Fulvestrant-3 Boronic Acid (ZB716): An Orally Bioavailable Selective Estrogen Receptor Downregulator (SERD)

J Med Chem. 2016 Sep 8;59(17):8134-40. doi: 10.1021/acs.jmedchem.6b00753. Epub 2016 Aug 29.

Abstract

Orally bioavailable SERDs may offer greater systemic drug exposure, improved clinical efficacy, and more durable treatment outcome for patients with ER-positive endocrine-resistant breast cancer. We report the design and synthesis of a boronic acid modified fulvestrant (5, ZB716), which binds to ERα competitively (IC50 = 4.1 nM) and effectively downregulates ERα in both tamoxifen-sensitive and tamoxifen-resistant breast cancer cells. Furthermore, It has superior oral bioavailability (AUC = 2547.1 ng·h/mL) in mice, indicating its promising clinical utility as an oral SERD.

Publication types

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

MeSH terms

  • Administration, Oral
  • Animals
  • Biological Availability
  • Boronic Acids / chemical synthesis
  • Boronic Acids / chemistry*
  • Boronic Acids / pharmacology
  • Breast Neoplasms
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Down-Regulation
  • Drug Resistance, Neoplasm
  • Estrogen Receptor alpha / metabolism
  • Female
  • Mice, Inbred C57BL
  • Selective Estrogen Receptor Modulators / chemical synthesis
  • Selective Estrogen Receptor Modulators / chemistry*
  • Selective Estrogen Receptor Modulators / pharmacology
  • Signal Transduction
  • Stereoisomerism
  • Sterols / chemical synthesis
  • Sterols / chemistry*
  • Sterols / pharmacology
  • Tamoxifen / pharmacology

Substances

  • Boronic Acids
  • Estrogen Receptor alpha
  • Selective Estrogen Receptor Modulators
  • Sterols
  • ZB716 compound
  • Tamoxifen