Abstract
The 1-azabicyclo[5.2.0]nonan-2-one lactam 1 adequately substituted on both cycles A and B as scaffolds mimics the conformationally constrained beta-turn of the tripeptide RGD signaling motif of fibronectin. Using an in vitro assay, we establish that trans diastereoisomer 1b dissociates a soluble fibronectin-integrin alpha(5)beta(1) complex at concentrations comparable to those of a linear RGDS peptide as a competitor.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Amino Acid Motifs
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Bridged Bicyclo Compounds / chemical synthesis*
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Bridged Bicyclo Compounds / pharmacology
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Drug Design
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Fibronectins / chemistry
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Integrin alpha5beta1 / chemistry
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Lactams / chemical synthesis*
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Lactams / chemistry
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Lactams / pharmacology
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Molecular Mimicry
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Oligopeptides / antagonists & inhibitors*
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Oligopeptides / chemistry
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Stereoisomerism
Substances
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1-azabicyclo(5.2.0)nonan-2-one lactam
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Bridged Bicyclo Compounds
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Fibronectins
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Integrin alpha5beta1
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Lactams
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Oligopeptides
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arginyl-glycyl-aspartic acid