Exploring structural effects in single-chain “folding” mediated by intramolecular thermal Diels–Alder chemistry

Hanlon, Ashley M.; Martin, Ian K.; Bright, Elizabeth R.; Chouinard, Jennifer; Rodriguez, Kyle J.; Patenotte, Gabriel E.; Berda, Erik B.

doi:10.1039/c7py00320j

Cited by 39 publications

(33 citation statements)

References 53 publications

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“…Interestingly, the SCPNs show similar RVs, that is, the increase in valency did not meet our original expectations of reducing hydrodynamic volume. Interestingly, our results deviate from a recent study by Berda and workers, who used bi‐ or tri‐maleimides to fold MMA and furfuryl methacrylate random copolymers . In their work, in contrast to ours, trivalent CL induced a smaller hydrodynamic volume.…”

Section: Resultscontrasting

confidence: 99%

Effect of intramolecular crosslinker properties on the mechanochemical fragmentation of covalently folded polymers

Levy

Goldstein

Brenman

et al. 2020

Journal of Polymer Science

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The mechanochemical stability of polymers in solution is enhanced if the chains are covalently folded. Under shear forces, the additional bonds absorb mechanical energy and inhibit unfolding, and as a result, slow down fragmentation. However, not all crosslinkers are equal in terms of their properties (length, strength, etc.). In order to understand the role of these added bonds in the polymers' stability under mechanical stress, a thorough study compares the rate of mechanochemistry on single‐chain polymer nanoparticles which have been folded with crosslinkers with different lengths, strengths, positioning, and valencies. The usage of bonds with different mechanical strengths in the crosslinkers was found to be the most powerful way to change the mechanochemical fragmentation rate. In addition, positioning and valency also play significant role in the mechanical stabilization mechanism. © 2020 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2020 © 2020 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2020, 58, 692–703

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Section: Resultscontrasting

confidence: 99%

Effect of intramolecular crosslinker properties on the mechanochemical fragmentation of covalently folded polymers

Levy

Goldstein

Brenman

et al. 2020

Journal of Polymer Science

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“…Several strategies have been explored trying to mimic (at a fundamental level) the folding of a natural non‐cyclized polypeptide to its native, functional conformation as observed, for example, in enzymes . Among them, the formation of single‐chain nanoparticles (SCNPs) via intra‐chain cross‐linking at high dilution to promote chain collapse in synthetic precursor polymers has shown to be one such promising approach . It is worth noting that polymer folding from synthetic polymer precursors proceeds via the random linking of the reactive pendant units along the polymer precursor chain, and hence the product inevitably entails structural heterogeneity.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of Single‐Ring Nanoparticles Mimicking Natural Cyclotides by a Stepwise Folding‐Activation‐Collapse Process

Rubio‐Cervilla

Frisch

Barner‐Kowollik

et al. 2018

Macromol. Rapid Commun.

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Cyclotides are small cyclic polypeptides found in a variety of organisms, ranging from bacteria to plants. Their ring structure endows those polypeptides with specific properties, such as improved stability against enzymatic degradation. Optimal cyclotide activity is often observed only in the presence of intra-ring disulfide bonds. Synthesis of soft nano-objects mimicking the conformation of natural cyclotides remains challenging. Here, a new class of natural cyclotide mimics synthesized by a stepwise folding-activation-collapse process at high dilution starting from simple synthetic precursor polymers is established. The initial folding step is carried out by a photoactivated hetero Diels-Alder (HDA) ring-closing reaction, which is accompanied by chain compaction of the individual precursor polymer chains as determined by size exclusion chromatography (SEC). The subsequent activation step comprises a simple azidation procedure, whereas the final collapse step is driven by CuAAC in the presence of an external cross-linker, providing additional compaction to the final single-ring nanoparticles (SRNPs). The unique structure and compaction degree of the SRNPs is established via a detailed comparison with conventional single-chain nanoparticles (SCNPs) prepared exclusively by chain collapse from the exact same precursor polymer (without the prefolding step). The stepwise folding-activation-collapse approach opens new avenues for the preparation of artificial cyclotide mimetics.

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“…Here, we observed a similar behaviour as the Berda team noted in their recent study. 55 With increasing amount of crosslinker, a major peak shift towards higher retention times is detected. By employing 1 in large excess (25 eq.…”

Section: Resultsmentioning

confidence: 96%

Self-reporting and refoldable profluorescent single-chain nanoparticles

Fischer

Spann

et al. 2018

Chem. Sci.

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Exploring structural effects in single-chain “folding” mediated by intramolecular thermal Diels–Alder chemistry

Abstract: We describe a method to fold single polymer chains into nanoparticles using simple thermal Diels–Alder (DA) chemistry.

Cited by 39 publications

References 53 publications

Effect of intramolecular crosslinker properties on the mechanochemical fragmentation of covalently folded polymers

Effect of intramolecular crosslinker properties on the mechanochemical fragmentation of covalently folded polymers

Synthesis of Single‐Ring Nanoparticles Mimicking Natural Cyclotides by a Stepwise Folding‐Activation‐Collapse Process

Self-reporting and refoldable profluorescent single-chain nanoparticles

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