Multiple N-methylation by a designed approach enhances receptor selectivity

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

doi:10.1021/jm701044r

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

School of Pharmacy

Research output: Contribution to journal › Article › peer-review

66 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 language	English
Pages (from-to)	5878-5881
Number of pages	4
Journal	Journal of Medicinal Chemistry
Volume	50
Issue number	24
DOIs	https://doi.org/10.1021/jm701044r
State	Published - 29 Nov 2007

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10.1021/jm701044r

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AU - Gilon, Chaim

AU - Kessler, Horst

PY - 2007/11/29

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Multiple N-methylation by a designed approach enhances receptor selectivity

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