title: Click synthesis of estradiol-cyclodextrin conjugates as cell compartment selective estrogens.
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 (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.
authors.affiliation: Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, 833 S. Wood Street, Chicago, IL 60612, United States.
authors.forename: Hye-Yeong
authors.initials: HY
authors.lastname: Kim
authors.forename: Johann
authors.initials: J
authors.lastname: Sohn
authors.forename: Gihani T
authors.initials: GT
authors.lastname: Wijewickrama
authors.forename: Praneeth
authors.initials: P
authors.lastname: Edirisinghe
authors.forename: Teshome
authors.initials: T
authors.lastname: Gherezghiher
authors.forename: Madhubani
authors.initials: M
authors.lastname: Hemachandra
authors.forename: Pei-Yi
authors.initials: PY
authors.lastname: Lu
authors.forename: R Esala
authors.initials: RE
authors.lastname: Chandrasena
authors.forename: Mary Ellen
authors.initials: ME
authors.lastname: Molloy
authors.forename: Debra A
authors.initials: DA
authors.lastname: Tonetti
authors.forename: Gregory R J
authors.initials: GR
authors.lastname: Thatcher
mesh_terms: D002463:Cell Membrane Permeability; D002478:Cells, Cultured; D018360:Crystallography, X-Ray; D003505:Cyclodextrins / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D003593:Cytoplasm / Q000737:chemistry / Q000378:metabolism; D004958:Estradiol / Q000737:chemistry* / Q000378:metabolism; D004967:Estrogens / Q000737:chemistry* / Q000378:metabolism; D006801:Humans; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D003505:Cyclodextrins; D004967:Estrogens; D004958:Estradiol