Abstract
Several histone deacetylase (HDAC) inhibiting bicyclic tetrapeptides have been designed and synthesized through intramolecular ring-closing metathesis (RCM) reaction and peptide cyclization. We designed bicyclic tetrapeptides based on CHAP31, trapoxin B and HC-toxin I. The HDAC inhibitory and p21 promoter assay results showed that the aliphatic loop position as well as the hydrophobicity plays an important role toward the activity of the bicyclic tetrapeptide HDAC inhibitors.
Keywords:
Aliphatic loop position; Bicyclic tetrapeptides; Histone deacetylase inhibitors; Ring-closing metathesis.
Copyright © 2014 Elsevier Ltd. All rights reserved.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Histone Deacetylase Inhibitors / chemical synthesis
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Histone Deacetylase Inhibitors / chemistry*
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Histone Deacetylase Inhibitors / metabolism
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Histone Deacetylases / chemistry
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Histone Deacetylases / metabolism
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Humans
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Hydrophobic and Hydrophilic Interactions
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Intercellular Signaling Peptides and Proteins
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Oligopeptides / chemical synthesis
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Oligopeptides / chemistry*
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Peptides / chemistry
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Peptides, Cyclic / chemical synthesis
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Peptides, Cyclic / chemistry*
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Peptides, Cyclic / metabolism
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Protein Binding
Substances
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Histone Deacetylase Inhibitors
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Intercellular Signaling Peptides and Proteins
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Oligopeptides
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Peptides
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Peptides, Cyclic
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cyclic hydroxamic acid-containing peptide 31
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trapoxin B
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HC toxin
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Histone Deacetylases