Discovery of targeting ligands for breast cancer cells using the one-bead one-compound combinatorial method

J Med Chem. 2009 Jan 8;52(1):126-33. doi: 10.1021/jm801062d.

Abstract

Four "one-bead one-compound" (OBOC) combinatorial libraries were designed, synthesized, and screened against MDA-MB-231 breast cancer cells. A novel cyclic peptide 1 (LXY1) with high binding specificity to alpha3 integrin was identified. Molecular interactions between alpha3 integrin and 1 were characterized by using a series of K562 cells transfected with various mutant alpha3 integrins. Using analytic flow cytometry, the binding affinity (K(d)) of 1 to alpha3 integrin on MDA-MB-231 breast cancer cells was determined to be approximately 0.4 microM. Based on the established structure-activity relationship (SAR) study, two highly focused cyclic peptide libraries were further designed, synthesized, and screened against MDA-MB-231 breast cancer cells under stringent conditions. A novel cyclic peptide 2 (LXY3) with a high binding affinity (IC(50) = 57 nM) was identified. Moreover, the targeting efficiency and specificity of 2 to the breast adenocarcinoma tumors in mouse xenografts were further confirmed by in vivo and ex vivo near-infrared fluorescence optical imaging.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Animals
  • Biomimetic Materials / chemical synthesis
  • Biomimetic Materials / chemistry
  • Biomimetic Materials / metabolism
  • Biotinylation
  • Breast Neoplasms / metabolism*
  • Breast Neoplasms / pathology
  • Cell Line, Tumor
  • Combinatorial Chemistry Techniques*
  • Databases, Protein
  • Drug Design
  • Female
  • Humans
  • Integrin alpha3 / metabolism
  • Ligands
  • Magnetic Resonance Spectroscopy
  • Mice
  • Mice, Nude
  • Molecular Structure
  • Peptides / chemical synthesis
  • Peptides / chemistry
  • Peptides / metabolism
  • Structure-Activity Relationship
  • Substrate Specificity
  • Xenograft Model Antitumor Assays

Substances

  • Integrin alpha3
  • Ligands
  • Peptides