Bicyclic tetrapeptides as potent HDAC inhibitors: effect of aliphatic loop position and hydrophobicity on inhibitory activity.

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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.

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Journal

Journal ID (iso-abbrev): Bioorg. Med. Chem.

Title: Bioorganic & medicinal chemistry

Publisher: Elsevier BV

ISSN (Electronic): 1464-3391

ISSN (Print): 0968-0896

Publication date (Electronic): Aug 01 2014

Volume: 22

Issue: 15

Affiliations

[1 ] Graduate School of Life Science and Systems Engineering, Kyushu Institute of Technology, Kitakyushu 808-0196, Japan; Department of Chemistry, Faculty of Science, University of Rajshahi, Rajshahi 6205, Bangladesh. Electronic address: mnurulchem@gmail.com.

[2 ] Graduate School of Life Science and Systems Engineering, Kyushu Institute of Technology, Kitakyushu 808-0196, Japan; Department of Chemistry, Faculty of Science, University of Rajshahi, Rajshahi 6205, Bangladesh.

[3 ] Graduate School of Life Science and Systems Engineering, Kyushu Institute of Technology, Kitakyushu 808-0196, Japan; Department of Biochemistry and Molecular Biology, Faculty of Science, University of Rajshahi, Rajshahi 6205, Bangladesh.

[4 ] Graduate School of Life Science and Systems Engineering, Kyushu Institute of Technology, Kitakyushu 808-0196, Japan.

[5 ] Chemical Genetics Laboratory/Chemical Genomics Research Group, RIKEN Advanced Science Institute, Saitama 351-0198, Japan.

Article

Publisher Item ID: S0968-0896(14)00477-5

DOI: 10.1016/j.bmc.2014.06.031

PubMed ID: 25022972

SO-VID: 1a01725a-687d-4364-af19-6fae91c83c55

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Keywords: Bicyclic tetrapeptides,Histone deacetylase inhibitors,Ring-closing metathesis,Aliphatic loop position

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Keywords: Bicyclic tetrapeptides, Histone deacetylase inhibitors, Ring-closing metathesis, Aliphatic loop position

Bicyclic tetrapeptides as potent HDAC inhibitors: effect of aliphatic loop position and hydrophobicity on inhibitory activity.

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