Bioinspired Poly(2-oxazoline)s

Hoogenboom, Richard; Schlaad, Helmut

doi:10.3390/polym3010467

Cited by 137 publications

(115 citation statements)

References 110 publications

(127 reference statements)

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“…On the other hand, copolymers bearing amino acid side-chains may not form -sheets or -helices, but are still of significant interest for their capacity to undergo self-assembly in response to external stimuli such as pH or temperature, to bind to metal ions or to interact with other polyelectrolytes. Bio-inspired poly(2-oxazolines) 6 and polymers derived from amino acid-based vinyl monomers 7,8 are the best examples of this category. The latter class of polymers draws on early work by Kulkarni and Morawetz, who first reported the synthesis of N-amino acid (meth)acrylamides without using protecting group chemistry by reaction of (meth)acryloyl chloride with amino acids.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of poly(amino acid methacrylate)-stabilized diblock copolymer nano-objects

et al. 2015

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International audienceAmino acids constitute one of Nature's most important building blocks. Their remarkably diverse properties (hydrophobic/hydrophilic character, charge density, chirality, reversible cross-linking etc.) dictate the structure and function of proteins. The synthesis of artificial peptides and proteins comprising main chain amino acids is of particular importance for nanomedicine. However, synthetic polymers bearing amino acid side-chains are more readily prepared and may offer desirable properties for various biomedical applications. Herein we describe an efficient route for the synthesis of poly(amino acid methacrylate)-stabilized diblock copolymer nano-objects. First, either cysteine or glutathione is reacted with a commercially available methacrylate-acrylate adduct to produce the corresponding amino acid-based methacrylic monomer (CysMA or GSHMA). Well-defined water-soluble macromolecular chain transfer agents (PCysMA or PGSHMA macro-CTAs) are then prepared via RAFT polymerization, which are then chain-extended via aqueous RAFT dispersion polymerization of 2-hydroxypropyl methacrylate. In situ polymerization- induced self-assembly (PISA) occurs to produce sterically-stabilized diblock copolymer nano-objects. Although only spherical nanoparticles could be obtained when PGSHMA was used as the sole macro-CTA, either spheres, worms or vesicles can be prepared using either PCysMA macro-CTA alone or binary mixtures of poly(glycerol monomethacrylate) (PGMA) with either PCysMA or PGSHMA macro-CTAs. The worms formed soft free-standing thermo-responsive gels that undergo degelation on cooling as a result of a worm-to-sphere transition. Aqueous electrophoresis studies indicate that all three copolymer morphologies exhibit cationic character below pH 3.5 and anionic character above pH 3.5. This pH sensitivity corresponds to the known behavior of the poly(amino acid methacrylate) steric stabilizer chains

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Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of poly(amino acid methacrylate)-stabilized diblock copolymer nano-objects

et al. 2015

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“…The most recent developments published in the last ten years have been focused on during the compilation of this review; crosslinked poly(2-oxazoline)s, which were reviewed in a recent publication, have been omitted from this compilation [10]. While this review focuses on the synthesis of poly(2-oxazoline)s and copoly(2-oxazoline)s as well as the derived materials, the properties of the polymers and materials themselves will be discussed only for dedicated examples, and the reader interested in more and/or more general details is referred to recent reviews in that area [11][12][13][14][15][16][17][18][19][20].…”

Section: Introductionmentioning

confidence: 99%

Design Strategies for Functionalized Poly(2-oxazoline)s and Derived Materials

2013

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Abstract:The polymer class of poly(2-oxazoline)s currently is under intensive investigation due to the versatile properties that can be tailor-made by the variation and manipulation of the functional groups they bear. In particular their utilization in the biomedic(in)al field is the subject of numerous studies. Given the mechanism of the cationic ring-opening polymerization, a plethora of synthetic strategies exists for the preparation of poly(2-oxazoline)s with dedicated functionality patterns, comprising among others the functionalization by telechelic end-groups, the incorporation of substituted monomers into (co)poly(2-oxazoline)s, and polymeranalogous reactions. This review summarizes the current state-of-the-art of poly(2-oxazoline) preparation and showcases prominent examples of poly(2-oxazoline)-based materials, which are retraced to the desktop-planned synthetic strategy and the variability of their properties for dedicated applications.

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“…Recently, poly(2-oxazoline)s have drawn attention with the finding of the potential biological and chemical favorability due to their some advantageous structural properties such as pH and temperature sensitive, ionic strength, chemical and biological stimuli [30][31][32][33][34]. These polymers can be obtained via living cationic ring opening polymerization (CROP) of 2-alkyl-oxazolines and functionalized by using either functional initiator or nucleophilic terminating agents [35][36][37][38][39]. Among them, poly(2-oxazoline)s with short side chains (ethyl, nand iso-propyl), except for 2-methyl-2-oxazoline, permit easy access to amphiphilic and well-defined block copolymers owing to the lower critical solution temperature (LCST) behavior in aqueous solutions and thermoresponsive properties [35][36][37][38][39].…”

mentioning

confidence: 99%

“…These polymers can be obtained via living cationic ring opening polymerization (CROP) of 2-alkyl-oxazolines and functionalized by using either functional initiator or nucleophilic terminating agents [35][36][37][38][39]. Among them, poly(2-oxazoline)s with short side chains (ethyl, nand iso-propyl), except for 2-methyl-2-oxazoline, permit easy access to amphiphilic and well-defined block copolymers owing to the lower critical solution temperature (LCST) behavior in aqueous solutions and thermoresponsive properties [35][36][37][38][39]. To date, poly(2-oxazoline)s are obtained utilizing various initiators including halides such as benzyl bromide, alkyl esters such as methyl tosylate, methyl triflate and Lewis acids such as boron trifluoride (BF 3 -OEt 2 ) [40][41][42].…”

mentioning

confidence: 99%