Click synthesis of estradiol-cyclodextrin conjugates as cell compartment selective estrogens

Bioorg Med Chem. 2010 Jan 15;18(2):809-21. doi: 10.1016/j.bmc.2009.11.046. Epub 2009 Nov 27.


Cyclodextrin (CD) is a well known drug carrier and excipient for enhancing aqueous solubility. CDs themselves are anticipated to have low membrane permeability because of relatively high hydrophilicity and molecular weight. CD derivatization with 17-beta estradiol (E(2)) was explored extensively using a number of different click chemistries and the cell membrane permeability of synthetic CD-E(2) conjugate was explored by cell reporter assays and confocal fluorescence microscopy. In simile with reported dendrimer-E(2) conjugates, CD-E(2) was found to be a stable, extranuclear receptor selective estrogen that penetrated into the cytoplasm.

Publication types

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

MeSH terms

  • Cell Membrane Permeability
  • Cells, Cultured
  • Crystallography, X-Ray
  • Cyclodextrins / chemical synthesis
  • Cyclodextrins / chemistry*
  • Cyclodextrins / metabolism
  • Cytoplasm / chemistry
  • Cytoplasm / metabolism
  • Estradiol / chemistry*
  • Estradiol / metabolism
  • Estrogens / chemistry*
  • Estrogens / metabolism
  • Humans
  • Models, Molecular
  • Molecular Structure
  • Stereoisomerism


  • Cyclodextrins
  • Estrogens
  • Estradiol