1D alignment of proteins and other nanoparticles by using reversible covalent bonds on cyclic peptide nanotubes

Granja, Juan R.; Montenegro, Javier; Louzao, Iria; Gallego, Iván; Priegue, Juan M.

doi:10.1039/d1qo01349a

Cited by 9 publications

(10 citation statements)

References 61 publications

(11 reference statements)

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“…[24] Another noteworthy advantage of cyclic peptides with alternative chirality is that the exposed surface could provide appropriate amino acid side chains for further modifications by incorporating natural or unnatural amino acids with functional groups. [25] The nanotubular structures in which all the side chains project perpendicularly toward the tube axis to provide ample spaces for conjugating with polymers or peptides. The report showed that cyclic d/l peptides could display superior solubility in water or lipophilicity to interact with biological membranes by tuning the hydrophilicity and hydrophobicity through side chains.…”

Section: Introductionmentioning

confidence: 99%

“…Another noteworthy advantage of cyclic peptides with alternative chirality is that the exposed surface could provide appropriate amino acid side chains for further modifications by incorporating natural or unnatural amino acids with functional groups [25] . The nanotubular structures in which all the side chains project perpendicularly toward the tube axis to provide ample spaces for conjugating with polymers or peptides.…”

Section: Introductionmentioning

confidence: 99%

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Recent Progress on Cyclic Peptides’ Assembly and Biomedical Applications

Wang

2023

ChemBioChem

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Cyclic peptides are important building blocks for forming functional structures and have been applied in various fields. Considering the significant structural and functional roles of cyclic peptides in materials science and the attributed biophysical advantages, we provide an overview of cyclic peptide types that can self‐assemble to form nanotubes, recent progress in stimuli‐triggered cyclic peptide assembly, and methods to construct peptide and polymer conjugates based on cyclic peptides with alternative chirality. Specifically, we highlight the roles that stimuli‐triggered cyclic peptides and their conjugates play in biomedical applications. Recent progress in other cyclic peptides acting as gelators in drug delivery and biomedicine are also summarized. These cyclic peptides with self‐assembly properties are expected to act as adaptive systems for drug delivery and selective disease targeting.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Recent Progress on Cyclic Peptides’ Assembly and Biomedical Applications

Wang

2023

ChemBioChem

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“…So far, most of the reported work of cyclic peptides produced via an irreversible amide coupling reaction, featuring a symmetrical backbone [16] self‐assemble to form 1D nanotubular structures and even 2D nanosheets [17] (Figure1a). Studies mainly focus on the modifications of nanotubes via a reversible covalent linkage through peptide side chains [9b,e,18] . However, the self‐assembly (SA) behaviors and the conformational tuning diversity of cyclic peptides with an asymmetrical backbone, such as incorporating a heterocycle has been less explored.…”

Section: Introductionmentioning

confidence: 99%

Dynamic Control of Cyclic Peptide Assembly to Form Higher‐Order Assemblies

Zhang

Kong

et al. 2023

Angew Chem Int Ed

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Chirality correction, asymmetry, ring‐chain tautomerism and hierarchical assemblies are fundamental phenomena in nature. They are geometrically related and may impact the biological roles of a protein or other supermolecules. It is challenging to study those behaviors within an artificial system due to the complexity of displaying these features. Herein, we design an alternating D,L peptide to recreate and validate the naturally occurring chirality inversion prior to cyclization in water. The resulting asymmetrical cyclic peptide containing a 4‐imidazolidinone ring provides an excellent platform to study the ring‐chain tautomerism, thermostability and dynamic assembly of the nanostructures. Different from traditional cyclic D,L peptides, the formation of 4‐imidazolidinone promotes the formation of intertwined nanostructures. Analysis of the nanostructures confirmed the left‐handedness, representing chirality induced self‐assembly. This proves that a rationally designed peptide can mimic multiple natural phenomena and could promote the development of functional biomaterials, catalysts, antibiotics, and supermolecules.

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“…[40][41] The highly ordered supramolecular structures have been employed as scaffolds to enable the precise arrangement of functional moieties, including drugs, π-conjugated chromophores, proteins, and nanoparticles. [42][43][44][45][46][47][48] More importantly, the densely packed polymer chains surrounding the cyclic peptide cores are expected to create a confined microenvironment. Therefore, we envisaged that by positioning the cyanine moieties near the core area within the supramolecular polymeric nanotubes, while molecularly dispensing them along the tubular structures, the undesired cis-trans photoisomerization and ACQ could be inhibited simultaneously, thus greatly boosting the fluorescence quantum yields of cyanine dyes.…”

Section: Introductionmentioning

confidence: 99%

Supra‐Cyanines: Ultrabright Cyanine‐Based Fluorescent Supramolecular Materials in Solution and in the Solid State

Lu,

Wang,

Hill

et al. 2023

Angew Chem Int Ed

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Fluorescent materials with high brightness play a crucial role in the advancement of various technologies such as bioimaging, photonics, and OLEDs. While significant efforts are dedicated to designing new organic dyes with improved performance, enhancing the brightness of existing dyes holds equal importance. In this study, we present a simple supramolecular strategy to develop ultrabright cyanine‐based fluorescent materials by addressing long‐standing challenges associated with cyanine dyes, including undesired cis–trans photoisomerization and aggregation‐caused quenching. Supra‐cyanines are obtained by incorporating cyanine moieties in a cyclic peptide‐based supramolecular scaffold, exhibiting high fluorescence quantum yield (up to 50%) in both solution and solid states. These findings offer a versatile approach for constructing highly emissive cyanine‐based supramolecular materials.

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1D alignment of proteins and other nanoparticles by using reversible covalent bonds on cyclic peptide nanotubes

Abstract: Self-assembling cyclic peptide nanotubes are supramolecular structures whose diameter and external surface properties are precisely controlled. In this communication we describe a general strategy to align different molecules on top...

Cited by 9 publications

References 61 publications

Recent Progress on Cyclic Peptides’ Assembly and Biomedical Applications

Recent Progress on Cyclic Peptides’ Assembly and Biomedical Applications

Dynamic Control of Cyclic Peptide Assembly to Form Higher‐Order Assemblies

Supra‐Cyanines: Ultrabright Cyanine‐Based Fluorescent Supramolecular Materials in Solution and in the Solid State

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