Literature DB >> 15685451

Endoxifen (4-hydroxy-N-desmethyl-tamoxifen) has anti-estrogenic effects in breast cancer cells with potency similar to 4-hydroxy-tamoxifen.

Young Chai Lim1, Zeruesenay Desta, David A Flockhart, Todd C Skaar.   

Abstract

PURPOSE: Tamoxifen is an effective drug for the treatment and prevention of breast cancer. It is extensively metabolized by the human cytochrome P450 enzyme system into several metabolites. Of these, 4-hydroxy-tamoxifen (4-OH-Tam) is an active metabolite, which has greater anti-estrogenic potency than the parent drug, tamoxifen. We reported recently that 4-hydroxy-N-desmethyl-tamoxifen (endoxifen) could also be active. The progesterone receptor (PR) messenger ribonucleic acid (mRNA) expression is commonly studied as a marker of estrogenic effect in breast cancer cells and PR levels in breast cancer patients are correlated with tamoxifen response. We, therefore, determined the effect of endoxifen and 4-OH-Tam on 17beta-estradiol (E2)-induced PR mRNA expression in an estrogen receptor-positive human breast cancer cell line.
METHODS: MCF-7 cells were treated with drugs for 24 h. The total ribonucleic acid (RNA) was harvested and transcribed into complementary deoxyribonucleic acids (cDNAs). The PR mRNA level was measured by using real-time reverse transcription polymerase chain reaction (RT-PCR). The PR expression data were normalized using a glyceraldehyde-3-phosphate dehydrogenase (GAPDH) gene expression. We measured the metabolite concentrations in the cultured media by high performance liquid chromatography (HPLC) to determine whether there was conversion of one metabolite to the other.
RESULTS: Consistent with previous reports, the dose-response of the E2 effect on the PR expression indicated an ED(50) value of approximately 60 pM and the maximum induction of PR mRNA was nearly ten-fold. When 10(-10) M E2 was used, induction of the PR expression was observed in 2 h and reached its maximum at 24 h. In this assay, neither endoxifen nor 4-OH-Tam alone produced any change in the PR mRNA expression. However, both endoxifen and 4-OH-Tam decreased the E2-induced PR expression with similar potency. There was very little interconversion between the two metabolites during the culture.
CONCLUSIONS: Since endoxifen is present at greater concentrations than 4-OH-Tam in human plasma of breast cancer patients receiving chronic tamoxifen, these results provide further evidence that endoxifen is as important as, or more important than, 4-OH-Tam to the anti-estrogenic action of tamoxifen.

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Year:  2005        PMID: 15685451     DOI: 10.1007/s00280-004-0926-7

Source DB:  PubMed          Journal:  Cancer Chemother Pharmacol        ISSN: 0344-5704            Impact factor:   3.333


  104 in total

1.  Pharmacogenomic diversity of tamoxifen metabolites and estrogen receptor genes in Hispanics and non-Hispanic whites with breast cancer.

Authors:  Leticia B A Rangel; Jodi L Taraba; Christopher R Frei; Lon Smith; Gladys Rodriguez; John G Kuhn
Journal:  Breast Cancer Res Treat       Date:  2014-11-14       Impact factor: 4.872

Review 2.  Uridine 5'-diphospho-glucuronosyltransferase genetic polymorphisms and response to cancer chemotherapy.

Authors:  Jacqueline Ramírez; Mark J Ratain; Federico Innocenti
Journal:  Future Oncol       Date:  2010-04       Impact factor: 3.404

3.  Endoxifen and other metabolites of tamoxifen inhibit human hydroxysteroid sulfotransferase 2A1 (hSULT2A1).

Authors:  Edwin J Squirewell; Xiaoyan Qin; Michael W Duffel
Journal:  Drug Metab Dispos       Date:  2014-08-25       Impact factor: 3.922

4.  Functional polymorphisms in UDP-glucuronosyl transferases and recurrence in tamoxifen-treated breast cancer survivors.

Authors:  Thomas P Ahern; Mariann Christensen; Deirdre P Cronin-Fenton; Kathryn L Lunetta; Håvard Søiland; Jennifer Gjerde; Jens Peter Garne; Carol L Rosenberg; Rebecca A Silliman; Henrik Toft Sørensen; Timothy L Lash; Stephen Hamilton-Dutoit
Journal:  Cancer Epidemiol Biomarkers Prev       Date:  2011-07-12       Impact factor: 4.254

5.  Germline pharmacogenetics of tamoxifen response: have we learned enough?

Authors:  Zeruesenay Desta; David A Flockhart
Journal:  J Clin Oncol       Date:  2007-11-20       Impact factor: 44.544

6.  A randomized phase II presurgical trial of transdermal 4-hydroxytamoxifen gel versus oral tamoxifen in women with ductal carcinoma in situ of the breast.

Authors:  Oukseub Lee; Katherine Page; David Ivancic; Irene Helenowski; Vamsi Parini; Megan E Sullivan; Julie A Margenthaler; Robert T Chatterton; Borko Jovanovic; Barbara K Dunn; Brandy M Heckman-Stoddard; Kathleen Foster; Miguel Muzzio; Julia Shklovskaya; Silvia Skripkauskas; Piotr Kulesza; David Green; Nora M Hansen; Kevin P Bethke; Jacqueline S Jeruss; Raymond Bergan; Seema A Khan
Journal:  Clin Cancer Res       Date:  2014-07-15       Impact factor: 12.531

Review 7.  Metabolism and transport of tamoxifen in relation to its effectiveness: new perspectives on an ongoing controversy.

Authors:  Deirdre P Cronin-Fenton; Per Damkier; Timothy L Lash
Journal:  Future Oncol       Date:  2014-01       Impact factor: 3.404

Review 8.  New insights into the metabolism of tamoxifen and its role in the treatment and prevention of breast cancer.

Authors:  V Craig Jordan
Journal:  Steroids       Date:  2007-07-27       Impact factor: 2.668

9.  Estrogen receptor genotypes, menopausal status, and the lipid effects of tamoxifen.

Authors:  N I Ntukidem; A T Nguyen; V Stearns; M Rehman; A Schott; T Skaar; Y Jin; P Blanche; L Li; S Lemler; J Hayden; R M Krauss; Z Desta; D A Flockhart; D F Hayes
Journal:  Clin Pharmacol Ther       Date:  2007-08-22       Impact factor: 6.875

10.  Regulation of aryl hydrocarbon receptor function by selective estrogen receptor modulators.

Authors:  Carolyn D DuSell; Erik R Nelson; Bryan M Wittmann; Jackie A Fretz; Dmitri Kazmin; Russell S Thomas; J Wesley Pike; Donald P McDonnell
Journal:  Mol Endocrinol       Date:  2009-11-09
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