Denting Nanospheres with a Short Peptide

Sha Lin; Hui Sun; Erik Jan Cornel; Jin-Hui Jiang; Yun-Qing Zhu; Zhen Fan; Jian-Zhong Du

doi:10.1007/s10118-021-2599-7

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Denting Nanospheres with a Short Peptide

ARTICLE | Updated：2021-06-18

- Denting Nanospheres with a Short Peptide
- Denting Nanospheres with a Short Peptide
- Chinese Journal of Polymer Science 2021年39卷第12期页码：1538-1549
- Affiliations：
  
  a.Department of Orthopedics, Shanghai Tenth People’s Hospital, Tongji University, Shanghai 200072, China
  b.Department of Polymeric Materials, School of Materials Science and Engineering, Tongji University, Shanghai 201804, China
- Author bio：
  
  jzdu@tongji.edu.cn
- Funds：
  
  J.D. is supported by the National Science Fund for Distinguished Young Scholars, NSFC (No. 21925505); Z.F. is supported by the National Natural Science Foundation of China (Nos. 51803152, 22075212), the program for professor of special appointment (Eastern Scholar) at Shanghai institutions of higher learning and Natural Science Foundation of Shanghai (19ZR1478800); Y.Z. is supported by the National Natural Science Foundation of China (No. 51903190) and Shanghai Pujiang Program (No. 19PJ140960); E.J.C. is supported by the China Postdoctoral Science Foundation (No. 2020M671197).
- DOI：10.1007/s10118-021-2599-7
  中图分类号：
- 收稿：2021-04-08，
  
  修回：2021-4-28，
  
  录用：2021-4-29，
  
  网络首发：2021-06-18，
  
  纸质出版：2021-10-18
- Accepted：
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Lin, S.; Sun, H.; Cornel, E. J.; Jiang, J. H.; Zhu, Y. Q.; Fan, Z.; Du, J. Z. Denting nanospheres with a short peptide. Chinese J. Polym. Sci. 2021, 39, 1538–1549

Sha Lin, Hui Sun, Erik Jan Cornel, et al. Denting Nanospheres with a Short Peptide[J]. Chinese Journal of Polymer Science, 2021, 39(12): 1538-1549.
Lin, S.; Sun, H.; Cornel, E. J.; Jiang, J. H.; Zhu, Y. Q.; Fan, Z.; Du, J. Z. Denting nanospheres with a short peptide. Chinese J. Polym. Sci. 2021, 39, 1538–1549 DOI： 10.1007/s10118-021-2599-7.

Sha Lin, Hui Sun, Erik Jan Cornel, et al. Denting Nanospheres with a Short Peptide[J]. Chinese Journal of Polymer Science, 2021, 39(12): 1538-1549. DOI： 10.1007/s10118-021-2599-7.

摘要

Abstract

Dented nanospheres show promising potential in drug delivery

nanomotors

etc

. However

it is still challenging to prepare them by homopolymer self-assembly because of the strict structural requirements of the homopolymer. Herein

we propose a strategy for preparing dented nanospheres from homopolymers by co-assembly with a short peptide. They were co-assembled from poly(2-hydroxy-3-((4-(ethoxycarbonyl)phenyl)amino)propyl methacrylate) (PHBzoMA

) and (

)-2-((

)-2-((((9

-fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanamido)-3-phenylpropanoic acid (Fmoc-FF-OH). PHBzoMA homopolymers can only self-assemble into nanospheres without dent

and the addition of a short peptide introduced hydrogen bonding and complementary

π-π

stacking interactions led to the final dented nanosphere morphology. The weight fractions of the short peptide can be adjusted to regulate the final morphology. It was confirmed that the radius of curvature of the dent on the surface was related to the organic bubble inside the protospheres prepared at critical aggregation concentration (CAC). The organic bubble can be adjusted by altering the kind of organic solvent and solution pH

which allowed control over the dented nanosphere dimension. The use of different organic solvents with various polarities allows adjustment of the interfacial tension

and hence the denting degree. This degree can also be controlled by manipulating the solution pH to (de)protonate the short peptide and homopolymer. Furthermore

the versatility of this method was highlighted by using a different homopolymer and the applicability of the resulting dented nanospheres was demonstrated by decoration with gold nanoparticles. Overall

this study provided important insights and a new simple strategy to prepare dented nanospheres in a controlled fashion.

关键词

Keywords

references

Sandanaraj, B. S.; Vutukuri, D. R.; Simard, J. M.; Klaikherd, A.; Hong, R.; Rotello, V. M.; Thayumanavan, S. . Noncovalent modification of chymotrypsin surface using an amphiphilic polymer scaffold: implications in modulating protein function . J. Am. Chem. Soc. , 2005 . 127 10693 - 10698 . DOI: 10.1021/ja051947+ http://doi.org/10.1021/ja051947+ .

Savariar, E. N.; Aathimanikandan, S. V.; Thayumanavan, S. . Supramolecular assemblies from amphiphilic homopolymers: testing the scope . J. Am. Chem. Soc. , 2006 . 128 16224 - 16230 . DOI: 10.1021/ja065213o http://doi.org/10.1021/ja065213o .

Chen, S.; Lin, S.; Xi, Y. J.; Xiao, Y. F.; Du, J. Z. . Polymersomes with inhomogeneous membranes, asymmetrical coronas and fused membranes and coronas . Chin. Sci. Bull. , 2020 . 65 2615 - 2626 . DOI: 10.1360/TB-2020-0472 http://doi.org/10.1360/TB-2020-0472 .

Liu, D. Q.; Sun, H.; Xiao, Y. F.; Chen, S.; Cornel, E. J.; Zhu, Y. Q.; Du, J. Z. . Design principles, synthesis and biomedical applications of polymer vesicles with inhomogeneous membranes . J. Control. Release , 2020 . 326 365 - 386 . DOI: 10.1016/j.jconrel.2020.07.018 http://doi.org/10.1016/j.jconrel.2020.07.018 .

Cornel, E. J.; Jiang, J. H.; Chen, S.; Du, J. Z. . Principles and characteristics of polymerization-induced self-assembly with various polymerization techniques . CCS Chem. , 2020 . 2104 - 2125 . .

Xiao, J. G.; Hu, Y.; Du, J. Z. . Polymer nanodisks by collapse of nanocapsules . Sci. China Chem. , 2018 . 61 569 - 575 . DOI: 10.1007/s11426-017-9209-3 http://doi.org/10.1007/s11426-017-9209-3 .

Sun, H.; Du, J. Z. . Intramolecular cyclization-induced crystallization-driven self-assembly of an amorphous poly(amic acid) . Macromolecules , 2020 . 53 11033 - 11039 . DOI: 10.1021/acs.macromol.0c02186 http://doi.org/10.1021/acs.macromol.0c02186 .

Chen, Z. J.; Yang, S. C.; Liu, X. L.; Gao, Y. H.; Dong, X.; Lai, X.; Zhu, M. H.; Feng, H. Y.; Zhu, X. D.; Lu, Q.; Zhao, M.; Chen, H. Z.; Lovell, J. F.; Fang, C. . Nanobowl-supported liposomes improve drug loading and delivery . Nano Lett. , 2020 . 20 4177 - 4187 . DOI: 10.1021/acs.nanolett.0c00495 http://doi.org/10.1021/acs.nanolett.0c00495 .

Li, X. M.; Zhou, L.; Wei, Y.; El-Toni, A. M.; Zhang, F.; Zhao, D. Y. . Anisotropic encapsulation-induced synthesis of asymmetric single-hole mesoporous nanocages . J. Am. Chem. Soc. , 2015 . 137 5903 - 5906 . DOI: 10.1021/jacs.5b03207 http://doi.org/10.1021/jacs.5b03207 .

Franken, L. E.; Wei, Y.; Chen, J.; Boekema, E. J.; Zhao, D.; Stuart, M. C. A.; Feringa, B. L. . Solvent mixing to induce molecular motor aggregation into bowl shaped particles: underlying mechanism, particle nature, and application to control motor behavior . J. Am. Chem. Soc. , 2018 . 140 7860 - 7868 . DOI: 10.1021/jacs.8b03045 http://doi.org/10.1021/jacs.8b03045 .

Peng, F.; Tu, Y. F.; van Hest, J. C. M.; Wilson, D. A. . Self-guided supramolecular cargo-loaded nanomotors with chemotactic behavior towards cells . Angew. Chem., Int. Ed. , 2015 . 54 11662 - 11665 . DOI: 10.1002/anie.201504186 http://doi.org/10.1002/anie.201504186 .

Liang, J.; Hu, H.; Park, H.; Xiao, C.; Ding, S.; Paik, U.; Lou, X. W. . Construction of hybrid bowl-like structures by anchoring NIO nanosheets on flat carbon hollow particles with enhanced lithium storage properties . Energy Environ. Sci. , 2015 . 8 1707 - 1711 . DOI: 10.1039/C5EE01125F http://doi.org/10.1039/C5EE01125F .

Lin, Z. X.; Tian, H.; Xu, F. G.; Yang, X. W.; Mai, Y. Y.; Feng, X. L. . Facile synthesis of bowl-shaped nitrogen-doped carbon hollow particles templated by block copolymer 'kippah vesicles' for high performance supercapacitors . Polym. Chem. , 2016 . 7 2092 - 2098 . DOI: 10.1039/C6PY00161K http://doi.org/10.1039/C6PY00161K .

Cheng, Z. F.; Luo, F. H.; Zhang, Z. X.; Ma, Y. Q. . Syntheses and applications of concave and convex colloids with precisely controlled shapes . Soft Matter , 2013 . 9 11392 - 11397 . DOI: 10.1039/c3sm52279b http://doi.org/10.1039/c3sm52279b .

Tanaka, T.; Komatsu, Y.; Fujibayashi, T.; Minami, H.; Okubo, M. . A novel approach for preparation of micrometer-sized, monodisperse dimple and hemispherical polystyrene particles . Langmuir , 2010 . 26 3848 - 3853 . DOI: 10.1021/la903309t http://doi.org/10.1021/la903309t .

Liu, D.; Peng, X.; Wu, B.; Zheng, X.; Chuong, T. T.; Li, J.; Sun, S.; Stuckyt, G. D. . Uniform concave polystyrene-carbon core-shell nanospheres by a swelling induced buckling process . J. Am. Chem. Soc. , 2015 . 137 9772 - 9775 . DOI: 10.1021/jacs.5b05027 http://doi.org/10.1021/jacs.5b05027 .

Mo, A. H.; Landon, P. B.; Emerson, C. D.; Zhang, C.; Anzenberg, P.; Akkiraju, S.; Lal, R. . Synthesis of nano-bowls with a janus template . Nanoscale , 2015 . 7 771 - 775 . DOI: 10.1039/C4NR05153J http://doi.org/10.1039/C4NR05153J .

Wang, Y. L.; Li, C. N.; He, X. H.; Zhu, J. T. . Preparation and assembly of concave polymer microparticles . RSC Adv. , 2015 . 5 36680 - 36686 . DOI: 10.1039/C5RA04110D http://doi.org/10.1039/C5RA04110D .

Liu, X.; Liu, J.; Jiang, M. . Spontaneous self-assembly of a mono-component polyimide bearing terminal hydrogen-bonding sites in a single solvent . Macromol. Rapid Commun. , 2009 . 30 892 - 896 . DOI: 10.1002/marc.200800773 http://doi.org/10.1002/marc.200800773 .

Wang, J.; Kuang, M.; Duan, H. W.; Chen, D. Y.; Jiang, M. . pH-dependent multiple morphologies of novel aggregates of carboxyl-terminated polymide in water . Eur. Phys. J. E , 2004 . 15 211 - 215 . DOI: 10.1140/epje/i2004-10049-5 http://doi.org/10.1140/epje/i2004-10049-5 .

Bucknall, D. G.; Anderson, H. L. . Polymers get organized . Science , 2003 . 302 1904 - 1905 . DOI: 10.1126/science.1091064 http://doi.org/10.1126/science.1091064 .

Hsu, C. Y.; Chang, S. C.; Hsu, K. Y.; Liu, Y. L. . Photoluminescent toroids formed by temperature-driven self-assembly of Rhodamine B end-capped poly( N -isopropylacrylamide) . Macromol. Rapid Commun. , 2013 . 34 689 - 694 . DOI: 10.1002/marc.201300038 http://doi.org/10.1002/marc.201300038 .

Zhu, Y. Q.; Fan, L.; Yang, B.; Du, J. Z. . Multifunctional homopolymer vesicles for facile immobilization of gold nanoparticles and effective water remediation . ACS Nano , 2014 . 8 5022 - 5031 . DOI: 10.1021/nn5010974 http://doi.org/10.1021/nn5010974 .

Zhu, Y. Q.; Liu, L.; Du, J. Z. . Probing into homopolymer self-assembly: how does hydrogen bonding influence morphology? . Macromolecules , 2013 . 46 194 - 203 . DOI: 10.1021/ma302176a http://doi.org/10.1021/ma302176a .

Ramireddy, R. R.; Prasad, P.; Finne, A.; Thayumanavan, S. . Zwitterionic amphiphilic homopolymer assemblies . Polym. Chem. , 2015 . 6 6083 - 6087 . DOI: 10.1039/C5PY00879D http://doi.org/10.1039/C5PY00879D .

Zhang, J.; Liu, K. L.; Mullen, K.; Yin, M. Z. . Self-assemblies of amphiphilic homopolymers: synthesis, morphology studies and biomedical applications . Chem. Commun. , 2015 . 51 11541 - 11555 . DOI: 10.1039/C5CC03016A http://doi.org/10.1039/C5CC03016A .

Li, Q. Y.; Lei, T.; Yao, Z. F.; Wang, J. Y.; Pei, J. . Multi-level self-assembly of conjugated polymers . Acta Polymerica Sinica (in Chinese) , 2019 . 50 1 - 12 . .

Sun, H.; Liu, D. Q.; Du, J. Z. . Nanobowls with controlled openings and interior holes driven by the synergy of hydrogen bonding and π-π interaction . Chem. Sci , 2019 . 10 657 - 664 . DOI: 10.1039/C8SC03995J http://doi.org/10.1039/C8SC03995J .

Huang, J.; Su, L. L.; Hang, Y. X.; Shi, B. B.; Wang, X. D.; Xu, H. . Water-soluble fluorescent nanobowls constructed by multiple supramolecular assembly . Macromolecules , 2020 . 53 10613 - 10622 . DOI: 10.1021/acs.macromol.0c01728 http://doi.org/10.1021/acs.macromol.0c01728 .

Wang, H.; Feng, Z.; Xu, B. . D-amino acid-containing supramolecular nanofibers for potential cancer therapeutics . Adv. Drug. Deliv. Rev. , 2017 . 110-111 102 - 111 . DOI: 10.1016/j.addr.2016.04.008 http://doi.org/10.1016/j.addr.2016.04.008 .

Adler-Abramovich, L.; Kol, N.; Yanai, I.; Barlam, D.; Shneck, R. Z.; Gazit, E.; Rousso, I. . Self-assembled organic nanostructures with metallic-like stiffness . Angew. Chem. Int. Ed. , 2010 . 49 9939 - 9942 . DOI: 10.1002/anie.201002037 http://doi.org/10.1002/anie.201002037 .

Raeburn, J.; Pont, G.; Chen, L.; Cesbron, Y.; Levy, R.; Adams, D. J. . Fmoc-diphenylalanine hydrogels: understanding the variability in reported mechanical properties . Soft Matter , 2012 . 8 1168 - 1174 . .

Brown, N.; Lei, J.; Zhan, C.; Shimon, L. J. W.; Adler-Abramovich, L.; Wei, G.; Gazit, E. . Structural polymorphism in a self-assembled tri-aromatic peptide system . ACS Nano , 2018 . 12 3253 - 3262 . DOI: 10.1021/acsnano.7b07723 http://doi.org/10.1021/acsnano.7b07723 .

Fleming, S.; Ulijn, R. V. . Design of nanostructures based on aromatic peptide amphiphiles . Chem. Soc. Rev. , 2014 . 43 8150 - 8177 . DOI: 10.1039/C4CS00247D http://doi.org/10.1039/C4CS00247D .

Wijerathne, N. K.; Kumar, M.; Ulijn, R. V. . Fmoc-dipeptide/porphyrin molar ratio dictates energy transfer efficiency in nanostructures produced by biocatalytic co-assembly . Chem. Eur. J. , 2019 . 25 11847 - 11851 . DOI: 10.1002/chem.201902819 http://doi.org/10.1002/chem.201902819 .

Smith, A. M.; Williams, R. J.; Tang, C.; Coppo, P.; Collins, R. F.; Turner, M. L.; Saiani, A.; Ulijn, R. V. . Fmoc-diphenylalanine self assembles to a hydrogel via a novel architecture based on π-π interlocked β -sheets . Adv. Mater. , 2008 . 20 37 - 41 . DOI: 10.1002/adma.200701221 http://doi.org/10.1002/adma.200701221 .

Tang, C.; Smith, A. M.; Collins, R. F.; Ulijn, R. V.; Saiani, A. . Fmoc-diphenylalanine self-assembly mechanism induces apparent p K a shifts . Langmuir , 2009 . 25 9447 - 9453 . DOI: 10.1021/la900653q http://doi.org/10.1021/la900653q .

Kale, T. S.; Klaikherd, A.; Popere, B.; Thayumanavan, S. . Supramolecular assemblies of amphiphilic homopolymers . Langmuir , 2009 . 25 9660 - 9670 . DOI: 10.1021/la900734d http://doi.org/10.1021/la900734d .

Feng, C.; Lu, G. L.; Li, Y. J.; Huang, X. Y. . Self-assembly of amphiphilic homopolymers bearing ferrocene and carboxyl functionalities: effect of polymer concentration, β -cyclodextrin, and length of alkyl linker . Langmuir , 2013 . 29 10922 - 10931 . DOI: 10.1021/la402335d http://doi.org/10.1021/la402335d .

Roy, B.; Govindaraju, T. . Amino acids and peptides as functional components in arylenediimide-based molecular architectonics . Bull. Chem. Soc. Jpn. , 2019 . 92 1883 - 1901 . DOI: 10.1246/bcsj.20190215 http://doi.org/10.1246/bcsj.20190215 .

Zhao, L.; Zou, Q.; Yan, X. . Self-assembling peptide-based nanoarchitectonics . Bull. Chem. Soc. Jpn. , 2019 . 92 70 - 79 . DOI: 10.1246/bcsj.20180248 http://doi.org/10.1246/bcsj.20180248 .

Han, J.; Li, Y.; Zhan, L.; Xue, J.; Sun, J.; Xiong, C.; Nie, Z. . A novel mass spectrometry method based on competitive non-covalent interaction for the detection of biomarkers . Chem. Commun. , 2018 . 54 10726 - 10729 . DOI: 10.1039/C8CC06100A http://doi.org/10.1039/C8CC06100A .

Zhang, L. F.; Eisenberg, A. . Thermodynamic vs kinetic aspects in the formation and morphological transitions of crew-cut aggregates produced by self-assembly of polystyrene- b -poly(acrylic acid) block copolymers in dilute solution . Macromolecules , 1999 . 32 2239 - 2249 . DOI: 10.1021/ma981039f http://doi.org/10.1021/ma981039f .

Wolffs, M.; Korevaar, P. A.; Jonkheijm, P.; Henze, O.; Feast, W. J.; Schenning, A. P. H. J.; Meijer, E. W. . The role of heterogeneous nucleation in the self-assembly of oligothiophenes . Chem. Commun. , 2008 . 4613 - 4615 . .

Riegel, I. C.; Eisenberg, A.; Petzhold, C. L.; Samios, D. . Novel bowl-shaped morphology of crew-cut aggregates from amphiphilic block copolymers of styrene and 5-( N , N -diethylamino)isoprene . Langmuir , 2002 . 18 3358 - 3363 . DOI: 10.1021/la015592t http://doi.org/10.1021/la015592t .

Liu, J.; Zhang, X.; Li, W.; Jiang, C.; Wang, Z.; Xiao, X. . Recent progress in periodic patterning fabricated by self-assembly of colloidal spheres for optical applications . Sci. China Mater. , 2020 . 63 1418 - 1437 . DOI: 10.1007/s40843-020-1284-8 http://doi.org/10.1007/s40843-020-1284-8 .

Bera, S.; Mondal, S.; Tang, Y. M.; Jacoby, G.; Arad, E.; Guterman, T.; Jelinek, R.; Beck, R.; Wei, G. H.; Gazit, E. . Deciphering the rules for amino acid co-assembly based on interlayer distances . ACS Nano , 2019 . 13 1703 - 1712 . .

Pearson, R. T.; Warren, N. J.; Lewis, A. L.; Armes, S. P.; Battaglia, G. . Effect of pH and temperature on PMPC-PDPA copolymer self-assembly . Macromolecules , 2013 . 46 1400 - 1407 . DOI: 10.1021/ma302228m http://doi.org/10.1021/ma302228m .

Yang, B.; Du, J. Z. . Ultrasound-responsive homopolymer nanoparticles . Chinese J. Polym. Sci. , 2020 . 38 349 - 356 . DOI: 10.1007/s10118-020-2345-6 http://doi.org/10.1007/s10118-020-2345-6 .

Burattini, S.; Greenland, B. W.; Merino, D. H.; Weng, W. G.; Seppala, J.; Colquhoun, H. M.; Hayes, W.; Mackay, M. E.; Hamley, I. W.; Rowan, S. J. . A healable supramolecular polymer blend based on aromatic π-π stacking and hydrogen-bonding interactions . J. Am. Chem. Soc. , 2010 . 132 12051 - 12058 . DOI: 10.1021/ja104446r http://doi.org/10.1021/ja104446r .

Rubino, J. T.; Yalkowsky, S. H. . Cosolvency and cosolvent polarity . Pharm. Res. , 1987 . 4 220 - 230 . DOI: 10.1023/A:1016456127893 http://doi.org/10.1023/A:1016456127893 .

Wei, W. S.; Xia, Y.; Ettinger, S.; Yang, S.; Yodh, A. G. . Molecular heterogeneity drives reconfigurable nematic liquid crystal drops . Nature , 2019 . 576 433 DOI: 10.1038/s41586-019-1809-8 http://doi.org/10.1038/s41586-019-1809-8 .

Sun, J. C.; Zhang, H.; Guo, K.; Yuan, S. L. . Self-assembly of dipeptide sodium salts derived from alanine: A molecular dynamics study . RSC Adv. , 2015 . 5 102182 - 102190 . DOI: 10.1039/C5RA19508J http://doi.org/10.1039/C5RA19508J .

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