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Progress in Chemistry 2023, Vol. 35 Issue (9): 1399-1414 DOI: 10.7536/PC221230 Previous Articles   

• Review •

NIR-Ⅱ Aggregation-Induced Emission for PDT-PTT Dual-Mode Synergistic Therapy

Hui Tang, Hairong Li, Xiaochun Liu, Yahui Zhang(), Zhouyu Wang(), Xiaoqi Yu()   

  1. Department of Chemistry, School of Science, Xihua University,Chengdu 610039, China
  • Received: Revised: Online: Published:
  • Contact: *e-mail: yahuizhang@mai.xhu.edu.cn(Yahui Zhang); wzyanne@163.com(Zhouyu Wang); xqyu@scu.edu.cn (Xiaoqi Yu)
  • Supported by:
    The National Natural Science Foundation of China(21905021); The Sichuan Province Science and Technology Support Program(2022NSFSC1269); The Sichuan Province Science and Technology Support Program(2023NSFSC1977)
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Due to the excellent optical properties, good biocompatibility, high reactive oxygen species yield and excellent photothermal conversion ability, aggregation-induced emission (AIE) materials show great potential applications in the fields of photodynamic and photothermal therapy. However, traditional fluorescent materials need light with short wavelength for emission, which has the problem of poor tissue penetration, and further restricts the clinical application. To overcome the problem, AIE materials with emission in the range of second near-infrared (NIR-Ⅱ) emission are employed, which promotes the feasibility of the clinical application. This review summarizes the application of NIR-Ⅱ AIEgens with donor-π-acceptor (D-π-A) and donor-acceptor-donor (D-A-D) structure in photodynamic-photothermal dual-mode synergistic therapy.

Contents

1 Introduction

2 NIR-Ⅱ AIE molecules with D-π-A and D-A-D structure for dual-mode synergistic therapy

2.1 D-π-A sructure

2.2 D-A-D sructure

3 Conclusion and outlook

Key words: aggregation-induced emission, the second near-infrared emission, photodynamic-photothermal dual-mode synergistic therapy
Fig.1 The depth of penetration of tissue by different wavelengths of light
Table 1 D-π-A structure of NIR-Ⅱ AIE molecules in PDT-PTT dual-mode synergistic therapy
Name Molecular stucture λex/λem (nm) Φf ROS PCE ref
BITT 590[a]/818[c] 5.8% 3.92% 35.76% 42
TTT-1 535[a]/750[b] 0.6% - 36.5% 43
TTT-2 540[a]/783[b] 0.4% - 42.6% 43
TTT-3 569[a]/782[b] 0.3% - 40.7% 43
TTT-4 568[a]/813[b] 0.3% - 39.9% 43
TI - - - - 44
TSI - - - - 44
TSSI 664[c]/992[b] - - 46% 44
TPEDCAc 580[b]/980[b] 0.4% - 44.8% 45
TAM 581[a]/840[a] 0.2% - - 46
TSAM 587[a]/933[a] 0.1% - - 46
TSSAM 595[a]/1022[a] 0.1% - 40.1% 46
Fig.2 (a) Chemical structures of ITT、BITT、ITB、BITB; (b) Plots of relative PL intensity (I/I0) of ITT、BITT、ITB、BITB versus hexane fraction; (c) The absorption and emission spectra of BITT NPs in aqueous solution; (d) CLSM imaging of intracellular ROS in 4T1 cells using DCFH-DA with BITT upon diverse treatment; (e) IR thermal images of 4T1 bearing-tumor mice injected with BITT NPs followed by laser irradiation. (f) Bodyweight changes of mice in different treatment groups; (g) Tumor bearing mice after 15-day different treatments[42]. Copyright 2021, Wiley-VCH GmbH
Fig.3 (a) Plots of the relative emission intensity (αAIE) versus hexane fraction; (b) Normalized absorption and (c) normalized emission spectra of these NPs in aqueous solution; (d) intracellular ROS level. (e) Thermal images, heating temperatures (at tumor sites) of tumor-bearing mice during continuous NIR irradiation at 12 h postinjection of TSSI NPs; (f) Time-dependent tumor growth curves of tumor-bearing mice with various treatments; (g) Photos of the tumors harvested at day 15 after different treatments[44].Copyright 2020, WIEY-VCH Verlag GmbH &Co. KgaA, Weinheim
Fig.4 (a) Plots of relative PL intensity (I/I0) of TAM、TSAM、TSSAM versus toluene fraction, Inset shows a summary table of the variation in PL intensity of TAM, TSAM, and TSSAM in aggregates (Iaggr.) and nanopaticles (NPs), compared with those in solution (Isol.); (b) Absorption spectra of TAM, TSAM, and TSSAM in film; (c) Fluorescence spectra of TAM, TSAM, and TSSAM aggregates (d) Intracellular ROS generation of TSSAM dots in 4T1 cells in the presence of DCFH-DA with light; (e) IR thermal images of 4T1 tumor-bearing mice intratumorally injected with TSSAM NPs, followed by laser irradiation; (f) (Left) Growth curves of the xenografted 4T1 tumors on the mice after receiving treatment with PBS alone, PBS, and laser light irradiation, TSSAM NPs alone, and TSSAM NPs and laser irradiation; (Right) Photographs of the 4T1 tumors extracted from the mice after the treatment described in panel; (g) Body weight curves of the xenografted 4T1 tumors extracted from the mice after the treatment described in panel[46].Copyright 2020, American Chemical Society
Fig.5 (a) PL spectra of TTT-4 in DMSO/toluene mixture with different toluene fraction(fT); (b) Normalized absorption of these AIEgens in DMSO solution; (c) Normalized PL spectra of AIEgens in the DMSO/toluene mixture with 99% toluene fraction. (d) Intracellular ROS generation (upper row) and live/dead cell staining (low row) of 4T1 cells treated with PBS, PBS+laser, TTT-4 NPs,and TTT-4 NPs +laser for 13 h; (e) IR thermal images of 4T1 tumor-bearing mice intratumorally injected with TTT-4 NPs, followed by laser irradiation; (f) Time-dependent tumor growth curves of tumor-bearing mice with various treatments; (g) Body weight change curves of mice in different treatment recorded during the treatment process[43].Copyright 2021, Elsevier Ltd
Fig.6 (a) PL spectra of TPEDCAc in DMSO/toluene mixture with different toluene fraction (fT); (b) Normalized absorption and (c) PL spectra of TPEDCPy, TPEDCQu and TPEDCAc in the aggregate state; (d) (upper row) Live/dead assay of MCF-7 cells co-stained with FDA and PI treated with PBS, PBS+L, TPEDCAc NPs,and TPEDCAc NPs + L for 30 min. (low row) intracellular ROS generation of TPEDCAc NPs in MCF-7 cells in the presence of DCFH-DA with light; (e) IR thermal images of MCF-7 tumor-bearing mice intratumorally injected with TPEDCAc NPs, followed by laser irradiation; (f) Growth curves of tumor-bearing mice with various treatments; (g) Body weight change curves of mice in different treatment recorded during the treatment process[45]. Copyright 2022, Wiley-VCH GmbH
Table 2 D-A-D structure of NIR-Ⅱ AIE molecules in PDT-PTT dual-mode synergistic therapy
Name Molecular structure λabs/λem Φf ROS PCE ref
ZSY-TPE 730[a]/1020[a] 3.1% 13.8% 28.4% 47
DDTB 687[b]/793[b] 0.16% 1.05% 30.7% 48
DPMD 524[a]/796[a] 5% - 32% 49
TPMD 564[a]/822[a] 19% - 42% 49
CTBT 682[a]/858[a] 16.92% - 57.7% 50
DCTBT 704[a]/995[a] 4.37% - 59.6% 50
Fig.7 (a) PL spectra of ZSY-TPE in THF/H2O mixture with different water fraction(fw); (b) Absorption and fluorescent emission spectra of ZSY-TPE in DCM; (c) ROS generation test against 4T1 cells after incubation with ZSY-TPE NPs for 2 h and co-staining with Lysotracker Green; (d) IR thermal images of the whole bodies of mice 24 h after the injection of ZSY-TPE NPs or PBS and laser irrdiation; (e) Variation in tumor temperature as a function of laser irradiation time; (f) Tumor growth inhibition (g) relative body weight curves after different treatments[47].Copyright 2020, Elsevier Ltd
Fig.8 (a) PL spectra of DCTBT in THF/H2O mixture with different water fraction(fw); (b) Normalized absorption spectra and (c) Normalized emission spectra of two NPs in aqueous solution; (d) ROS detection in PANC-1cells using DCFH as fluorescence indicator; (e) Thermal images, heating temperatures (at tumor sites) of tumor-bearing mice during continuous laser irradiation at 8 h postinjection of lip-DCTBT NPs; (f) Relative tumor volume changes for various treatment groups; (g) Tumor images harvested at 17 day after different treatments[50]. Copyright 2022, Elsevier Ltd
Fig.9 (a) PL spectra of DDTB in THF/H2O mixture with different water fraction(fw); (b) Absorption and emission spectra of the NPs in aqueous solution; (c) Detection of intracellular ROS generation by DCFH-DA in HeLa cells after incubation with DDTB NPs and PBS, follwed by laser irradiation; (d) Temperature changes at the tumor sites as a function of the laser irradiating time; (e) Average tumor growth curves in different groups; (f) Body weight of HeLa-tumor-bearing mice in different groups[48]. Copyright 2021, Wiley-VCH GmbH
[1]
Wang D, Lee M M S, Xu W H, Kwok R T K, Lam J W Y, Tang B Z. Theranostics, 2018, 8(18): 4925.

doi: 10.7150/thno.27787
[2]
Yang M Q, Deng J R., Su H F, Gu S X, Zhang J, Zhong A G, Wu F S. Mat. Chem. Front., 2021, 5(1): 406.
[3]
Gao J, Li J, Geng W C, Chen F Y, Duan X C, Zheng Z, Ding D, Guo D S. J. Am. Chem. Soc., 2018, 140(14): 4945.

doi: 10.1021/jacs.8b02331
[4]
Li X S, Kwon N, Guo T, Liu Z, Yoon J. Angew. Chem.Int. Ed., 2018, 57(36): 11522.
[5]
Cheng Y H, Cheng H, Jiang C X, Qiu X F, Wang K K, Huan W, Yuan A, Wu J H, Hu Y Q. Nat. Commun., 2015, 6 : 8.
[6]
Qu R, Zhen X, Jiang X Q. CCS Chem., 2022, 4(2): 401.

doi: 10.31635/ccschem.021.202101302
[7]
Chen W J, Chen H J, Huang Y R, Tan Y, Tan C Y, Xie Y, Yin J. ACS Appl. Bio. Mater., 2022, 5(7): 3428.

doi: 10.1021/acsabm.2c00363
[8]
Li C N, Zhang W, Liu S, Hu X L, Xie Z G. ACS Appl. Mater. Inter., 2020, 12 (27): 30077.

doi: 10.1021/acsami.0c06144
[9]
Ethirajan M, Chen Y H, Joshi P, Pandey R K. Chem. Soc. Rev., 2011, 40(1): 340.

doi: 10.1039/B915149B
[10]
Luo J, Xie Z, Lam J W, Cheng L, Chen H, Qiu C, Kwok H S, Zhan X, Liu Y, Zhu D, Tang B Z. Chem. Commun., (Cambridge, England) 2001, 18 : 1740.
[11]
Mei J, Leung N L C, Kwok R T K, Lam J W Y, Tang B Z. Chem. Rev., 2015, 115(21): 11718.

doi: 10.1021/acs.chemrev.5b00263 pmid: 26492387
[12]
Saini V, Venkatesh V, Pt B, Bhosale R S, Singh V. Prog.Mol.Biol.Transl., 2021, 185 : 45.
[13]
Liu S S, Feng G X, Tang B Z, Liu B. Chem. Sci., 2021, 12(19): 6488.

doi: 10.1039/D1SC00045D
[14]
Zhang M, Wang W T, Mohammadniaei M, Zheng T, Zhang Q C, Ashley J, Liu S J, Sun Y, Tang B Z. Adv. Mater., 2021, 33(22):12.
[15]
Song S L, Zhao Y, Kang M M, Zhang Z J, Wu Q, Fu S, Li Y M, Wen H F, Wang D, Tang B Z. Adv. Funct. Mater., 2021, 31(51): 14.
[16]
Hu F, Huang Y Y, Zhang G X, Zhao R, Yang H, Zhang D Q. Anal. Chem., 2014, 86(15): 7987.

doi: 10.1021/ac502103t
[17]
Gu X G, Zhang X Y, Ma H L, Jia S R, Zhang P F, Zhao Y J, Liu Q, Wang J G, Zheng X Y, Lam J W Y, Ding D, Tang B Z. Adv. Mater., 2018, 30(26): 9.
[18]
Liu S J, Zhou X, Zhang H K, Ou H L, Lam J W Y, Liu Y, Shi L Q, Ding D, Tang B Z. J. Am. Chem. Soc., 2019, 141(13): 5359.

doi: 10.1021/jacs.8b13889
[19]
Liang P P, Huang X Y, Wang Y, Chen D P, Ou C J, Zhang Q, Shao J J, Huang W Dong, X C. ACS Nano., 2018, 12(11): 11446.

doi: 10.1021/acsnano.8b06478
[20]
Chen D P, Tang Y Y, Zhu J W, Zhang J J, Song X J, Wang W J, Shao J J, Huang W, Chen P, Dong X C. Biomaterials, 2019, 221 : 11.
[21]
Zhao X Z, Long S R, Li M L, Cao J F, Li Y C, Guo L Y, Sun W, Du J J, Fan J L, Peng X J. J. Am. Chem. Soc., 2020, 142(3): 1510.

doi: 10.1021/jacs.9b11800
[22]
Wang Y J, Gong N Q, Li Y J, Lu Q C, Wang X, Li J H. J. Am. Chem. Soc., 2020, 142(4): 1735.

doi: 10.1021/jacs.9b11553
[23]
Xu Z R, Jiang Y H, Fan M Z, Tang S, Liu M X, Law W C, Yang C B, Ying M, Ma M Z, Dong B Q, Yong K T, Xu G X. Adv. Opt. Mater., 2021, 9(20): 27.
[24]
Deng J R, Yang M Q, Li C, Liu G Y, Sun Q, Luo X G, Wu F S. Dyes Pigments., 2021, 187 : 7.
[25]
Hong G S, Diao S, Chang J L, Antaris A L, Chen C X, Zhang B, Zhao S, Atochin D N,. Huang P L, Andreasson K I, Kuo C J, Dai H J. Nat. Photonics, 2014, 8(9): 723.

doi: 10.1038/nphoton.2014.166
[26]
Hong G S, Antaris A L, Dai H J. Nat. Biomed. Eng., 2017, 1(1): 22.

doi: 10.1038/s41551-016-0022
[27]
Jiang S S, Huang K, Qu J L, Lin J, Huang P. View, 2021, 2(1): 15.
[28]
Liu S J, Chen C, Li Y Y, Zhang H K, Liu J K, Wang R, Wong S T H, Lam J W Y, Ding D, Tang B Z. Adv. Funct. Mater., 2020, 30(7): 10.
[29]
He B R, Situ B, Zhao Z J, Zheng L. Small Methods, 2020, 4(4): 32.
[30]
Fan X X, Xia Q M, Zhang Y Y, Li Y R, Feng Z, Zhou J, Qi J, Tang B Z, Qian J, Lin H. Adv. Healthc. Mater., 2021, 10(24): 12.
[31]
Zhao Z, Chen C, Wu W T, Wang F F, Du L L, Zhang X Y, Xiong Y, He X W, Cai Y J, Kwok R T K, Lam J W Y, Gao X K, Sun P C, Phillips D L, Ding D, Tang B Z. Nat. Commun., 2019, 10(1): 768.

doi: 10.1038/s41467-019-08722-z
[32]
Deng G J, Peng X H, Su Z H, Zheng W, Yu J, Du L L, Chen H J, Gong P, Zhang P F, Cai L T, Tang B Z. ACS Nano, 2020, 14(9): 11452.

doi: 10.1021/acsnano.0c03824
[33]
Shi P J, Zhang X X, Liu Y, Duan Y A, Li Y P, Li Z F, Han T Y. Mater. Lett., 2020, 263: 4.
[34]
Zhao Z, Su H F, Zhang P F, Cai Y J, Kwok R T K, Chen Y C, He Z K, Gu X G, He X W, Sung H H Y, Willimas I D, Lam J W Y, Zhang Z F, Tang B Z. J. Mater. Chem., 2017, 5 (8): 1650.
[35]
Kang M M, Zhou C C, Wu S M, Yu B R., Zhang Z J, Song N, Lee M M S, Xu W H, Xu F J, Wang D, Wang L, Tang B Z. J. Am. Chem. Soc., 2019, 141 (42):16781.

doi: 10.1021/jacs.9b07162
[36]
Li D, Li Y M, Wu Q, Xiao P H, Wang L, Wang D, Tang B Z. Small, 2021, 17(37): 9.
[37]
Feng G X, Zhang G Q, Ding D. Chem. Soc. Rev., 2020, 49(22): 8179.

doi: 10.1039/D0CS00671H
[38]
Ren F, Shi J B, Tong B, Cai Z X, Dong Y P. Progress in Chemistry, 2021, 33(3): 341.
(任飞, 石建兵, 佟斌, 蔡政旭, 董宇平. 化学进展, 2021, 33(3): 341.).

doi: 10.7536/PC200614
[39]
Zhang R Y, Duan Y K, Liu B. Nanoscale, 2019, 11(41): 19241.

doi: 10.1039/C9NR06012J
[40]
Alifu N, Zebibula A, Qi J, Zhang H Q, Sun C W, Yu X M, Xue D W, Lam J W Y, Li G H, Qian J, Tang B Z. ACS Nano, 2018, 12(11): 11282.

doi: 10.1021/acsnano.8b05937
[41]
Zhao Y Z, Cai M M, Qian Y, Xie L H, Huang W. Progress in Chemistry, 2013, 25(Z1): 296.
(赵跃智, 蔡敏敏, 钱妍, 解令海, 黄维. 化学进展, 2013, 25(Z1): 296.).
[42]
Zhu W, Kang M M, Wu Q, Zhang Z J, Wu Y, Li C B, Li K, Wang L, Wang D, Tang B Z. Adv. Funct. Mater., 2021, 31(3): 11.
[43]
Wen H F, Zhang Z J, Kang M M, Li H X, Xu W H, Guo H, Li Y M, Tan Y H, Wen Z Y, Wu Q, Huang J C, Xi L, Li K, Wang L, Wang D, Tang B Z. Biomaterials, 2021, 274 : 10.
[44]
Zhang Z J, Xu W H, Kang M M, Wen H F, Guo H, Zhang P F, Xi L, Li K, Wang L, Wang D, Tang B Z. Adv. Mater., 2020, 32(36): 11.
[45]
Zhang T F, Zhang J Y, Wang F B, Cao H, Zhu D M, Chen X Y, Xu C H, Yang X Q, Huang W B, Wang Z Y, Wang J F, He Z K, Zheng Z, Lam J W Y, Tang B Z. Adv. Funct. Mater., 2022, 32 (16): 10.
[46]
Xu W H, Zhang Z J, Kang M M, Guo H, Li Y M, Wen H F, Lee M M S, Wang Z Y, Kwok R T K, Lam J W Y, Li K, Xi L, Chen S J, Wang D, Tang B Z. ACS Mater. Lett., 2020, 2(8): 1033.
[47]
Xu Y L, Zhang Y, Li J, An J S, Li C L, Bai S Y, Sharma A, Deng G Z, Kim J S, Sun Y. Biomaterials, 2020, 259 : 8.
[48]
Jiang R M, Dai J, Dong X Q, Wang Q, Meng Z J, Guo J J, Yu Y J, Wang S X, Xia F, Zhao Z J, Lou X D, Tang B Z. Adv. Mater., 2021, 33(22): 13.
[49]
Liu L Q, Wang X, Wang L J, Guo L Q, Li Y B, Bai B, Fu F, Lu H G, Zhao X W. ACS Appl. Mater. Inter., 2021, 13(17): 19668.

doi: 10.1021/acsami.1c02260
[50]
Li D, Chen X H, Wang D L, Wu H Z, Wen H F, Wang L, Jin Q, Wang D, Ji J, Tang B Z. Biomaterials, 2022, 283 : 13.
[51]
Yang G, Ni J S, Li Y X, Zha M L, Tu Y, Li K. Angew. Chem.Int. Ed., 2021, 60(10): 5386.
[52]
Qu J M, Zhang Y H, Cai Z X, Tong B, Xie H Y, Dong Y P, Shi J B. Nanoscale, 2022, 14(38): 14064.

doi: 10.1039/D2NR02273G
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