Anionic Polymerization of β-Butyrolactone Initiated with Sodium Phenoxides. The Effect of the Initiator Basicity/Nucleophilicity on the ROP Mechanism

Domiński, Adrian; Konieczny, Tomasz; Zięba, Magdalena; Klim, Magdalena; Kurcok, Piotr

doi:10.3390/polym11071221

Cited by 22 publications

(18 citation statements)

References 42 publications

(57 reference statements)

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“…One of the most popular products coming from β-butyrolactone is polyhydroxybutyrate (PHB). It belongs to the group of polyhydroxyalkanoates, which are future "green" polymeric materials for biomedical applications, packaging and controlled drug release systems [40]. Unfortunately, it has poor mechanical properties due to its fragility and tendency toward thermal degradation.…”

Section: Products Produced From Lactones and Their Applicationsmentioning

confidence: 99%

Recent Developments in Lactone Monomers and Polymer Synthesis and Application

2021

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Lactones are a group of compounds that have been known for several decades. The commercial importance of lactones results from the possibility of manufacturing of a broad scope of derivatives and polymers with a wide spectrum of applications. In this work the synthesis and characterization of simple lactones are described, which due to the easy methods of the synthesis are of high importance for the industry. The chemical as well as biochemical methods are included with special attention paid to the methods that avoid metal catalysts, initiators or toxic solvents, allowing the use of the final products for the medical applications, e.g., for controlled drug-release systems, resorbable surgical threads, implants, tissue scaffolds or for the production of drugs. Lactone-based derivatives, such as polymers, copolymers, composites or three-dimensional structures are also presented. The work is focused on the methods for the synthesis of lactones and lactones derivates, as well as on the special properties and application of the studied compounds.

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Section: Products Produced From Lactones and Their Applicationsmentioning

confidence: 99%

Recent Developments in Lactone Monomers and Polymer Synthesis and Application

2021

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“…Synthetic and natural poly(3-hydroxybutyrate)s are very popular in biomedical applications due to their excellent biodegradability and biocompatibility. PHB can be synthesized by biotechnological processes or as a result of a chemical reaction, such as the polymerization of β-butyrolactone [104]. The mixing of the amphiphilic PEG-PHB-PEG triblock copolymer with α-CD synthesized a hydrogel.…”

Section: α-Cyclodextrin/linear Polymer-based Polypseudorotaxane Hydromentioning

confidence: 99%

α-Cyclodextrin-Based Polypseudorotaxane Hydrogels

2019

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Supramolecular hydrogels that are based on inclusion complexes between α-cyclodextrin and (co)polymers have gained significant attention over the last decade. They are formed via dynamic noncovalent bonds, such as host-guest interactions and hydrogen bonds, between various building blocks. In contrast to typical chemical crosslinking (covalent linkages), supramolecular crosslinking is a type of physical interaction that is characterized by great flexibility and it can be used with ease to create a variety of "smart" hydrogels. Supramolecular hydrogels based on the self-assembly of polypseudorotaxanes formed by a polymer chain "guest" and α-cyclodextrin "host" are promising materials for a wide range of applications. α-cyclodextrin-based polypseudorotaxane hydrogels are an attractive platform for engineering novel functional materials due to their excellent biocompatibility, thixotropic nature, and reversible and stimuli-responsiveness properties. The aim of this review is to provide an overview of the current progress in the chemistry and methods of designing and creating α-cyclodextrin-based supramolecular polypseudorotaxane hydrogels. In the described systems, the guests are (co)polymer chains with various architectures or polymeric nanoparticles. The potential applications of such supramolecular hydrogels are also described.

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“…To further its applications in drug delivery systems, it is crucial to obtain PHB in a highly controlled manner with the desired stereochemistry, which is essential for its physicochemical properties [10,11]. Therefore, extensive studies have focused on the ring-opening polymerization of β-lactones to obtain the polymer with the desired molar mass, low dispersity, microstructure, and reduced side reactions [12][13][14][15][16]. The isotactic poly ([R]-3-hydroxybutyrate) is synthesized both biotechnologically through bacterial fermentation and chemically by the polymerization of β-butyrolactone (β-BL) [17].…”

Section: Introductionmentioning

confidence: 99%

Shell-Sheddable Micelles Based on Poly(ethylene glycol)-hydrazone-poly[R,S]-3-hydroxybutyrate Copolymer Loaded with 8-Hydroxyquinoline Glycoconjugates as a Dual Tumor-Targeting Drug Delivery System

et al. 2022

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The development of selective delivery of anticancer drugs into tumor tissues to avoid systemic toxicity is a crucial challenge in cancer therapy. In this context, we evaluated the efficacy of a combination of nanocarrier pH-sensitivity and glycoconjugation of encapsulated drugs, since both vectors take advantage of the tumor-specific Warburg effect. Herein, we synthesized biodegradable diblock copolymer, a poly(ethylene glycol)-hydrazone linkage-poly[R,S]-3-hydroxybutyrate, which could further self-assemble into micelles with a diameter of ~55 nm. The hydrazone bond was incorporated between two copolymer blocks under an acidic pH, causing the shell-shedding of micelles which results in the drug’s release. The micelles were stable at pH 7.4, but decompose in acidic pH, as stated by DLS studies. The copolymer was used as a nanocarrier for 8-hydroxyquinoline glucose and galactose conjugates as well as doxorubicin, and exhibited pH-dependent drug release behavior. In vitro cytotoxicity, apoptosis, and life cycle assays studies of blank and drug-loaded micelles were performed on Normal Human Dermal Fibroblasts-Neonatal (NHDF-Neo), colon carcinoma (HCT-116), and breast cancer (MCF-7) for 24, 48, and 72 h. A lack of toxicity of blank micelles was demonstrated, whereas the glycoconjugates-loaded micelles revealed enhanced selectivity to inhibit the proliferation of cancer cells. The strategy of combining pH-responsive nanocarriers with glycoconjugation of the drug molecule provides an alternative to the modus operandi of designing multi-stimuli nanocarriers to increase the selectivity of anticancer therapy.

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Anionic Polymerization of β-Butyrolactone Initiated with Sodium Phenoxides. The Effect of the Initiator Basicity/Nucleophilicity on the ROP Mechanism

Cited by 22 publications

References 42 publications

Recent Developments in Lactone Monomers and Polymer Synthesis and Application

Recent Developments in Lactone Monomers and Polymer Synthesis and Application

α-Cyclodextrin-Based Polypseudorotaxane Hydrogels

Shell-Sheddable Micelles Based on Poly(ethylene glycol)-hydrazone-poly[R,S]-3-hydroxybutyrate Copolymer Loaded with 8-Hydroxyquinoline Glycoconjugates as a Dual Tumor-Targeting Drug Delivery System

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