Amino-Acid-Encoded Bioinspired Supramolecular Self-Assembly of Multimorphological Nanocarriers
Yifan Huang
Key Laboratory of Precision and Intelligent Chemistry, University of Science and Technology of China, Hefei, Anhui, 230031 China
Department of Radiation Oncology, The First Affiliated Hospital of USTC, Division of Life Sciences and Medicine, University of Science and Technology of China, Hefei, Anhui, 230026 China
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230031 China
Search for more papers by this authorGuokun Yang
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230031 China
Hefei National Research Center for Physical Sciences at the Microscale, University of Science and Technology of China, Hefei, Anhui, 230026 China
Search for more papers by this authorZian Yu
Key Laboratory of Precision and Intelligent Chemistry, University of Science and Technology of China, Hefei, Anhui, 230031 China
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230031 China
Search for more papers by this authorTong Tong
Key Laboratory of Precision and Intelligent Chemistry, University of Science and Technology of China, Hefei, Anhui, 230031 China
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230031 China
Search for more papers by this authorYan Huang
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230031 China
Hefei National Research Center for Physical Sciences at the Microscale, University of Science and Technology of China, Hefei, Anhui, 230026 China
Search for more papers by this authorQianzijing Zhang
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230031 China
Hefei National Research Center for Physical Sciences at the Microscale, University of Science and Technology of China, Hefei, Anhui, 230026 China
Search for more papers by this authorYajian Hong
Key Laboratory of Precision and Intelligent Chemistry, University of Science and Technology of China, Hefei, Anhui, 230031 China
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230031 China
Search for more papers by this authorJun Jiang
Key Laboratory of Precision and Intelligent Chemistry, University of Science and Technology of China, Hefei, Anhui, 230031 China
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230031 China
Search for more papers by this authorCorresponding Author
Guozhen Zhang
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230031 China
Hefei National Research Center for Physical Sciences at the Microscale, University of Science and Technology of China, Hefei, Anhui, 230026 China
E-mail: [email protected]; [email protected]
Search for more papers by this authorCorresponding Author
Yue Yuan
Key Laboratory of Precision and Intelligent Chemistry, University of Science and Technology of China, Hefei, Anhui, 230031 China
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230031 China
E-mail: [email protected]; [email protected]
Search for more papers by this authorYifan Huang
Key Laboratory of Precision and Intelligent Chemistry, University of Science and Technology of China, Hefei, Anhui, 230031 China
Department of Radiation Oncology, The First Affiliated Hospital of USTC, Division of Life Sciences and Medicine, University of Science and Technology of China, Hefei, Anhui, 230026 China
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230031 China
Search for more papers by this authorGuokun Yang
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230031 China
Hefei National Research Center for Physical Sciences at the Microscale, University of Science and Technology of China, Hefei, Anhui, 230026 China
Search for more papers by this authorZian Yu
Key Laboratory of Precision and Intelligent Chemistry, University of Science and Technology of China, Hefei, Anhui, 230031 China
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230031 China
Search for more papers by this authorTong Tong
Key Laboratory of Precision and Intelligent Chemistry, University of Science and Technology of China, Hefei, Anhui, 230031 China
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230031 China
Search for more papers by this authorYan Huang
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230031 China
Hefei National Research Center for Physical Sciences at the Microscale, University of Science and Technology of China, Hefei, Anhui, 230026 China
Search for more papers by this authorQianzijing Zhang
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230031 China
Hefei National Research Center for Physical Sciences at the Microscale, University of Science and Technology of China, Hefei, Anhui, 230026 China
Search for more papers by this authorYajian Hong
Key Laboratory of Precision and Intelligent Chemistry, University of Science and Technology of China, Hefei, Anhui, 230031 China
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230031 China
Search for more papers by this authorJun Jiang
Key Laboratory of Precision and Intelligent Chemistry, University of Science and Technology of China, Hefei, Anhui, 230031 China
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230031 China
Search for more papers by this authorCorresponding Author
Guozhen Zhang
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230031 China
Hefei National Research Center for Physical Sciences at the Microscale, University of Science and Technology of China, Hefei, Anhui, 230026 China
E-mail: [email protected]; [email protected]
Search for more papers by this authorCorresponding Author
Yue Yuan
Key Laboratory of Precision and Intelligent Chemistry, University of Science and Technology of China, Hefei, Anhui, 230031 China
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230031 China
E-mail: [email protected]; [email protected]
Search for more papers by this authorAbstract
Supramolecular self-assembly has emerged as an efficient tool to construct well-organized nanostructures for biomedical applications by small organic molecules. However, the physicochemical properties of self-assembled nanoarchitectures are greatly influenced by their morphologies, mechanical properties, and working mechanisms, making it challenging to design and screen ideal building blocks. Herein, using a biocompatible firefly-sourced click reaction between the cyano group of 2-cyano-benzothiazole (CBT) and the 1,2-aminothiol group of cysteine (Cys), an amino-acid-encoded supramolecular self-assembly platform Cys(SEt)-X-CBT (X represents any amino acid) is developed to incorporate both covalent and noncovalent interactions for building diverse morphologies of nanostructures with bioinspired response mechanism, providing a convenient and rapid strategy to construct site-specific nanocarriers for drug delivery, cell imaging, and enzyme encapsulation. Additionally, it is worth noting that the biodegradation of Cys(SEt)-X-CBT generated nanocarriers can be easily tracked via bioluminescence imaging. By caging either the thiol or amino groups in Cys with other stimulus-responsive sites and modifying X with probes or drugs, a variety of multi-morphological and multifunctional nanomedicines can be readily prepared for a wide range of biomedical applications.
Conflict of Interest
The authors declare no conflict of interest.
Open Research
Data Availability Statement
The data that support the findings of this study are available from the corresponding author upon reasonable request.
Supporting Information
| Filename | Description |
|---|---|
| smll202311351-sup-0001-SuppMat.pdf3 MB | Supporting Information |
| smll202311351-sup-0002-MovieS1.MP433 MB | Supplemental Movie 1 |
| smll202311351-sup-0003-MovieS2.MP421.7 MB | Supplemental Movie 2 |
| smll202311351-sup-0004-MovieS3.MP423.1 MB | Supplemental Movie 3 |
| smll202311351-sup-0005-MovieS4.MP422.9 MB | Supplemental Movie 4 |
| smll202311351-sup-0006-MovieS5.MP429.7 MB | Supplemental Movie 5 |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
References
- 1a) G. M. Whitesides, J. P. Mathias, C. T. Seto, Science 1991, 254, 1312; b) N. J. Sinha, M. G. Langenstein, D. J. Pochan, C. J. Kloxin, J. G. Saven, Chem. Rev. 2021, 121, 13915.
- 2a) S. Yagai, A. Kitamura, Chem. Soc. Rev. 2008, 37, 1520; b) B. J. Kim, D. Yang, B. Xu, Trends Chem. 2020, 2, 71; c) D. Pochan, O. Scherman, Chem. Rev. 2021, 121, 13699.
- 3a) G. Ghosh, R. Barman, A. Mukherjee, U. Ghosh, S. Ghosh, G. Fernández, Angew. Chem., Int. Ed. 2022, 61, e202113403; b) M. K. Klein, H. A. Kassam, R. H. Lee, W. Bergmeier, E. B. Peters, D. C. Gillis, B. R. Dandurand, J. R. Rouan, M. R. Karver, M. D. Struble, T. D. Clemons, L. C. Palmer, B. Gavitt, T. A. Pritts, N. D. Tsihlis, S. I. Stupp, M. R. Kibbe, ACS Nano 2020, 14, 6649; c) Z. Feng, H. Wang, S. Wang, Q. Zhang, X. Zhang, A. A. Rodal, B. Xu, J. Am. Chem. Soc. 2018, 140, 9566.
- 4a) M. Reches, E. Gazit, Science 2003, 300, 625; b) Z. Yang, G. Liang, B. Xu, Acc. Chem. Res. 2008, 41, 315; c) J. Ryu, C. B. Park, Adv. Mater. 2008, 20, 3754.
- 5a) B. A. Grzybowski, W. T. S. Huck, Nat. Nanotechnol. 2016, 11, 585; b) M. Kumar, N. L. Ing, V. Narang, N. K. Wijerathne, A. I. Hochbaum, R. V. Ulijn, Nat. Chem. 2018, 10, 696.
- 6a) H. Ren, F. Xiao, K. Zhan, Y.-P. Kim, H. Xie, Z. Xia, J. Rao, Angew. Chem., Int. Ed. 2009, 48, 9658; b) G. Liang, H. Ren, J. Rao, Nat. Chem. 2010, 2, 239; c) M. Zhang, Y. Guan, Z. Dang, P. Zhang, Z. Zheng, L. Chen, W. Kuang, C. Wang, G. Liang, Sci. Adv. 2020, 6, eaba3190; d) Y. Yuan, D. Li, J. Zhang, X. Chen, C. Zhang, Z. Ding, L. Wang, X. Zhang, J. Yuan, Y. Li, Y. Kang, G. Liang, Chem. Sci. 2015, 6, 6425; e) Y. Yuan, J. Zhang, X. Qi, S. Li, G. Liu, S. Siddhanta, I. Barman, X. Song, M. T. McMahon, J. W. M. Bulte, Nat. Mater. 2019, 18, 1376.
- 7a) A. Dragulescu-Andrasi, S.-R. Kothapalli, G. A. Tikhomirov, J. Rao, S. S. Gambhir, J. Am. Chem. Soc. 2013, 135, 11015; b) S. Liu, A. Tang, M. Xie, Y. Zhao, J. Jiang, G. Liang, Angew. Chem., Int. Ed. 2015, 54, 3639; c) Z. Zheng, P. Chen, M. Xie, C. Wu, Y. Luo, W. Wang, J. Jiang, G. Liang, J. Am. Chem. Soc. 2016, 138, 11128.
- 8a) Y. Yuan, P. Raj, J. Zhang, S. Siddhanta, I. Barman, J. W. M. Bulte, Angew. Chem., Int. Ed. 2021, 60, 3825; b) C. Wang, W. Du, C. Wu, S. Dan, M. Sun, T. Zhang, B. Wang, Y. Yuan, G. Liang, Angew. Chem., Int. Ed. 2022, 61, e202114766; c) Y. Yuan, L. Wang, W. Du, Z. Ding, J. Zhang, T. Han, L. An, H. Zhang, G. Liang, Angew. Chem., Int. Ed. 2015, 54, 9700; d) Y. Yuan, F. Wang, W. Tang, Z. Ding, L. Wang, L. Liang, Z. Zheng, H. Zhang, G. Liang, ACS Nano 2016, 10, 7147; e) J. Lin, D. Gao, S. Wang, G. Lv, X. Wang, C. Lu, Y. Peng, L. Qiu, J. Am. Chem. Soc. 2022, 144, 7667.
- 9M. J. Mulski, K. A. Connors, Supramol. Chem. 1995, 4, 271.
- 10a) X. Yan, P. Zhu, J. Li, Chem. Soc. Rev. 2010, 39, 1877; b) Q. Ma, E. E. Remsen, C. G. Clark, T. Kowalewski, K. L. Wooley, Proc. Natl. Acad. Sci. USA 2002, 99, 5058.
- 11T. O. Mason, T. C. T. Michaels, A. Levin, C. M. Dobson, E. Gazit, T. P. J. Knowles, A. K. Buell, J. Am. Chem. Soc. 2017, 139, 16134.
- 12a) S. Gan, W. Wu, G. Feng, Z. Wang, B. Liu, B. Z. Tang, Small 2022, 18, 2202242; b) J. Hao, W. Y. Lv, C. M. Li, B. Wang, L. Q. Xu, New J. Chem. 2018, 42, 14709.
- 13a) P. Du, S. Xu, Z.-K. Xu, Z.-G. Wang, Adv. Funct. Mater. 2021, 31, 2104819; b) Y. Lin, M. R. Thomas, A. Gelmi, V. Leonardo, E. T. Pashuck, S. A. Maynard, Y. Wang, M. M. Stevens, J. Am. Chem. Soc. 2017, 139, 13592; c) Y. Zhang, S. Tsitkov, H. Hess, Nat. Commun. 2016, 7, 13982; d) M. Fogel, J. W. Hastings, Proc. Natl. Acad. Sci. USA 1972, 69, 690.
- 14J. Kim, T. H. Han, Y.-I. Kim, J. S. Park, J. Choi, D. G. Churchill, S. O. Kim, H. Ihee, Adv. Mater. 2010, 22, 583.
- 15C. Wu, R. Zhang, W. Du, L. Cheng, G. Liang, Nano Lett. 2018, 18, 7749.
- 16R. Yan, Y. Hu, F. Liu, S. Wei, D. Fang, A. J. Shuhendler, H. Liu, H.-Y. Chen, D. Ye, J. Am. Chem. Soc. 2019, 141, 10331.
- 17G. von Maltzahn, S. Vauthey, S. Santoso, S. Zhang, Langmuir 2003, 19, 4332.
- 18a) J. G. Huang, J. C. Li, Y. Lyu, Q. Q. Miao, K. Y. Pu, Nat. Mater. 2019, 18, 1133; b) P. H. Cheng, K. Y. Pu, Nat. Rev. Mater. 2021, 6, 1095.
- 19a) R. M. Friedlander, N. Engl. J. Med. 2003, 348, 1365; b) M. P. Mattson, Nat. Rev. Mol. Cell Biol. 2000, 1, 120.
