Polymers made from cholic acid derivatives: selected properties

Zhang, Y. H.; Zhu, Xiaoxia

doi:10.1002/macp.1996.021971032

Cited by 26 publications

(34 citation statements)

References 19 publications

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“…The OH at C3 position has been turned into NH 2 and the methacrylamide derivatives of bile acids have been compared with methacrylate derivatives. The former are found to undergo more feasible (free radical) polymerization resulting in more hydrophilic polymer [214,215]. The stereoisomerism of the polymerizable moieties has also been studied.…”

Section: Bile Acid-derived Monomersmentioning

confidence: 97%

Synthesis of Terpene-Based Polymers

Zhao¹,

Schlaad²

2012

Advances in Polymer Science

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Terpenes or terpenoids are a large class of diverse biological compounds derived from isoprene. Due to their abundance in nature and desirable properties, there has been great interest in producing polymers with terpenes as either functional entities or as the main constituent. Terpene-based polymers have found applications as biomedical or liquid crystalline materials and, more importantly, have greatly contributed to the concept of sustainable polymer chemistry. The design and preparation of terpene-based polymers have involved different chemical strategies and a wide variety of polymerization techniques, making use of the chemical functionalities in terpene molecules, e.g. (conjugated) double bonds, hydroxyl and carboxyl groups. This review describes the synthetic methodologies for terpene-based polymers, classified by the position of terpene entities in the polymer chains, i.e., main chain, terminal or central group, and pendant group.

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Section: Bile Acid-derived Monomersmentioning

confidence: 97%

Synthesis of Terpene-Based Polymers

Zhao¹,

Schlaad²

2012

Advances in Polymer Science

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“…Indeed, in our group, we have prepared and modified various acrylamide-based block copolymers with CAs as pendant chains to study their effect on the tuning of the LCST. [45][46][47][48][49] Bile acids have the property of associating with ␤-cyclodextrin (␤-CD), due to the compatibility of the size and shape of bile acids with the cavity of ␤-CD. [50][51][52][53][54][55] This reversible association allows the tuning of the thermoresponsive properties via the addition of a supramolecular host.…”

Section: Thermoresponsive Polymers and Hydrogelsmentioning

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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“…The products were oily and were obtained in yields of 33, 28, and 19% for 3 c, 3 d and 3 e, respectively. Methyl 3amethacryloyl-7a,12a-dihydroxy-5b-cholan-24-ate (4 a): This monomer was prepared as described in a previous report 19) .…”

Section: Monomer Synthesismentioning

confidence: 99%

“…In our effort to explore the use of bile acids in the preparation of polymeric hydrogels [17][18][19][20] , we sought to improve the hydrophilicity of the polymers. The bile acid-containing monomers were copolymerized with more hydrophilic comonomers, such as methacrylic acid and 2-hydroxyethyl methacrylate 18,20) .…”

Section: Introductionmentioning

confidence: 99%

“…Furthermore, more hydrophilic derivatives of cholic acid, 3a-and 3b-methacrylamides, were prepared and used in the synthesis of the polymers 17) . Polymers made from monomers with a 3b-configuration showed interesting advantages 19,20) including higher yield, higher molecular weight, better solubility and lower polydispersity index. Therefore, stereoselective synthesis of 3b-monomers was carried out 21) .…”

Section: Introductionmentioning

confidence: 99%

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Hydrophilic polymethacrylates containing cholic acid-ethylene glycol derivatives as pendant groups

Benrebouh

Zhang

Zhu³

2000

Macromol. Rapid Commun.

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In an effort to improve the hydrophilicity of bile acid containing polymers, we have synthesized new methacrylate monomers by incorporating ethylene glycol and oligo(ethylene glycol) spacers of different lengths between cholic acid and methacrylate residues. The monomers were subsequently polymerized by free radical reaction in solution. The methyl ester protecting groups on the cholic acid residue were selectively hydrolyzed to restore the carboxylic acid group of cholic acid. Water absorption tests showed that the hydrophilicity of the polymers was improved with increasing length of oligo(ethylene glycol) spacers and upon restoration of the carboxylic acid group of the cholic acid residue.

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Polymers made from cholic acid derivatives: selected properties

Cited by 26 publications

References 19 publications

Synthesis of Terpene-Based Polymers

Synthesis of Terpene-Based Polymers

Polymers made of bile acids: from soft to hard biomaterials

Hydrophilic polymethacrylates containing cholic acid-ethylene glycol derivatives as pendant groups

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