Applications of Hyaluronic Acid Nanomaterials in Fluorescence/Photoacoustic Imaging and Phototherapy
Received date: 2021-05-17
Online published: 2021-07-29
Supported by
Ministry of Education of China(IRT1148); Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD); Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM); open research fund of State Key Laboratory of Organic Electronics and Information Displays
The biomedical applications of fluorescence/photoacoustic imaging and phototherapy have attracted more and more attention. However, many fluorescent/photoacoustic contrast agents have some common problems, such as poor biocompatibility, lack of tumor targeting, low signal-to-noise ratio, single function and so on, which seriously limit their application in diagnosis and treatment. Hyaluronic acid (HA) exhibits excellent biocompatibility and active tumor targeting, can be degraded by hyaluronidase, and is easy to be chemically modified and realize the cooperation of a variety of supramolecular weak interactions. Therefore, HA has been combined with fluorescent/photoacoustic contrast agents to prepare nanomaterials, which greatly improves the labeling performance and therapeutic effects in cells and even in vivo. In this paper, the preparation methods of nanomaterials by combining these two kinds of materials are reviewed, and the relationships between the structure and performance of nanomaterials are emphasized, which provides guidance for their future design and development. Finally, the main problems and important research directions in the future are analyzed and prospected.
Lixiang Pan , Yanqin Huang , Kuang Sheng , Rui Zhang , Quli Fan , Wei Huang . Applications of Hyaluronic Acid Nanomaterials in Fluorescence/Photoacoustic Imaging and Phototherapy[J]. Acta Chimica Sinica, 2021 , 79(9) : 1097 -1106 . DOI: 10.6023/A21050219
| [1] | Torre, L. A.; Bray, F.; Siegel, R. L.; Ferlay, J.; Lortet-Tieulent, J.; Jemal, A. Ca-Cancer J. Clin. 2015, 65, 87. |
| [2] | Chen, W. Q.; Zheng, R. S.; Baade, P. D.; Zhang, S. W.; Zeng, H. M.; Bray, F.; Jemal, A.; Yu, X. Q.; He, J. Ca-Cancer J. Clin. 2016, 66, 115. |
| [3] | Kobayashi, H.; Ogawa, M.; Alford, R.; Choyke, P. L.; Urano, Y. Chem. Rev. 2010, 110, 2620. |
| [4] | Kim, D.; Ryu, H. G.; Ahn, K. H. Org. Biomol. Chem. 2014, 12, 4550. |
| [5] | Wang, X.; Xie, X.; Ku, G.; Wang, L. V. J. Biomed. Opt. 2006, 11, 024015. |
| [6] | Luo, S. L.; Zhang, E. L.; Su, Y. P.; Cheng, T. M.; Shi, C. M. Biomaterials 2011, 32, 7127. |
| [7] | Lu, X. M.; Chen, P. F.; Hu, W. B.; Tang, Y. F.; Huang, W.; Fan, Q. L. Prog. Chem. 2017, 29, 119. |
| [8] | Gao, P.; Pan, W.; Li, N.; Tang, B. Chem. Sci. 2019, 10, 6035. |
| [9] | Antaris, A. L.; Chen, H.; Diao, S.; Ma, Z. R.; Zhang, Z.; Zhu, S. J.; Wang, J.; Lozano, A. X.; Fan, Q. L.; Chew, L. L.; Zhu, M.; Cheng, K.; Hong, X. C.; Dai, H. J.; Cheng, Z. Nat. Commun. 2017, 8, 11. |
| [10] | Ren, X. J.; Lu, X. M.; Fan, Q. L.; Huang, W. Prog. Chem. 2013, 25, 1739. |
| [11] | Sang, R. Y.; Xu, X. P.; Wang, Q.; Fan, Q. L.; Huang, W. Acta Chim. Sinica 2020, 78, 901. |
| [12] | Ren, T. B.; Wang, Z. Y.; Xiang, Z.; Lu, P.; Lai, H. H.; Yuan, L.; Zhang, X. B.; Tan, W. H. Angew. Chem. Int. Ed. 2021, 60, 800. |
| [13] | Lei, Z. H.; Zhang, F. Angew. Chem. Int. Ed. 2021, 60, 16294. |
| [14] | Song, K. H.; Stein, E. W.; Margenthaler, J. A.; Wang, L. V. J. Biomed. Opt. 2008, 13, 054033. |
| [15] | Pu, K. Y.; Shuhendler, A. J.; Jokerst, J. V.; Mei, J. G.; Gambhir, S. S.; Bao, Z. N.; Rao, J. H. Nat. Nanotechnol. 2014, 9, 233. |
| [16] | 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.; Huang, W.; Zhao, H.; Cheng, Z. Adv. Mater. 2015, 27, 843. |
| [17] | Yang, Z.; Dai, Y. L.; Yin, C.; Fan, Q. L.; Zhang, W. S.; Song, J.; Yu, G. C.; Tang, W.; Fan, W. P.; Yung, B. C.; Li, J.; Li, X.; Li, X. C.; Tang, Y. F.; Huang, W.; Song, J. B.; Chen, X. Y. Adv. Mater. 2018, 30, 8. |
| [18] | Liu, Y. J.; Bhattarai, P.; Dai, Z. F.; Chen, X. Y. Chem. Soc. Rev. 2019, 48, 2053. |
| [19] | Hu, W. B.; He, T. C.; Jiang, R. C.; Yin, J.; Li, L.; Lu, X. M.; Zhao, H.; Zhang, L.; Huang, L.; Sun, H. D.; Huang, W.; Fan, Q. L. Chem. Commun. 2017, 53, 1680. |
| [20] | Wang, Q.; Dai, Y. N.; Xu, J. Z.; Cai, J.; Niu, X. R.; Zhang, L.; Chen, R. F.; Shen, Q. M.; Huang, W.; Fan, Q. L. Adv. Funct. Mater. 2019, 29, 12. |
| [21] | Li, J.; Jiang, R. C.; Wang, Q.; Li, X.; Hu, X. M.; Yuan, Y.; Lu, X. M.; Wang, W. J.; Huang, W.; Fan, Q. L. Biomaterials 2019, 217, 9. |
| [22] | Wang, Q.; Xia, B.; Xu, J. Z.; Niu, X. R.; Cai, J.; Shen, Q. M.; Wang, W. J.; Huang, W.; Fan, Q. L. Mat. Chem. Front. 2019, 3, 650. |
| [23] | Xie, N.; Feng, K.; Chen, B.; Zhao, M.; Peng, S.; Zhang, L. P.; Tung, C. H.; Wu, L. Z. J. Mater. Chem. B 2014, 2, 502. |
| [24] | Garland, M.; Yim, J. J.; Bogyo, M. Cell Chem. Biol. 2016, 23, 122. |
| [25] | Li, K.; Liu, B. Chem. Soc. Rev. 2014, 43, 6570. |
| [26] | Yan, T.; Liu, Z. H.; Song, X. Y.; Zhang, S. S. Acta Chim. Sinica 2020, 78, 657. |
| [27] | Toole, B. P. Nat. Rev. Cancer 2004, 4, 528. |
| [28] | Tripodo, G.; Trapani, A.; Torre, M. L.; Giammona, G.; Trapani, G.; Mandracchia, D. Eur. J. Pharm. Biopharm. 2015, 97, 400. |
| [29] | Saravanakumar, G.; Deepagan, V. G.; Jayakumar, R.; Park, J. H. J. Biomed. Nanotechnol. 2014, 10, 17. |
| [30] | Jiang, G.; Park, K.; Kim, J.; Kim, K. S.; Hahn, S. K. Mol. Pharm. 2009, 6, 727. |
| [31] | Luo, Y.; Prestwich, G. D. Bioconjugate Chem. 1999, 10, 755. |
| [32] | Luo, Y.; Prestwich, G. D. Bioconjugate Chem. 2001, 12, 1085. |
| [33] | Shi, H. X.; Sun, W. C.; Liu, C. B.; Gu, G. Y.; Ma, B.; Si, W. L.; Fu, N. N.; Zhang, Q.; Huang, W.; Dong, X. C. J. Mater. Chem. B 2016, 4, 113. |
| [34] | Bhang, S. H.; Won, N.; Lee, T. J.; Jin, H.; Nam, J.; Park, J.; Chung, H.; Park, H. S.; Sung, Y. E.; Hahn, S. K.; Kim, B. S.; Kim, S. ACS Nano 2009, 3, 1389. |
| [35] | Hill, T. K.; Abdulahad, A.; Kelkar, S. S.; Marini, F. C.; Long, T. E.; Provenzale, J. M.; Mohs, A. M. Bioconjugate Chem. 2015, 26, 294. |
| [36] | Yoon, H. Y.; Koo, H.; Choi, K. Y.; Lee, S. J.; Kim, K.; Kwon, I. C.; Leary, J. F.; Park, K.; Yuk, S. H.; Park, J. H.; Choi, K. Biomaterials 2012, 33, 3980. |
| [37] | Jalani, G.; Naccache, R.; Rosenzweig, D. H.; Lerouge, S.; Haglund, L.; Vetrone, F.; Cerruti, M. Nanoscale 2015, 7, 11255. |
| [38] | Wang, H. N.; Sun, H. F.; Wei, H.; Xi, P.; Nie, S. M.; Ren, Q. S. J. Nanopart. Res. 2014, 16, 13. |
| [39] | Huang, Y. Q.; Yao, X.; Zhang, R.; Lang, O. Y.; Jiang, R. C.; Liu, X. F.; Song, C. X.; Zhang, G. W.; Fan, Q. L.; Wang, L. H.; Huang, W. ACS Appl. Mater. Interfaces 2014, 6, 19144. |
| [40] | Huang, Y. Q.; Song, C. X.; Li, H. C.; Zhang, R.; Jiang, R. C.; Liu, X. F.; Zhang, G. W.; Fan, Q. L.; Wang, L. H.; Huang, W. ACS Appl. Mater. Interfaces 2015, 7, 21529. |
| [41] | Wu, W. T.; Shen, J.; Banerjee, P.; Zhou, S. Q. Biomaterials 2010, 31, 7555. |
| [42] | Lee, H.; Lee, K.; Kim, I. K.; Park, T. G. Adv. Funct. Mater. 2009, 19, 1884. |
| [43] | Lee, H.; Lee, K.; Kim, I. K.; Park, T. G. Biomaterials 2008, 29, 4709. |
| [44] | Jeong, E. H.; Jung, G.; Hong, C. A.; Lee, H. Arch. Pharm. Res. 2014, 37, 53. |
| [45] | Zhang, L. W.; Gao, S.; Zhang, F.; Yang, K.; Ma, Q. J.; Zhu, L. ACS Nano 2014, 8, 12250. |
| [46] | Wang, X.; Chen, J. T.; Zhu, H. M.; Chen, X. Y.; Yan, X. P. Anal. Chem. 2013, 85, 10225. |
| [47] | Chen, Z. W.; Liu, Z.; Li, Z. H.; Ju, E. G.; Gao, N.; Zhou, L.; Ren, J. S.; Qu, X. G. Biomaterials 2015, 39, 15. |
| [48] | Gong, H.; Peng, R.; Liu, Z. Adv. Drug Deliv. Rev. 2013, 65, 1951. |
| [49] | Mani, V.; Chen, S. M.; Lou, B. S. Int. J. Electrochem. Sci. 2013, 8, 11641. |
| [50] | Lim, S. Y.; Shen, W.; Gao, Z. Q. Chem. Soc. Rev. 2015, 44, 362. |
| [51] | Hou, L.; Yang, X. M.; Ren, J. X.; Wang, Y. C.; Zhang, H. J.; Feng, Q. H.; Shi, Y. Y.; Shan, X. N.; Yuan, Y. J.; Zhang, Z. Z. Int. J. Nanomed. 2016, 11, 607. |
| [52] | Xie, L. S.; Wang, G. H.; Zhou, H.; Zhang, F.; Guo, Z. D.; Liu, C.; Zhang, X. Z.; Zhu, L. Biomaterials 2016, 103, 219. |
| [53] | Liu, S. Y.; Zhao, N.; Cheng, Z.; Liu, H. G. Nanoscale 2015, 7, 6836. |
| [54] | Abdullah-Al, N.; Lee, J. E.; Jeong, J. H.; Park, S. Y. Biomacromolecules 2013, 14, 4082. |
| [55] | Swierczewska, M.; Choi, K. Y.; Mertz, E. L.; Huang, X.; Zhang, F.; Zhu, L.; Yoon, H. Y.; Park, J. H.; Bhirde, A.; Lee, S.; Chen, X. Nano Lett. 2012, 12, 3613. |
| [56] | Zhu, C. L.; Liu, L. B.; Yang, Q.; Lv, F. T.; Wang, S. Chem. Rev. 2012, 112, 4687. |
| [57] | Song, W.; Yin, C.; Jiang, R.; Lu, X.; Quan, Y.; Tian, C.; Li, J.; Hu, W.; Sun, P.; Deng, W.; Fan, Q.; Huang, W. Polym. Chem. 2015, 6, 5295. |
| [58] | Huang, Y. Q.; Sun, L. J.; Zhang, R.; Hu, J.; Liu, X. F.; Jiang, R. C.; Fan, Q. L.; Wang, L. H.; Huang, W. ACS Appl. Bio Mater. 2019, 2, 2421. |
| [59] | Wang, Y. F.; Zhang, W. S.; Sun, P. F.; Cai, Y.; Xu, W. G.; Fan, Q. L.; Hu, Q. G.; Han, W. Theranostics 2019, 9, 391. |
| [60] | Huang, Y. Q.; Zhang, R.; Zhao, Y. K.; Chen, H.; Jiang, R. C.; Liu, X. F.; Fan, Q. L.; Wang, L. H.; Huang, W. New J. Chem. 2017, 41, 4998. |
| [61] | Wang, X. C.; Chang, G.; Cao, R. J.; Meng, L. J. Prog. Chem. 2015, 27, 794. |
| [62] | Cho, H. J.; Yoon, H. Y.; Koo, H.; Ko, S. H.; Shim, J. S.; Cho, J. H.; Park, J. H.; Kim, K.; Kwon, I. C.; Kim, D.-D. J. Controlled Release 2012, 162, 111. |
| [63] | Liang, X. L.; Fang, L.; Li, X. D.; Zhang, X.; Wang, F. Biomaterials 2017, 132, 72. |
| [64] | Sun, W.; Guo, S. G.; Hu, C.; Fan, J. L.; Peng, X. J. Chem. Rev. 2016, 116, 7768. |
| [65] | Mok, H.; Jeong, H.; Kim, S. J.; Chung, B. H. Chem. Commun. 2012, 48, 8628. |
| [66] | Kim, J.; Chong, Y.; Mok, H. Macromol. Biosci. 2014, 14, 881. |
| [67] | Park, H. S.; Lee, J. E.; Cho, M. Y.; Hong, J. H.; Cho, S. H.; Lim, Y. T. Macromol. Rapid Commun. 2012, 33, 1549. |
| [68] | Miki, K.; Inoue, T.; Kobayashi, Y.; Nakano, K.; Matsuoka, H.; Yamauchi, F.; Yano, T.; Ohe, K. Biomacromolecules 2015, 16, 219. |
| [69] | Wang, G.; Zhang, F.; Tian, R.; Zhang, L.; Fu, G.; Yang, L.; Zhu, L. ACS Appl. Mater. Interfaces 2016, 8, 5608. |
| [70] | Zhang, H. J.; Pei, Y. M.; Zhang, X. G.; Zhu, L.; Hou, L.; Chang, J. B.; Zhang, Z. Z. Appl. Mater. Today 2020, 18, 15. |
| [71] | Yu, F.; Zhu, M. S.; Li, N. N.; Ao, M. T.; Li, Y.; Zhong, M. Y.; Yuan, Q.; Chen, H. Y.; Fan, Z. X.; Wang, Y.; Hou, Z. Q.; Qi, Z. Q.; Shen, Y. M.; Chen, X. D. Chem. Eng. J. 2020, 380, 12. |
| [72] | Boens, N.; Leen, V.; Dehaen, W. Chem. Soc. Rev. 2012, 41, 1130. |
| [73] | Miki, K.; Enomoto, A.; Inoue, T.; Nabeshima, T.; Saino, S.; Shimizu, S.; Matsuoka, H.; Ohe, K. Biomacromolecules 2017, 18, 249. |
| [74] | Sun, H.; Benjaminsen, R. V.; Almdal, K.; Andresen, T. L. Bioconjugate Chem. 2012, 23, 2247. |
| [75] | Baier, G.; Fichter, M.; Kreyes, A.; Klein, K.; Maeilaender, V.; Gehring, S.; Landfester, K. Biomacromolecules 2016, 17, 148. |
| [76] | Song, Y. C.; Wang, Z.; Li, L. H.; Shi, W.; Li, X. H.; Ma, H. M. Chem. Commun. 2014, 50, 15696. |
| [77] | Yang, Y.; Zhang, Y. M.; Chen, Y.; Chen, J. T.; Liu, Y. Sci. Rep. 2016, 6, 10. |
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