Janus cyclic peptide–polymer nanotubes

Danial, Maarten; Tran, Carmen M.-N.; Young, Philip G.; Perrier, Sébastien; Jolliffe, Katrina A.

doi:10.1038/ncomms3780

Cited by 99 publications

(100 citation statements)

References 70 publications

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“…42,43 Cyclic, (hyper-)branched and multiarm star architectures with three or more segments have not received less attention as building blocks for MCNs formation so far, but individual studies give a glimpse of their structuring potential. [44][45][46][47][48] Monomer functionality. The strength of microphase separation depends on the segment-segment incompatibility, χ, which is an intrinsic property of the employed monomers and higher values correspond to stronger enthalpic repulsion.…”

Section: Controlled and Directed Self-assemblymentioning

confidence: 99%

Self-assembly concepts for multicompartment nanostructures

2015

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Compartmentalization is ubiquitous to many biological and artificial systems, be it for the separate storage of incompatible matter or to isolate transport processes. Advancements in the synthesis of sequential block copolymers offer a variety of tools to replicate natural design principles with tailor-made soft matter for the precise spatial separation of functionalities on multiple length scales. Here, we review recent trends in the self-assembly of amphiphilic block copolymers to multicompartment nanostructures (MCNs) under (semi-)dilute conditions, with special emphasis on ABC triblock terpolymers. The intrinsic immiscibility of connected blocks induces short-range repulsion into discrete nano-domains stabilized by a third, soluble block or molecular additive. Polymer blocks can be synthesized from an arsenal of functional monomers directing self-assembly through packing frustration or response to various fields. The mobility in solution further allows the manipulation of self-assembly processes into specific directions by clever choice of environmental conditions. This review focuses on practical concepts that direct self-assembly into predictable nanostructures, while narrowing particle dispersity with respect to size, shape and internal morphology. The growing understanding of underlying self-assembly mechanisms expands the number of experimental concepts providing the means to target and manipulate progressively complex superstructures.

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Section: Controlled and Directed Self-assemblymentioning

confidence: 99%

Self-assembly concepts for multicompartment nanostructures

2015

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“…41 The desired cyclic peptide chain transfer agent CP-PABTC 3 was then obtained by coupling the chain transfer agent (CTA) N-hydroxysuccinimide (propanoic acid)yl butyl trithiocarbonate (NHS-PABTC, 1) to the lysine residues of CP 2 (Scheme 1). Mass spectrometry monitoring indicated that the coupling reaction was quantitative, as no residual CP 2 or mono-functionalized product was detected, affording CP-PABTC 3 in high yield.…”

Section: Synthesis Of the Cyclic Peptide Chain Transfer Agentmentioning

confidence: 99%

“…41 Despite the numerous individual approaches to create CPpolymer conjugates, no comprehensive comparison between the grafting-from and the grafting-to approach has been reported. Therefore, we designed this systematic study comparing the two approaches to clearly determine the advantages and disadvantages of each strategy.…”

Section: Introductionmentioning

confidence: 99%

Cyclic peptide–polymer conjugates: Grafting‐to vs grafting‐from

Larnaudie

Brendel

Jolliffe

et al. 2015

J. Polym. Sci. Part A: Polym. Chem.

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A systematic comparison between the grafting-to (convergent) and grafting-from (divergent) synthetic routes leading to cyclic peptide-polymer conjugates is described. The reversible addition-fragmentation chain transfer (RAFT) process was used to control the polymerizations and the couplings between cyclic peptide and polymer or RAFT agent were performed using N-hydroxysuccinimide (NHS) active ester ligation. The kinetics of polymerization and polymer conjugation to cyclic peptides were studied for both grafting-to and grafting-from synthetic routes, using N-acryloyl morpholine as a model monomer. The cyclic peptide chain transfer agent was able to mediate polymerization as efficiently as a traditional RAFT agent, reaching high conversion in the same time scale while maintaining excellent control over the molecular weight distribution. The conjugation of polymers to cyclic peptides proceeded to high conversion, and the nature of the carbon at the a-position to the NHS group was found to play a crucial role in the reaction kinetics. The study was extended to a wider range of monomers, including hydrophilic and temperature responsive acrylamides, hydrophilic and hydrophobic acrylates, and hydrophobic and pH responsive methacrylates. Both approaches lead to similar peptide-polymer conjugates in most cases, while some exceptions highlight the advantages of one or the other method, thereby demonstrating their complementarity.

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“…More recently, Perrier's group adopted a click chemistry reaction to couple a cyclic l , d ‐α‐peptide pattern to various responsive polymers. Hybrids with different degrees of functionalization and sensitivity to the environmental stimuli were produced …”

Section: Dl‐α‐peptide‐based Building Blocks To Generate Hybrid Matermentioning

confidence: 99%

Peptides with regularly alternating enantiomeric sequence: From ion channel models to bioinspired nanotechnological applications

et al. 2018

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Peptides are versatile building blocks that have been extensively used as peptide‐based organizers to generate bioinspired hybrid materials. Among them, those peptides characterized by regularly alternating enantiomeric sequences (l,d‐peptides) have attracted much interest. Their structures, which are not accessible to the corresponding homochiral peptides, have been exploited to achieve hybrid conjugates, the chemical and structural properties of which can be predetermined by correct design. Molecules that self‐assemble into hollow tubular architectures with side chains on the outer surface can form, allowing the introduction of new functionalities on amino acid residues containing reactive side chains. This provides an effective strategy to develop engineered nanotubes with the surface suitably tuned for applications in different fields, spanning from electronics to medicine.

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Janus cyclic peptide–polymer nanotubes

Cited by 99 publications

References 70 publications

Self-assembly concepts for multicompartment nanostructures

Self-assembly concepts for multicompartment nanostructures

Cyclic peptide–polymer conjugates: Grafting‐to vs grafting‐from

Peptides with regularly alternating enantiomeric sequence: From ion channel models to bioinspired nanotechnological applications

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