Isoindigo nanoparticles for photoacoustic imaging-guided tumor photothermal therapy

doi:10.1016/j.cjche.2024.05.010

Chinese Journal of Chemical Engineering ›› 2024, Vol. 72 ›› Issue (8): 19-25.DOI: 10.1016/j.cjche.2024.05.010

Isoindigo nanoparticles for photoacoustic imaging-guided tumor photothermal therapy

Yao Pei¹, Ran Wang¹, Xiang Rong¹, Xiang Xia², Hexiang Wang¹, Zongwei Zhang¹, Tian Qiu¹, Saran Long^1,2, Jianjun Du^1,2, Jiangli Fan^1,2, Wen Sun^1,2, Xiaojun Peng¹

1 State Key Laboratory of Fine Chemicals, Frontiers Science Center for Smart Materials Oriented Chemical Engineering, Dalian University of Technology, Dalian 116024, China;
2 Ningbo Institute of Dalian University of Technology, Ningbo 315016, China

Received:2024-02-26 Revised:2024-05-11 Online:2024-10-17 Published:2024-08-28
Contact: Wen Sun,E-mail:sunwen@dlut.edu.cn
Supported by:
This work was financially supported by the National Natural Science Foundation of China (22078046), Fundamental Research Fundamental Funds for the Central Universities (DUT22LAB601), Liaoning Binhai Laboratory (LBLB-2023-03), and China Postdoctoral Science Foundation (2023M740487).

Isoindigo nanoparticles for photoacoustic imaging-guided tumor photothermal therapy

Yao Pei¹, Ran Wang¹, Xiang Rong¹, Xiang Xia², Hexiang Wang¹, Zongwei Zhang¹, Tian Qiu¹, Saran Long^1,2, Jianjun Du^1,2, Jiangli Fan^1,2, Wen Sun^1,2, Xiaojun Peng¹

1 State Key Laboratory of Fine Chemicals, Frontiers Science Center for Smart Materials Oriented Chemical Engineering, Dalian University of Technology, Dalian 116024, China;
2 Ningbo Institute of Dalian University of Technology, Ningbo 315016, China

通讯作者: Wen Sun,E-mail:sunwen@dlut.edu.cn
基金资助:
This work was financially supported by the National Natural Science Foundation of China (22078046), Fundamental Research Fundamental Funds for the Central Universities (DUT22LAB601), Liaoning Binhai Laboratory (LBLB-2023-03), and China Postdoctoral Science Foundation (2023M740487).

Abstract

Abstract: The key factor in photothermal therapy lies in the selection of photothermal agents. Traditional photothermal agents generally have problems such as poor photothermal stability and low photothermal conversion efficiency. Herein, we have designed and synthesized an isoindigo (IID) dye. We used isoindigo as the molecular center and introduced common triphenylamine and methoxy groups as rotors. In order to improve the photothermal stability and tumor targeting ability, we encapsulated IID into nanoparticles. As a result, the nanoparticles exhibited high photothermal stability and photothermal conversion efficiency (67%) upon 635 nm laser irradiation. Thus, the nanoparticles demonstrated a significant inhibitory effect on live tumors in photothermal therapy guided by photoacoustic imaging and provided a viable strategy to overcome the treatment challenges.

Key words: Photothermal therapy, Isoindigo, Nanoparticles, Photoacoustic imaging

摘要： The key factor in photothermal therapy lies in the selection of photothermal agents. Traditional photothermal agents generally have problems such as poor photothermal stability and low photothermal conversion efficiency. Herein, we have designed and synthesized an isoindigo (IID) dye. We used isoindigo as the molecular center and introduced common triphenylamine and methoxy groups as rotors. In order to improve the photothermal stability and tumor targeting ability, we encapsulated IID into nanoparticles. As a result, the nanoparticles exhibited high photothermal stability and photothermal conversion efficiency (67%) upon 635 nm laser irradiation. Thus, the nanoparticles demonstrated a significant inhibitory effect on live tumors in photothermal therapy guided by photoacoustic imaging and provided a viable strategy to overcome the treatment challenges.

关键词: Photothermal therapy, Isoindigo, Nanoparticles, Photoacoustic imaging

Yao Pei, Ran Wang, Xiang Rong, Xiang Xia, Hexiang Wang, Zongwei Zhang, Tian Qiu, Saran Long, Jianjun Du, Jiangli Fan, Wen Sun, Xiaojun Peng. Isoindigo nanoparticles for photoacoustic imaging-guided tumor photothermal therapy[J]. Chinese Journal of Chemical Engineering, 2024, 72(8): 19-25.

References

[1] P.P. Liang, Q.Y. Tang, Y. Cai, G.Y. Liu, W.L. Si, J.J. Shao, W. Huang, Q. Zhang, X.C. Dong, Self-quenched ferrocenyl diketopyrrolopyrrole organic nanoparticles with amplifying photothermal effect for cancer therapy, Chem. Sci. 8 (11) (2017) 7457-7463.
[2] G.X. Feng, G.Q. Zhang, D. Ding, Design of superior phototheranostic agents guided by Jablonski diagrams, Chem. Soc. Rev. 49 (22) (2020) 8179-8234.
[3] Y.J. Zhu, Q.G. Li, C.J. Wang, Y. Hao, N.L. Yang, M.J. Chen, J.S. Ji, L.Z. Feng, Z. Liu, Rational design of biomaterials to potentiate cancer thermal therapy, Chem. Rev. 123 (11) (2023) 7326-7378.
[4] C. Li, G. Jiang, J. Yu, W. Ji, L. Liu, P. Zhang, J. Du, C. Zhan, J. Wang, B.Z. Tang, Fluorination enhances NIR-II emission and photothermal conversion efficiency of phototheranostic agents for imaging-guided cancer therapy, Adv. Mater. 35 (3) (2023) e2208229.
[5] Y.M. Yao, Y. Zhang, J.W. Zhang, X.D. Yang, D. Ding, Y. Shi, H.E. Xu, X.K. Gao, Azulene-containing squaraines for photoacoustic imaging and photothermal therapy, ACS Appl. Mater. Interfaces 14 (17) (2022) 19192-19203.
[6] Q. Cheng, Y.L. Tian, H.P. Dang, C.C. Teng, K. Xie, D.L. Yin, L.F. Yan, Antiquenching macromolecular NIR-II probes with high-contrast brightness for imaging-guided photothermal therapy under 1064 nm irradiation, Adv. Healthc. Mater. 11 (1) (2022) e2101697.
[7] H. Gu, W.J. Liu, S.J. Zhen, S.R. Long, W. Sun, J.F. Cao, X.Z. Zhao, J.J. Du, J.L. Fan, X.J. Peng, “Internal and external combined” nonradiative decay-based nanoagents for photoacoustic image-guided highly efficient photothermal therapy, ACS Appl. Mater. Interfaces 13 (39) (2021) 46353-46360.
[8] J. Qi, Y. Fang, R.T.K. Kwok, X. Zhang, X. Hu, J.W.Y. Lam, D. Ding, B.Z. Tang, Highly stable organic small molecular nanoparticles as an advanced and biocompatible phototheranostic agent of tumor in living mice, ACS Nano 11 (7) (2017) 7177-7188.
[9] X. Rong, X. Xia, R. Wang, Z.H. Su, T. Liu, Z.W. Zhang, S.R. Long, J.J. Du, J.L. Fan, W. Sun, X.J. Peng, Near-infrared and highly photostable squaraine-based nanoparticles for photoacoustic imaging guided photothermal therapy, Dyes Pigm. 211 (2023) 111055.
[10] D.M. Xi, M. Xiao, J.F. Cao, L.Y. Zhao, N. Xu, S.R. Long, J.L. Fan, K. Shao, W. Sun, X.H. Yan, X.J. Peng, NIR light-driving barrier-free group rotation in nanoparticles with an 88.3% photothermal conversion efficiency for photothermal therapy, Adv. Mater. 32 (11) (2020) e1907855.
[11] L. Cheng, W.W. He, H. Gong, C. Wang, Q. Chen, Z.P. Cheng, Z. Liu, PEGylated micelle nanoparticles encapsulating a non-fluorescent near-infrared organic dye as a safe and highly-effective photothermal agent for in vivo cancer therapy, Adv. Funct. Mater. 23 (47) (2013) 5893-5902.
[12] Y.J. Liu, P. Bhattarai, Z.F. Dai, X.Y. Chen, Photothermal therapy and photoacoustic imaging via nanotheranostics in fighting cancer, Chem. Soc. Rev. 48 (7) (2019) 2053-2108.
[13] K.W. Chang, Y.B. Liu, D.H. Hu, Q.F. Qi, D.Y. Gao, Y.T. Wang, D.L. Li, X.J. Zhang, H.R. Zheng, Z.H. Sheng, Z. Yuan, Highly stable conjugated polymer dots as multifunctional agents for photoacoustic imaging-guided photothermal therapy, ACS Appl. Mater. Interfaces 10 (8) (2018) 7012-7021.
[14] C. Yin, X.Z. Li, Y. Wang, Y.Y. Liang, S. Zhou, P.C. Zhao, C.S. Lee, Q.L. Fan, W. Huang, Organic semiconducting macromolecular dyes for NIR-II photoacoustic imaging and photothermal therapy, Adv. Funct. Mater. 31 (37) (2021) 2104650.
[15] L. Zhang, W. Zhuang, Y. Yuan, J.J. Shen, W.W. Shi, G. Liu, W.B. Wu, Q. Zhang, G.Q. Shao, Q.B. Mei, Q.L. Fan, Novel glutathione activated smart probe for photoacoustic imaging, photothermal therapy, and safe postsurgery treatment, ACS Appl. Mater. Interfaces 14 (21) (2022) 24174-24186.
[16] Y. Zhang, Q. Shen, Q. Li, P.P. He, J.Y. Li, F. Huang, J. Wang, Y.F. Duan, C. Shen, F. Saleem, Z.M. Luo, L.H. Wang, Ultrathin two-dimensional plasmonic PtAg nanosheets for broadband phototheranostics in both NIR-I and NIR-II biowindows, Adv. Sci. 8 (17) (2021) e2100386.
[17] F. Chen, D.L. Yang, H.F. Shen, M. Deng, Y. Zhang, G.L. Zhong, Y.L. Hu, L.X. Weng, Z.M. Luo, L.H. Wang, Hydrothermal synthesis of novel rhombic dodecahedral SnS nanocrystals for highly efficient photothermal therapy, Chem. Commun. 55 (19) (2019) 2789-2792.
[18] X.Y. Qu, Y. Hong, H. Cai, X. Sun, Q. Shen, D.L. Yang, X.C. Dong, A.H. Jiao, P. Chen, J.J. Shao, Promoted intramolecular photoinduced-electron transfer for multi-mode imaging-guided cancer photothermal therapy, Rare Met. 41 (1) (2022) 56-66.
[19] Y. Ding, Z. Yuan, J.W. Hu, K. Xu, H. Wang, P. Liu, K.Y. Cai, Surface modification of titanium implants with micro-nano-topography and NIR photothermal property for treating bacterial infection and promoting osseointegration, Rare Met. 41 (2) (2022) 673-688.
[20] S. Hong, D.W. Zheng, C. Zhang, Q.X. Huang, S.X. Cheng, X.Z. Zhang, Vascular disrupting agent induced aggregation of gold nanoparticles for photothermally enhanced tumor vascular disruption, Sci. Adv. 6 (23) (2020) eabb0020.
[21] Y.W. Chen, Y.L. Su, S.H. Hu, S.Y. Chen, Functionalized graphene nanocomposites for enhancing photothermal therapy in tumor treatment, Adv. Drug Deliv. Rev. 105 (Pt B) (2016) 190-204.
[22] W. Liu, X.Y. Zhang, L. Zhou, L. Shang, Z.Q. Su, Reduced graphene oxide (rGO) hybridized hydrogel as a near-infrared (NIR)/pH dual-responsive platform for combined chemo-photothermal therapy, J. Colloid Interface Sci. 536 (2019) 160-170.
[23] C.B. Leng, X. Zhang, F.X. Xu, Y. Yuan, H. Pei, Z.H. Sun, L. Li, Z.H. Bao, Engineering gold nanorod-copper sulfide heterostructures with enhanced photothermal conversion efficiency and photostability, Small 14 (12) (2018) e1703077.
[24] Y. Zhang, Y. Li, J.Y. Li, F. Mu, J. Wang, C. Shen, H. Wang, F. Huang, B. Chen, Z.M. Luo, L.H. Wang, DNA-templated Ag@Pd nanoclusters for NIR-II photoacoustic imaging-guided photothermal-augmented nanocatalytic therapy, Adv. Healthc. Mater. 12 (22) (2023) e2300267.
[25] Y. Zhang, H.F. Du, P.P. He, C. Shen, Q. Li, Y.F. Duan, Z.W. Shao, F. Mu, F. Huang, P.Y. Li, P.Q. Gao, P. Yu, Z.M. Luo, L.H. Wang, Exfoliated FePS3 nanosheets for T1-weighted magnetic resonance imaging-guided near-infrared photothermal therapy in vivo, Sci. China Mater. 64 (10) (2021) 2613-2623.
[26] X.S. Wang, Q. Chen, C. Shen, J. Dai, C. Zhu, J.Y. Zhang, Z.W. Wang, Q.S. Song, L. Wang, H. Li, Q. Wang, Z. Liu, Z.M. Luo, X. Huang, W. Huang, Spatially controlled preparation of layered metallic-semiconducting metal chalcogenide heterostructures, ACS Nano 15 (7) (2021) 12171-12179.
[27] H.S. Jung, P. Verwilst, A. Sharma, J. Shin, J.L. Sessler, J.S. Kim, Organic molecule-based photothermal agents: an expanding photothermal therapy universe, Chem. Soc. Rev. 47 (7) (2018) 2280-2297.
[28] C.Y. Yang, L.X. Guo, K.X. Zhang, G. Wang, Q.S. Yu, Z.H. Gan, X.G. Gu, Diradical-featured organic small-molecule photothermal material based on 4, 6-di(2-thienyl) thieno[3, 4-c][1, 2, 5]thiadiazole for photothermal immunotherapy, Adv. Funct. Mater. 33 (52) (2023) 2306360.
[29] Y.Z. Liu, X.Y. Ran, D.H. Zhou, H. Zhang, Y.J. Chen, J.X. Xu, S.Y. Chen, Q.Q. Kong, X.Q. Yu, K. Li, Novel dibenzofulvene-based NIR-II emission phototheranostic agent with an 82.6% photothermal conversion efficiency for photothermal therapy, Adv. Funct. Mater. 34 (8) (2024) 2311365.
[30] B. Guo, Z.M. Huang, Q. Shi, E. Middha, S.D. Xu, L. Li, M. Wu, J.W. Jiang, Q.L. Hu, Z.W. Fu, B. Liu, Organic small molecule based photothermal agents with molecular rotors for malignant breast cancer therapy, Adv. Funct. Mater. 30 (5) (2020) 1907093.
[31] X.H. Zhang, S.S. Xue, W. Pan, H.Y. Wang, K.Y. Wang, N. Li, B. Tang, A heat shock protein-inhibiting molecular photothermal agent for mild-temperature photothermal therapy, Chem. Commun. 59 (2) (2022) 235-238.
[32] H.Y. Wang, J.J. Chang, M.W. Shi, W. Pan, N. Li, B. Tang, A dual-targeted organic photothermal agent for enhanced photothermal therapy, Angew. Chem. Int. Ed Engl. 58 (4) (2019) 1057-1061.
[33] C. Aumaitre, C. Rodriguez-Seco, J. Jover, O. Bardagot, F. Caffy, Y. Kervella, N. Lopez, E. Palomares, R. Demadrille, Visible and near-infrared organic photosensitizers comprising isoindigo derivatives as chromophores: synthesis, optoelectronic properties and factors limiting their efficiency in dye solar cells, J. Mater. Chem. A 6 (21) (2018) 10074-10084.
[34] N.M. Randell, C.L. Radford, J.L. Yang, J. Quinn, D.L. Hou, Y.N. Li, T.L. Kelly, Effect of acceptor unit length and planarity on the optoelectronic properties of isoindigo-thiophene donor-acceptor polymers, Chem. Mater. 30 (14) (2018) 4864-4873.
[35] Y. Rout, V. Chauhan, R. Misra, Synthesis and characterization of isoindigo-based push-pull chromophores, J. Org. Chem. 85 (7) (2020) 4611-4618.
[36] S.M. Vijayan, N. Sparks, J.K. Roy, C. Smith, C. Tate, N.I. Hammer, J. Leszczynski, D.L. Watkins, Evaluating donor effects in isoindigo-based small molecular fluorophores, J. Phys. Chem. A 124 (51) (2020) 10777-10786.
[37] S. Liu, X. Zhou, H. Zhang, H. Ou, J.W.Y. Lam, Y. Liu, L. Shi, D. Ding, B.Z. Tang, Molecular motion in aggregates: manipulating TICT for boosting photothermal theranostics, J. Am. Chem. Soc. 141 (13) (2019) 5359-5368.
[38] G.C. Qing, X.X. Zhao, N.Q. Gong, J. Chen, X.L. Li, Y.L. Gan, Y.C. Wang, Z. Zhang, Y.X. Zhang, W.S. Guo, Y. Luo, X.J. Liang, Thermo-responsive triple-function nanotransporter for efficient chemo-photothermal therapy of multidrug-resistant bacterial infection, Nat. Commun. 10 (1) (2019) 4336.

Isoindigo nanoparticles for photoacoustic imaging-guided tumor photothermal therapy

Isoindigo nanoparticles for photoacoustic imaging-guided tumor photothermal therapy

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Junbo Feng, Junyan Wu, Dongdong Yan, Yadong Zhang. Porous silica nano-flowers stabilized Pt-Pd bimetallic nanoparticles as heterogeneous catalyst for efficiently synthesizing guaiacol from 2-methoxycyclohexanol [J]. Chinese Journal of Chemical Engineering, 2024, 70(6): 222-233.
[2]	Mohamed Mobarak, Saleh Qaysi, Mohamed Saad Ahmed, Yasser F. Salama, Ahmed Mohamed Abbass, Mohamed Abd Elrahman, Hamdy A. Abdel-Gawwad, Moaaz K. Seliem. Insights into the adsorption performance and mechanism of Cr(VI) onto porous nanocomposite prepared from gossans and modified coal interface: Steric, energetic, and thermodynamic parameters interpretations [J]. Chinese Journal of Chemical Engineering, 2023, 61(9): 118-128.
[3]	Wenting Fan, Fang Zhao, Ming Chen, Jian Li, Xuhong Guo. An efficient microreactor with continuous serially connected micromixers for the synthesis of superparamagnetic magnetite nanoparticles [J]. Chinese Journal of Chemical Engineering, 2023, 59(7): 85-91.
[4]	Masoumeh Sheikh Hosseini Lori, Mohammad Delnavaz, Hoda Khoshvaght. Synthesizing and characterizing the magnetic EDTA/chitosan/CeZnO nanocomposite for simultaneous treating of chromium and phenol in an aqueous solution [J]. Chinese Journal of Chemical Engineering, 2023, 58(6): 76-88.
[5]	Jingran Liu, Yue Wu, Jie Tang, Tao Wang, Feng Ni, Qiumin Wu, Xijiao Yang, Ayyaz Ahmad, Naveed Ramzan, Yisheng Xu. Polymeric assembled nanoparticles through kinetic stabilization by confined impingement jets dilution mixer for fluorescence switching imaging [J]. Chinese Journal of Chemical Engineering, 2023, 56(4): 89-96.
[6]	Lianlian Zhao, Fufu Di, Xiaonan Wang, Sumbal Farid, Suzhen Ren. Constructing a hollow core-shell structure of RuO₂ wrapped by hierarchical porous carbon shell with Ru NPs loading for supercapacitor [J]. Chinese Journal of Chemical Engineering, 2023, 55(3): 93-100.
[7]	Xueqing Chen, Weiqun Gao, Yan Sun, Xiaoyan Dong. Multiple effects of polydopamine nanoparticles on Cu²⁺-mediated Alzheimer's β-amyloid aggregation [J]. Chinese Journal of Chemical Engineering, 2023, 54(2): 144-152.
[8]	Zhesai Zhao, Qingwen Han, Wenwen He, Xiaolong Han. Preparation of ZIF-8@PEBAX/PVDF nanocomposite membrane by the combination of self-assembly and in-situ growth for removing thiophene from the model gasoline [J]. Chinese Journal of Chemical Engineering, 2023, 64(12): 177-187.
[9]	Lijian Shi, Yaping Zhang, Yujia Tong, Wenlong Ding, Weixing Li. Plant-inspired biomimetic hybrid PVDF membrane co-deposited by tea polyphenols and 3-amino-propyl-triethoxysilane for high-efficiency oil-in-water emulsion separation [J]. Chinese Journal of Chemical Engineering, 2023, 53(1): 170-180.
[10]	Baolong Niu, Min Li, Jianhong Jia, Lixuan Ren, Xin Gang, Bin Nie, Yanying Fan, Xiaojie Lian, Wenfeng Li. Preparation and functional study of pH-sensitive amorphous calcium phosphate nanocarriers [J]. Chinese Journal of Chemical Engineering, 2022, 48(8): 244-252.
[11]	Yingmeng Zhang, Luting Liu, Qingwei Deng, Wanlin Wu, Yongliang Li, Xiangzhong Ren, Peixin Zhang, Lingna Sun. Hybrid CuO-Co₃O₄ nanosphere/RGO sandwiched composites as anode materials for lithium-ion batteries [J]. Chinese Journal of Chemical Engineering, 2022, 47(7): 185-192.
[12]	Dongze Ma, Ye Tian, Tiefei He, Xiaobiao Zhu. Preparation of novel magnetic nanoparticles as draw solutes in forward osmosis desalination [J]. Chinese Journal of Chemical Engineering, 2022, 46(6): 223-230.
[13]	Yang Gui, Kai Cheng, Ruojiao Wang, Sirui Liu, Chenyang Zhao, Rui Zhang, Ming Wang, Zhen Cheng, Meng Yang. Photoacoustic detection of follicular thyroid carcinoma using targeted Nano-Au-Tripods [J]. Chinese Journal of Chemical Engineering, 2022, 44(4): 1-7.
[14]	Chen Gu, Wenqiang Weng, Cong Lu, Peng Tan, Yao Jiang, Qiang Zhang, Xiaoqin Liu, Linbing Sun. Decorating MXene with tiny ZIF-8 nanoparticles: An effective approach to construct composites for water pollutant removal [J]. Chinese Journal of Chemical Engineering, 2022, 42(2): 42-48.
[15]	Yaping Wang, Songyue Cheng, Wendi Fan, Yikun Jiang, Jie Yang, Zaizai Tong, Guohua Jiang. Dual responsive block copolymer coated hollow mesoporous silica nanoparticles for glucose-mediated transcutaneous drug delivery [J]. Chinese Journal of Chemical Engineering, 2022, 51(11): 35-42.