Synthesis of novel cholic acid functionalized branched oligo/poly(ε‐caprolactone)s for biomedical applications

Fu, Huili; Yu, Lian; Zhang, Hua; Zhang, Xian‐Zheng; Cheng, Si‐Xue; Zhuo, Ren‐Xi

doi:10.1002/jbm.a.30924

Cited by 16 publications

(21 citation statements)

References 23 publications

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“…Such polymers are known to be less crystalline and have a high number of end‐groups compared to their linear analogs 3–5. The type and number of end‐groups present, play an important role in the properties and degradation of biodegradable aliphatic polyesters 6–10. As an example, carboxylic acid groups change the hydrophilicity of a polymer and can accelerate degradation by hydrolysis 6.…”

Section: Introductionmentioning

confidence: 99%

AB₂ Functional Polyesters via Ring Opening Polymerization: Synthesis and Characterization

Velthoen

Dijkstra

Feijén

2009

Macro Chemistry & Physics

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Aliphatic AB2 functional polyesters were conveniently prepared by the ring opening polymerization of ε‐caprolactone and L‐lactide in the presence of the AB2 functional initiator 2,2‐bis(hydroxymethyl)propionic acid (bis‐MPA) and Sn(Oct)2 as the catalyst. In L‐lactide polymerization, both bis‐MPA hydroxyl groups initiated the polymerization reaction, but for ε‐caprolactone polymerization this depended on the monomer to initiator to catalyst ratio. Initiation at two hydroxyl groups occurred at high monomer to initiator ([M]/[I]) ratio and at high Sn(Oct)2 to monomer ratio. The melting temperatures of the AB2‐functional PLLA and PCL polymers were comparable to linear polymers with a $\overline {DP}$ equal to the $\overline {DP}$ per arm in the polymer.

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Section: Introductionmentioning

confidence: 99%

AB₂ Functional Polyesters via Ring Opening Polymerization: Synthesis and Characterization

Velthoen

Dijkstra

Feijén

2009

Macro Chemistry & Physics

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“…A series of star-shaped polymers were prepared with cholic acid as the core and DL-lactide, ε-caprolactone or other carbonates as branches through ring-opening polymerization by the group of Zhuo (Figure 8, A-D). These polymers can be useful in applications such as drug release [38][39][40][41][42] and gene delivery [43] , and can serve as scaffolds to promote cell attachment and growth [44,45] . When thermo-sensitive groups were attached onto position 24 of cholic acid, ringopening polymerization yielded thermo-sensitive drug carriers [46] .…”

Section: Bile Acids As the Core Of Star-shaped Polymersmentioning

confidence: 99%

Biomaterials made of bile acids

Zhang

Zhu

2009

Sci. China Ser. B-Chem.

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The use of natural compounds in the preparation of new materials can improve the biocompatibility of the materials and avoid any potential toxicity of the degradation products when used for biomedical applications. Bile acids are amphiphilic molecules biosynthesized in the liver. They are used to prepare various polymers and oligomers. These polymers made of bile acids are promising materials in both biomedical and pharmaceutical fields.

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“…Ring-opening polymerization has been a method of choice, where the hydroxyl groups at positions C-3, C-7, and C-12 can be used as initiating points in the presence of DL-lactide, -caprolactone, or other cyclic ester monomers. [19][20][21][22][23][24][25] Zhuo et al exploited the hydroxyl groups of cholic acid (CA) to prepare a three arm star shaped polylactide with potential applications in drug delivery and as scaffolds for promoting cell adhesion and proliferation. However, high polydispersities and uneven chain lengths are shortcomings of ring-opening polymerization in the present context.…”

Section: Self-assembled Systemsmentioning

confidence: 99%

Polymers made of bile acids: from soft to hard biomaterials

Cunningham

Zhu

2016

Can. J. Chem.

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Bile acids are gaining increasing importance as building blocks in the development of novel polymeric materials. This is evidenced by the growing number of publications advocating the advantages of their incorporation in the design and construction of materials. Composed of a rigid steroid backbone, functional groups with potential towards diverse reactions, and a biocompatible framework, there are various ways in which these molecules can be utilized to afford biomaterials via distinct architectures. Soft materials utilize the intrinsic capacity of bile acids to self-assemble and have seen a range of applications, most notably in the field of drug delivery. On the other hand, there is also the possibility of including bile acids in the polymer backbone, which has been used in the preparation of elastomers. This review discusses a selection of materials that can be prepared using bile acids and the advantages afforded by these molecules. Focus will be on the development of soft and hard materials, where soft materials are described as being held by weak intermolecular interactions, whereas hard materials are mechanically stronger with bile acids covalently incorporated in the polymer network.Key words: bile acids, polymers, biomaterials, drug delivery, dental composites. Résumé :Les acides biliaires sont des synthons de plus en plus importants dans la mise au point de nouveaux matériaux à base de polymères, comme en témoigne le nombre croissant de publications préconisant leur incorporation dans la conception et la fabrication de ces matériaux. Composées d'un squelette stéroïdien rigide, de groupes fonctionnels au potentiel réactionnel diversifié, et d'une structure biocompatible, ces molécules, de par leurs différentes architectures, présentent diverses possibilités d'application dans le domaine des biomatériaux. La capacité intrinsèque des acides biliaires à s'autoassembler permet de produire des matériaux souples dont les applications sont variées, notamment dans le domaine de la libération des médica-ments. Par ailleurs, la possibilité d'intégrer des acides biliaires dans le squelette de polymères a aussi été explorée dans le cadre de la fabrication d'élastomères. Le présent article de synthèse porte sur une sélection de matériaux pouvant être préparés à partir d'acides biliaires et sur les avantages que comportent ces molécules. Une attention particulière est accordée à la mise au point de matériaux souples et de matériaux rigides. On y décrit les matériaux souples comme étant maintenus par des interactions intermoléculaires faibles, tandis que les matériaux rigides, dans lesquels les acides biliaires sont incorporés dans le réseau polymérique par des liaisons covalentes, sont mécaniquement plus solides. [Traduit par la Rédaction]

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Synthesis of novel cholic acid functionalized branched oligo/poly(ε‐caprolactone)s for biomedical applications

Cited by 16 publications

References 23 publications

AB₂ Functional Polyesters via Ring Opening Polymerization: Synthesis and Characterization

AB₂ Functional Polyesters via Ring Opening Polymerization: Synthesis and Characterization

Biomaterials made of bile acids

Polymers made of bile acids: from soft to hard biomaterials

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Synthesis of novel cholic acid functionalized branched oligo/poly(ε‐caprolactone)s for biomedical applications

Cited by 16 publications

References 23 publications

AB2 Functional Polyesters via Ring Opening Polymerization: Synthesis and Characterization

AB2 Functional Polyesters via Ring Opening Polymerization: Synthesis and Characterization

Biomaterials made of bile acids

Polymers made of bile acids: from soft to hard biomaterials

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AB₂ Functional Polyesters via Ring Opening Polymerization: Synthesis and Characterization

AB₂ Functional Polyesters via Ring Opening Polymerization: Synthesis and Characterization