The flavanolignan silybin and its hemisynthetic derivatives, a novel series of potential modulators of P-glycoprotein

Bioorg Med Chem Lett. 2000 Jan 17;10(2):157-60. doi: 10.1016/s0960-894x(99)00636-8.

Abstract

A new series of potential flavonoidic modulators of P-glycoprotein activity has been prepared. The flavanolignan silybin was first oxidised to dehydrosilybin and then C-alkylated with either prenyl or geranyl bromide. The resulting isoprenoid dehydrosilybins were shown to display high in vitro affinities for direct binding to P-glycoprotein, which ranged them among the best flavonoids ever tested.

MeSH terms

  • ATP Binding Cassette Transporter, Subfamily B, Member 1 / chemistry*
  • Drug Resistance, Multiple
  • Flavonoids / chemical synthesis*
  • Flavonols
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Plants, Medicinal
  • Protein Binding
  • Quercetin / analogs & derivatives
  • Quercetin / chemistry
  • Silybum marianum / chemistry
  • Silymarin / analogs & derivatives*

Substances

  • ATP Binding Cassette Transporter, Subfamily B, Member 1
  • Flavonoids
  • Flavonols
  • Silymarin
  • Quercetin
  • taxifolin