Citation: 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[J]. Chinese Chemical Letters, ;2024, 35(10): 109452. doi: 10.1016/j.cclet.2023.109452 shu

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

Xuejian Xing ^{a, b, 1} ,
Pan Zhu ^{a, 1} ,
E Pang ^a ,
Shaojing Zhao ^a ,
Yu Tang ^a ,
Zheyu Hu ^{c, d} ,
Quchang Ouyang ^{c, d, *,} ,
Minhuan Lan ^{a, *,}

a.
Key Laboratory of Hunan Province for Water Environment and Agriculture Product Safety, College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, China
b.
School of Chemistry and Chemical Engineering, Neijiang Normal University, Neijiang 641100, China
c.
Medical Department of Breast Cancer, Hunan Cancer Hospital, Changsha 410083, China
d.
Medical Department of Breast Cancer, The Affiliated Cancer Hospital of Xiangya School of Medicine, Central South University, Changsha 410083, China

oyqc1969@126.com

minhuanlan@csu.edu.cn

Received Date: 26 September 2023
Revised Date: 21 December 2023
Accepted Date: 22 December 2023
Available Online: 26 December 2023

Figures(4)

Clinical phototheranostic agents suffer from low absorption in near-infrared (NIR) region, decreasing singlet oxygen quantum yield (¹O₂ QY) caused by aggregation in water, and low photothermal conversion efficiency (PCE), all of which are factors weakening their phototheranostic efficacy. Herein, we designed and synthesized a donor-acceptor-donor (D-A-D) structured boron-dipyrromethene derivative (B-2TPA) which exhibited NIR absorption and fluorescence. After being encapsulated in amphiphilic distearoyl phosphoethanolamine polyethyleneglycol 2000 (DSPE-PEG-2000), the water-soluble B-2TPA nanoparticles (NPs) had increasing ¹O₂ QY (6.7%) due to the intermolecular aggregation-induced decrease in the energy gap between singlet and triplet excited states. Moreover, the quenched fluorescence and stable twisted intramolecular charge transfer in aggregates further increased the PCE of B-2TPA NPs to 60.1%. In vitro and in vivo studies confirmed that B-2TPA NPs could be used in NIR fluorescence and photoacoustic imaging-guided synergistic photodynamic and photothermal therapy in tumor treatment.
- Boron-dipyrromethene,
- Aggregation,
- Intersystem crossing,
- Twisted intramolecular charge transfer,
- Photodynamic therapy,
- Photothermal therapy
1. [1]
  S. Wang, W. Ren, J.T. Hou, et al., Chem. Soc. Rev. 50 (2021) 8887–8902. doi: 10.1039/D1CS00083G
2. [2]
  X. Qin, F. Li, Y. Zhang, et al., Anal. Chem. 90 (2018) 9381–9385. doi: 10.1021/acs.analchem.8b01992
3. [3]
  X. Yue, B. Wang, M. Lan, et al., Chem. Commun. 59 (2023) 4676–4679. doi: 10.1039/D3CC00214D
4. [4]
  H. Wang, J. Chang, M. Shi, et al., Angew. Chem. Int. Ed. 58 (2019) 1057–1061. doi: 10.1002/anie.201811273
5. [5]
  K. Yang, F. Long, W. Liu, et al., ACS Appl. Mater. Interfaces 14 (2022) 18043–18052. doi: 10.1021/acsami.1c22444
6. [6]
  X. Li, F. Fang, B. Sun, et al., Nanoscale Horiz. 6 (2021) 177–185. doi: 10.1039/D0NH00672F
7. [7]
  Q. Cheng, Z. Li, Y. Xia, et al., NPG Asia Mater. 11 (2019) 63. doi: 10.1038/s41427-019-0164-4
8. [8]
  L. Zhang, Y. Geng, L. Li, et al., Chem. Sci. 12 (2021) 5918–5925. doi: 10.1039/D1SC00126D
9. [9]
  A. Kano, Y. Taniwaki, I. Nakamura, et al., J. Control. Release 167 (2013) 315–321. doi: 10.1016/j.jconrel.2013.02.016
10. [10]
  W. Park, S.J. Park, K. Na, Biomaterials 32 (2011) 8261–8270. doi: 10.1016/j.biomaterials.2011.07.023
11. [11]
  M. Hou, W. Chen, J. Zhao, et al., Chin. Chem. Lett. 33 (2022) 4101–4106. doi: 10.1016/j.cclet.2022.01.049
12. [12]
  J. Jin, Y. Zhu, Z. Zhang, et al., Angew. Chem. Int. Ed. 57 (2018) 16354–16358. doi: 10.1002/anie.201808811
13. [13]
  E.A. Owens, M. Henary, G. El Fakhri, et al., Acc. Chem. Res. 49 (2016) 1731–1740. doi: 10.1021/acs.accounts.6b00239
14. [14]
  P. Xue, R. Yang, L. Sun, et al., Nano-Micro Lett. 10 (2018) 74. doi: 10.1007/s40820-018-0227-z
15. [15]
  L. Cheng, W. He, H. Gong, et al., Adv. Funct. Mater. 23 (2013) 5893–5902. doi: 10.1002/adfm.201301045
16. [16]
  N. Jing, Z. Zhou, W. Xiong, et al., Chin. Chem. Lett. 32 (2021) 3948–3953. doi: 10.1016/j.cclet.2021.06.053
17. [17]
  Y. Wan, G. Lu, W.C. Wei, et al., ACS Nano 14 (2020) 9917–9928. doi: 10.1021/acsnano.0c02767
18. [18]
  B. Lu, Y. Huang, Z. Zhang, et al., Mater. Chem. Front. 6 (2022) 2968–2993. doi: 10.1039/D2QM00752E
19. [19]
  Z. Cheng, T. Zhang, W. Wang, et al., Chin. Chem. Lett. 32 (2021) 1580–1585. doi: 10.1016/j.cclet.2021.02.017
20. [20]
  R. Jiang, J. Dai, X. Dong, et al., Adv. Mater. 33 (2021) 2101158. doi: 10.1002/adma.202101158
21. [21]
  J. Zhang, S. Mukamel, J. Jiang, J. Phys. Chem. B 124 (2020) 2238–2244. doi: 10.1021/acs.jpcb.0c00654
22. [22]
  J. Zhao, K. Yan, G. Xu, et al., Adv. Funct. Mater. 31 (2021) 2008325. doi: 10.1002/adfm.202008325
23. [23]
  G. Xu, C. Li, C. Chi, et al., Nat. Commun. 13 (2022) 3064. doi: 10.1038/s41467-022-30721-w
24. [24]
  S. Liu, Y. Li, R.T. Kwok, Chem. Sci. 12 (2021) 3427. doi: 10.1039/D0SC02911D
25. [25]
  R. Liu, J. Liu, W. Xu, et al., Adv. Mater. 35 (2023) 2303212. doi: 10.1002/adma.202303212
26. [26]
  D. Xi, M. Xiao, J. Cao, et al., Adv. Mater. 32 (2020) 1907855. doi: 10.1002/adma.201907855
27. [27]
  Z.R. Grabowski, K. Rotkiewicz, W. Rettig, Chem. Rev. 103 (2003) 3899–4032. doi: 10.1021/cr940745l
28. [28]
  X. Lv, C. Gao, T. Han, et al., Chem. Commun. 56 (2020) 715–718. doi: 10.1039/C9CC09138F
29. [29]
  C. Wang, W. Chi, Q. Qiao, et al., Chem. Soc. Rev. 50 (2021) 12656–12678. doi: 10.1039/D1CS00239B
30. [30]
  S. Liu, X. Zhou, H. Zhang, et al., J. Am. Chem. Soc. 41 (2019) 5359–5368.
31. [31]
  Z. Zhao, C. Chen, W. Wu, et al., Nat. Commun. 10 (2019) 768. doi: 10.1038/s41467-019-08722-z
32. [32]
  B. Li, E Pang, S. Zhao, et al., Chem. Biomed. Imaging 1 (2023) 541–549. doi: 10.1021/cbmi.2c00004
33. [33]
  J. Ma, Z. Liu, Z. Wang, et al., Mater. Chem. Front. 1 (2017) 2547–2553. doi: 10.1039/C7QM00307B
34. [34]
  Y. Zhang, M. Shi, Z. Yan, et al., Adv. Healthc. Mater. 9 (2020) 2001042. doi: 10.1002/adhm.202001042
35. [35]
  K. Li, X. Duan, Z. Jiang, et al., Nat. Commun. 12 (2021) 2376. doi: 10.1038/s41467-021-22686-z
36. [36]
  Z.R. Grabowski, K. Rotkiewicz, A. Siemiarczuk, J. Lumin. 18-19 (1979) 420-424.
37. [37]
  X.Y. Shen, W. Yuan, Y. Liu, et al., J. Phys. Chem. C 116 (2012) 10541–10547. doi: 10.1021/jp303100a
38. [38]
  J. Cao, Q. Liu, S. Bai, et al., ACS Appl. Mater. Interfaces 11 (2019) 29814–29820. doi: 10.1021/acsami.9b07677
39. [39]
  D. Wu, H.C. Daly, E. Conroy, et al., Eur. J. Med. Chem. 161 (2019) 343–353. doi: 10.1016/j.ejmech.2018.10.046
40. [40]
  W. Hu, X. Miao, H. Tao, et al., ACS Nano 13 (2019) 12006–12014. doi: 10.1021/acsnano.9b06208
41. [41]
  X. Li, L. Liu, S. Li, et al., ACS Nano 13 (2019) 12901–12911. doi: 10.1021/acsnano.9b05383
42. [42]
  H. Ma, Y. Lu, Z. Huang, et al., J. Am. Chem. Soc. 144 (2022) 3477–3486. doi: 10.1021/jacs.1c11886
43. [43]
  X. Xing, K. Yang, B. Li, et al., J. Phys. Chem. Lett. 13 (2022) 7939–7946. doi: 10.1021/acs.jpclett.2c02122
44. [44]
  H. Gao, Y. Gao, C. Wang, et al., ACS Appl. Mater. Interfaces 10 (2018) 14956–14965. doi: 10.1021/acsami.7b13444
45. [45]
  S. Liu, C. Chen, Y. Li, et al., Adv. Funct. Mater. 30 (2020) 1908125. doi: 10.1002/adfm.201908125
46. [46]
  W. Zhang, B. Hao, C. Gao, et al., Eur. J. Pharm. Biopharm. 179 (2020) 206–220.
47. [47]
  K.M. Tsoi, S. MacParland, X. Ma, et al., Nat. Mater. 15 (2016) 1212–1221. doi: 10.1038/nmat4718
48. [48]
  Z. Li, Y. Zhu, H. Zeng, et al., Nat. Commun. 14 (2023) 14337.
1. [1]
  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
2. [2]
  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
3. [3]
  Yihao Zhang , Yang Jiao , Xianchao Jia , Qiaojia Guo , Chunying Duan . Highly effective self-assembled porphyrin MOCs nanomaterials for enhanced photodynamic therapy in tumor. Chinese Chemical Letters, 2024, 35(5): 108748-. doi: 10.1016/j.cclet.2023.108748
4. [4]
  Yiling Li , Zekun Gao , Xiuxiu Yue , Minhuan Lan , Xiuli Zheng , Benhua Wang , Shuang Zhao , Xiangzhi Song . FRET-based two-photon benzo[a] phenothiazinium photosensitizer for fluorescence imaging-guided photodynamic therapy. Chinese Chemical Letters, 2024, 35(7): 109133-. doi: 10.1016/j.cclet.2023.109133
5. [5]
  Hao Cai , Xiaoyan Wu , Lei Jiang , Feng Yu , Yuxiang Yang , Yan Li , Xian Zhang , Jian Liu , Zijian Li , Hong Bi . Lysosome-targeted carbon dots with a light-controlled nitric oxide releasing property for enhanced photodynamic therapy. Chinese Chemical Letters, 2024, 35(4): 108946-. doi: 10.1016/j.cclet.2023.108946
6. [6]
  Xin Lu , Haoran Sun , Xiaomeng Li , Chunrui Li , Jinfeng Wang , Dandan Zhou . C14-HSL limits the mycelial morphology of pathogen Trichosporon cells but enhances their aggregation: Mechanisms and implications. Chinese Chemical Letters, 2024, 35(6): 108936-. doi: 10.1016/j.cclet.2023.108936
7. [7]
  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
8. [8]
  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
9. [9]
  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
10. [10]
  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
11. [11]
  Kun-Heng Li , Hong-Yang Zhao , Dan-Dan Wang , Ming-Hui Qi , Zi-Jian Xu , Jia-Mi Li , Zhi-Li Zhang , Shi-Wen Huang . Mitochondria-targeted nano-AIEgens as a powerful inducer for evoking immunogenic cell death. Chinese Chemical Letters, 2024, 35(5): 108882-. doi: 10.1016/j.cclet.2023.108882
12. [12]
  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
13. [13]
  Xinyue Lan , Junguang Liang , Churan Wen , Xiaolong Quan , Huimin Lin , Qinqin Xu , Peixian Chen , Guangyu Yao , Dan Zhou , Meng Yu . Photo-manipulated polyunsaturated fatty acid-doped liposomal hydrogel for flexible photoimmunotherapy. Chinese Chemical Letters, 2024, 35(4): 108616-. doi: 10.1016/j.cclet.2023.108616
14. [14]
  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
15. [15]
  Xin Huang , Yi Zhao , Wanzhen Liang . Vibronic coupling effect on intersystem crossing rates of TADF emitters. Chinese Journal of Structural Chemistry, 2024, 43(6): 100278-100278. doi: 10.1016/j.cjsc.2024.100278
16. [16]
  Jinyu Guo , Yandai Lin , Shaohua He , Yueqing Chen , Fenglu Li , Renjie Ruan , Gaoxing Pan , Hexin Nan , Jibin Song , Jin Zhang . Utilizing dual-responsive iridium(Ⅲ) complex for hepatocellular carcinoma: Integrating photoacoustic imaging with chemotherapy and photodynamic therapy. Chinese Chemical Letters, 2024, 35(9): 109537-. doi: 10.1016/j.cclet.2024.109537
17. [17]
  Jiaqi Huang , Renjiang Kong , Yanmei Li , Ni Yan , Yeyang Wu , Ziwen Qiu , Zhenming Lu , Xiaona Rao , Shiying Li , Hong Cheng . Feedback enhanced tumor targeting delivery of albumin-based nanomedicine to amplify photodynamic therapy by regulating AMPK signaling and inhibiting GSTs. Chinese Chemical Letters, 2024, 35(8): 109254-. doi: 10.1016/j.cclet.2023.109254
18. [18]
  Zhe Li , Ping-Zhao Liang , Li Xu , Fei-Yu Yang , Tian-Bing Ren , Lin Yuan , Xia Yin , Xiao-Bing Zhang . Three positive charge nonapoptotic-induced photosensitizer with excellent water solubility for tumor therapy. Chinese Chemical Letters, 2024, 35(8): 109190-. doi: 10.1016/j.cclet.2023.109190
19. [19]
  Zhaomin Tang , Qian He , Jianren Zhou , Shuang Yan , Li Jiang , Yudong Wang , Chenxing Yao , Huangzhao Wei , Keda Yang , Jiajia Wang . Active-transporting of charge-reversal Cu(Ⅱ)-doped mesoporous silica nanoagents for antitumor chemo/chemodynamic therapy. Chinese Chemical Letters, 2024, 35(7): 109742-. doi: 10.1016/j.cclet.2024.109742
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(128)
HTML views(5)

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