Citation: Miao Wang, Hongning Zheng, Fei Xu. Collagen-like Peptide Self-Assembly via Phenyl Isocyanate Induction[J]. Acta Physico-Chimica Sinica, ;2021, 37(10): 191103. doi: 10.3866/PKU.WHXB201911039 shu

Collagen-like Peptide Self-Assembly via Phenyl Isocyanate Induction

Miao Wang ^† ,
Hongning Zheng ^† ,
Fei Xu ^,

Key Laboratory of Sugar Chemistry and Biotechnology, Ministry of Education, School of Biological Engineering, Jiangnan University, Wuxi 214122, Jiangsu Province, China

Corresponding author: Fei Xu, feixu@jiangnan.edu.cn

^†

Received Date: 20 November 2019
Revised Date: 18 December 2019
Accepted Date: 23 December 2019
Available Online: 27 December 2019
Fund Project: the National Natural Science Foundation of China 21603088the National Natural Science Foundation of China 51603089the China Postdoctoral Science Foundation 2017M611687

Synthetic matrices provide powerful tools for dissecting molecular interactions involved in the organization of the extracellular matrix (ECM), establishment of cell axis polarity, and suppression of neoplasticity in pre-cancerous endothelial cells. Collagen is the most abundant protein in extracellular matrix. A de novo approach is essential for the synthesis of collagen matrices which can have a broad impact on the understanding of matrix biology and our capacity to construct safe and medically useful biomaterials. Conventionally, the ECM has been studied by an analytical "top-down" approach, where the individual components of the matrix are first isolated and then characterized to explore their biochemical and functional properties. Since native collagen is difficult to modify and can engender pathogenic and immunological side effects, its application on tissue regeneration is limited. Therefore, we attempted to synthesize artificial collagen directly through small organic molecule recognition. The collagen-like peptides possess various benefits such as being clean, programmable, and easy to modify; therefore, in recent years, they have been used as ideal substrates for the synthesis of collagen nanomaterials. The self-assembly of collagen-like peptides is mainly driven by various non-covalent interactions such as electrostatic attraction, π-π stacking, and metal coordination. This renders a difficulty in the rational design of uniform nanostructures from short synthesized peptides and demands a novel strategy. To date, small organic molecules have been rarely used for the self-assembly of collagen-like peptides. In the present study, we attempted to use the small organic molecules for the combined supramolecular self-assembly of collagen-like peptides. Initially, the collagen-like peptides, (POG)₆ and (POG)₈, synthesized by the solid-phase synthesis technique, were both modified chemically using 4, 4'-methylene bis(phenyl isocyanate) to obtain the collagen-like hybrid peptides, AP₆ and AP₈, respectively. Phenyl isocyanate contributes to the formation of potential weak forces, such as hydrogen bonds and π-π stacking at the N-terminal regions of the collagen-like hybrid peptides. The purity and molecular weight of the collagen-like hybrid peptides were analyzed using analytical high-performance liquid chromatography (HPLC) and matrix-assisted laser desorption ionization time of flight (MALDI-TOF), respectively. The stability of AP₆ and AP₈ triple helices was analyzed by circular dichroism (CD) spectroscopy. The small organic molecule 4, 4'-methylene bis(phenyl isocyanate) promoted the unfolding of (POG)₆ and increased the melting temperature (T_m) of (POG)₈ from 37.7 to 58.8 ℃to form a triple helix. The hydrodynamic radii of collagen-like hybrid peptides were measured by dynamic light scattering (DLS). Atomic force microscopy (AFM) and transmission electron microscopy (TEM) were used to analyze the morphology of the aggregation states. AFM results showed that the collagen-like hybrid peptides, AP₆ and AP₈, formed nanofibers spontaneously. Consistent with the AFM results, TEM showed that the AP₆ and AP₈ collagen-like hybrid peptides also formed nanofiber structures. The formation of stable complexes was attributed to the presence of multiple weak interactions such as hydrogen bonding, π-π stacking, and hydrophobic interactions. In the present study, we demonstrated that the chemical modification of collagen-like polypeptides at the N-terminus via the small organic molecule, 4, 4'-methylene bis(phenyl isocyanate), promoted the intramolecular and intermolecular assembly of collagen-like peptides. A simple and effective strategy has been developed in this study to promote the self-assembly of collagen-like peptides.
- Collagen-like peptide,
- Triple helix,
- Phenyl isocyanate,
- Weak interaction,
- Self-assembly,
- Nanofibers,
- Nano materials
1. [1]
  Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science 1991, 254 (5036), 1312. doi: 10.1126/science.1962191 doi: 10.1126/science.1962191
2. [2]
  Whitesides, G. M.; Grzybowski, B. Science 2002, 295 (5564), 2418. doi: 10.1126/science.1070821 doi: 10.1126/science.1070821
3. [3]
  Seeman, N. C.; Fan, C.; Wang, S.; Schanze, K.; Fernandez, L. ACS Appl. Mater. Interfaces 2019, 11 (15), 13833. doi: 10.1021/acsami.9b04482 doi: 10.1021/acsami.9b04482
4. [4]
  Baker, E. G.; Bartlett, G. J.; Porter Goff, K. L.; Woolfson, D. N. Acc. Chem. Res. 2017, 50 (9), 2085. doi: 10.1021/acs.accounts.7b00186 doi: 10.1021/acs.accounts.7b00186
5. [5]
  Xing, R. R.; Zou, Q. L.; Yan, X. H. Acta Phys. -Chim. Sin. 2020, 36 (10), 1909048. doi: 10.3866/PKU.WHXB201909048
6. [6]
  Xu, X. J.; Xiao, X. Q.; Xu, S. H.; Liu, H. L. Acta Phys. -Chim. Sin. 2019, 35 (6), 598. doi: 10.3866/PKU.WHXB201806034
7. [7]
  Du, C. B.; Han, B. X. Acta Phys. -Chim. Sin. 2019, 35 (10), 1045. doi: 10.3866/PKU.WHXB201905058
8. [8]
  Yuan, C.; Ji, W.; Xing, R.; Li, J.; Gazit, E.; Yan, X. Nat. Rev. Chem. 2019, 3 (10), 567. doi: 10.1038/s41570-019-0129-8 doi: 10.1038/s41570-019-0129-8
9. [9]
  Bai, Y.; Luo, Q.; Liu, J. Chem. Soc. Rev. 2016, 45 (10), 2756. doi: 10.1039/c6cs00004 doi: 10.1039/c6cs00004
10. [10]
  Gelse, K.; Pöschl, E.; Aigner, T. Adv. Drug Deliv. Rev. 2003, 55 (12), 1531. doi: 10.1016/j.addr.2003.08.002 doi: 10.1016/j.addr.2003.08.002
11. [11]
  Shoulders, M. D.; Raines, R. T. Annu. Rev. Biochem. 2009, 78 (1), 929. doi: 10.1146/annurev.biochem.77.032207.120833 doi: 10.1146/annurev.biochem.77.032207.120833
12. [12]
  Kotch, F. W.; Raines, R. T. Proc. Natl. Acad. Sci. U. S. A. 2006, 103 (9), 3028. doi: 10.1073/pnas.0508783103 doi: 10.1073/pnas.0508783103
13. [13]
  O'Leary, L. E.; Fallas, J. A.; Bakota, E. L.; Kang, M. K.; Hartgerink, J. D. Nat. Chem. 2011, 3 (10), 821. doi: 10.1038/nchem.1123 doi: 10.1038/nchem.1123
14. [14]
  Tanrikulu, I. C.; Forticaux, A.; Jin, S.; Raines, R. T. Nat. Chem. 2016, 8 (11), 1008. doi: 10.1038/nchem.2556 doi: 10.1038/nchem.2556
15. [15]
  Cejas, M. A.; Kinney, W. A.; Chen, C.; Vinter, J. G.; Almond, H. R. Jr.; Balss, K. M.; Maryanoff, C. A.; Schmidt, U.; Breslav, M.; Mahan, A.; et al. Proc. Natl. Acad. Sci. U. S. A. 2008, 105 (25), 8513. doi: 10.1073/pnas.080029110 doi: 10.1073/pnas.080029110
16. [16]
  Cejas, M. A.; Kinney, W. A.; Chen, C.; Leo, G. C.; Tounge, B. A.; Vinter, J. G.; Joshi, P. P.; Maryanoff, B. E. J. Am. Chem. Soc. 2007, 129 (8), 2202. doi: 10.1021/ja066986f doi: 10.1021/ja066986f
17. [17]
  Przybyla, D. E.; Chmielewski, J. J. Am. Chem. Soc. 2008, 130 (38), 12610. doi: 10.1021/ja804942w doi: 10.1021/ja804942w
18. [18]
  Przybyla, D.; Rubert Pérez, C. M.; Gleaton, J.; Nandwana, V.; Chmielewski. J. J. Am. Chem. Soc. 2013, 135 (9), 3418. doi: 10.1021/ja307651e doi: 10.1021/ja307651e
19. [19]
  Pires, M. M.; Chmielewski, J. J. Am. Chem. Soc. 2009, 131 (7), 2706. doi: 10.1021/ja8088845 doi: 10.1021/ja8088845
20. [20]
  He, M.; Wang, L.; Wu, J; Xiao, J. Chem. -Eur. J. 2016, 22 (6), 1914. doi: 10.1002/chem.20150437 doi: 10.1002/chem.20150437
21. [21]
  Holmgren, S. K.; Bretscher, L. E.; Taylor, K. M.; Raines, R. T. Chem. Biol. 1999, 6 (2), 63. doi: 10.1016/S1074-5521(99)80003-9 doi: 10.1016/S1074-5521(99)80003-9
22. [22]
  Feng, Y.; Melacini, G.; Goodman, M. Biochemistry 1997, 36 (29), 8716. doi: 10.1021/bi962980z doi: 10.1021/bi962980z
23. [23]
  Luo, J.; Tong, Y. W. ACS Nano 2011, 5 (10), 7739. doi: 10.1021/nn202822f doi: 10.1021/nn202822f
24. [24]
  Persikov, A. V.; Ramshaw, J. A.; Brodsky, B. J. Biol. Chem. 2005, 280 (19), 19343. doi: 10.1074/jbc.M501657200 doi: 10.1074/jbc.M501657200
25. [25]
  Bai, W.; Jiang, Z.; Ribbe, A. E.; Thayumanavan, S. Angew. Chem. Int. Edit. 2016, 55 (36), 10707. doi: 10.1002/anie.201605050 doi: 10.1002/anie.201605050
26. [26]
  Liang, J.; Lai, D. Y.; Wu, W. L.; Li, G. Z.; Li, J. B.; Fang, C. L. Acta Phys. -Chim. Sin. 2015, 31 (4), 722. doi: 10.3866/PKU.WHXB20150303
27. [27]
  Lee, E. S.; Gao, Z.; Kim, D.; Park, K.; Kwon, I. C.; Bae, Y. H. J. Control. Release 2008, 129 (3), 228. doi: 10.1016/j.jconrel.2008.04.024 doi: 10.1016/j.jconrel.2008.04.024
28. [28]
  Xu, X. D.; Lin, B. B.; Feng, J.; Wang, Y.; Cheng, S. X.; Zhang, X. Z.; Zhuo, R. X. Macromol. Rapid Commun. 2012, 33 (5), 426. doi: 10.1002/marc.201100689 doi: 10.1002/marc.201100689
29. [29]
  Wiranharma, N.; Tong, Y. W.; Yang, Y. Y. Biomaterials 2009, 30 (17), 3100. doi: 10.1016/j.biomaterials.2009.03.006 doi: 10.1016/j.biomaterials.2009.03.006
30. [30]
  Kubo, T.; Morikawa, M.; Ohba, H.; Fujii, M. Org. Lett. 2003, 5 (15), 2623. doi: 10.1021/ol034721p doi: 10.1021/ol034721p
31. [31]
  Brown, F. R.; Di Corato, A.; Lorenzi, G. P.; Blout, E. R. J. Mol. Biol. 1972, 63 (1), 85. doi: 10.1016/0022-2836(72)90523-2 doi: 10.1016/0022-2836(72)90523-2
32. [32]
  Sakakibara, S.; Kishida, Y.; Okuyama, K.; Tanaka, N.; Ashida, T.; Kakudo, M. J. Mol. Biol. 1972, 65 (2), 371. doi: 10.1016/0022-2836(72)90288-4 doi: 10.1016/0022-2836(72)90288-4
33. [33]
  Kar, K.; Amin, P.; Bryan, M. A.; Persikov, A. V.; Mohs, A.; Wang, Y. H.; Brodsky, B. J. Biol. Chem. 2006, 281 (44), 33283. doi: 10.1074/jbc.M605747200 doi: 10.1074/jbc.M605747200
34. [34]
  Parmar, A. S.; James, J. K.; Grisham, D. R.; Pike, D. H.; Nanda, V. J. Am. Chem. Soc. 2016, 138 (13), 4362. doi: 10.1021/jacs.5b10304 doi: 10.1021/jacs.5b10304
1. [1]
  Juan WANG , Zhongqiu WANG , Qin SHANG , Guohong WANG , Jinmao LI . NiS and Pt as dual co-catalysts for the enhanced photocatalytic H₂ production activity of BaTiO₃ nanofibers. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1719-1730. doi: 10.11862/CJIC.20240102
2. [2]
  Zunyuan Xie , Lijin Yang , Zixiao Wan , Xiaoyu Liu , Yushan He . Exploration of the Preparation and Characterization of Nano Barium Titanate and Its Application in Inorganic Chemistry Laboratory Teaching. University Chemistry, 2024, 39(4): 62-69. doi: 10.3866/PKU.DXHX202310137
3. [3]
  Juan Yuan , Bin Zhang , Jinping Wu , Mengfan Wang . Design of a Comprehensive Experiment on Preparation and Characterization of Cu₂(Salen)₂ Nanomaterials with Two Distinct Morphologies. University Chemistry, 2024, 39(10): 420-425. doi: 10.3866/PKU.DXHX202402014
4. [4]
  Simin Fang , Wei Huang , Guanghua Yu , Cong Wei , Mingli Gao , Guangshui Li , Hongjun Tian , Wan Li . Integrating Science and Education in a Comprehensive Chemistry Design Experiment: The Preparation of Copper(I) Oxide Nanoparticles and Its Application in Dye Water Remediation. University Chemistry, 2024, 39(8): 282-289. doi: 10.3866/PKU.DXHX202401023
5. [5]
  Jin Tong , Shuyan Yu . Crystal Engineering for Supramolecular Chirality. University Chemistry, 2024, 39(3): 86-93. doi: 10.3866/PKU.DXHX202308113
6. [6]
  Ruoxi Sun , Yiqian Xu , Shaoru Rong , Chunmiao Han , Hui Xu . The Enchanting Collision of Light and Time Magic: Exploring the Footprints of Long Afterglow Lifetime. University Chemistry, 2024, 39(5): 90-97. doi: 10.3866/PKU.DXHX202310001
7. [7]
  Wenjun Zheng . Application in Inorganic Synthesis of Ionic Liquids. University Chemistry, 2024, 39(8): 163-168. doi: 10.3866/PKU.DXHX202401020
8. [8]
  Shihui Shi , Haoyu Li , Shaojie Han , Yifan Yao , Siqi Liu . Regioselectively Synthesis of Halogenated Arenes via Self-Assembly and Synergistic Catalysis Strategy. University Chemistry, 2024, 39(5): 336-344. doi: 10.3866/PKU.DXHX202312002
9. [9]
  Xiaofei NIU , Ke WANG , Fengyan SONG , Shuyan YU . Self-assembly of [Pd₆(L)₄]⁸⁺-type macrocyclic complexes for fluorescent sensing of HSO₃^-. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1233-1242. doi: 10.11862/CJIC.20240057
10. [10]
  Guangming YIN , Huaiyao WANG , Jianhua ZHENG , Xinyue DONG , Jian LI , Yi'nan SUN , Yiming GAO , Bingbing WANG . Preparation and photocatalytic degradation performance of Ag/protonated g-C₃N₄ nanorod materials. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1491-1500. doi: 10.11862/CJIC.20240086
11. [11]
  Qingtang ZHANG , Xiaoyu WU , Zheng WANG , Xiaomei WANG . Performance of nano Li₂FeSiO₄/C cathode material co-doped by potassium and chlorine ions. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1689-1696. doi: 10.11862/CJIC.20240115
12. [12]
  Qi Li , Pingan Li , Zetong Liu , Jiahui Zhang , Hao Zhang , Weilai Yu , Xianluo Hu . Fabricating Micro/Nanostructured Separators and Electrode Materials by Coaxial Electrospinning for Lithium-Ion Batteries: From Fundamentals to Applications. Acta Physico-Chimica Sinica, 2024, 40(10): 2311030-. doi: 10.3866/PKU.WHXB202311030
13. [13]
  Xiufang Wang , Donglin Zhao , Kehua Zhang , Xiaojie Song . “Preparation of Carbon Nanotube/SnS₂ Photoanode Materials”: A Comprehensive University Chemistry Experiment. University Chemistry, 2024, 39(4): 157-162. doi: 10.3866/PKU.DXHX202308025
14. [14]
  Haiyuan Wang , Yiming Tang , Haoran Guo , Guohui Chen , Yajing Sun , Chao Zhao , Zhen Zhang . Comprehensive Chemistry Experimental Teaching Design Based on the Integration of Science and Education: Preparation and Catalytic Properties of Silver Nanomaterials. University Chemistry, 2024, 39(10): 219-228. doi: 10.12461/PKU.DXHX202404067
15. [15]
  Chunmei GUO , Weihan YIN , Jingyi SHI , Jianhang ZHAO , Ying CHEN , Quli FAN . Facile construction and peroxidase-like activity of single-atom platinum nanozyme. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1633-1639. doi: 10.11862/CJIC.20240162
16. [16]
  Min LI , Xianfeng MENG . Preparation and microwave absorption properties of ZIF-67 derived Co@C/MoS₂ nanocomposites. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1932-1942. doi: 10.11862/CJIC.20240065
17. [17]
  Yinyin Qian , Rui Xu . Utilizing VESTA Software in the Context of Material Chemistry: Analyzing Twin Crystal Nanostructures in Indium Antimonide. University Chemistry, 2024, 39(3): 103-107. doi: 10.3866/PKU.DXHX202307051
18. [18]
  Jinyi Sun , Lin Ma , Yanjie Xi , Jing Wang . Preparation and Electrocatalytic Nitrogen Reduction Performance Study of Vanadium Nitride@Nitrogen-Doped Carbon Composite Nanomaterials: A Recommended Comprehensive Chemistry Experiment. University Chemistry, 2024, 39(4): 184-191. doi: 10.3866/PKU.DXHX202310094
19. [19]
  Junli Liu . Practice and Exploration of Research-Oriented Classroom Teaching in the Integration of Science and Education: a Case Study on the Synthesis of Sub-Nanometer Metal Oxide Materials and Their Application in Battery Energy Storage. University Chemistry, 2024, 39(10): 249-254. doi: 10.12461/PKU.DXHX202404023
20. [20]
  Jinghua Wang , Yanxin Yu , Yanbiao Ren , Yesheng Wang . Integration of Science and Education: Investigation of Tributyl Citrate Synthesis under the Promotion of Hydrate Molten Salts for Research and Innovation Training. University Chemistry, 2024, 39(11): 232-240. doi: 10.3866/PKU.DXHX202402057

Get Citation

PDF

XML

Metrics

PDF Downloads(9)
Abstract views(240)
HTML views(26)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142