Citation: 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[J]. Chinese Chemical Letters, ;2024, 35(12): 109735. doi: 10.1016/j.cclet.2024.109735 shu

Engineering aggregates of julolidine-substituted aza-BODIPY nanoparticles for NIR-II photothermal therapy

Lulu Cao ^{a, 1} ,
Yikun Li ^{b, 1} ,
Dongxiang Zhang ^a ,
Shuai Yue ^a ,
Rong Shang ^c ,
Xin-Dong Jiang ^{a, *,} ,
Jianjun Du ^{b, *,}

a.
Liaoning & Shenyang Key Laboratory of Functional Dye and Pigment, Shenyang University of Chemical Technology, Shenyang 110142, China
b.
State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, China
c.
Department of Chemistry, Graduate School of Advanced Science and Engineering, Hiroshima University, Higashi-Hiroshima 7398526, Japan

xdjiang@syuct.edu.cn

dujj@dlut.edu.cn

Received Date: 24 December 2023
Revised Date: 20 February 2024
Accepted Date: 21 February 2024
Available Online: 8 March 2024

Figures(5)

Near infrared-II (NIR-II) dyes have unique advantages in biomedical applications owing to the powerful ability in penetrating biological tissues. Herein, NIR-II aza-BODIPY dye, QLD-BDP, was developed with julolidine at 1,7-sites and p-dimethylaminophenyl group at 3,5-sites. According to X-ray analysis, QLD-BDP exhibits significant distortion, and this molecule appears a bowl shaped structure. The photothermal conversion efficiency of the self-assembled QLD-BDP nanoparticles (QLD-BDP-NPs) can reach 50.5%, with maximum emission at 998 nm by the aggregate. QLD-BDP-NPs can cause the complete destruction of 4T1 multicellular spheroids (MCSs), indicating a photothermal therapy (PTT) effect.
- Aggregate,
- NIR-II,
- Julolidine,
- Aza-BODIPY,
- PTT
1. [1]
  S. Diao, G. Hong, A.L. Antaris, et al., Nano Res. 8 (2015) 3027–3034. doi: 10.1007/s12274-015-0808-9
2. [2]
  G. Hong, A.L. Antaris, H. Dai, Nat. Biomed. Eng. 1 (2017) 0010. doi: 10.1038/s41551-016-0010
3. [3]
  Z. Lei, F. Zhang, Angew. Chem. Int. Ed. 60 (2021) 16294–16308. doi: 10.1002/anie.202007040
4. [4]
  C. Li, G. Chen, Y. Zhang, et al., J. Am. Chem. Soc. 142 (2020) 14789–14804. doi: 10.1021/jacs.0c07022
5. [5]
  S. Wang, H. Shi, L. Wang, et al., J. Am. Chem. Soc. 144 (2022) 23668–23676. doi: 10.1021/jacs.2c11223
6. [6]
  J. Cao, B. Zhu, K. Zheng, et al., Front. Bioeng. Biotechnol. 7 (2020) 487. doi: 10.3389/fbioe.2019.00487
7. [7]
  S. He, J. Song, J. Qu, et al., Chem. Soc. Rev. 47 (2018) 4258–4278. doi: 10.1039/C8CS00234G
8. [8]
  G. Hong, J.C. Lee, J.T. Robinson, et al., Nat. Med. 18 (2012) 1841–1846. doi: 10.1038/nm.2995
9. [9]
  G. Hong, Y. Zou, A.L. Antaris, et al., Nat. Commun. 5 (2014) 4206. doi: 10.1038/ncomms5206
10. [10]
  Z. Hu, C. Fang, B. Li, et al., Nat. Biomed. Eng. 4 (2019) 259–271. doi: 10.1038/s41551-019-0494-0
11. [11]
  Y. Jiang, K. Pu, Adv. Biosyst. 2 (2018) 1700262. doi: 10.1002/adbi.201700262
12. [12]
  M.H. Lee, A. Sharma, M.J. Chang, et al., Chem. Soc. Rev. 47 (2018) 28–52. doi: 10.1039/C7CS00557A
13. [13]
  Q. Shen, S. Wang, N. -D. Yang, et al., J. Lumin. 225 (2020) 117338. doi: 10.1016/j.jlumin.2020.117338
14. [14]
  A.M. Smith, M.C. Mancini, S. Nie, Nat. Nanotechnol. 4 (2009) 710–711. doi: 10.1038/nnano.2009.326
15. [15]
  S. Zhu, B.C. Yung, S. Chandra, et al., Theranostics 8 (2018) 4141–4151. doi: 10.7150/thno.27995
16. [16]
  Y. Zhang, Y. Jia, S. Zhu, SmartMat 5 (2024) e1245. doi: 10.1002/smm2.1245
17. [17]
  T. Li, T. Meyer, R. Meerheim, et al., J. Mater. Chem. A 5 (2017) 10696–10703. doi: 10.1039/C7TA02133J
18. [18]
  Y. Liu, D. Gao, M. Xu, et al., J. Biophotonics 12 (2018) e201800237.
19. [19]
  Z. Shi, X. Han, W. Hu, et al., Chem. Soc. Rev. 49 (2020) 7533–7567. doi: 10.1039/D0CS00234H
20. [20]
  M. Strobl, A. Walcher, T. Mayr, et al., Anal. Chem. 89 (2017) 2859–2865. doi: 10.1021/acs.analchem.6b04045
21. [21]
  M. Liu, S. Ma, M. She, et al., Chin. Chem. Lett. 30 (2019) 1815–1824. doi: 10.1016/j.cclet.2019.08.028
22. [22]
  M. Kaur, A. Janaagal, N. Balsukuri, et al., Coord. Chem. Rev. 498 (2024) 215428. doi: 10.1016/j.ccr.2023.215428
23. [23]
  Y. Wang, D. Zhang, K. Xiong, et al., Chin. Chem. Lett. 33 (2022) 115–122. doi: 10.1016/j.cclet.2021.06.083
24. [24]
  Y. Su, Q. Hu, D. Zhang, et al., Chem. Eur. J. 28 (2022) e202103571. doi: 10.1002/chem.202103571
25. [25]
  S.Z. Wang, Y. Guo, X. Zhang, et al., Adv. Funct. Mater. 33 (2023) 2303328. doi: 10.1002/adfm.202303328
26. [26]
  A.M. Scott, T. Miura, A.B. Ricks, et al., J. Am. Chem. Soc. 131 (2009) 17655–17666. doi: 10.1021/ja907625k
27. [27]
  H. Dang, D. Yin, Y. Tian, et al., J. Mater. Chem. B 10 (2022) 5279–5290. doi: 10.1039/D2TB00705C
28. [28]
  K. Okino, S. Hira, Y. Inoue, et al., Angew. Chem. Int. Ed. 56 (2017) 16597–16601. doi: 10.1002/anie.201710354
29. [29]
  G. Wu, F. Kong, J. Li, et al., J. Power Sources 243 (2013) 131–137. doi: 10.1016/j.jpowsour.2013.05.188
30. [30]
  L. Bai, P. Sun, Y. Liu, et al., Chem. Commun. 55 (2019) 10920–10923. doi: 10.1039/C9CC03378E
31. [31]
  Z. Shi, H. Bai, J. Wu, et al., Research 6 (2023) 0169. doi: 10.34133/research.0169
32. [32]
  C. Li, Y. Xu, L. Tu, et al., Chem. Sci. 13 (2022) 6541–6549. doi: 10.1039/D2SC01518H
33. [33]
  F. Würthner, T.E. Kaiser, C.R. Saha-Möller, Angew. Chem. Int. Ed. 50 (2011) 3376–3410. doi: 10.1002/anie.201002307
34. [34]
  M.H.Y. Cheng, K.M. Harmatys, D.M. Charron, et al., Angew. Chem. Int. Ed. 58 (2019) 13394–13399. doi: 10.1002/anie.201907754
35. [35]
  X. Zhang, H. Wang, D. Li, et al., Macromolecules 53 (2020) 3747–3755. doi: 10.1021/acs.macromol.0c00469
36. [36]
  Y. Qu, W. Jin, Y. Wan, et al., Chin. Chem. Lett. 35 (2024) 108493. doi: 10.1016/j.cclet.2023.108493
37. [37]
  N. Yang, S. Song, M.H. Akhtar, et al., J. Mater. Chem. B 11 (2023) 9712–9720. doi: 10.1039/D3TB01280H
38. [38]
  A. Gorman, J. Killoran, C. O'Shea, et al., J. Am. Chem. Soc. 126 (2004) 10619–10631. doi: 10.1021/ja047649e
39. [39]
  J.N. Schrauben, J.L. Ryerson, J. Michl, et al., J. Am. Chem. Soc. 136 (2014) 7363–7373. doi: 10.1021/ja501337b
40. [40]
  W. Zhang, B. Li, H. Ma, et al., ACS Appl. Mater. Interfaces 8 (2016) 21465–21471. doi: 10.1021/acsami.6b05817
41. [41]
  M.L. Agazzi, M.B. Ballatore, E. Reynoso, et al., Eur. J. Med. Chem. 126 (2017) 110–121. doi: 10.1016/j.ejmech.2016.10.001
42. [42]
  Z. Li, C. Liu, H. Abroshan, et al., ACS Catal. 7 (2017) 3368–3374. doi: 10.1021/acscatal.7b00239
43. [43]
  X. Wang, Y. Yu, K. Cheng, et al., Mikrochim. Acta 186 (2019) 842. doi: 10.1007/s00604-019-3924-5
44. [44]
  S. Jiang, X. Wang, Z. Zhang, et al., Int. J. Nanomedicine 11 (2016) 5505–5518. doi: 10.2147/IJN.S115428
45. [45]
  J. Chen, A.C. Sedgwick, S. Sen, et al., Chem. Sci. 12 (2021) 9916–9921. doi: 10.1039/D1SC01591E
46. [46]
  H. Ning, Y. Yang, C. Lv, et al., Nano Res. 16 (2023) 12294–12303. doi: 10.1007/s12274-023-5923-4
47. [47]
  Y.H. Kim, D.H. Jeong, D. Kim, et al., J. Am. Chem. Soc. 123 (2000) 76–86.
48. [48]
  T.L.C. Jansen, Chem 5 (2019) 3010–3012. doi: 10.1016/j.chempr.2019.11.011
49. [49]
  Y. Li, T. Ma, H. Jiang, et al., Angew. Chem. Int. Ed. 61 (2022) e202203093. doi: 10.1002/anie.202203093
50. [50]
  C. Li, H. Ge, D. Zhang, et al., Sens. Actuator. B: Chem. 344 (2021) 130213. doi: 10.1016/j.snb.2021.130213
51. [51]
  J. Huang, X. Sun, Y. Wang, et al., Ecotoxicol. Environ. Saf. 264 (2023) 115447. doi: 10.1016/j.ecoenv.2023.115447
52. [52]
  M. Azharuddin, K. Roberg, A.K. Dhara, et al., Sci. Rep. 9 (2019) 20066. doi: 10.1038/s41598-019-56273-6
53. [53]
  M. Wan, Q. Wang, X. Li, et al., Angew. Chem. Int. Ed. 59 (2020) 14458–14465. doi: 10.1002/anie.202002452
54. [54]
  Y. Lu, F. Xu, Y. Wang, et al., Biomaterials 278 (2021) 121167. doi: 10.1016/j.biomaterials.2021.121167
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]
  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
3. [3]
  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
4. [4]
  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
5. [5]
  Jing Guo . New electrolyte concept: Compact ion-pair aggregate electrolyte. Chinese Chemical Letters, 2025, 36(4): 110512-. doi: 10.1016/j.cclet.2024.110512
6. [6]
  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
7. [7]
  Yuyang Zhou , Ziwang Mao , Jing-Juan Xu . Recent advances in near infrared (NIR) electrochemiluminescence luminophores. Chinese Chemical Letters, 2024, 35(11): 109622-. doi: 10.1016/j.cclet.2024.109622
8. [8]
  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
9. [9]
  Yan-Li Li , Zhi-Ming Li , Kai-Kai Wang , Xiao-Long He . Beyond 1,4-addition of in-situ generated (aza-)quinone methides and indole imine methides. Chinese Chemical Letters, 2024, 35(7): 109322-. doi: 10.1016/j.cclet.2023.109322
10. [10]
  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
11. [11]
  Linjing Li , Wenlai Xu , Jianyong Ning , Yaping Zhong , Chuyue Zhang , Jiane Zuo , Zhicheng Pan . Revealing the intrinsic mechanisms for accelerating nitrogen removal efficiency in the Anammox reactor by adding Fe(II) at low temperature. Chinese Chemical Letters, 2024, 35(8): 109243-. doi: 10.1016/j.cclet.2023.109243
12. [12]
  Ji Qi , Jianan Zhu , Yanxu Zhang , Jiahao Yang , Chunting Zhang . Visible Color Change of Copper (II) Complexes in Reversible SCSC Transformation: The Effect of Structure on Color. University Chemistry, 2024, 39(3): 43-57. doi: 10.3866/PKU.DXHX202307050
13. [13]
  Jiaxuan Wang , Tonghe Liu , Bingxiang Wang , Ziwei Li , Yuzhong Niu , Hou Chen , Ying Zhang . Synthesis of polyhydroxyl-capped PAMAM dendrimer/silica composites for the adsorption of aqueous Hg(II) and Ag(I). Chinese Chemical Letters, 2024, 35(12): 109900-. doi: 10.1016/j.cclet.2024.109900
14. [14]
  Muhammad Riaz , Rakesh Kumar Gupta , Di Sun , Mohammad Azam , Ping Cui . Selective adsorption of organic dyes and iodine by a two-dimensional cobalt(II) metal-organic framework. Chinese Journal of Structural Chemistry, 2024, 43(12): 100427-100427. doi: 10.1016/j.cjsc.2024.100427
15. [15]
  Yongpo Zhang , Xinfeng Li , Yafei Song , Mengyao Sun , Congcong Yin , Chunyan Gao , Jinzhong Zhao . Synthesis of Chlorine-Bridged Binuclear Cu(I) Complexes Based on Conjugation-Driven Cu(II) Oxidized Secondary Amines. University Chemistry, 2024, 39(5): 44-51. doi: 10.3866/PKU.DXHX202309092
16. [16]
  Xinhao Yan , Guoliang Hu , Ruixi Chen , Hongyu Liu , Qizhi Yao , Jiao Li , Lingling Li . Polyethylene Glycol-Ammonium Sulfate-Nitroso R Salt System for the Separation of Cobalt (II). University Chemistry, 2024, 39(6): 287-294. doi: 10.3866/PKU.DXHX202310073
17. [17]
  Xiaohui Fu , Yanping Zhang , Juan Liao , Zhen-Hua Wang , Yong You , Jian-Qiang Zhao , Mingqiang Zhou , Wei-Cheng Yuan . Palladium-catalyzed enantioselective decarboxylation of vinyl cyclic carbamates: Generation of amide-based aza-1,3-dipoles and application to asymmetric 1,3-dipolar cycloaddition. Chinese Chemical Letters, 2024, 35(12): 109688-. doi: 10.1016/j.cclet.2024.109688
18. [18]
  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
19. [19]
  Biao Huang , Tao Tang , Fushou Liu , Shi-Hui Chen , Zhi-Ling Zhang , Mingxi Zhang , Ran Cui . Quantum dots boost large-view NIR-Ⅱ imaging with high fidelity for fluorescence-guided tumor surgery. Chinese Chemical Letters, 2024, 35(12): 109694-. doi: 10.1016/j.cclet.2024.109694
20. [20]
  Xiaoshuai Wu , Bailei Wang , Yichen Li , Xiaoxuan Guan , Mingjing Yin , Wenquan Lv , Yin Chen , Fei Lu , Tao Qin , Huyang Gao , Weiqian Jin , Yifu Huang , Cuiping Li , Ming Gao , Junyu Lu . NIR driven catalytic enhanced acute lung injury therapy by using polydopamine@Co nanozyme via scavenging ROS. Chinese Chemical Letters, 2025, 36(2): 110211-. doi: 10.1016/j.cclet.2024.110211

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(381)
HTML views(12)

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