Click synthesis of estradiol-cyclodextrin conjugates as cell compartment selective estrogens.
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.
Kim
Hye-Yeong
HY
Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, 833 S. Wood Street, Chicago, IL 60612, United States.
Sohn
Johann
J
Wijewickrama
Gihani T
GT
Edirisinghe
Praneeth
P
Gherezghiher
Teshome
T
Hemachandra
Madhubani
M
Lu
Pei-Yi
PY
Chandrasena
R Esala
RE
Molloy
Mary Ellen
ME
Tonetti
Debra A
DA
Thatcher
Gregory R J
GR
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
D003505:Cyclodextrins; D004967:Estrogens; D004958:Estradiol