Polymeric Materials Containing Bile Acids

Zhu, Xiaoxia; Nichifor, Marieta

doi:10.1021/ar0101180

Cited by 136 publications

(91 citation statements)

References 57 publications

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“…and a hydrophilic ␤-side (10, 13). The natural physicochemical and enterohepatic circulation properties of the bile acids could be utilized for the preparation of new drugs (4,7,8,16). Our concept was to design a delivery carrier based on bile acid molecules that could physically interact with oppositely charged hydrophilic, and thus poorly absorbable, drugs.…”

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confidence: 99%

Pharmacokinetics of a New, Orally Available Ceftriaxone Formulation in Physical Complexation with a Cationic Analogue of Bile Acid in Rats

Lee

Kim

Lee

et al. 2006

Antimicrob Agents Chemother

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Oral administration of ceftriaxone associated with a bile acid-based new oral carrier, cholylethylenediamine, in 50% propylene glycol to rats at doses of 25 and 50 mg/kg of body weight resulted in a significant increase in intestinal absorption, as evidenced by 55% improvement in the bioavailability, whereas ceftriaxone alone showed a bioavailability of less than 1%.The introduction of new oral cephalosporins, or formulation development of existing and highly promising parenteral cephalosporins, provides a possibility for follow-up oral treatment after initial parenteral treatment, thus reducing hospitalization time and costs (5,6,14). Ceftriaxone (CRO) is a widely used injectable broad-spectrum cephalosporin that exhibits potent activity against gram-positive and gram-negative bacteria (1, 2, 11, 12). However, the therapeutic utility of ceftriaxone is limited, as it requires parenteral infusion for its administration. In this respect, the development of an oral formulation of CRO would be helpful in rapid and proper step-down therapy that would lead to better patient compliance without compromising the therapeutic activity.In a previous study, we developed a new oral delivery carrier based on bile acids, which could improve the oral bioavailability of therapeutically active peptides without damaging the tissue structure of the mucous membrane (8, 9). Based on the observation that associated bile acid could increase the absorption of a poorly absorbable drug in the intestine, we prepared a positively charged carrier by simple modification of bile acid, cholic acid, with ethylenediamine for the negatively charged small organic molecules, CRO. This scheme was designed with the goal of preparing a carrier that could physically associate with the drug by ion pair interaction to improve its lipophilicity without altering the structure of the native drug. In the present study, we show that the positively charged bile acid analogue forms a complex with CRO and report the impact of this association on the oral bioavailability.Cholylethylendiamine (CEA) was synthesized by using cholic acid and ethylenediamine as precursors. A delivery agent was composed of the hydrophobic part of bile acid and the positive charge of ethylenediamine, thereby facilitating an ionpairing interaction with anionic drug, CRO. The complex formation in aqueous medium was reversible and dependent on the molar ratio between CRO and the delivery agent. Since CRO/CEA complexes showed significantly reduced solubility in water, the lyophilized drug complex was reformulated by the addition of one of the most common water-soluble solvents, propylene glycol (PG) (15), as a prototype formulation.The partition coefficients of CRO/CEA complexes were investigated in an n-octanol/water system. CRO concentrations were analyzed on a reversed-phase high-performance liquid chromatograph (RP-HPLC) (Shimadzu, Tokyo, Japan) as previously described (3). Briefly, a 50-l aliquot of supernatant was injected into an RP-HPLC fitted with an Eclipse XDB analytical column (25...

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confidence: 99%

Pharmacokinetics of a New, Orally Available Ceftriaxone Formulation in Physical Complexation with a Cationic Analogue of Bile Acid in Rats

Lee

Kim

Lee

et al. 2006

Antimicrob Agents Chemother

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“…此外胆酸还含有手性碳原子, 在手性领域具有很好的应用潜能. 良好的生物相容性、甾环的高稳定性、分子的两亲性和手性、分子的自组装能力等 [15] , 使胆酸近年来在生物医药和化学领域引起了广泛兴趣, 已被成功用于不对称合成、分子识别、药物传送体系和高分子生物材料等方面 [16] . 本文中我们首先通过硅烷偶联剂将叠氮基团引入到 GO 表面, 再将经过炔基化的胆酸通过 Click 反应接在 GO 表面, 以此实现了对 GO 的手性功能化, 同时制备了一种新型的手性石墨烯杂化材料.…”

Section: Doi: 106023/a14080614unclassified

Cholic Acid/Graphene Oxide Chiral Hybrid Material: Preparation and Characterizations

Huang¹,

Ren²,

Chen³

et al. 2014

Acta Chim. Sinica

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“…1,[8][9][10][11] Notwithstanding their physiological importance, bile acids are rapidly gaining impetus as frameworks for the development of novel materials with considerable importance in the pharmacological, biochemical, and nanotechnological fields. 2,12,13 Although they have found potential applications in the treatment of liver diseases, 14,15 and as antifungal 16 and antiviral agents, 17 the present review will provide an account of the use of bile acids as platforms for the preparation of soft and hard materials. Central to this idea, we will begin with a glance at the physicochemical properties of bile acids followed by examples of their exploitation for the development of soft materials such as self-healing gels and nanoparticles for drug delivery and in their development of hard materials such as elastomers and dental resins.…”

Section: Introductionmentioning

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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Polymeric Materials Containing Bile Acids

Cited by 136 publications

References 57 publications

Pharmacokinetics of a New, Orally Available Ceftriaxone Formulation in Physical Complexation with a Cationic Analogue of Bile Acid in Rats

Pharmacokinetics of a New, Orally Available Ceftriaxone Formulation in Physical Complexation with a Cationic Analogue of Bile Acid in Rats

Cholic Acid/Graphene Oxide Chiral Hybrid Material: Preparation and Characterizations

Polymers made of bile acids: from soft to hard biomaterials

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