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Enantiomeric cyclic peptides with different Caco-2 permeability suggest carrier-mediated transport

Marelli, Udaya Kiran and Bezençon, Jacqueline and Puig, Eduard and Ernst, Beat and Kessler, Horst. (2015) Enantiomeric cyclic peptides with different Caco-2 permeability suggest carrier-mediated transport. Chemistry - A European Journal, 21 (22). pp. 8023-8027.

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Official URL: http://edoc.unibas.ch/40921/

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Abstract

Recently, oral absorption of cyclic hexapeptides was improved by N-methylation of their backbone amides. However, the number and position of N-methylations or of solvent exposed NHs did not correlate to intestinal permeability, measured in a Caco-2 model. In this study, we investigate enantiomeric pairs of three polar and two lipophilic peptides to demonstrate the participation of carrier-mediated transporters. As expected, all the enantiomeric peptides exhibited identical lipophilicity (logD7.4) and passive transcellular permeability determined by the parallel artificial membrane permeability assay (PAMPA). However, the enantiomeric polar peptides exhibited different Caco-2 permeability (Papp) in both directions a-b and b-a. The same trend was observed for one of the lipophilic peptide, whereas the second lipophilic enantiomer pair showed identical Caco-2 permeability (within the errors). These findings provide the first evidence for the involvement of carrier-mediated transport for peptides, especially for those of polar nature.
Faculties and Departments:05 Faculty of Science > Departement Pharmazeutische Wissenschaften > Pharmazie > Molekulare Pharmazie (Ernst)
UniBasel Contributors:Ernst, Beat and Bezençon, Jacqueline
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:Wiley
ISSN:0947-6539
e-ISSN:1521-3765
Note:Publication type according to Uni Basel Research Database: Journal article
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Last Modified:28 Nov 2017 11:11
Deposited On:11 Aug 2016 08:07

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