Bile salts and derivatives: Rigid unconventional amphiphiles as dispersants, carriers and superstructure building blocks

Galantini, Luciano; Gregorio, Maria Chiara di; Gubitosi, Marta; Travaglini, Leana; Tato, José Vázquez; Jover, Aida; Meijide, Francisco; Tellini, Víctor Hugo Soto; Pavel, Nicolae Viorel

doi:10.1016/j.cocis.2015.08.004

Cited by 91 publications

(66 citation statements)

References 104 publications

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“…Consequently, the hydrophobic-hydrophilic balance of the compound is either increased or reduced, thus modifying its self-aggregation in aqueous solution. Several papers dealing with the physicochemical properties and applications in fields such as supramolecular chemistry, biomedicine, and pharmaceutics have been reported [18,[22][23][24][25][26][27][28].…”

Section: R1mentioning

confidence: 99%

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A Standard Structure for Bile Acids and Derivatives

et al. 2018

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Abstract:The crystal structures of two ester compounds (a monomer in its methyl ester form, with an amino isophthalic group, and a dimer in which the two steroid units are linked by a urea bridge recrystallized from ethyl acetate/methanol) derived from cholic acid are described. Average bond lengths and bond angles from the crystal structures of 26 monomers and four dimers (some of them in several solvents) of bile acids and esters (and derivatives) are used for proposing a standard steroid nucleus. The hydrogen bond network and conformation of the lateral chain are also discussed. This standard structure was used to compare with the structures of both progesterone and cholesterol.

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Section: R1mentioning

confidence: 99%

“…In aqueous solution they behave as surfactants, the aggregates showing a wide range of structures. The subject has been reviewed recently [18]. On the other hand, the head-tail structure of BS allows the synthesis of head-to-head [19], head-to-tail [20], and tail-to-tail [21] dimers.…”

Section: Introductionmentioning

confidence: 99%

A Standard Structure for Bile Acids and Derivatives

et al. 2018

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“…It is expected that the facile and innovative design of supramolecular material by the ISA strategy could be used as pH detection probes and microreactors. Recently, one kind of biomolecule, bile salts, has been developed as building blocks for various functional nanomaterials [28,29]. All of the bile salts possess a rigid, nearly planar hydrophobic steroid backbone and have polar hydroxyl groups on the concave α-face and methyl groups on the convex β-face [30,31].…”

Section: Dye-surfactant Isa Materialsmentioning

confidence: 99%

Supramolecular Materials Based on Ionic Self‐Assembly: Structure, Property, and Application

Shen¹,

Yuan²,

Xin³

2017

Molecular Self-Assembly in Nanoscience and Nanotechnology

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The technique of ionic self-assembly (ISA), on the basis of electrostatic interactions, is a powerful tool to create new material nanostructures and chemical objects due to its advantages of facility, reliability, cost saving, flexibility, and universality. It has attracted great attention because of its promising applications in catalysis, drug delivery, and molecular detection. This review focuses on recent advances in the construction of self-assemblies with different morphologies on the basis of ISA strategy and its applications. The ISA method provides an opportunity to generate complex and hierarchical assemblies with tunable properties, which is regarded as a very promising case of supramolecular chemistry.

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“…On the one hand, they enhance absorption by increasing drug solubility and the rate of dissolution or provide protection from degradation; on the other hand they are able to alter the membrane permeability through interaction with the membranes phospholipids (28). Yet, BS have been mainly applied as penetration enhancers in drug formulations to support mucosal absorption especially due to the membrane destabilizing properties (29)(30)(31). It was shown that BS significantly enhances the intestinal permeability of CEF and increasing the absorption rate up to 2-times (32).…”

Section: Introductionmentioning

confidence: 99%

Nanosized Liposomes Containing Bile Salt: A Vesicular Nanocarrier for Enhancing Oral Bioavailability of BCS Class III Drug

et al. 2017

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-PURPOSE: Liposomes have been studied as a colloidal carrier in drug delivery systems, especially for oral administration. However, their low structural integrity in the gut is still a major shortcoming. Membrane disruptive effects of physiological bile salts in the small intestine result in premature drug release prior to intestinal absorption. Thus, we analyzed the stabilizing effect of sodium deoxycholate when incorporated into nano-sized liposomes. METHOD: Cefotaxime-loaded liposomes were prepared with different sodium deoxycholate concentrations (3.75-30 mM) by rotary film evaporation followed by nanosize reduction. The physical integrity of liposomes was evaluated by monitoring cefotaxime leakage, particle sizes in different simulated physiological media. The oral bioavailability and pharmacokinetics of cefotaxime was assessed in rats (n = 6 per group) after single dose of drug-encapsulated in liposomes containing bile salt, drug in conventional liposomes, and cefotaxime solution (oral and intravenous). RESULTS: Simulated gastric fluid with low pH showed less effect on the stability of liposomes in comparison to media containing physiological bile salts. Liposomes containing 15 mM sodium deoxycholate were most stable in size and retained the majority of encapsulated cefotaxime even in fed state of simulated intestinal fluid being the most destructive media. Pharmacokinetics data showed an increase in Cmax and AUC0-inf in the following order: cefotaxime solution < conventional liposomes < liposomes made with bile salts. The total oral bioavailability of cefotaxime in liposomes containing bile salt was found to be 5-times higher compared to cefotaxime solution and twice as much as in conventional liposomes. CONCLUSION: Incorporation of bile salts, initially used as membrane permeation enhancer, also acted as a stabilizer against physiological bile salts. The nanosized liposomes containing sodium deoxycholate were able to reduce the leakage of encapsulated cefotaxime in the gut due to the improved vesicle stability and to enhance the oral bioavailability of acid-labile drugs up to 5-fold.

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Bile salts and derivatives: Rigid unconventional amphiphiles as dispersants, carriers and superstructure building blocks

Cited by 91 publications

References 104 publications

A Standard Structure for Bile Acids and Derivatives

A Standard Structure for Bile Acids and Derivatives

Supramolecular Materials Based on Ionic Self‐Assembly: Structure, Property, and Application

Nanosized Liposomes Containing Bile Salt: A Vesicular Nanocarrier for Enhancing Oral Bioavailability of BCS Class III Drug

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