The use of thiolated polymers as carrier matrix in oral peptide delivery—Proof of concept

Bernkop‐Schnürch, Andreas; Pinter, Yvonne; Guggi, D.; Kahlbacher, Hermann; Schöffmann, Gudrun; Schuh, Maximilian; Schmerold, Ivo; Curto, Del; D'Antonio, M.; Esposito, P.; Huck, Christian W.

doi:10.1016/j.jconrel.2005.04.004

Cited by 50 publications

(23 citation statements)

References 19 publications

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“…(and R REL of 3.2%) [431]. In a similar study, an enteric-coated oral tablet (10mg) containing insulin (2.8 mg) chitosan TBA (5mg) and two peptide inhibitor conjugates of chitosan (chitosan-BBI (0.75 mg) and chitosan-elastatinal (0.75 mg), as well as CA (0.1 M) was tested in rats [433].…”

Section: Case 16: Chitosan and Its Derivativesmentioning

confidence: 99%

“…Several thiomers sustain drug release from tablets [431] and mini-tablets [67,432]. Given that thiomers are mucoadhesive and can inhibit peptidase activity, it is not surprising that they retain the ability to improve intestinal permeability, although whether this is directly due to permeation enhancement or whether such enhancement can effectively translate to man is unknown.…”

Section: Case 16: Chitosan and Its Derivativesmentioning

confidence: 99%

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Intestinal permeation enhancers for oral peptide delivery

Maher

Mrsny

Brayden

2016

Advanced Drug Delivery Reviews

290

201

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Publication informationAdvanced Drug Delivery Reviews, (Part B): 277-319 Publisher ElsevierItem record/more information http://hdl.handle.net/10197/7800Publisher's statement þÿ T h i s i s t h e a u t h o r s v e r s i o n o f a w o r k t h a t w a s a c c e p t e d f o r p u b l i c a t i o n i n A d v a n c e d D r u g Delivery Reviews. Changes resulting from the publishing process, such as peer review,

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Section: Case 16: Chitosan and Its Derivativesmentioning

confidence: 99%

Section: Case 16: Chitosan and Its Derivativesmentioning

confidence: 99%

Intestinal permeation enhancers for oral peptide delivery

Maher

Mrsny

Brayden

2016

Advanced Drug Delivery Reviews

290

201

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“…Examples of bioadhesive polymers (99) include carbomer (100), chitosan (101), and modified chitosan (102,103). Thiolated polymers or 'thiomers' are typically chitosan-based and induce effective mucoadhesion by in situ formation of disulfide bonds (104). Ultra-pure preparations of chitosan have enabled evaluation of its commercial viability in this application, though thiomers are not yet available with the required safety testing for pharmaceutical use or at commercial scale.…”

Section: Oral Peptide Formulationmentioning

confidence: 99%

Physicochemical and Formulation Developability Assessment for Therapeutic Peptide Delivery—A Primer

Bak

Leung

Barrett

et al. 2014

AAPS J

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Abstract. Peptides are an important class of endogenous ligands that regulate key biological cascades. As such, peptides represent a promising therapeutic class with the potential to alleviate many severe disease states. Despite their therapeutic potential, peptides frequently pose drug delivery challenges to scientists. This review introduces the physicochemical, biophysical, biopharmaceutical, and formulation developability aspects of peptides pertinent to the drug discovery-to-development interface. It introduces the relevance of these properties with respect to the delivery modalities available for peptide pharmaceuticals, with the parenteral route being the most prevalent route of administration. This review also presents characterization strategies for oral delivery of peptides with the aim of illuminating developability issues with the drug candidate. A brief overview of other routes of administration, including inhaled, transdermal, and intranasal routes, is provided as these routes are generally preferred by patients over injectables. Finally, this review presents formulation techniques to mitigate some of the developability obstacles associated with peptide delivery. The authors emphasize opportunities for the thoughtful application of pharmaceutical science to the development of peptide drugs and to the general advancement of this promising class of pharmaceuticals.

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“…When a thiolated chitosan was introduced into the formulation, however, an improved uptake of the drug was found. The absolute and relative bioavailability of these formulations were calculated to be 1.1% and 3.2% increased, respectively [74].…”

Section: Oral Drug Deliverymentioning

confidence: 99%

Chitosan and Thiolated Chitosan

Sarti

Bernkop‐Schnürch

2011

Advances in Polymer Science

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Thiolated chitosans constitute an integral part of designated "thiomers", which are thiolated polymers widely investigated for non-invasive drug delivery. In brief, thiomers display thiol-group-bearing ligands on their polymer backbone. Through thiol/disulfide exchange reactions and/or a simple oxidation process, disulfide bonds are formed between such polymers and the cysteine-rich subdomains of mucus glycoproteins, thus building up the mucus gel layer. Most chemical modifications of chitosan are performed at the free amino groups of the glucosamine units. So far, the alkyl thiomers chitosan-cysteine, chitosan-thiobutylamidine, chitosan-thioglycolic acid, chitosan-N-acetylcysteine, and chitosan-thioethylamidine and the aryl thiomers chitosan-6-mercaptonicotinic acid and chitosan-4-mercaptobenzoic acid have been generated. Due to the immobilization of thiol groups on the chitosan backbone, its mucoadhesive, permeation enhancing, in situ gelling, efflux pump inhibitory, and controlled drug release properties are improved. The great benefits of this new generation of chitosans in comparison to the corresponding unmodified polymers has been verified via numerous in vivo studies on various mucosal membranes. A proof of concept for oral, nasal and buccal drug delivery is provided. This chapter includes an overview of the mechanism of adhesion and the design of thiomers as well as of delivery systems comprising thiolated chitosans and their in vivo performance.

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The use of thiolated polymers as carrier matrix in oral peptide delivery—Proof of concept

Cited by 50 publications

References 19 publications

Intestinal permeation enhancers for oral peptide delivery

Intestinal permeation enhancers for oral peptide delivery

Physicochemical and Formulation Developability Assessment for Therapeutic Peptide Delivery—A Primer

Chitosan and Thiolated Chitosan

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