Synthesis and Characterization of Stimuli‐Responsive Star‐Like Polypept(o)ides: Introducing Biodegradable PeptoStars

Holm, Regina; Weber, Benjamín; Heller, Philipp; Klinker, Kristina; Westmeier, Dana; Docter, Dominic; Stauber, Roland H.; Barz, Matthias

doi:10.1002/mabi.201600514

Cited by 23 publications

(30 citation statements)

References 43 publications

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“…[77] Treatment of the star-shaped polymers with glutathione SCHEME 8 DBU-mediated ZROPs of Bu-NCAs to afford cyclic PNBGs. [69] Reprinted with permission from American Chemical Society …”

Section: Fig Urementioning

confidence: 99%

“…[77] Adapted with permission from John Wiley and Sons copolymer than the PNPgG homopolymer. [68] This was attributed to the strong tendency of PNPgG to aggregate in solution, limiting the access of the propargyl groups by the azide and Cu catalyst.…”

Section: Postpolymerization Modification Of Polypeptoidsmentioning

confidence: 99%

“…[19] Adapted with permission from the Royal Society of Chemistry for all samples, reduction of cell viability was found to occur in a cellline dependent manner. [77] For example, the tri-arm star-shaped polysarcosine (arm DP 5 HepG2 cells were used in the study. [86] Adapted with permission from American Chemical Society SCHEME 11 Synthesis of redox-responsive and core-cleavable or noncore-cleavable micelles based on amphiphilic block copolypeptoids PNEG-b-P(NPgG-r-NDG) further used to investigate the effect of ABC hydrogel on hASCs metabolic activity.…”

Section: Cytotoxicitymentioning

confidence: 99%

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Polypeptoid polymers: Synthesis, characterization, and properties

et al. 2017

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Polypeptoids, a class of peptidomimetic polymers, have emerged at the forefront of macromolecular and supramolecular science and engineering as the technological relevance of these polymers continues to be demonstrated. The chemical and structural diversity of polypeptoids have enabled access to and adjustment of a variety of physicochemical and biological properties (eg, solubility, charge characteristics, chain conformation, HLB, thermal processability, degradability, cytotoxicity and immunogenicity). These attributes have made this synthetic polymer platform a potential candidate for various biomedical and biotechnological applications. This review will provide an overview of recent development in synthetic methods to access polypeptoid polymers with well-defined structures and highlight some of the fundamental physicochemical and biological properties of polypeptoids that are pertinent to the future development of functional materials based on polypeptoids. | I N TR ODU C TI ONPolypeptoids composed of N-substituted polyglycine backbones are structural mimics of polypeptides ( Figure 1). Because of N-substitution, polypeptoids lack stereogenic centers and hydrogen bonding interactions along the main chains, in sharp contrast to polypeptides.As a result, the global conformations of polypeptoids are strongly dependent on the N-substituent structures, giving rise to random coils or well-defined secondary structures [eg, polyproline I (PPI) helix [1][2][3][4][5][6] and R-sheets] [7][8][9][10][11][12] that are reminiscent of those of polypeptides. The polypeptoid backbone containing tertiary amide linkages is highly polar and hydrophilic. The physicochemical properties of polypeptoids can be tailored by the N-substituent structures, enabling control over the hydrophilicity and lipophilicity balance (HLB), charge characteristics, [13,14] backbone conformation, [1][2][3][4][5][6][7][8][9][10][11][12] solubility, [15][16][17][18][19][20] thermal and crystallization properties of the polypeptoids. [21][22][23][24] Without extensive hydrogen bonding, polypeptoids are thermally processable similar to conventional thermoplastics, [20][21][22][23][24] whereas polypeptides undergo thermal degradation before they can be melt-processed due to the extensive hydrogen bonding interactions. While polypeptoids exhibited enhanced proteolytic stability relative to peptides, [25,26] they can be oxidatively degraded under conditions that mimic tissue inflammation, [27] suggesting their potential in vivo uses as biodegradable materials.Recent advances in the controlled polymerization methods have enabled access to a suite of structurally well-defined polypeptoids with various N-substituent structures and molecular architectures, setting the stage for the future development of polypeptoid materials for various targeted applications. Several review articles on the synthesis, properties, and application of polypeptoids for biomedical or nonbiomedical uses have been published in recent years. [28][29][30][31][32] As a result, this...

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“…[77] Treatment of the star-shaped polymers with glutathione SCHEME 8 DBU-mediated ZROPs of Bu-NCAs to afford cyclic PNBGs. [69] Reprinted with permission from American Chemical Society …”

Section: Fig Urementioning

confidence: 99%

Section: Postpolymerization Modification Of Polypeptoidsmentioning

confidence: 99%

Section: Cytotoxicitymentioning

confidence: 99%

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Polypeptoid polymers: Synthesis, characterization, and properties

et al. 2017

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“…The high demand for reactive thiols enabling bioreversible conjugation to polypeptides by disulfide bonds is eminent, as illustrated by the well established incorporation of disulfide bonds in initiators, in the main or side chain of polypeptides In addition, reactive polypeptides enable a variety of post‐polymerization modification techniques . A multitude of chemoselective modifications, for example, alkylation, azide‐alkyne, thiol‐ene and ‐yne reactions is available.…”

Section: Synthesis Of Polypeptidesmentioning

confidence: 99%

“…Polypeptides synthesized by this method have already entered clinical trails or,a si nt he case of copaxone, becamemulti-billiond ollar drugs. [155,156] The high demandf or reactive thiols enabling bioreversible conjugation to polypeptides by disulfide bonds is eminent, as illustrated by the well established incorporation of disulfide bonds in initiators, in the main or side chain of polypeptides [164][165][166][167] In addition, reactive polypeptides enable av ariety of post-polymerization modification techniques. [157,168] Am ultitude of chemoselectivem odifications, for example, alkylation, [158] azide-alkyne, [159] thiol-ene and -yne reactions [160][161][162] is available.…”

Section: Nca Polymerizationmentioning

confidence: 99%

Of Thiols and Disulfides: Methods for Chemoselective Formation of Asymmetric Disulfides in Synthetic Peptides and Polymers

Schäfer

Barz

2018

Chemistry A European J

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In protein or peptide chemistry, thiols are frequently chosen as a chemical entity for chemoselective modification reactions. Although it is a well-established methodology to address cysteines and homocysteines in aqueous media to form S-C bonds, possibilities for the chemoselective formation of asymmetric disulfides have been less approached. Focusing on bioreversibility in conjugation chemistry, the formation of disulfide bonds is highly desirable for the attachment of thiol-containing bioactive agents to proteins or in cross-linking reactions, because disulfide bonds can combine stability in blood with degradability inside cells. In this Concept article, recent approaches in the field of activating groups for thiol moieties incorporated in peptide and polymer materials are highlighted. Advantageous combinations of stability during synthesis of the material with high reactivity towards thiols are explored focusing on simplification and prevention of side reactions as well as additional deprotection and activation steps prior to disulfide formation. Moreover, applications of this chemistry are highlighted and future perspectives are envisioned.

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Capturing “Extraordinary” Soft‐Assembled Charge‐Like Polypeptides as a Strategy for Nanocarrier Design

et al. 2017

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The rational design of nanomedicines is a challenging task given the complex architectures required for the construction of nanosized carriers with embedded therapeutic properties and the complex interface of these materials with the biological environment. Herein, an unexpected charge-like attraction mechanism of self-assembly for star-shaped polyglutamates in nonsalty aqueous solutions is identified, which matches the ubiquitous "ordinary-extraordinary" phenomenon previously described by physicists. For the first time, a bottom-up methodology for the stabilization of these nanosized soft-assembled star-shaped polyglutamates is also described, enabling the translation of theoretical research into nanomaterials with applicability within the drug-delivery field. Covalent capture of these labile assemblies provides access to unprecedented architectures to be used as nanocarriers. The enhanced in vitro and in vivo properties of these novel nanoconstructs as drug-delivery systems highlight the potential of this approach for tumor-localized as well as lymphotropic delivery.

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Synthesis and Characterization of Stimuli‐Responsive Star‐Like Polypept(o)ides: Introducing Biodegradable PeptoStars

Cited by 23 publications

References 43 publications

Polypeptoid polymers: Synthesis, characterization, and properties

Polypeptoid polymers: Synthesis, characterization, and properties

Of Thiols and Disulfides: Methods for Chemoselective Formation of Asymmetric Disulfides in Synthetic Peptides and Polymers

Capturing “Extraordinary” Soft‐Assembled Charge‐Like Polypeptides as a Strategy for Nanocarrier Design

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