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

doi:10.1016/j.bmc.2009.11.046

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 journal › Article › peer-review

31 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 language	English (US)
Pages (from-to)	809-821
Number of pages	13
Journal	Bioorganic and Medicinal Chemistry
Volume	18
Issue number	2
DOIs	https://doi.org/10.1016/j.bmc.2009.11.046
State	Published - Jan 15 2010
Externally published	Yes

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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10.1016/j.bmc.2009.11.046

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Kim, H. Y., Sohn, J., Wijewickrama, G. T., Edirisinghe, P., Gherezghiher, T., Hemachandra, M., Lu, P. Y., Chandrasena, R. E., Molloy, M. E., Tonetti, D. A., & Thatcher, G. R. J. (2010). Click synthesis of estradiol-cyclodextrin conjugates as cell compartment selective estrogens. Bioorganic and Medicinal Chemistry, 18(2), 809-821. https://doi.org/10.1016/j.bmc.2009.11.046

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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 (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.",

keywords = "Bioconjugate, Cyclodextrin, Estrogen, Membrane, Nuclear receptor",

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T1 - Click synthesis of estradiol-cyclodextrin conjugates as cell compartment selective estrogens

AU - Kim, Hye Yeong

AU - Sohn, Johann

AU - Wijewickrama, Gihani T.

AU - Edirisinghe, Praneeth

AU - Gherezghiher, Teshome

AU - Hemachandra, Madhubani

AU - Lu, Pei Yi

AU - Chandrasena, R. Esala

AU - Molloy, Mary Ellen

AU - Tonetti, Debra A.

AU - Thatcher, Gregory R.J.

PY - 2010/1/15

Y1 - 2010/1/15

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AB - 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.

KW - Bioconjugate

KW - Cyclodextrin

KW - Estrogen

KW - Membrane

KW - Nuclear receptor

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JO - Bioorganic and Medicinal Chemistry

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IS - 2

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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