Synthesis and screening of a cyclic peptide library: discovery of small-molecule ligands against human prolactin receptor

Bioorg Med Chem. 2009 Feb 1;17(3):1026-33. doi: 10.1016/j.bmc.2008.01.015. Epub 2008 Jan 13.

Abstract

Prolactin receptor is involved in normal lactation and reproduction; however, excessive prolactin levels can cause various reproductive disorders such as prolactinomas. Small-molecule antagonists against the human prolactin receptor (hPRLr) thus have potential clinical applications and may serve as useful molecular probes in biomedical research. In this work, we synthesized a large, support-bound cyclic peptide library (theoretical diversity of 1.2x10(7)) on 90-microm TentaGel beads and screened it against the extracellular domain of hPRLr. To facilitate hit identification, each TentaGel bead was spatially segregated into outer and inner layers, with a cyclic peptide displayed on the bead surface while the bead interior contained the corresponding linear peptide. The identity of a positive bead was revealed by sequencing the linear encoding peptide within the bead by partial Edman degradation/mass spectrometry. Screening of the library resulted in 20 hits, two of which were selected for further analysis and shown to bind to hPRLr with dissociation constants of 2-3 microM.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Amino Acid Sequence
  • Combinatorial Chemistry Techniques
  • Humans
  • Ligands
  • Microspheres
  • Peptide Library*
  • Peptides / chemical synthesis
  • Peptides / chemistry
  • Peptides, Cyclic / chemical synthesis*
  • Peptides, Cyclic / chemistry
  • Receptors, Prolactin / antagonists & inhibitors*
  • Receptors, Prolactin / metabolism
  • Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
  • Surface Plasmon Resonance

Substances

  • Ligands
  • Peptide Library
  • Peptides
  • Peptides, Cyclic
  • Receptors, Prolactin