Cited by 69Chemical Synthesis and AnalysisEstrogen and related hormone effectsProtein Structure and Dynamics

Thioether side chain cyclization for helical peptide formation: inhibitors of estrogen receptor–coactivator interactions

Galande, A.K., Bramlett, K.S., Burris, T.P., Wittliff, J.L., Spatola, A.F.·2004·The Journal of Peptide Research

Abstract

Abstract: Cystine, lanthionine, and cystathionine containing cyclic peptides incorporating the signature nuclear receptor (NR) box (LXXLL) motif have been synthesized and the abilities of these peptides to inhibit estrogen receptor (ER)–coactivator interactions have been determined. We found that helicity of these peptides directly correlated with their bioactivity. Cystathionine proved to be a redox‐stable, isosteric replacement for the cystine disulfide. Cystathionine containing peptide 3 showed higher helical character and a lower inhibition constant (Ki, 7 n m) when compared with its cystine counterpart.

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Crossref · 10.1111/j.1399-3011.2004.00152.x

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Authors
Galande, A. K., Bramlett, K. S., Burris, T. P., Wittliff, J. L., & Spatola, A. F.
Affiliations
University of Louisville (US)
Corresponding author
Wittliff, J.L.
Venue
The Journal of Peptide Research
Publisher
Wiley
Published
2004-03
Volume
63
Issue
3
Pages
297-302
ISSN
1397-002X (ISSN-L)
OpenAlex
W2076247712
Cited by
69
References
28
Citations by year
2026: 1 · 2024: 3 · 2023: 1 · 2022: 3 · 2021: 3 · 2020: 3 · 2019: 2 · 2018: 3 · 2017: 6 · 2016: 7 · 2015: 5 · 2014: 5 · 2013: 3 · 2012: 4
FWCI
1.30
Type
journal article
Language
en
Open access
closed
Locations
  • Journal of Peptide Research (publishedVersion)
  • PubMed (publishedVersion)
Topics
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Chemical Synthesis and Analysis
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Genetics › Estrogen and related hormone effects
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Protein Structure and Dynamics
Keywords
helical peptides, estrogen receptor, coactivator binding, LXXLL motif, cystathionine, lanthionine, cyclic peptides, redox stability, peptide inhibitors
MeSH terms
Amino Acids, Sulfur, Binding, Competitive, Oligopeptides, Peptides, Cyclic, Receptors, Estrogen, Sulfides, Transcription Factors, Molecular Structure, Amino Acid Motifs

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