Engineering pH-responsive switching of donor–π–acceptor chromophore alignments along a peptide nanotube scaffold

Tabata, Yuki; Kamano, Yusuke; Kimura, Shunsaku; Uji, Hirotaka

doi:10.1039/d0ra00231c

Cited by 6 publications

(6 citation statements)

References 33 publications

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“…Previously, we demonstrated the formation of pHresponsive bundles and single PNTs repeatedly in aqueous solution, where the charged groups introduced at the side chain cause electrostatic repulsion between the PNTs and prevent bundling. 31 Therefore, in this study, it can be presumed that the partial charge of the helical peptide at the C-terminus decreases the dipole−dipole interaction between the PNTs, causing the PNT crystals to disassemble into a single PNT during sonication treatment.…”

Section: ■ Results and Discussionmentioning

confidence: 87%

“…29 α,γ-PNTs bearing fullerene side chains were also reported to form a defined bundle structure due to self-assembly of fullerene arrangements. 30 Recently, the introduction of charged side-chain moieties, such as naphthalimide (Npi) groups 31 or chloranil groups, 32 to cyclic βpeptides was found to lead to the formation of single PNTs in aqueous solutions, preventing bundle formation by electrostatic repulsion. These ionic functional groups can affect the piezoelectric properties; therefore, it is necessary to construct single PNTs with nonionic functional moieties.…”

Section: ■ Introductionmentioning

confidence: 99%

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Construction and Piezoelectric Properties of a Single-Peptide Nanotube Composed of Cyclic β-peptides with Helical Peptides on the Side Chains

et al. 2021

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To develop nanopiezoelectronics, it is necessary to investigate the relationship between the sizes and piezoelectric properties of the material. Peptide nanotubes (PNTs) composed of cyclic β-peptides have been studied as leading candidates for nanopiezoelectric materials. The current drawback of PNTs is aggregation to form a PNT bundle structure due to strong dipole–dipole interactions between PNTs. Here, we report the construction and piezoelectric properties of single PNTs without nonspecific aggregation by side-chain modification of helical peptides. A cyclic tri-β-peptide with a helical peptide was prepared by multiple-step liquid-phase peptide synthesis and assembled into PNTs by the vapor diffusion method. These nanotubes were characterized by polarized light microscopy and Fourier transform infrared (FTIR) spectroscopy. Additionally, atomic force microscopy (AFM) topographic images showed nanotubes with a height of 4 nm, which corresponds to the diameter of a PNT on a gold-coated mica substrate, indicating that a single PNT was prepared successfully. The converted piezoelectric response of a single PNT was determined to be 1.39 ± 0.12 pm/V. This value was consistent with that of a PNT bundle, which reveals that the piezoelectricity of PNTs is induced by deformation of their cyclic skeletons and is independent of the bundled structure. This finding not only demonstrates a new molecular design strategy to construct these smallest piezoelectric biomaterials by controlling the supramolecular hierarchical structures but also provides insights into the correlation between molecular assembly morphology and size-dependent piezoelectric properties.

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Section: ■ Results and Discussionmentioning

confidence: 87%

Section: ■ Introductionmentioning

confidence: 99%

Construction and Piezoelectric Properties of a Single-Peptide Nanotube Composed of Cyclic β-peptides with Helical Peptides on the Side Chains

et al. 2021

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“…Later on, a nanotube-forming α-alt( d,l )-cyclic peptide bearing four NDI units was shown to self-assemble into electronically delocalized nanotubes in aqueous media because of the alignment of the NDI moieties promoted by the directed backbone hydrogen bonding interactions between the cyclic peptides . Moreover, the alignment of other π-conjugated moieties such as fullerene, pyrene, and tetrathiafulvalene was also realized by the use of either cyclic α,γ-peptides or cyclic β-peptides as scaffolds. ,− More interestingly, as shown in Figure , the pyrene-modified SCPNs were further applied to noncovalently interact with single-walled carbon nanotubes (SWCNTs) or subnanometric silver metal clusters, resulting in functional hybrid nanomaterials. , Thus, intermolecular peptide self-assembly proved to be an effective template for the construction of one-dimensional nanomaterials with potential applications, such as optical and electronic devices.…”

Section: Design and Functionalization Of Cyclic Peptidesmentioning

confidence: 99%

Molecular Self-Assembly and Supramolecular Chemistry of Cyclic Peptides

et al. 2021

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This Review focuses on the establishment and development of self-assemblies governed by the supramolecular interactions between cyclic peptides. The Review first describes the type of cyclic peptides able to assemble into tubular structures to form supramolecular cyclic peptide nanotubes. A range of cyclic peptides have been identified to have such properties, including α-peptides, β-peptides, α,γ-peptides, and peptides based on δ- and ε-amino acids. The Review covers the design and functionalization of these cyclic peptides and expands to a recent advance in the design and application of these materials through their conjugation to polymer chains to generate cyclic peptide–polymer conjugates nanostructures. The Review, then, concentrates on the challenges in characterizing these systems and presents an overview of the various analytical and characterization techniques used to date. This overview concludes with a critical survey of the various applications of the nanomaterials obtained from supramolecular cyclic peptide nanotubes, with a focus on biological and medical applications, ranging from ion channels and membrane insertion to antibacterial materials, anticancer drug delivery, gene delivery, and antiviral applications.

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“…Further, upon applying a coercive electric field, the pairing of TTF and chloranil will be rearranged to generate the dipole of the charge-transfer complex in the direction opposite to that without the applied electric field but with low energy dissipation on the same PNT scaffold. [21] Therefore, molecular dipole switching materials without accompanying molecular assembling structural changes are attainable by using a donor-acceptor complex along the PNT.…”

Section: Introductionmentioning

confidence: 99%

“…When one cyclic peptide carrying a TTF and another with chloranil alternatingly stack together to form a PNT with the help of stabilization energy upon charge‐transfer complex formation, the pairing of TTF and chloranil along the PNT will occur to generate a dipole of the charge‐transfer complex pointing parallel to the electric field of the PNT scaffold. Further, upon applying a coercive electric field, the pairing of TTF and chloranil will be rearranged to generate the dipole of the charge‐transfer complex in the direction opposite to that without the applied electric field but with low energy dissipation on the same PNT scaffold [21] . Therefore, molecular dipole switching materials without accompanying molecular assembling structural changes are attainable by using a donor‐acceptor complex along the PNT.…”

Section: Introductionmentioning

confidence: 99%

Piezoelectric properties reflecting nanostructures of tetrathiafulvalene and chloranil complexes using cyclic peptide nanotube scaffolds

et al. 2020

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Tetrathiafulvalene (TTF) and chloranil were introduced at the side chains of different cyclic tripeptides, which were self-assembled into peptide nanotubes (PNTs). PNTs were used as scaffolds for alignment of the charge-transfer complexes between TTF and chloranil, and they were prepared via two methods, one is that mixing a PNT comprising only TTF with a PNT comprising only chloranil (method 1), and the other is that one pot mixing of cyclic tripeptides with TTF and cyclic tripeptides with chloranil to be self-assembled into PNTs (method 2). These PNTs naturally associated to form PNT bundles. The surface potentials of the PNT bundles became larger for the PNTs carrying charge-transfer complexes along the PNT (method 2) than those between PNTs (method 1). This bundle of PNT carrying charge-transfer complexes along the PNT (method 2) showed a hysteresis response in the piezoelectric force curve with varying bias voltages according to piezoelectric force microscope measurements.

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Engineering pH-responsive switching of donor–π–acceptor chromophore alignments along a peptide nanotube scaffold

Abstract: pH-Responsive switching between a left-handed chiral and random alignments of D–π–A naphthalimides along a peptide nanotube (PNT) composed of tri-β-cyclic peptides was attained in response to repeated pH changes.

Cited by 6 publications

References 33 publications

Construction and Piezoelectric Properties of a Single-Peptide Nanotube Composed of Cyclic β-peptides with Helical Peptides on the Side Chains

Construction and Piezoelectric Properties of a Single-Peptide Nanotube Composed of Cyclic β-peptides with Helical Peptides on the Side Chains

Molecular Self-Assembly and Supramolecular Chemistry of Cyclic Peptides

Piezoelectric properties reflecting nanostructures of tetrathiafulvalene and chloranil complexes using cyclic peptide nanotube scaffolds

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