Dual stimuli‐responsive polypeptide prepared by thiol‐ene click reaction of poly(<scp>l</scp>‐cysteine) and <i>N</i>, <i>N</i>‐dimethylaminoethyl acrylate

Xiao, Yan; Tang, Chenna; Yang, Czau‐Siung; Lang, Meidong

doi:10.1002/bip.23318

Cited by 14 publications

(8 citation statements)

References 53 publications

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“…Recently, Xiao and his coworkers used poly(L‐cysteine) as a clickable polymeric precursor to produce stimuli‐responsive polypeptides. [ 43 ] They used triphosgene to transform the thiol‐protected cysteine into NCA, and the thiol‐containing poly(L‐cysteine) was obtained by controlled ROP followed by deprotection of a benzyl group ( Figure ). After the postmodification with N , N ‐dimethylaminoethyl acrylate (DMAEA) via the thiol‐ene addition, a thermo‐ and pH‐dual responsive polymer was produced ( Figure ).…”

Section: Synthesis Of Stimuli‐responsive Polymers By Postmodificationmentioning

confidence: 99%

Postpolymerization Modification: A Powerful Tool for the Synthesis and Function Tuning of Stimuli‐Responsive Polymers

Michinobu

2021

Macro Chemistry & Physics

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Stimuli‐responsive polymers are a type of functional polymers showing a change in their physicochemical properties in response to external stimuli, such as temperature, pH, and electrochemical potential application, and they can be used in biosensors, biomedicine, and separation technology. Postmodification of polymers plays an important role in designing stimuli‐responsive polymers in terms of their synthesis, tuning of their thermoresponsivity, and functionalization. A variety of topological polymer structures, such as a comb, sphere, and dendrimer, can be produced, and the resultant tuning of the transition temperatures and phase types (lower critical solution temperature‐ or upper critical solution temperature‐type) can be achieved. Furthermore, postmodification techniques are employed as a useful tool to functionalize precursor polymers or improve the responsive properties of the polymers, which expands the applicable fields of these polymers. In this review, click chemistry‐related reactions, the esterification reaction, and surface‐initiated polymerization are the focus as efficient postmodification reactions to produce high‐performance stimuli‐responsive polymers.

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Section: Synthesis Of Stimuli‐responsive Polymers By Postmodificationmentioning

confidence: 99%

Postpolymerization Modification: A Powerful Tool for the Synthesis and Function Tuning of Stimuli‐Responsive Polymers

Michinobu

2021

Macro Chemistry & Physics

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“…On the other hand, polymerizations of 𝛼-amino acid NTAs in amide polar solvents are still regarded difficult as the bimolecular termination is inevitable, whereas polar solvents such as DMF are common for NCA polymerizations. [109][110][111] Due to limited initiators and slow polymerization rates, designs of efficient catalysts and initiators for controlled polymerizations of NTAs are an intriguing topic. Moreover, the polymerizations of NTA and NNTA monomers with unprotected functional groups, especially thiol and hydroxyl groups, are rarely reported.…”

Section: Advantages and Unsettled Problemsmentioning

confidence: 99%

An Inspection into Multifarious Ways to Synthesize Poly(Amino Acid)s

Zheng

Bai

Tao

et al. 2021

Macromol. Rapid Commun.

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Poly(𝜶-amino acid)s (PAAs) attract growing attention due to their essential role in the application as biomaterials. To synthesize PAAs with desired structures and properties, scientists have developed various synthetic techniques with respective advantages. Here, different approaches to preparing PAAs are inspected. Basic features and recent progresses of these methods are summarized, including polymerizations of amino acid N-carboxyanhydrides (NCAs), amino acid N-thiocarboxyanhydrides (NTAs), and N-phenoxycarbonyl amino acids (NPCs), as well as other synthetic routes. NCA is the most classical monomer to prepare PAAs with high molecular weights (MWs). NTA polymerizations are promising alternative pathways to produce PAAs, which can tolerate nucleophiles including alcohols, mercaptans, carboxyl acids, and water. By various techniques including choosing appropriate solvents or using organic acids as promoters, NTAs polymerize to produce polypeptoids and polypeptides with narrow dispersities and designed MWs up to 55.0 and 57.0 kg mol −1 , respectively. NPC polymerizations are phosgene-free ways to synthesize polypeptides and polypeptoids. For the future prospects, detail investigations into polymerization mechanisms of NTA and NPC are expected. The synthesis of PAAs with designed topologies and assembly structures is another intriguing topic. The advantages and unsettled problems in various synthetic ways are discussed for readers to choose appropriate approaches for PAAs.

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“…Generally, the control unit is composed of a stimuli-response structure or material. Until now, the pH-responsive unit, photoresponsive unit, electric-responsive unit, magnetic responsive unit, and chemical responsive unit have been investigated as control units (Dong and Chen, 2011;Guragain et al, 2015;Kim et al, 2015;Liu et al, 2015;Lorenzo et al, 2015;Wang et al, 2015;Bian et al, 2016a;Cao and Wang, 2016;Dong et al, 2017;Xiao et al, 2019). Azobenzene (AZO) has photoisomerizing characteristic, which provides possibilities as a photo switch (Li et al, 2014;Pang et al, 2014).…”

Section: Introductionmentioning

confidence: 99%

Design and Fabrication of Photo-Responsive Hydrogel for the Application of Functional Contact Lens

et al. 2021

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Traditional hydrogel has usually had restricted application in the biomedical field due to lack of a control unit. Herein, Azobenzene (AZO), as a typical kind of photo-response molecule, was introduced into hydrogel by polymerization to provide a control unit for hydrogel. Simultaneously, the immobilization of AZO end group would solve the problems of uncontrollable recovery and light fatigue for AZO small molecules according to previous research. In the research, two kinds of crosslinkable AZO molecules, namely AZO crosslinker and AZO monomer, were synthesized as functional monomers or crosslinkers. Further, AZO copolymerized hydrogel and AZO crosslinked hydrogel were obtained. In order to estimate fundamental properties for contact lenses, gelation time and swelling ratio of hydrogels as a function of AZO concentration as well as crosslinking type were investigated. Moreover, synthesized hydrogels exhibited typical porous morphology, but their size and homogeneity were dependent on the type of hydrogel. In order to evaluate photo-responsive performance, detailed photo induced isomerization of both AZO copolymerized hydrogel and crosslinked hydrogel were tracked by UV spectra. The results confirmed the reversible, stable, and controllable photo responsive process. In vitro evaluation was used to investigate drug release behavior using orfloxacin and puerarin as model drugs. It was found that AZO addition as well as hydrogel type would influence puerarin release, but would have little effect on the orfloxacin release behavior in hydrogels. Furthermore, the isomer type in the hydrogel would have some effects on drug release behavior including orfloxacin and puerarin.

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Dual stimuli‐responsive polypeptide prepared by thiol‐ene click reaction of poly(l‐cysteine) and N, N‐dimethylaminoethyl acrylate

Cited by 14 publications

References 53 publications

Postpolymerization Modification: A Powerful Tool for the Synthesis and Function Tuning of Stimuli‐Responsive Polymers

Postpolymerization Modification: A Powerful Tool for the Synthesis and Function Tuning of Stimuli‐Responsive Polymers

An Inspection into Multifarious Ways to Synthesize Poly(Amino Acid)s

Design and Fabrication of Photo-Responsive Hydrogel for the Application of Functional Contact Lens

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