Facile thiolation of hydroxyl functional polymers

Andrén, Oliver C. J.; Malkoch, Michael

doi:10.1039/c7py01097d

Cited by 6 publications

(9 citation statements)

References 34 publications

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“…Similar phenomena were reported in previous in vitro drug release study. 9 An addition of 10 mM GSH to the pH 5.0 medium further promotes drug release to 87% within the duration for H40-PCL 15 -SS-POEGMA 24 micelles, in contrast to the drug release of 62% for H40-PCL 15 -b-POEGMA 23 micelles, which indicates that the cleavage of the disulfide links in H40-PCL 15 -SS-POEGMA 24 micelles by GSH destabilizes the micelle structure and accelerates the DOX release as expected. The results demonstrate that reducible H40-PCL 15 -SS-POEGMA 24 micelles possess greater drug-loading capacity as well as higher accumulative drug release amount in the intracellular acidic and reducing environment than the non-reducible analogues.…”

Section: In Vitro Drug Releasementioning

confidence: 71%

“…S3(b)]. The very similar characterization data acquired for both reducible H40-PCL 15 -SS-POEGMA 24 and nonreducible H40-PCL 15 -SS-POEGMA 24 micelle constructs demonstrate the insignificant Reduction-Triggered Disassembly of H40-PCL 15 -SS-POEGMA 24 Micelles To investigate the reduction-triggered disassembly behaviors, the size changes of reducible micelles incubated with 10 mM GSH, mimicking the intracellular reducing environment, for various periods was monitored by DLS (Fig. 6).…”

Section: Characterization Of Reducible Micellesmentioning

confidence: 77%

“…Hyperbranched Amphiphilic Block Copolymer, H40-PCL 15 -SS-POEGMA 24 The synthesis of reduction-responsive hyperbranched amphiphilic block copolymer, H40-PCL 15 -SS-POEGMA 24 , is illustrated in Scheme 3.…”

Section: Synthesis and Characterization Of Reduction-responsivementioning

confidence: 99%

“…Among these systems, the reduction‐sensitive micelles containing disulfide bond seems of particular importance, owing to the large concentration gradient of glutathione (GSH) between the reducing intracellular compartment (∼10 mM) and mildly oxidizing extracellular environment (∼0.002 mM). The disulfide links tend to be cleaved by the reducing agents such as glutathione (GSH), leading to the destabilization of reduction‐sensitive micelles and subsequent release of the encapsulated drug with high efficacy …”

Section: Introductionmentioning

confidence: 99%

“…The disulfide links tend to be cleaved by the reducing agents such as glutathione (GSH), leading to the destabilization of reduction-sensitive micelles and subsequent release of the encapsulated drug with high efficacy. [22][23][24] Taken together, the preparation of H40-based stimuli-responsive amphiphilic block copolymers provides one solution to the tradeoff between the extracellular stability and intracellular high therapeutic efficacy of drug delivery systems.…”

mentioning

confidence: 99%

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Optimization of bioreducible micelles self‐assembled from amphiphilic hyperbranched block copolymers for drug delivery

Yang

Zhao

Zhang

et al. 2018

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

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Dendritic polymers‐based unimolecular micelles with enhanced stability are attractive carriers. However, the preparation of dendrimers or dendrons with higher generation remains substantially synthetic challenge due to the increased steric hindrance, multistep and tedious preparation, and low yields. The adoption of Boltorn H40, a commercially available dendritic polymer of Boltorn family containing multiple hydroxyl groups with various functionalities as a dendrimer‐based starting core template for the generation of hyperbranched polymers, offers a straightforward solution to address this problem. To develop universal strategies toward H40‐based amphiphilic block copolymers, the “grafting from” and “grafting to” approaches were both applied in this study. The reduction‐insensitive block copolymers, H40‐b‐poly(ɛ‐caprolactone)‐b‐poly(oligo(ethylene glycol) monomethyl ether methacrylate) (H40‐b‐PCL‐b‐POEGMA), were synthesized by “grafting from” including sequential ring‐opening polymerization (ROP) and atom transfer radical polymerization (ATRP). The core structure and the polymer composition of the nonreducible amphiphilic hyperbranched block copolymers were optimized toward better properties and performance for drug delivery applications, and H40‐PCL15‐b‐POEGMA23 was screened as the best polymer construct relative to H20‐PCL15‐b‐POEGMA23 and H40‐PCL15‐b‐POEGMA32 in terms of micelle stability and drug loading capacity. Therefore, the reducible H40‐b‐PCL‐SS‐POEGMA with an identical core and polymer composition to that of H40‐PCL15‐b‐POEGMA23 was further prepared by “grafting to” using click coupling between H40‐PCL‐azide and P(OEGMA)‐alkyne. The delivery efficacy evaluated by an in vitro cytotoxicity study revealed that the resulting DOX‐loaded reducible micelles of H40‐PCL15‐SS‐POEGMA23 produced greater cytotoxicity in cancer cells than in normal cells and macrophages, therefore, are promising carriers for anticancer drug delivery. © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2018, 56, 1383–1394

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Section: In Vitro Drug Releasementioning

confidence: 71%

Section: Characterization Of Reducible Micellesmentioning

confidence: 77%

Section: Synthesis and Characterization Of Reduction-responsivementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

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Optimization of bioreducible micelles self‐assembled from amphiphilic hyperbranched block copolymers for drug delivery

Yang

Zhao

Zhang

et al. 2018

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

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Thiolated Poly‐ and Oligosaccharide‐Based Hydrogels for Tissue Engineering and Wound Healing

Noreen,

Bernkop‐Schnürch

2023

Adv Funct Materials

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Due to thiolation of poly‐ and oligosaccharides numerous favorable properties for tissue engineering and wound healing can be introduced. Poly‐ and oligosaccharides can be thiolated via hydroxyl‐to‐thiol conversions or the covalent attachment of sulfhydryl ligands to hydroxyl, carbonic acid or amino groups on them. Since thiolated poly‐ and oligosaccharides can cross‐link via disulfide bonds, they form stable 3D networks with defined microarchitecture, stiffness, elasticity, and degradability. Furthermore, thiol groups can enhance cell adhesion since cells exhibit cysteine‐rich subdomains on their surface that form disulfide bonds with them. Sulfhydryl groups can also participate in cell signaling pathways favoring various cellular processes like proliferation, migration, spreading, and differentiation that are beneficial for tissue engineering and wound healing. In addition, a controlled release of active ingredients such as growth factors being bound via disulfide bonds to thiolated poly‐ and oligosaccharides can be achieved via thiol/disulfide exchange reactions. Over the last two decades, the number of thiolated poly‐ and oligosaccharides such as thiolated hyaluronic acid and thiolated chitosan used for tissue engineering and wound healing has increased tremendously. Within this review, an overview is provided about the chemistry of thiolated poly‐ and oligosaccharides, their key properties, applications and performance in clinical trials and as marketed products.

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Thiolated polymers: Bioinspired polymers utilizing one of the most important bridging structures in nature

Leichner

Jelkmann

Bernkop‐Schnürch

2019

Advanced Drug Delivery Reviews

100

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Facile thiolation of hydroxyl functional polymers

Abstract: A simple synthetic pathway to broaden the accessibility of thiol-functional polymers including formation of dendritic hydrogelsviaTEC chemistry.

Cited by 6 publications

References 34 publications

Optimization of bioreducible micelles self‐assembled from amphiphilic hyperbranched block copolymers for drug delivery

Optimization of bioreducible micelles self‐assembled from amphiphilic hyperbranched block copolymers for drug delivery

Thiolated Poly‐ and Oligosaccharide‐Based Hydrogels for Tissue Engineering and Wound Healing

Thiolated polymers: Bioinspired polymers utilizing one of the most important bridging structures in nature

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