Non-ionic water-soluble “clickable” α-helical polypeptides: synthesis, characterization and side chain modification

Cao, Jinbao; Hu, Ping; Lu, Lu; Chan, Brandon A.; Luo, Bing Hao; Zhang, Donghui

doi:10.1039/c4py01560f

Cited by 18 publications

(18 citation statements)

References 34 publications

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“…Then, they also synthesized methylated mono and di(ethylene glycol)-functionalized poly( L -serine) and poly( l -cysteine) [ 32 ]. Subsequently, Zhang and coworkers synthesized OEGylated poly( l -glutamic acid) encoding pendant alkyne side groups that were amendable to further modifications [ 33 ]. Inspired by these pioneer works, the OEGylated poly(amino acid)s were prepared as thermoresponsive materials with difference amino acids, and different OEG topological structures (e.g., linear, Y-shaped) and length; the expansion of structural diversity provides more possibilities for its applications.…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in Thermoresponsive OEGylated Poly(amino acid)s

Geng

Wang

2021

Polymers

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Thermoresponsive polymers have been widely studied in the past decades due to their potential applications in biomedicine, nanotechnology, and so on. As is known, poly(N-isopropylacrylamide) (PNIPAM) and poly(oligo(ethylene glycol)methacrylates) (POEGMAs) are the most popular thermoresponsive polymers, and have been studied extensively. However, more advanced thermoresponsive polymers with excellent biocompatibility, biodegradability, and bioactivity also need to be developed for biomedical applications. OEGylated poly(amino acid)s are a kind of novel polymer which are synthesized by attaching one or multiple oligo(ethylene glycol) (OEG) chains to poly(amino acid) (PAA).These polymers combine the great solubility of OEG, and the excellent biocompatibility, biodegradability and well defined secondary structures of PAA. These advantages allow them to have great application prospects in the field of biomedicine. Therefore, the study of OEGylated poly(amino acid)s has attracted more attention recently. In this review, we summarized the development of thermoresponsive OEGylated poly(amino acid)s in recent years, including the synthesis method (such as ring-opening polymerization, post-polymerization modification, and Ugi reaction), stimuli-response behavior study, and secondary structure study. We hope that this periodical summary will be more conducive to design, synthesis and application of OEGylated poly(amino acid)s in the future.

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Section: Introductionmentioning

confidence: 99%

Recent Advances in Thermoresponsive OEGylated Poly(amino acid)s

Geng

Wang

2021

Polymers

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“…Polypeptides are attractive materials with protein‐like structures for numerous applications in biochemical and biomedicine due to their excellent biocompatibility with blood and tissue, biodegradability, and biorecognition properties . Amino acids (AAs) with various side groups qualify polypeptides with various properties, fascinating researchers with great interests . For example, polylysine and poly(glutamic acid), bearing amino groups and carboxyl groups, respectively, are widely used in stimuli‐responsive biomaterials .…”

Section: Introductionmentioning

confidence: 99%

Hydroxyl‐tolerated polymerization of N‐phenoxycarbonyl α‐amino acids: A simple way to polypeptides bearing hydroxyl groups

Yang

Bai

Ling

et al. 2019

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

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Differing from the moisture‐sensitive α‐amino acid N‐carboxyanhydrides (AA‐NCAs) monomers, N‐phenoxycarbonyl α‐amino acids (AA‐NPCs) can be prepared and stored in open air. In this contribution, we report that the controlled polymerizations of AA‐NPC monomers of O‐tert‐butyl‐dl‐serine (BRS‐NPC), Nε‐benzyloxycarbonyl‐l‐lysine (ZLL‐NPC) and Nε‐trifluoroacetyl‐l‐lysine (FLL‐NPC) initiated by amines are surprisingly able to tolerate common nucleophilic impurities such as water and alcohols at a level of monomer concentration. The structures of polypeptides synthesized in the presence of water or alcohols agree well with the designed ones in the case of repeated chain extensions. Detailed mechanism study and density functional theory calculation reveal that the low concentration of AA‐NCA and the high activity of amines are the key factors to the controllability of AA‐NPC polymerizations. The water‐ and alcohol‐tolerant property in polymerizations of AA‐NPCs encourages the following studies on unprotected (phenolic) hydroxyl groups containing AA‐NPCs. The controllable polymerizations of N‐phenoxycarbonyl l‐tyrosine (LT‐NPC) and N‐phenoxycarbonyl S‐(3‐hydroxypropyl)‐l‐cysteine (HLC‐NPC) initiated by amines are confirmed and reported for the first time, which extends the library of AA‐NPCs and polypeptides as well. All the universality of library, the convenience of monomer preparation, and the controllability and water‐ and alcohol‐tolerant property of polymerization of AA‐NPCs significantly enhance the feasibility of polypeptide synthesis, making AA‐NPC approach a promising synthetic method of polypeptides. © 2019 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 907–916

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“…18, 24-26 Their broad applicability is attributed to the precisely-defined nano- and microstructures derived from hierarchical assembly of polypeptides, and the variety of stimuli-responsive behaviors exhibited by natural and synthetic polypeptides. 27-29 Secondary structures, especially the α-helix and β-sheet conformations, can serve as the driving forces to form well-defined fibrous structures, which further assemble into noncovalently crosslinked three-dimensional networks that can encapsulate aqueous media to form hydrogels. 24, 30, 31 Recently, Chen and co-workers reported a biocompatible polypeptide hydrogelator, poly(ethylene glycol)- block -poly(γ-propargyl- l -glutamate) (PEG- b -PPLG), with a temperature-triggered sol–to–gel transition driven by the formation of β-sheet structures.…”

Section: Introductionmentioning

confidence: 99%

Multi-responsive polypeptide hydrogels derived from N-carboxyanhydride terpolymerizations for delivery of nonsteroidal anti-inflammatory drugs

Fan

Wang

et al. 2017

Org. Biomol. Chem.

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A polypeptide-based hydrogel system, when prepared from a diblock polymer with a ternary copolypeptide as one block, exhibited thermo-, mechano- and enzyme-responsive properties, which enabled the encapsulation of naproxen (Npx) during the sol–gel transition and its release in the gel state. Statistical terpolymerizations of l-alanine (Ala), glycine (Gly) and l–isoleucine (Ile) NCAs at a 1:1:1 feed ratio initiated by monomethoxy monoamino-terminated poly(ethylene glycol) afforded a series of methoxy poly(ethylene glycol)-block-poly(l-alanine-co-glycine-co-l-isoleucine) (mPEG-b-P(A-G-I)) block polymers. β-Sheets were the dominant secondary structures within the polypeptide segements, which facilitated a heat-induced sol–to-gel transition, resulting from the supramolecular assembly of β-sheets into nanofibrils. Deconstruction of the three–dimensional networks by mechanical force (sonication) triggered the reverse gel–to–sol transition. Certain enzymes could accelerate the breakdown of the hydrogel, as determined by in vitro gel weight loss profiles. The hydrogels were able to encapsulate and release Npx over 6 days, demonstrating the potential application of these polypeptide hydrogels as an injectable local delivery system for small molecule drugs.

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Non-ionic water-soluble “clickable” α-helical polypeptides: synthesis, characterization and side chain modification

Abstract: Non-ionic water-soluble helical polypeptides bearing reactive side chains can be efficiently modified with hydrophobic or hydrophilic moieties to produce water-soluble conjugates.

Cited by 18 publications

References 34 publications

Recent Advances in Thermoresponsive OEGylated Poly(amino acid)s

Recent Advances in Thermoresponsive OEGylated Poly(amino acid)s

Hydroxyl‐tolerated polymerization of N‐phenoxycarbonyl α‐amino acids: A simple way to polypeptides bearing hydroxyl groups

Multi-responsive polypeptide hydrogels derived from N-carboxyanhydride terpolymerizations for delivery of nonsteroidal anti-inflammatory drugs

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