Dominican University of California
 

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Presentation or Panel Title

Synthesis of Isoflav-3-enes

Location

Guzman 112

Start Date

4-15-2016 2:00 PM

End Date

4-15-2016 2:15 PM

Department

Natural Sciences and Mathematics

Student Type

Undergraduate

Faculty Mentor

Maria Carranza, Ph.D.

Presentation Format

Oral Presentation

Abstract/Description

Synthesis of Isoflav-3-ene

Estrogen receptors (ERs) are members of the nuclear receptor (NR) superfamily of ligand regulated transcription factors. ERs mediate the physiological effects of both endogenous and synthetic estrogens in reproductive tissues, the brain, bone and cardiovascular system. Estrogen receptor alpha (ERα), known to be overexpressed in 70% of breast cancers, is well characterized as a mediator of cell proliferation. In breast cancer cells, ERα drives cell growth in the presence of estrogen. Endocrine therapy for breast cancer involves selective estrogen receptor modulators (SERMS) such as tamoxifen, an ERα antagonist which can compete to bind to estrogen. ERα is therefore an important drug target for breast cancer and related diseases. Isoflav-3-enes are one class of phytoestrogens, often referred to as “weak estrogens”, because of their estrogen-like structures. Phytoestrogens are primarily found in plants from the legume family, which includes soybeans, and other grains. The ability of isoflav-3-enes to bind to ERs, particularly ERα, makes them valuable lead structures in the search for possible treatments for breast cancer. Eryvarin H is an isoflav-3-ene initially discovered in 2003 in the root of Erythrina variegata, a member of the Leguminosae family. Eryvarin H has only been synthesized once by Koo and co-workers in 2013 via a 12 step synthesis and initial studies delineated its potential estrogenic properties. The purpose of the present study is to chemically synthesize and characterize Erivaryn H and its analogs (via an improved route) and to evaluate their biological effect on ERα.

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Apr 15th, 2:00 PM Apr 15th, 2:15 PM

Synthesis of Isoflav-3-enes

Guzman 112

Synthesis of Isoflav-3-ene

Estrogen receptors (ERs) are members of the nuclear receptor (NR) superfamily of ligand regulated transcription factors. ERs mediate the physiological effects of both endogenous and synthetic estrogens in reproductive tissues, the brain, bone and cardiovascular system. Estrogen receptor alpha (ERα), known to be overexpressed in 70% of breast cancers, is well characterized as a mediator of cell proliferation. In breast cancer cells, ERα drives cell growth in the presence of estrogen. Endocrine therapy for breast cancer involves selective estrogen receptor modulators (SERMS) such as tamoxifen, an ERα antagonist which can compete to bind to estrogen. ERα is therefore an important drug target for breast cancer and related diseases. Isoflav-3-enes are one class of phytoestrogens, often referred to as “weak estrogens”, because of their estrogen-like structures. Phytoestrogens are primarily found in plants from the legume family, which includes soybeans, and other grains. The ability of isoflav-3-enes to bind to ERs, particularly ERα, makes them valuable lead structures in the search for possible treatments for breast cancer. Eryvarin H is an isoflav-3-ene initially discovered in 2003 in the root of Erythrina variegata, a member of the Leguminosae family. Eryvarin H has only been synthesized once by Koo and co-workers in 2013 via a 12 step synthesis and initial studies delineated its potential estrogenic properties. The purpose of the present study is to chemically synthesize and characterize Erivaryn H and its analogs (via an improved route) and to evaluate their biological effect on ERα.