H. Jin, et al., J. Am. Chem. Soc. 142 (2020) 9231-9239. doi: 10.1021/jacs.9b13982
31. [31]
  S. Choi, J. Bouffard, Y. Kim, Chem. Sci. 5 (2014) 751-755. doi: 10.1039/C3SC52495G
32. [32]
  J.B. Grimm, B.P. English, J. Chen, et al., Nat. Methods 12 (2015) 244-250. doi: 10.1038/nmeth.3256
1. [1]
  Chuanfeng Fan , Jian Gao , Yingkai Gao , Xintong Yang , Gaoning Li , Xiaochun Wang , Fei Li , Jin Zhou , Haifeng Yu , Yi Huang , Jin Chen , Yingying Shan , Li Chen . A non-peptide-based chymotrypsin-targeted long-wavelength emission fluorescent probe with large Stokes shift and its application in bioimaging. Chinese Chemical Letters, 2024, 35(10): 109838-. doi: 10.1016/j.cclet.2024.109838
2. [2]
  Beitong Zhu , Xiaorui Yang , Lirong Jiang , Tianhong Chen , Shuangfei Wang , Lintao Zeng . A portable and versatile fluorescent platform for high-throughput screening of toxic phosgene, diethyl chlorophosphate and volatile acyl chlorides. Chinese Chemical Letters, 2025, 36(1): 110222-. doi: 10.1016/j.cclet.2024.110222
3. [3]
  Haixian Ren , Yuting Du , Xiaojing Yang , Fangjun Huo , Le Zhang , Caixia Yin . Development of ESIPT-based specific fluorescent probes for bioactive species based on the protection-deprotection of the hydroxyl. Chinese Chemical Letters, 2025, 36(2): 109867-. doi: 10.1016/j.cclet.2024.109867
4. [4]
  Fan Zheng , Runsha Xiao , Shuai Huang , Zhikang Chen , Chen Lai , Anyao Bi , Heying Yao , Xueping Feng , Zihua Chen , Wenbin Zeng . Accurate visualization colorectal cancer by monitoring viscosity variations with a novel mitochondria-targeted fluorescent probe. Chinese Chemical Letters, 2025, 36(2): 109876-. doi: 10.1016/j.cclet.2024.109876
5. [5]
  Lixian Fu , Yiyun Tan , Yue Ding , Weixia Qing , Yong Wang . Water–soluble and polarity–sensitive near–infrared fluorescent probe for long–time specific cancer cell membranes imaging and C. Elegans label. Chinese Chemical Letters, 2024, 35(4): 108886-. doi: 10.1016/j.cclet.2023.108886
6. [6]
  Qihang Wu , Hui Wen , Wenhai Lin , Tingting Sun , Zhigang Xie . Alkyl chain engineering of boron dipyrromethenes for efficient photodynamic antibacterial treatment. Chinese Chemical Letters, 2024, 35(12): 109692-. doi: 10.1016/j.cclet.2024.109692
7. [7]
  Bin Fang , Jiaqi Yang , Limin Wang , Haoqin Li , Jiaying Guo , Jiaxin Zhang , Qingyuan Guo , Bo Peng , Kedi Liu , Miaomiao Xi , Hua Bai , Li Fu , Lin Li . A mitochondria-targeted H₂S-activatable fluorogenic probe for tracking hepatic ischemia-reperfusion injury. Chinese Chemical Letters, 2024, 35(6): 108913-. doi: 10.1016/j.cclet.2023.108913
8. [8]
  Zengchao Guo , Weiwei Liu , Tengfei Liu , Jinpeng Wang , Hui Jiang , Xiaohui Liu , Yossi Weizmann , Xuemei Wang . Engineered exosome hybrid copper nanoscale antibiotics facilitate simultaneous self-assembly imaging and elimination of intracellular multidrug-resistant superbugs. Chinese Chemical Letters, 2024, 35(7): 109060-. doi: 10.1016/j.cclet.2023.109060
9. [9]
  Yunlong Li , Xinyu Zhang , Shuang Liu , Chunsheng Li , Qiang Wang , Jin Ye , Yong Lu , Jiating Xu . Engineered iron-based metal-organic frameworks nanoplatforms for cancer theranostics: A mini review. Chinese Chemical Letters, 2025, 36(2): 110501-. doi: 10.1016/j.cclet.2024.110501
10. [10]
  Meiling Zhao , Yao Lu , Yutao Zhang , Haoyun Xue , Zhiqian Guo . Ultra-high signal-to-noise ratio near-infrared chemiluminescent probe for in vivo sensing singlet oxygen. Chinese Chemical Letters, 2025, 36(5): 110105-. doi: 10.1016/j.cclet.2024.110105
11. [11]
  Jian Li , Yu Zhang , Rongrong Yan , Kaiyuan Sun , Xiaoqing Liu , Zishang Liang , Yinan Jiao , Hui Bu , Xin Chen , Jinjin Zhao , Jianlin Shi . 高效靶向示踪钙钛矿纳米系统光电增效抗肿瘤. Acta Physico-Chimica Sinica, 2025, 41(5): 100042-. doi: 10.1016/j.actphy.2024.100042
12. [12]
  Lina Feng , Guoyu Jiang , Xiaoxia Jian , Jianguo Wang . Application of Organic Radical Materials in Biomedicine. University Chemistry, 2025, 40(4): 253-260. doi: 10.12461/PKU.DXHX202405171
13. [13]
  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
14. [14]
  Wenjuan Jin , Zelong Chen , Yi Wang , Jiaxuan Li , Jiahui Li , Yuxin Pei , Zhichao Pei . Nano metal-photosensitizer based on Aza-BODIPY-Cu complex for CDT-enhanced dual phototherapy. Chinese Chemical Letters, 2024, 35(7): 109328-. doi: 10.1016/j.cclet.2023.109328
15. [15]
  Lulu Cao , Yikun Li , Dongxiang Zhang , Shuai Yue , Rong Shang , Xin-Dong Jiang , Jianjun Du . Engineering aggregates of julolidine-substituted aza-BODIPY nanoparticles for NIR-II photothermal therapy. Chinese Chemical Letters, 2024, 35(12): 109735-. doi: 10.1016/j.cclet.2024.109735
16. [16]
  Mengjie Gao , Zhiqiang Cui , Yue Shen , Yikun Li , Dongxiang Zhang , Xiaoyan Gao , Yaguang Sun , Xin-Dong Jiang , Jianjun Du , Xiaohong Sun . NIR-II emissive aza-BODIPY-based nanoparticles for triggering glioblastoma apoptosis in brain. Chinese Chemical Letters, 2025, 36(5): 110098-. doi: 10.1016/j.cclet.2024.110098
17. [17]
  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
18. [18]
  Yan Zhu , Jia Liu , Meiheng Lv , Tingting Wang , Dongxiang Zhang , Rong Shang , Xin-Dong Jiang , Jianjun Du , Guiling Wang . Heavy-atom-free orthogonal configurative dye 1,7-di-anthra-aza-BODIPY for singlet oxygen generation. Chinese Chemical Letters, 2024, 35(10): 109446-. doi: 10.1016/j.cclet.2023.109446
19. [19]
  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
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(794)
HTML views(43)

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