Peptoids on steroids: Precise multivalent estradiol-peptidomimetic conjugates generated via azide-alkyne [3 + 2] cycloaddition reactions

Justin M. Holub, Michael J. Garabedian, Kent Kirshenbaum

Research output: Contribution to journalArticle

Abstract

We have developed a family of functionalized peptidomimetic oligomers for the multivalent display of bioactive ligands in a site-directed manner. Sequence-specific N-substituted glycine peptoid oligomer scaffolds were synthesized on solid phase to include up to six azidoalkyl sidechains. These constructs were used as substrates for Cu(I)-catalyzed azide-alkyne [3+2] cycloaddition reactions. 17a-ethynylestradiol was conjugated at up to six positions along the peptoid backbone, generating estradiol-peptidomimetic conjugates in good yield. We evaluate how the binding avidities of these compounds to the estrogen receptor are enhanced when the valency of hormone ligand presentation is increased.

Original languageEnglish (US)
Pages (from-to)1175-1180
Number of pages6
JournalQSAR and Combinatorial Science
Volume26
Issue number11-12
DOIs
StatePublished - Dec 1 2007

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Keywords

  • Click chemistry
  • Estrogen receptor
  • Hormone
  • Peptidomimetic
  • Polymer therapeutics

ASJC Scopus subject areas

  • Drug Discovery
  • Computer Science Applications
  • Organic Chemistry

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