Insight into estrogenicity of phytoestrogens using in silico simulation

Biochem Biophys Res Commun. 2009 Jan 30;379(1):139-44. doi: 10.1016/j.bbrc.2008.12.046. Epub 2008 Dec 25.


Phytoestrogens, including miroestrol and deoxymiroestrol, have the ability to act through competition with estrogen for binding to the estrogen receptor (ER). Here, we utilize manual ligand docking followed by molecular dynamics simulations and binding free energy calculations with the linear interaction energy method to predict the binding modes and the binding affinities of phytoestrogens on the ligand binding domain of ER (ERalpha-LBD). The calculations brought about the good correlation between the calculated binding free energy and the bioassays. Furthermore, consideration of Lennard-Jones and Coulomb interaction energies of miroestrol and deoxymiroestrol on ERalpha-LBD provided the information to develop the phytoestrogen derivatives as the preferred drug for ER positive breast cancer treatment.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry*
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Antineoplastic Agents, Phytogenic / therapeutic use
  • Breast Neoplasms / drug therapy
  • Computer Simulation
  • Coumarins / chemistry
  • Coumarins / pharmacology
  • Coumarins / therapeutic use
  • Drug Discovery / methods*
  • Entropy
  • Estrogen Receptor alpha / agonists*
  • Estrogen Receptor alpha / chemistry*
  • Humans
  • Models, Chemical
  • Molecular Structure
  • Phytoestrogens / chemistry*
  • Phytoestrogens / pharmacology
  • Phytoestrogens / therapeutic use
  • Static Electricity
  • Steroids / chemistry
  • Steroids / pharmacology
  • Steroids / therapeutic use
  • Thermodynamics


  • Antineoplastic Agents, Phytogenic
  • Coumarins
  • Estrogen Receptor alpha
  • Phytoestrogens
  • Steroids
  • deoxymiroestrol