Design and synthesis of a series of novel, cationic liposaccharide derivatives as potential penetration enhancers for oral drug delivery

Abdelrahim, Adel S.; Ziora, Zyta M.; Bergeon, Julie A.; Moss, Anne R.; Tóth, István

doi:10.1016/j.tet.2009.08.072

Cited by 11 publications

(3 citation statements)

References 33 publications

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“…A number of penetration enhancers were shown to improve oral availability of heparins. In this strategy, chemical structure of heparins is preserved [ 82 ] and once the complex crosses the membrane, penetration enhancers dissociate spontaneously from the therapeutic agent [ 52 ]. However, systemic toxic side effects of these compounds cannot be excluded [ 83 ].…”

Section: Co-administration With Penetration Enhancersmentioning

confidence: 99%

Strategies to Overcome Heparins’ Low Oral Bioavailability

et al. 2016

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Even after a century, heparin is still the most effective anticoagulant available with few side effects. The poor oral absorption of heparins triggered the search for strategies to achieve oral bioavailability since this route has evident advantages over parenteral administration. Several approaches emerged, such as conjugation of heparins with bile acids and lipids, formulation with penetration enhancers, and encapsulation of heparins in micro and nanoparticles. Some of these strategies appear to have potential as good delivery systems to overcome heparin’s low oral bioavailability. Nevertheless, none have reached the market yet. Overall, this review aims to provide insights regarding the oral bioavailability of heparin.

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Section: Co-administration With Penetration Enhancersmentioning

confidence: 99%

Strategies to Overcome Heparins’ Low Oral Bioavailability

et al. 2016

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“…In all of the glycolipopeptides constructed, two lipoamino acids were introduced to modulate lipophilicity and to assist microsphere formation via a self-assembly process. 14,18,19 The glycosyl azides 1a-g were synthesized according to known procedures. [20][21][22][23][24][25][26][27] The glycosyl units 2a-h were obtained by the acylation and in situ hydrogenation 28 of 1a-h (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of glycolipopeptidic building blocks for carbohydrate receptor discovery

Ziora

Wimmer

New

et al. 2011

Carbohydrate Research

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“…ITC is a sensitive, routine method which allows determining the critical micelles/aggregates concentration (CMC/CAC) and provides access to thermodynamic parameters such as enthalpy (ΔH), entropy (ΔS) and Gibbs free energy (ΔG) of micellization/aggregation [12,13]. Titration of concentrated mixture of compounds 1a-d or 2a-c into water allowed disaggregation and formation of new particles (aggregates/micelles).…”

Section: Introductionmentioning

confidence: 99%

Lipopeptides for the Fragment-Based Pharmaceutics Design

Ziora¹,

Wimmer²,

New³

et al. 2012

IJOC

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This paper describes the synthesis of peptide fragments for use in a new type of combinatorial discovery technology, in which the building blocks are brought together by non-covalent interactions, rather than direct chemical bonding. The building blocks of interest-in this case different amino acids-are converted to amphiphiles by attachment to lipid tails. The amphiphiles, when mixed together in aqueous phase, are designed so that they aggregate spontaneously to form micelles. The building blocks form the headgroups of each of the amphiphiles, and these headgroups cover the surface of the micelle in a dynamic close-packed fluid mosaic array. These building blocks come together so closely that twoor three-dimensional structures are created on the surface of the micelles, and these can be screened in biological assays to find out which combination of building blocks is able to elicit a biological response. Lipopeptides consisting of two residues of lipoamino acid and other amino acids moieties have been designed, synthesized, characterized and the ability of these constructs to form supra-molecular assemblies is demonstrated.

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Design and synthesis of a series of novel, cationic liposaccharide derivatives as potential penetration enhancers for oral drug delivery

Cited by 11 publications

References 33 publications

Strategies to Overcome Heparins’ Low Oral Bioavailability

Strategies to Overcome Heparins’ Low Oral Bioavailability

Synthesis of glycolipopeptidic building blocks for carbohydrate receptor discovery

Lipopeptides for the Fragment-Based Pharmaceutics Design

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