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

Hye Yeong Kim, Johann Sohn, Gihani T. Wijewickrama, Praneeth Edirisinghe, Teshome Gherezghiher, Madhubani Hemachandra, Pei Yi Lu, R. Esala Chandrasena, Mary Ellen Molloy, Debra A. Tonetti, Gregory R.J. Thatcher

Research output: Contribution to journalArticlepeer-review

27 Scopus citations

Abstract

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 (E2) was explored extensively using a number of different click chemistries and the cell membrane permeability of synthetic CD-E2 conjugate was explored by cell reporter assays and confocal fluorescence microscopy. In simile with reported dendrimer-E2 conjugates, CD-E2 was found to be a stable, extranuclear receptor selective estrogen that penetrated into the cytoplasm.

Original languageEnglish (US)
Pages (from-to)809-821
Number of pages13
JournalBioorganic and Medicinal Chemistry
Volume18
Issue number2
DOIs
StatePublished - Jan 15 2010
Externally publishedYes

Keywords

  • Bioconjugate
  • Cyclodextrin
  • Estrogen
  • Membrane
  • Nuclear receptor

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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