Multiple N-methylation by a designed approach enhances receptor selectivity

Jayanta Chatterjee, Oded Ovadia, Grit Zahn, Luciana Marinelli, Amnon Hoffman, Chaim Gilon, Horst Kessler*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

65 Scopus citations

Abstract

An unselective cyclic peptide integrin ligand was sequentially N-methylated by a designed approach, where only the externally oriented (solvent exposed) amide bonds were N-methylated. The N-methylation resulted in tremendous enhancement in selectivity among the different integrin receptor subtypes (α5β1, αvβ93, and αIIbβ3). Conformational and docking studies were performed, which suggested that the receptor selectivity is principally caused by reduced backbone flexibility due to N-methylation.

Original languageAmerican English
Pages (from-to)5878-5881
Number of pages4
JournalJournal of Medicinal Chemistry
Volume50
Issue number24
DOIs
StatePublished - 29 Nov 2007

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