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Nano Research 2017, 10(3): 794-801 https://doi.org/10.1007/s12274-016-1332-2
Research Article | Issue | Published: 23 December 2016

Small-molecule diketopyrrolopyrrole-based therapeutic nanoparticles for photoacoustic imaging-guided photothermal therapy

Show Author's Information Yu Cai1,§,  Weili Si1,§,  Qianyun Tang1,  Pingping Liang1,  Chengwu Zhang1,  Peng Chen2,  Qi Zhang3( ),  Wei Huang1( ),  Xiaochen Dong1( )
Key Laboratory of Flexible Electronics (KLOFE) & Institute of Advanced Materials (IAM) Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM) Nanjing Tech University (NanjingTech), 30 South Puzhu Road Nanjing 211816 China
School of Chemical and Biomedical Engineering Nanyang Technological University, 70 Nanyang Drive, N1.3-B3-08 Singapore
School of Pharmaceutical Sciences Nanjing Tech University (NanjingTech), 30 South Puzhu Road Nanjing 211816 China

§ These authors contributed equally to this work.

Keywords:
photoacoustic imaging, photothermal therapy, diketopyrrolopyrrole, donor-acceptor-donor
Cite this article:
Cai Y, Si W, Tang Q, et al. Small-molecule diketopyrrolopyrrole-based therapeutic nanoparticles for photoacoustic imaging-guided photothermal therapy. Nano Research, 2017, 10(3): 794-801. https://doi.org/10.1007/s12274-016-1332-2
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Abstract Full text Electronic supplementary material About this article

Therapeutic nanoparticles (NPs) based on the donor-acceptor-donor structured small organic molecule diketopyrrolopyrrole (SDPP) were prepared using a simple reprecipitation approach. These near-infrared radiation-absorbing NPs have high photothermal conversion efficiency and are able to selectively target cancer tissues through the enhanced permeability and retention effect. Benefiting from these advantages, SDPP NPs can serve as an excellent therapeutic agent for highly efficient and noninvasive photoacoustic imaging-guided photothermal therapy. Experiments using mouse tumor models showed that the SDPP NPs exhibited exceptional tumor ablation ability under laser irradiation (660 nm, 1.0 W·cm-2), even at a low dose (0.16 mg·kg-1).


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About this article

Small-molecule diketopyrrolopyrrole-based therapeutic nanoparticles for photoacoustic imaging-guided photothermal therapy

Show Author's information Yu Cai1,§, Weili Si1,§, Qianyun Tang1, Pingping Liang1, Chengwu Zhang1, Peng Chen2, Qi Zhang3( ), Wei Huang1( ), Xiaochen Dong1( )
Key Laboratory of Flexible Electronics (KLOFE) & Institute of Advanced Materials (IAM) Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM) Nanjing Tech University (NanjingTech), 30 South Puzhu Road Nanjing 211816 China
School of Chemical and Biomedical Engineering Nanyang Technological University, 70 Nanyang Drive, N1.3-B3-08 Singapore
School of Pharmaceutical Sciences Nanjing Tech University (NanjingTech), 30 South Puzhu Road Nanjing 211816 China

§ These authors contributed equally to this work.

Abstract

Therapeutic nanoparticles (NPs) based on the donor-acceptor-donor structured small organic molecule diketopyrrolopyrrole (SDPP) were prepared using a simple reprecipitation approach. These near-infrared radiation-absorbing NPs have high photothermal conversion efficiency and are able to selectively target cancer tissues through the enhanced permeability and retention effect. Benefiting from these advantages, SDPP NPs can serve as an excellent therapeutic agent for highly efficient and noninvasive photoacoustic imaging-guided photothermal therapy. Experiments using mouse tumor models showed that the SDPP NPs exhibited exceptional tumor ablation ability under laser irradiation (660 nm, 1.0 W·cm-2), even at a low dose (0.16 mg·kg-1).

Keywords: photoacoustic imaging, photothermal therapy, diketopyrrolopyrrole, donor-acceptor-donor

References(43)

1

Zhu, C. L.; Liu, L. B.; Yang, Q.; Lv, F. T.; Wang, S. Water-soluble conjugated polymers for imaging, diagnosis, and therapy. Chem. Rev. 2012, 112, 4687-4735.
DOI Google Scholar
2

Liu, T.; Wang, C.; Gu, X.; Gong, H.; Cheng, L.; Shi, X. Z.; Feng, L. Z.; Sun, B. Q.; Liu, Z. Drug delivery with PEGylated MoS2 nano-sheets for combined photothermal and chemotherapy of cancer. Adv. Mater. 2014, 26, 3433-3440.
DOI Google Scholar
3

Shi, S. X.; Chen, F.; Ehlerding, E. B.; Cai, W. B. Surface engineering of graphene-based nanomaterials for biomedical applications. Bioconjugate Chem. 2014, 25, 1609-1619.
DOI Google Scholar
4

Cai, Y.; Tang, Q. Y.; Wu, X. J.; Si, W. L.; Zhang, Q.; Huang, W.; Dong, X. C. Bromo-substituted diketopyrrolopyrrole derivative with specific targeting and high efficiency for photodynamic therapy. ACS Appl. Mater. Interfaces 2016, 8, 10737-10742.
DOI Google Scholar
5

Shi, H. X.; Sun, W. C.; Liu, C. B.; Gu, G. Y.; Ma, B.; Si, W. L.; Fu, N.; Zhang, Q.; Huang, W.; Dong, X. C. Tumor-targeting, enzyme-activated nanoparticles for simultaneous cancer diagnosis and photodynamic therapy. J. Mater. Chem. B 2016, 4, 113-120.
DOI Google Scholar
6

Huang, Y. J.; Hu, H.; Li, R. Q.; Yu, B. R.; Xu, F. J. Versatile types of MRI-visible cationic nanoparticles involving pullulan polysaccharides for multifunctional gene carriers. ACS Appl. Mater. Interfaces 2016, 8, 3919-3927.
DOI Google Scholar
7

Zhu, X. J.; Feng, W.; Chang, J.; Tan, Y. W.; Li, J. C.; Chen, M.; Sun, Y.; Li, F. Y. Temperature-feedback upconversion nanocomposite for accurate photothermal therapy at facile temperature. Nat. Commun. 2016, 7, 10437.
DOI Google Scholar
8

Huang, P.; Rong, P. F.; Lin, J.; Li, W. W.; Yan, X. F.; Zhang, M. G.; Nie, L. M.; Niu, G.; Lu, J.; Wang, W. et al. Triphase interface synthesis of plasmonic gold bellflowers as near-infrared light mediated acoustic and thermal theranostics. J. Am. Chem. Soc. 2014, 136, 8307-8313.
DOI Google Scholar
9

Song, G. S.; Hao, J. L.; Liang, C.; Liu, T.; Gao, M.; Cheng, L.; Hu, J. Q.; Liu, Z. Degradable molybdenum oxide nanosheets with rapid clearance and efficient tumor homing capabilities as a therapeutic nanoplatform. Angew. Chem., Int. Ed. 2016, 55, 2122-2126.
DOI Google Scholar
10

Song, X. J.; Chen, Q.; Liu, Z. Recent advances in the development of organic photothermal nano-agents. Nano Res. 2015, 8, 340-354.
DOI Google Scholar
11

Lokerse, W. J. M.; Kneepkens, E. C. M.; ten Hagen, T. L. M.; Eggermont, A. M. M.; Grüll, H.; Koning, G. A. In depth study on thermosensitive liposomes: Optimizing formulations for tumor specific therapy and in vitro to in vivo relations. Biomaterials 2016, 82, 138-150.
DOI Google Scholar
12

Zhou, Z. G.; Sun, Y.; Shen, J. C.; Wei, J.; Yu, C.; Kong, B.; Liu, W.; Yang, H.; Yang, S. P.; Wang, W. Iron/iron oxide core/shell nanoparticles for magnetic targeting MRI and near-infrared photothermal therapy. Biomaterials 2014, 35, 7470-7478.
DOI Google Scholar
13

Yang, K.; Xu, H.; Cheng, L.; Sun, C. Y.; Wang, J.; Liu, Z. In vitro and in vivo near-infrared photothermal therapy of cancer using polypyrrole organic nanoparticles. Adv. Mater. 2012, 24, 5586-5592.
DOI Google Scholar
14

Liu, Y. L.; Yang, M.; Zhang, J. P.; Zhi, X.; Li, C.; Zhang, C. L.; Pan, F.; Wang, K.; Yang, Y. M.; Martinez de la Fuentea, J. et al. Human induced pluripotent stem cells for tumor targeted delivery of gold nanorods and enhanced photothermal therapy. ACS Nano 2016, 10, 2375-2385.
DOI Google Scholar
15

Huang, P.; Lin, J.; Wang, S. J.; Zhou, Z. J.; Li, Z. M.; Wang, Z.; Zhang, C. L.; Yue, X. Y.; Niu, G.; Yang, M. et al. Photosensitizer-conjugated silica-coated gold nanoclusters for fluorescence imaging-guided photodynamic therapy. Biomaterials 2013, 34, 4643-4654.
DOI Google Scholar
16

Li, W. W.; Rong, P. F.; Yang, K.; Huang, P.; Sun, K.; Chen, X. Y. Semimetal nanomaterials of antimony as highly efficient agent for photoacoustic imaging and photothermal therapy. Biomaterials 2015, 45, 18-26.
DOI Google Scholar
17

Piao, J. G.; Liu, D.; Hu, K.; Wang, L. M.; Gao, F.; Xiong, Y. J.; Yang, L. H. Cooperative nanoparticle system for photothermal tumor treatment without skin damage. ACS Appl. Mater. Interfaces 2016, 8, 2847-2856.
DOI Google Scholar
18

Gao, S.; Zhang, L. W.; Wang, G. H.; Yang, K.; Chen, M. L.; Tian, R.; Ma, Q. J.; Zhu, L. Hybrid graphene/Au activatable theranostic agent for multimodalities imaging guided enhanced photothermal therapy. Biomaterials 2016, 79, 36-45.
DOI Google Scholar
19

Chen, D. Q.; Wang, C.; Nie, X.; Li, S. M.; Li, R. M.; Guan, M. R.; Liu, Z.; Chen, C. Y.; Wang, C. R.; Shu, C. Y. et al. Photoacoustic imaging guided near-infrared photothermal therapy using highly water-dispersible single-walled carbon nanohorns as theranostic agents. Adv. Funct. Mater. 2014, 24, 6621-6628.
DOI Google Scholar
20

Chen, L.; Zhong, X. Y.; Yi, X.; Huang, M.; Ning, P.; Liu, T.; Ge, C. C.; Chai, Z. F.; Liu, Z.; Yang, K. Radionuclide (131)I labeled reduced graphene oxide for nuclear imaging guided combined radio- and photothermal therapy of cancer. Biomaterials 2015, 66, 21-28.
DOI Google Scholar
21

Wang, L.; Yang, P. P.; Zhao, X. X.; Wang, H. Self-assembled nanomaterials for photoacoustic imaging. Nanoscale 2016, 8, 2488-2509.
DOI Google Scholar
22

Muhanna, N.; Jin, C. S.; Huynh, E.; Chan, H.; Qiu, Y.; Jiang, W. L.; Cui, L. Y.; Burgess, L.; Akens, M. K.; Chen, J. et al. Phototheranostic porphyrin nanoparticles enable visualization and targeted treatment of head and neck cancer in clinically relevant models. Theranostics 2015, 5, 1428-1443.
DOI Google Scholar
23

Hu, Y.; Zhou, Y. Q.; Zhao, N. N.; Liu, F. S.; Xu, F. J. Multifunctional pDNA-conjugated polycationic Au nanorod-coated Fe3O4 hierarchical nanocomposites for trimodal imaging and combined photothermal/gene therapy. Small 2016, 12, 2459-2468.
DOI Google Scholar
24

Zhao, N.; Li, J.; Zhou, Y. Q.; Hu, Y.; Wang, R. R.; Ji, Z. X.; Liu, F. S.; Xu,F.-J. Hierarchical nanohybrids of gold nanorods and PGMA-based polycations for multifunctional theranostics. Adv. Funct. Mater. 2016, 26, 5848-5861.
DOI Google Scholar
25

Kaur, M.; Choi, D. H. Diketopyrrolopyrrole: Brilliant red pigment dye-based fluorescent probes and their applications. Chem. Soc. Rev. 2015, 44, 58-77.
DOI Google Scholar
26

Bürckstummer, H.; Weissenstein, A.; Bialas, D.; Würthner, F. Synthesis and characterization of optical and redox properties of bithiophene-functionalized diketopyrrolopyrrole chromophores. J. Org. Chem. 2011, 76, 2426-2432.
DOI Google Scholar
27

Yi, Z. R.; Wang, S.; Liu, Y. Q. Design of high-mobility diketopyrrolopyrrole-based π-conjugated copolymers for organic thin-film transistors. Adv. Mater. 2015, 27, 3589-3606.
DOI Google Scholar
28

Shen, X. Y.; Wang, Y. J.; Zhang, H. K.; Qin, A. J.; Sun, J. Z.; Tang, B. Z. Conjugates of tetraphenylethene and diketopyrrolopyrrole: Tuning the emission properties with phenyl bridges. Chem. Commun. 2014, 50, 8747-8750.
DOI Google Scholar
29

Zhang, Y.; Kim, C.; Lin, J.; Nguyen,T.-Q. Solution-processed ambipolar field-effect transistor based on diketopyrrolopyrrole functionalized with benzothiadiazole. Adv. Funct. Mater. 2012, 22, 97-105.
DOI Google Scholar
30

Zou, Y. P.; Gendron, D.; Neagu-Plesu, R.; Leclerc, M. Synthesis and characterization of new low-bandgap diketopyrrolopyrrole-based copolymers. Macromolecules 2009, 42, 6361-6365.
DOI Google Scholar
31

Lan, M. H.; Zhang, J. F.; Zhu, X. Y.; Wang, P. F.; Chen, X. F.; Lee,C.-S.; Zhang, W. J. Highly stable organic fluorescent nanorods for living-cell imaging. Nano Res. 2015, 8, 2380-2389.
DOI Google Scholar
32

Schmitt, J.; Heitz, V.; Sour, A.; Bolze, F.; Ftouni, H.; Nicoud, J. F.; Flamigni, L.; Ventura, B. Diketopyrrolopyrrole-porphyrin conjugates with high two-photon absorption and singlet oxygen generation for two-photon photodynamic therapy. Angew. Chem., Int. Ed. 2015, 54, 169-173.
DOI Google Scholar
33

Kanimozhi, C.; Yaacobi-Gross, N.; Chou, K. W.; Amassian, A.; Anthopoulos, T. D.; Patil, S. Diketopyrrolopyrrole-diketopyrrolopyrrole-based conjugated copolymer for high-mobility organic field-effect transistors. J. Am. Chem. Soc. 2012, 134, 16532-16535.
DOI Google Scholar
34

Kline, R. J.; McGehee, M. D.; Kadnikova, E. N.; Liu, J. S.; Fréchet, J. M. J.; Toney, M. F. Dependence of regioregular poly(3-hexylthiophene) film morphology and field-effect mobility on molecular weight. Macromolecules 2005, 38, 3312-3319.
DOI Google Scholar
35

Lee, O. P.; Yiu, A. T.; Beaujuge, P. M.; Woo, C. H.; Holcombe, T. W.; Millstone, J. E.; Douglas, J. D.; Chen, M. S.; Fréchet, J. M. J. Efficient small molecule bulk heterojunction solar cells with high fill factors via pyrene-directed molecular self-assembly. Adv. Mater. 2011, 23, 5359-5363.
DOI Google Scholar
36

Jana, A.; Devi, K. S. P.; Maiti, T. K.; Singh, N. D. P. Perylene-3-ylmethanol: Fluorescent organic nanoparticles as a single-component photoresponsive nanocarrier with real-time monitoring of anticancer drug release. J. Am. Chem. Soc. 2012, 134, 7656-7659.
DOI Google Scholar
37

Peng, H. S.; Chiu, D. T. Soft fluorescent nanomaterials for biological and biomedical imaging. Chem. Soc. Rev. 2015, 44, 4699-4722.
DOI Google Scholar
38

Hauert, S.; Bhatia, S. N. Mechanisms of cooperation in cancer nanomedicine: Towards systems nanotechnology. Trends Biotechnol. 2014, 32, 448-455.
DOI Google Scholar
39

Fan, Q. L.; Cheng, K.; Yang, Z.; Zhang, R. P.; Yang, M.; Hu, X.; Ma, X. W.; Bu, L. H.; Lu, X. M.; Xiong, X. X. et al. Perylene-diimide-based nanoparticles as highly efficient photoacoustic agents for deep brain tumor imaging in living mice. Adv. Mater. 2015, 27, 843-847.
DOI Google Scholar
40

Grzybowski, M.; Hugues, V.; Blanchard-Desce, M.; Gryko, D. T. Two-photon-induced fluorescence in new π-expanded diketopyrrolopyrroles. Chem. -Eur. J. 2014, 20, 12493-12501.
DOI Google Scholar
41

Aioub, M.; El-Sayed, M. A. A real-time surface enhanced raman spectroscopy study of plasmonic photothermal cell death using targeted gold nanoparticles. J. Am. Chem. Soc. 2016, 138, 1258-1264.
DOI Google Scholar
42

Wang, Z. H.; Sun, J. H.; Qiu, Y. Q.; Li, W.; Guo, X. M.; Li, Q. P.; Zhang, H. B.; Zhou, J. L.; Du, Y. Z.; Yuan, H. et al. Specific photothermal therapy to the tumors with high EphB4 receptor expression. Biomaterials 2015, 68, 32-41.
DOI Google Scholar
43

Saravanakumar, G.; Lee, J.; Kim, J.; Kim, W. J. Visible light-induced singlet oxygen-mediated intracellular disassembly of polymeric micelles co-loaded with a photosensitizer and an anticancer drug for enhanced photodynamic therapy. Chem. Commun. 2015, 51, 9995-9998.
DOI Google Scholar
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Publication history
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Acknowledgements

Publication history

Received: 31 August 2016
Revised: 08 October 2016
Accepted: 12 October 2016
Published: 23 December 2016
Issue date: March 2017

Copyright

© Tsinghua University Press and Springer-Verlag Berlin Heidelberg 2016

Acknowledgements

Acknowledgements

The work was supported by the National Basic Research Program of China (No. 2014CB660808), the National Natural Science Foundation of China (Nos. 61525402 and 21275076), Key University Science Research Project of Jiangsu Province (No. 15KJA430006), Program for New Century Excellent Talents in University (No. NCET-13-0853), QingLan Project, Jiangsu Province Science Foundation for Six Great Talent Peak (No. XCL-018).

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