journal article·2020-07Open access

Peptoid-based hierarchically-structured biomimetic nanomaterials: Synthesis, characterization and applications

Jianli Liu, Bin Cai, Lifeng Cui, Chun-Long Chen

Science China Materials· Volume 63· Issue 7

Abstract

Peptoids (or poly- N -substituted glycines) are a promising class of bioinspired sequence-defined polymers due to their highly efficient synthesis, high chemical stability, enzyme hydrolysis resistance, and biocompatibility. By tuning the side chain chemistry of peptoids, it allows for precise control over sequences and achieving a large side-chain diversity. Due to these unique features, in the last several years, many amphiphilic peptoids were designed as highly tunable building blocks for the preparation of biomimetic nanomaterials with well-defined hierarchical structures and desired functionalities. Herein, we provide an overview of the recent achievements in this area by dividing them into the following three aspects. First, mica- and silica-templated peptoid self-assembly are summarized. The presence of inorganic substrates provides the guarantee of investigating their self-assembly mechanisms and interactions between peptoids and substrates using nanoscale characterization techniques, particularly in situ atomic force microscopy (AFM) and AFM-based dynamic force spectroscopy (AFM-DFS). Second, solution-phase self-assembly of peptoids into nanotubes and nanosheets is presented, as well as their self-repair properties. Third, the applications of peptoid-based nanomaterials are outlined, including the construction of catalytic nanomaterials as a template and cytosolic delivery as cargoes.
Source: openaire · Quality: candidate unverified · Source record ↗

Research context

OpenAlex topics: Chemical Synthesis and Analysis · Advanced biosensing and bioanalysis techniques · Supramolecular Self-Assembly in Materials

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

References (56)

Show source-provided references
1. Sun J, Zuckermann RN. Peptoid polymers: A highly designable bioinspired material. ACS Nano, 2013, 7: 4715–473210.1021/nn4015714 ↗
2. Knight AS, Zhou EY, Francis MB, et al. Sequence programmable peptoid polymers for diverse materials applications. Adv Mater, 2015, 27: 5665–569110.1002/adma.201500275 ↗
3. Liu R, Hudalla GA. Using self-assembling peptides to integrate biomolecules into functional supramolecular biomaterials. Molecules, 2019, 24: 145010.3390/molecules24081450 ↗
4. Lin Y, Mao C. Bio-inspired supramolecular self-assembly towards soft nanomaterials. Front Mater Sci, 2011, 5: 247–26510.1007/s11706-011-0141-5 ↗
5. Lutz JF, Ouchi M, Liu DR, et al. Sequence-controlled polymers. Science, 2013, 341: 123814910.1126/science.1238149 ↗
6. Chang B, Li X, Sun T. Self-assembled chiral materials from achiral components or racemates. Eur Polym J, 2019, 118: 365–38110.1016/j.eurpolymj.2019.05.061 ↗
7. Robertson EJ, Battigelli A, Proulx C, et al. Design, synthesis, assembly, and engineering of peptoid nanosheets. Acc Chem Res, 2016, 49: 379–38910.1021/acs.accounts.5b00439 ↗
8. Luo Y, Song Y, Wang M, et al. Bioinspired peptoid nanotubes for targeted tumor cell imaging and chemo-photodynamic therapy. Small, 2019, 15: 190248510.1002/smll.201902485 ↗
9. Jin H, Jian T, Ding YH, et al. Solid-phase synthesis of three-armed star-shaped peptoids and their hierarchical self-assembly. Biopolymers, 2019, 110: e2325810.1002/bip.23258 ↗
10. Jiao F, Wu X, Jian T, et al. Hierarchical assembly of peptoid-based cylindrical micelles exhibiting efficient resonance energy transfer in aqueous solution. Angew Chem Int Ed, 2019, 58: 12223–1223010.1002/anie.201904598 ↗
11. Yan F, Liu L, Walsh TR, et al. Controlled synthesis of highly-branched plasmonic gold nanoparticles through peptoid engineering. Nat Commun, 2018, 9: 232710.1038/s41467-018-04789-2 ↗
12. Jin H, Ding YH, Wang M, et al. Designable and dynamic singlewalled stiff nanotubes assembled from sequence-defined peptoids. Nat Commun, 2018, 9: 27010.1038/s41467-017-02059-1 ↗
13. Murray DJ, Kim JH, Grzincic EM, et al. Uniform, large-area, highly ordered peptoid monolayer and bilayer films for sensing applications. Langmuir, 2019, 35: 13671–1368010.1021/acs.langmuir.9b02557 ↗
14. Jin H, Jiao F, Daily MD, et al. Highly stable and self-repairing membrane-mimetic 2D nanomaterials assembled from lipid-like peptoids. Nat Commun, 2016, 7: 1225210.1038/ncomms12252 ↗
15. Jiao F, Chen Y, Jin H, et al. Self-repair and patterning of 2D membrane-like peptoid materials. Adv Funct Mater, 2016, 26: 8960–896710.1002/adfm.201602365 ↗
16. Chen CL, Zuckermann RN, DeYoreo JJ. Surface-directed assembly of sequence-defined synthetic polymers into networks of hexagonally patterned nanoribbons with controlled functionalities. ACS Nano, 2016, 10: 5314–532010.1021/acsnano.6b01333 ↗
17. Song Y, Wang M, Li S, et al. Efficient cytosolic delivery using crystalline nanoflowers assembled from fluorinated peptoids. Small, 2018, 14: 180354410.1002/smll.201803544 ↗
18. Zhu L, Zhao Z, Cheng P, et al. Antibody-mimetic peptoid nanosheet for label-free serum-based diagnosis of Alzheimer’s disease. Adv Mater, 2017, 29: 170005710.1002/adma.201700057 ↗
19. Zuckermann RN, Kerr JM, Kent SBH, et al. Efficient method for the preparation of peptoids [oligo(N-substituted glycines)] by submonomer solid-phase synthesis. J Am Chem Soc, 1992, 114: 10646–1064710.1021/ja00052a076 ↗
20. Horn T, Lee BC, Dill KA, et al. Incorporation of chemoselective functionalities into peptoids via solid-phase submonomer synthesis. Bioconjugate Chem, 2004, 15: 428–43510.1021/bc0341831 ↗
21. Fowler SA, Luechapanichkul R, Blackwell HE. Synthesis and characterization of nitroaromatic peptoids: Fine tuning peptoid secondary structure through monomer position and functionality. J Org Chem, 2009, 74: 1440–144910.1021/jo8023363 ↗
22. Malkin AJ, Kuznetsov YG, McPherson A. In situ atomic force microscopy studies of surface morphology, growth kinetics, defect structure and dissolution in macromolecular crystallization. J Cryst Growth, 1999, 196: 471–48810.1016/S0022-0248(98)00823-9 ↗
23. Engel A. Atomic force microscopy: A powerful tool to observe biomolecules at work. Trends Cell Biol, 1999, 9: 77–8010.1016/S0962-8924(98)01415-9 ↗
24. Takeuchi O, Miyakoshi T, Taninaka A, et al. Dynamic-force spectroscopy measurement with precise force control using atomic-force microscopy probe. J Appl Phys, 2006, 100: 07431510.1063/1.2355432 ↗
25. Liu J, Zhang X, Wang X, et al. Single-molecule force spectroscopy study of the effect of cigarette carcinogens on thrombomodulin-thrombin interaction. Sci Bull, 2016, 61: 1187–119410.1007/s11434-016-1084-0 ↗
26. De Yoreo JJ, Chung S, Friddle RW. In situ atomic force microscopy as a tool for investigating interactions and assembly dynamics in biomolecular and biomineral systems. Adv Funct Mater, 2013, 23: 2525–253810.1002/adfm.201203424 ↗
27. Chan BA, Xuan S, Li A, et al. Polypeptoid polymers: Synthesis, characterization, and properties. Biopolymers, 2018, 109: e2307010.1002/bip.23070 ↗
28. Battigelli A. Design and preparation of organic nanomaterials using self-assembled peptoids. Biopolymers, 2019, 110: e2326510.1002/bip.23265 ↗
29. Nam KT, Shelby SA, Choi PH, et al. Free-floating ultrathin two-dimensional crystals from sequence-specific peptoid polymers. Nat Mater, 2010, 9: 454–46010.1038/nmat2742 ↗
30. Robertson EJ, Olivier GK, Qian M, et al. Assembly and molecular order of two-dimensional peptoid nanosheets through the oil-water interface. Proc Natl Acad Sci USA, 2014, 111: 13284–1328910.1073/pnas.1414843111 ↗
31. Sanii B, Kudirka R, Cho A, et al. Shaken, not stirred: Collapsing a peptoid monolayer to produce free-floating, stable nanosheets. J Am Chem Soc, 2011, 133: 20808–2081510.1021/ja206199d ↗
32. Olivier GK, Cho A, Sanii B, et al. Antibody-mimetic peptoid nanosheets for molecular recognition. ACS Nano, 2013, 7: 9276–928610.1021/nn403899y ↗
33. Kudirka R, Tran H, Sanii B, et al. Folding of a single-chain, information-rich polypeptoid sequence into a highly ordered nanosheet. Biopolymers, 2011, 96: 586–59510.1002/bip.21590 ↗
34. Murnen HK, Rosales AM, Jaworski JN, et al. Hierarchical self-assembly of a biomimetic diblock copolypeptoid into homochiral superhelices. J Am Chem Soc, 2010, 132: 16112–1611910.1021/ja106340f ↗
35. Ma X, Zhang S, Jiao F, et al. Tuning crystallization pathways through sequence engineering of biomimetic polymers. Nat Mater, 2017, 16: 767–77410.1038/nmat4891 ↗
36. Mu P, Zhou G, Chen CL. 2D nanomaterials assembled from sequence-defined molecules. Nano-Struct Nano-Objects, 2018, 15: 153–16610.1016/j.nanoso.2017.09.010 ↗
37. Jariwala D, Sangwan VK, Lauhon LJ, et al. Carbon nanomaterials for electronics, optoelectronics, photovoltaics, and sensing. Chem Soc Rev, 2013, 42: 2824–286010.1039/C2CS35335K ↗
38. Yang G, Zhu C, Du D, et al. Graphene-like two-dimensional layered nanomaterials: Applications in biosensors and nanomedicine. Nanoscale, 2015, 7: 14217–1423110.1039/C5NR03398E ↗
39. Velický M, Toth PS. From two-dimensional materials to their heterostructures: An electrochemist’s perspective. Appl Mater Today, 2017, 8: 68–10310.1016/j.apmt.2017.05.003 ↗
40. Choi CH, Lee DJ, Sung JH, et al. A study of AFM-based scratch process on polycarbonate surface and grating application. Appl Surf Sci, 2010, 256: 7668–767110.1016/j.apsusc.2010.06.025 ↗
41. Balasubramanian R, Prayakarao S, Han S, et al. Tunable gold nanostructures with nanocapsules as template reaction vessels. RSC Adv, 2012, 2: 11668–1167110.1039/c2ra21986g ↗
42. Xu WL, Smith MD, Krause JA, et al. Single crystal to single crystal polymerization of a self-assembled diacetylene macrocycle affords columnar polydiacetylenes. Cryst Growth Des, 2014, 14: 993–100210.1021/cg401380a ↗
43. Hsieh WH, Liaw J. Applications of cyclic peptide nanotubes (cPNTs). J Food Drug Anal, 2019, 27: 32–4710.1016/j.jfda.2018.09.004 ↗
44. Zhao X, Pan F, Xu H, et al. Molecular self-assembly and applications of designer peptide amphiphiles. Chem Soc Rev, 2010, 39: 3480–349810.1039/b915923c ↗
45. Young TJ, Monclus MA, Burnett TL, et al. The use of the Peak-Force™ quantitative nanomechanical mapping AFM-based method for high-resolution Young’s modulus measurement of polymers. Meas Sci Technol, 2011, 22: 12570310.1088/0957-0233/22/12/125703 ↗
46. Morales-Rivas L, González-Orive A, Garcia-Mateo C, et al. Nanomechanical characterization of nanostructured bainitic steel: Peak force microscopy and nanoindentation with AFM. Sci Rep, 2015, 5: 1716410.1038/srep17164 ↗
47. Adler-Abramovich L, Gazit E. The physical properties of supra-molecular peptide assemblies: From building block association to technological applications. Chem Soc Rev, 2014, 43: 6881–689310.1039/C4CS00164H ↗
48. Yu SH, Chen SF. Recent advances in polymer directed crystal growth and mediated self-assembly of nanoparticles. CNANO, 2006, 2: 81–9210.2174/157341306776875767 ↗
49. Lazzari M, Rodríguez-Abreu C, Rivas J, et al. Self-assembly: A minimalist route to the fabrication of nanomaterials. J Nanosci Nanotech, 2006, 6: 892–90510.1166/jnn.2006.172 ↗
50. An Y, Ren Y, Bick M, et al. Highly fluorescent copper nanoclusters for sensing and bioimaging. Biosens Bioelectron, 2020, 154: 11207810.1016/j.bios.2020.112078 ↗
51. Tang J, Qin N, Chong Y, et al. Nanowire arrays restore vision in blind mice. Nat Commun, 2018, 9: 78610.1038/s41467-018-03212-0 ↗
52. Merrill NA, Yan F, Jin H, et al. Tunable assembly of biomimetic peptoids as templates to control nanostructure catalytic activity. Nanoscale, 2018, 10: 12445–1245210.1039/C8NR03852J ↗
53. Aparicio-Blanco J, Sebastián V, Rodríguez-Amaro M, et al. Size-tailored design of highly monodisperse lipid nanocapsules for drug delivery. J Biomed Nanotechnol, 2019, 15: 1149–116110.1166/jbn.2019.2765 ↗
54. Jiang Y, Tang R, Duncan B, et al. Direct cytosolic delivery of siRNA using nanoparticle-stabilized nanocapsules. Angew Chem Int Ed, 2014, 54: 506–51010.1002/anie.201409161 ↗
55. Schröder T, Niemeier N, Afonin S, et al. Peptoidic amino- and guanidinium-carrier systems: Targeted drug delivery into the cell cytosol or the nucleus. J Med Chem, 2008, 51: 376–37910.1021/jm070603m ↗
56. Dowdy SF. Overcoming cellular barriers for RNA therapeutics. Nat Biotechnol, 2017, 35: 222–22910.1038/nbt.3802 ↗