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Improving Oral Bioavailability of Peptides by Multiple N‐Methylation: Somatostatin Analogues

2008; Wiley; Volume: 47; Issue: 14 Linguagem: Inglês

10.1002/anie.200705797

1521-3773

Éric Biron, Jayanta Chatterjee, Oded Ovadia, Daniel Langenegger, Joseph Brueggen, Daniël Hoyer, Herbert Schmid, Raz Jelinek, Chaim Gilon, Amnon Hoffman, Horst Kessler,

Click Chemistry and Applications

Full methyl jacket? A complete library of the N-methylated somatostatin cyclopeptidic analogue Veber–Hirschmann peptide cyclo(-PFwKTF-) has been prepared with the aim of improving its bioavailability. Several analogues from the library were found to bind to the somatostatin receptor in the nanomolar range and one of them shows a significant oral bioavailability of 10 %. Conformational analysis shows that N-methylation is allowed at specific positions without affecting the bioactive conformation. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2008/z705797_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.