4-hydroxytamoxifen (BioDeep_00000409843)
代谢物信息卡片
(E/Z)-4-hydroxy Tamoxifen
化学式: C26H29NO2 (387.2198174)
中文名称: 4-羟基三苯氧胺
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CCC(=C(C1=CC=C(O)C=C1)C1=CC=C(OCCN(C)C)C=C1)C1=CC=CC=C1
InChI: InChI=1S/C26H29NO2/c1-4-25(20-8-6-5-7-9-20)26(21-10-14-23(28)15-11-21)22-12-16-24(17-13-22)29-19-18-27(2)3/h5-17,28H,4,18-19H2,1-3H3
描述信息
CONFIDENCE standard compound; INTERNAL_ID 2716
同义名列表
2 个代谢物同义名
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
0 个相关的物种来源信息
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：
- PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。
文献列表
- Kazuki Nishimoto, Nobuyuki Okahashi, Masaharu Maruyama, Yoshihiro Izumi, Kohta Nakatani, Yuki Ito, Junko Iida, Takeshi Bamba, Fumio Matsuda. Lipidome and metabolome analyses reveal metabolic alterations associated with MCF-7 apoptosis upon 4-hydroxytamoxifen treatment.
Scientific reports.
2023 10; 13(1):18549. doi:
10.1038/s41598-023-45764-2. [PMID: 37899460] - Alisia K Dalhäusser, Oliver G Rössler, Gerald Thiel. Regulation of c-Fos gene transcription by stimulus-responsive protein kinases.
Gene.
2022 May; 821(?):146284. doi:
10.1016/j.gene.2022.146284. [PMID: 35143939] - Stefan Rehnmark, Ivan Shabo, Håkan Randahl, Yvonne Wengström, Per Rydberg, Elham Hedayati. Preliminary results using a kit to measure tamoxifen and metabolites concentrations in capillary blood samples from women with breast cancer.
Scientific reports.
2022 01; 12(1):1643. doi:
10.1038/s41598-022-05443-0. [PMID: 35102224] - Yung-Yi Cheng, Elise T Tuzo, Jeffrey W Dalley, Tung-Hu Tsai. Dose-dependent effects of Hedyotis diffusa extract on the pharmacokinetics of tamoxifen, 4-hydroxytamoxifen, and N-desmethyltamoxifen.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie.
2022 Jan; 145(?):112466. doi:
10.1016/j.biopha.2021.112466. [PMID: 34839255] - Julia Ortiz, Francisco J Aranda, José A Teruel, Antonio Ortiz. Dissimilar action of tamoxifen and 4-hydroxytamoxifen on phosphatidylcholine model membranes.
Biophysical chemistry.
2021 11; 278(?):106681. doi:
10.1016/j.bpc.2021.106681. [PMID: 34530285] - Maria Lucia Souza Siqueira, Sara Michelli Vieira Andrade, José Luiz Fernandes Vieira, Marta Chagas Monteiro. A preliminary study on the association of tamoxifen, endoxifen, and 4-hydroxytamoxifen with blood lipids in patients with breast cancer.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie.
2021 Oct; 142(?):111972. doi:
10.1016/j.biopha.2021.111972. [PMID: 34391185] - Yan Cao, Rongyang Li, Ming Shen, Chengyu Li, Yan Zou, Qiang Jiang, Shuo Liu, Chunwan Lu, Honglin Li, Honglin Liu, Yafei Cai. DDRGK1, a crucial player of ufmylation system, is indispensable for autophagic degradation by regulating lysosomal function.
Cell death & disease.
2021 04; 12(5):416. doi:
10.1038/s41419-021-03694-9. [PMID: 33879777] - Andre Heinen, Stefanie Gödecke, Ulrich Flögel, Dominika Miklos, Katharina Bottermann, André Spychala, Axel Gödecke. 4-hydroxytamoxifen does not deteriorate cardiac function in cardiomyocyte-specific MerCreMer transgenic mice.
Basic research in cardiology.
2021 02; 116(1):8. doi:
10.1007/s00395-020-00841-9. [PMID: 33544211] - João P Ximenez, Vera L Lanchote, Marcelo A Bello, Fernanda H S Iocken, Renata C M Obadia, Valéria P de Sousa, Guilherme Suarez-Kurtz. Post-marketing assessment of generic tamoxifen in Brazilian breast cancer patients.
Basic & clinical pharmacology & toxicology.
2020 May; 126(5):432-436. doi:
10.1111/bcpt.13368. [PMID: 31758654] - Aliyah Almomen, Hadir M Maher, Nourah Z Alzoman, Shereen M Shehata, Shorog M Al-Taweel, Ashwaq A Alanazi. Development and validation of UPLC-MS/MS method for studying the pharmacokinetic interaction of dasabuvir and tamoxifen, 4-hydroxytamoxifen in Wistar rats.
Scientific reports.
2020 02; 10(1):3521. doi:
10.1038/s41598-020-60613-2. [PMID: 32103133] - João Paulo Bianchi Ximenez, Jurandyr Moreira de Andrade, Maria Paula Marques, Eduardo Barbosa Coelho, Guilherme Suarez-Kurtz, Vera Lucia Lanchote. Hormonal status affects plasma exposure of tamoxifen and its main metabolites in tamoxifen-treated breast cancer patients.
BMC pharmacology & toxicology.
2019 12; 20(Suppl 1):81. doi:
10.1186/s40360-019-0358-y. [PMID: 31852530] - Ta-Chung Chao, Wen-Chi Pan, Yi-Fang Tsai, Yueh-Ching Chou, Yu-Rong Liu, Sheng-Fan Wang, Ying-Jen Chen, Pavel Souček, Yune-Fang Ueng. Plasma endoxifen and 4-hydroxytamoxifen levels in CYP2D6(C100T) carrying breast cancer patients and association with serum cholesterol.
Toxicology and applied pharmacology.
2019 09; 378(?):114619. doi:
10.1016/j.taap.2019.114619. [PMID: 31195002] - Priya Hari, Fraser R Millar, Nuria Tarrats, Jodie Birch, Andrea Quintanilla, Curtis J Rink, Irene Fernández-Duran, Morwenna Muir, Andrew J Finch, Valerie G Brunton, João F Passos, Jennifer P Morton, Luke Boulter, Juan Carlos Acosta. The innate immune sensor Toll-like receptor 2 controls the senescence-associated secretory phenotype.
Science advances.
2019 06; 5(6):eaaw0254. doi:
10.1126/sciadv.aaw0254. [PMID: 31183403] - Usha Sundralingam, Tahir Mehmood Khan, Sumita Elendran, Saravanan Muniyandy, Uma D Palanisamy. Review: Patient-controlled transdermal 4-hydroxytamoxifen (4-OHT) vs. oral tamoxifen: A systematic review and meta analysis.
Pakistan journal of pharmaceutical sciences.
2019 May; 32(3):1121-1128. doi:
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Breast cancer research and treatment.
2018 Oct; 171(3):701-708. doi:
10.1007/s10549-018-4876-x. [PMID: 29980881] - J-Pablo Salvador, Ester Vila-Roca, Núria Monfort, Rosa Ventura, M-Pilar Marco. New approach based on immunochemical techniques for monitoring of selective estrogen receptor modulators (SERMs) in human urine.
Journal of pharmaceutical and biomedical analysis.
2018 Jul; 156(?):147-152. doi:
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Integrative cancer therapies.
2018 03; 17(1):99-105. doi:
10.1177/1534735416684014. [PMID: 28008779] - Lesley J Mills, W Matthew Henderson, Saro Jayaraman, Ruth E Gutjahr-Gobell, Gerald E Zaroogian, Doranne Borsay Horowitz, Susan C Laws. Approaches for predicting effects of unintended environmental exposure to an endocrine active pharmaceutical, tamoxifen.
Environmental toxicology.
2016 Dec; 31(12):1834-1850. doi:
10.1002/tox.22184. [PMID: 26303313] - Natalia Sutiman, Joanne Siok Liu Lim, Thomas E Muerdter, Onkar Singh, Yin Bun Cheung, Raymond Chee Hui Ng, Yoon Sim Yap, Nan Soon Wong, Peter Cher Siang Ang, Rebecca Dent, Werner Schroth, Matthias Schwab, Chiea Chuen Khor, Balram Chowbay. Pharmacogenetics of UGT1A4, UGT2B7 and UGT2B15 and Their Influence on Tamoxifen Disposition in Asian Breast Cancer Patients.
Clinical pharmacokinetics.
2016 10; 55(10):1239-1250. doi:
10.1007/s40262-016-0402-7. [PMID: 27098059] - Wei Xiong, Jia-jia Zhao, Ling Wang, Xue-hua Jiang, Xiao-qiu Tao. [Advances in the research of pharmacogenomics of tamoxifen].
Yao xue xue bao = Acta pharmaceutica Sinica.
2016 09; 51(9):1356-67. doi:
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Therapeutic drug monitoring.
2016 Apr; 38(2):239-45. doi:
10.1097/ftd.0000000000000257. [PMID: 26485084] - Rishabh Kala, Trygve O Tollefsbol. A Novel Combinatorial Epigenetic Therapy Using Resveratrol and Pterostilbene for Restoring Estrogen Receptor-α (ERα) Expression in ERα-Negative Breast Cancer Cells.
PloS one.
2016; 11(5):e0155057. doi:
10.1371/journal.pone.0155057. [PMID: 27159275] - Oukseub Lee, David Ivancic, Subhashini Allu, Ali Shidfar, Kara Kenney, Irene Helenowski, Megan E Sullivan, Miguel Muzzio, Denise Scholtens, Robert T Chatterton, Kevin P Bethke, Nora M Hansen, Seema A Khan. Local transdermal therapy to the breast for breast cancer prevention and DCIS therapy: preclinical and clinical evaluation.
Cancer chemotherapy and pharmacology.
2015 Dec; 76(6):1235-46. doi:
10.1007/s00280-015-2848-y. [PMID: 26560487] - Marina V Antunes, Tatiana Aparecida da Fontoura Timm, Vanessa de Oliveira, Dilana E Staudt, Suziane Raymundo, Gustavo Gössling, Jorge V Biazús, José A Cavalheiro, Daniela D Rosa, Pierre Wallemacq, Vincent Haufroid, Rafael Linden, Gilberto Schwartsmann. Influence of CYP2D6 and CYP3A4 Phenotypes, Drug Interactions, and Vitamin D Status on Tamoxifen Biotransformation.
Therapeutic drug monitoring.
2015 Dec; 37(6):733-44. doi:
10.1097/ftd.0000000000000212. [PMID: 25853922] - Noelia Negreira, Jorge Regueiro, Miren López de Alda, Damià Barceló. Transformation of tamoxifen and its major metabolites during water chlorination: Identification and in silico toxicity assessment of their disinfection byproducts.
Water research.
2015 Nov; 85(?):199-207. doi:
10.1016/j.watres.2015.08.036. [PMID: 26320721] - Kanumuri Siva Rama Raju, Isha Taneja, Guru Raghavendra Valicherla, Murali Krishna Challagundla, Mamunur Rashid, Anees Ahmed Syed, Jiaur Rahman Gayen, Sheelendra Pratap Singh, Muhammad Wahajuddin. No effect on pharmacokinetics of tamoxifen and 4-hydroxytamoxifen by multiple doses of red clover capsule in rats.
Scientific reports.
2015 Nov; 5(?):16126. doi:
10.1038/srep16126. [PMID: 26530625] - Qiu Zhong, Changde Zhang, Qiang Zhang, Lucio Miele, Shilong Zheng, Guangdi Wang. Boronic prodrug of 4-hydroxytamoxifen is more efficacious than tamoxifen with enhanced bioavailability independent of CYP2D6 status.
BMC cancer.
2015 Sep; 15(?):625. doi:
10.1186/s12885-015-1621-2. [PMID: 26354796] - Samy A F Morad, Myles C Cabot. Tamoxifen regulation of sphingolipid metabolism--Therapeutic implications.
Biochimica et biophysica acta.
2015 Sep; 1851(9):1134-45. doi:
10.1016/j.bbalip.2015.05.001. [PMID: 25964209] - Ying Hui, Lijun Luo, Lingtian Zhang, Katsuhisa Kurogi, Chunyang Zhou, Yoichi Sakakibara, Masahito Suiko, Ming-Cheh Liu. Sulfation of afimoxifene, endoxifen, raloxifene, and fulvestrant by the human cytosolic sulfotransferases (SULTs): A systematic analysis.
Journal of pharmacological sciences.
2015 Jul; 128(3):144-9. doi:
10.1016/j.jphs.2015.06.004. [PMID: 26169578] - Marina Venzon Antunes, Suziane Raymundo, Vanessa de Oliveira, Dilana Elisabeth Staudt, Gustavo Gössling, Giovana Piva Peteffi, Jorge Villanova Biazús, José Antônio Cavalheiro, Marie Tre-Hardy, Arnaud Capron, Vincent Haufroid, Pierre Wallemacq, Gilberto Schwartsmann, Rafael Linden. Ultra-high performance liquid chromatography tandem mass spectrometric method for the determination of tamoxifen, N-desmethyltamoxifen, 4-hydroxytamoxifen and endoxifen in dried blood spots--development, validation and clinical application during breast cancer adjuvant therapy.
Talanta.
2015 Jan; 132(?):775-84. doi:
10.1016/j.talanta.2014.10.040. [PMID: 25476377] - Juan Peris-Vicente, Enrique Ochoa-Aranda, Devasish Bose, Josep Esteve-Romero. Determination of tamoxifen and its main metabolites in plasma samples from breast cancer patients by micellar liquid chromatography.
Talanta.
2015 Jan; 131(?):535-40. doi:
10.1016/j.talanta.2014.07.093. [PMID: 25281137] - Marina Venzon Antunes, Vanessa de Oliveira, Suziane Raymundo, Dilana Elisabeth Staudt, Gustavo Gössling, Jorge Villanova Biazús, José Antônio Cavalheiro, Daniela Dornelles Rosa, Geneviève Mathy, Pierre Wallemacq, Rafael Linden, Gilberto Schwartsmann, Vincent Haufroid. CYP3A4*22 is related to increased plasma levels of 4-hydroxytamoxifen and partially compensates for reduced CYP2D6 activation of tamoxifen.
Pharmacogenomics.
2015; 16(6):601-17. doi:
10.2217/pgs.15.13. [PMID: 25893704] - Brandie N Radde, Margarita M Ivanova, Huy Xuan Mai, Joshua K Salabei, Bradford G Hill, Carolyn M Klinge. Bioenergetic differences between MCF-7 and T47D breast cancer cells and their regulation by oestradiol and tamoxifen.
The Biochemical journal.
2015 Jan; 465(1):49-61. doi:
10.1042/bj20131608. [PMID: 25279503] - Joel M Reid, Matthew P Goetz, Sarah A Buhrow, Chad Walden, Stephanie L Safgren, Mary J Kuffel, Kathryn E Reinicke, Vera Suman, Paul Haluska, Xiaonan Hou, Matthew M Ames. Pharmacokinetics of endoxifen and tamoxifen in female mice: implications for comparative in vivo activity studies.
Cancer chemotherapy and pharmacology.
2014 Dec; 74(6):1271-8. doi:
10.1007/s00280-014-2605-7. [PMID: 25318936] - Philipp Y Maximov, Russell E McDaniel, Daphne J Fernandes, Valeriy R Korostyshevskiy, Puspanjali Bhatta, Thomas E Mürdter, David A Flockhart, V Craig Jordan. Simulation with cells in vitro of tamoxifen treatment in premenopausal breast cancer patients with different CYP2D6 genotypes.
British journal of pharmacology.
2014 Dec; 171(24):5624-35. doi:
10.1111/bph.12864. [PMID: 25073551] - Leticia B A Rangel, Jodi L Taraba, Christopher R Frei, Lon Smith, Gladys Rodriguez, John G Kuhn. Pharmacogenomic diversity of tamoxifen metabolites and estrogen receptor genes in Hispanics and non-Hispanic whites with breast cancer.
Breast cancer research and treatment.
2014 Dec; 148(3):571-80. doi:
10.1007/s10549-014-3191-4. [PMID: 25395315] - Cécile Arellano, Ben Allal, Anwar Goubaa, Henri Roché, Etienne Chatelut. An UPLC-MS/MS method for separation and accurate quantification of tamoxifen and its metabolites isomers.
Journal of pharmaceutical and biomedical analysis.
2014 Nov; 100(?):254-261. doi:
10.1016/j.jpba.2014.07.033. [PMID: 25173109] - Alice I Nichols, Shannon Lubaczewski, Yali Liang, Kyle Matschke, Gabriel Braley, Tanya Ramey. Open-label, 2-period sequential drug interaction study to evaluate the effect of a 100-mg dose of desvenlafaxine on the pharmacokinetics of tamoxifen when coadministered in healthy postmenopausal female subjects.
International journal of clinical pharmacology and therapeutics.
2014 10; 52(10):830-41. doi:
10.5414/cp201958. [PMID: 25138680] - 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. A randomized phase II presurgical trial of transdermal 4-hydroxytamoxifen gel versus oral tamoxifen in women with ductal carcinoma in situ of the breast.
Clinical cancer research : an official journal of the American Association for Cancer Research.
2014 Jul; 20(14):3672-82. doi:
10.1158/1078-0432.ccr-13-3045. [PMID: 25028506] - Philipp Y Maximov, Daphne J Fernandes, Russell E McDaniel, Cynthia B Myers, Ramona F Curpan, V Craig Jordan. Influence of the length and positioning of the antiestrogenic side chain of endoxifen and 4-hydroxytamoxifen on gene activation and growth of estrogen receptor positive cancer cells.
Journal of medicinal chemistry.
2014 Jun; 57(11):4569-83. doi:
10.1021/jm500569h. [PMID: 24805199] - Yong Liu, Yizhou He, Aiwen Jin, Andrey P Tikunov, Lishi Zhou, Laura A Tollini, Patrick Leslie, Tae-Hyung Kim, Lei O Li, Rosalind A Coleman, Zhennan Gu, Yong Q Chen, Jeffrey M Macdonald, Lee M Graves, Yanping Zhang. Ribosomal protein-Mdm2-p53 pathway coordinates nutrient stress with lipid metabolism by regulating MCD and promoting fatty acid oxidation.
Proceedings of the National Academy of Sciences of the United States of America.
2014 Jun; 111(23):E2414-22. doi:
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Fitoterapia.
2014 Apr; 94(?):62-9. doi:
10.1016/j.fitote.2014.01.027. [PMID: 24508860] - Anne-Laure Lainé, Eric Adriaenssens, Anne Vessières, Gérard Jaouen, Cyril Corbet, Emilie Desruelles, Pascal Pigeon, Robert-Alain Toillon, Catherine Passirani. The in vivo performance of ferrocenyl tamoxifen lipid nanocapsules in xenografted triple negative breast cancer.
Biomaterials.
2013 Sep; 34(28):6949-56. doi:
10.1016/j.biomaterials.2013.05.065. [PMID: 23777919] - Wei Lv, Jinzhong Liu, Deshun Lu, David A Flockhart, Mark Cushman. Synthesis of mixed (E,Z)-, (E)-, and (Z)-norendoxifen with dual aromatase inhibitory and estrogen receptor modulatory activities.
Journal of medicinal chemistry.
2013 Jun; 56(11):4611-8. doi:
10.1021/jm400364h. [PMID: 23731360] - Marina Venzon Antunes, Daniela Dornelles Rosa, Tamyris Dos Santos Viana, Huander Andreolla, Tiago Ozelame Fontanive, Rafael Linden. Sensitive HPLC-PDA determination of tamoxifen and its metabolites N-desmethyltamoxifen, 4-hydroxytamoxifen and endoxifen in human plasma.
Journal of pharmaceutical and biomedical analysis.
2013 Mar; 76(?):13-20. doi:
10.1016/j.jpba.2012.12.005. [PMID: 23291438] - Juhyun Kim, Christopher C Coss, Christina M Barrett, Michael L Mohler, Casey E Bohl, Chien-Ming Li, Yali He, Karen A Veverka, James T Dalton. Role and pharmacologic significance of cytochrome P-450 2D6 in oxidative metabolism of toremifene and tamoxifen.
International journal of cancer.
2013 Mar; 132(6):1475-85. doi:
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International journal of pharmaceutics.
2012 Oct; 436(1-2):574-81. doi:
10.1016/j.ijpharm.2012.07.045. [PMID: 22850290] - N G L Jager, H Rosing, S C Linn, J H M Schellens, J H Beijnen. Importance of highly selective LC-MS/MS analysis for the accurate quantification of tamoxifen and its metabolites: focus on endoxifen and 4-hydroxytamoxifen.
Breast cancer research and treatment.
2012 Jun; 133(2):793-8. doi:
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ACS medicinal chemistry letters.
2012 Feb; 3(4):268-272. doi:
10.1021/ml2002554. [PMID: 22611478] - Y A Cho, W Lee, J S Choi. Effects of curcumin on the pharmacokinetics of tamoxifen and its active metabolite, 4-hydroxytamoxifen, in rats: possible role of CYP3A4 and P-glycoprotein inhibition by curcumin.
Die Pharmazie.
2012 Feb; 67(2):124-30. doi:
NULL. [PMID: 22512082] - Sheelendra Pratap Singh, Wahajuddin, K S R Raju, Mushir M Ali, Kanchan Kohli, Girish Kumar Jain. Reduced bioavailability of tamoxifen and its metabolite 4-hydroxytamoxifen after oral administration with biochanin A (an isoflavone) in rats.
Phytotherapy research : PTR.
2012 Feb; 26(2):303-7. doi:
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Molecular endocrinology (Baltimore, Md.).
2011 Dec; 25(12):2029-40. doi:
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Archives of pharmacal research.
2011 Nov; 34(11):1965-72. doi:
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Atherosclerosis.
2011 Oct; 218(2):435-42. doi:
10.1016/j.atherosclerosis.2011.06.048. [PMID: 21820658] - Sheelendra Pratap Singh, Wahajuddin, Mushir M Ali, Kanchan Kohli, Girish Kumar Jain. Liquid chromatography-mass spectrometry method for the quantification of tamoxifen and its metabolite 4-hydroxytamoxifen in rat plasma: application to interaction study with biochanin A (an isoflavone).
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2011 Oct; 879(27):2845-51. doi:
10.1016/j.jchromb.2011.07.036. [PMID: 21890435] - P Bourassa, S Dubeau, Ghulam M Maharvi, Abdul H Fauq, T J Thomas, H A Tajmir-Riahi. Locating the binding sites of anticancer tamoxifen and its metabolites 4-hydroxytamoxifen and endoxifen on bovine serum albumin.
European journal of medicinal chemistry.
2011 Sep; 46(9):4344-53. doi:
10.1016/j.ejmech.2011.07.005. [PMID: 21777996] - Cheng Li, Sung-Cil Lim, Jin Kim, Jun-Shik Choi. Effects of myricetin, an anticancer compound, on the bioavailability and pharmacokinetics of tamoxifen and its main metabolite, 4-hydroxytamoxifen, in rats.
European journal of drug metabolism and pharmacokinetics.
2011 Sep; 36(3):175-82. doi:
10.1007/s13318-011-0036-y. [PMID: 21442417] - P Bourassa, S Dubeau, Ghulam M Maharvi, Abdul H Fauq, T J Thomas, H A Tajmir-Riahi. Binding of antitumor tamoxifen and its metabolites 4-hydroxytamoxifen and endoxifen to human serum albumin.
Biochimie.
2011 Jul; 93(7):1089-101. doi:
10.1016/j.biochi.2011.03.006. [PMID: 21439346] - Na Li, Weiwei Jiang, Kaifeng Rao, Mei Ma, Zijian Wang, Satyanarayanan Senthik Kumaran. Estrogen-related receptor gamma disruption of source water and drinking water treatment processes extracts.
Journal of environmental sciences (China).
2011; 23(2):301-6. doi:
10.1016/s1001-0742(10)60406-8. [PMID: 21517005] - Minji Kim, Lucy Erin O'Brien, Sang-Ho Kwon, Keith E Mostov. STAT1 is required for redifferentiation during Madin-Darby canine kidney tubulogenesis.
Molecular biology of the cell.
2010 Nov; 21(22):3926-33. doi:
10.1091/mbc.e10-02-0112. [PMID: 20861313] - Emily L Rickert, Sean Oriana, Cori Hartman-Frey, Xinghua Long, Timothy T Webb, Kenneth P Nephew, Ross V Weatherman. Synthesis and characterization of fluorescent 4-hydroxytamoxifen conjugates with unique antiestrogenic properties.
Bioconjugate chemistry.
2010 May; 21(5):903-10. doi:
10.1021/bc900461h. [PMID: 20420372] - Giorgia Urbinati, Davide Audisio, Véronique Marsaud, Vincent Plassat, Silvia Arpicco, Brigitte Sola, Elias Fattal, Jack-Michel Renoir. Therapeutic potential of new 4-hydroxy-tamoxifen-loaded pH-gradient liposomes in a multiple myeloma experimental model.
Pharmaceutical research.
2010 Feb; 27(2):327-39. doi:
10.1007/s11095-009-0023-z. [PMID: 20033476] - Cheul-Seong Kim, Sang-Jun Choi, Chi-Young Park, Cheng Li, Jun-Shik Choi. Effects of silybinin on the pharmacokinetics of tamoxifen and its active metabolite, 4-hydroxytamoxifen in rats.
Anticancer research.
2010 Jan; 30(1):79-85. doi:
NULL. [PMID: 20150620] - Sang-Chul Shin, Jun-Shik Choi. Effects of epigallocatechin gallate on the oral bioavailability and pharmacokinetics of tamoxifen and its main metabolite, 4-hydroxytamoxifen, in rats.
Anti-cancer drugs.
2009 Aug; 20(7):584-8. doi:
10.1097/cad.0b013e32832d6834. [PMID: 19491656] - Yukimasa Takeda, Xiaohui Liu, Miho Sumiyoshi, Ayami Matsushima, Miki Shimohigashi, Yasuyuki Shimohigashi. Placenta expressing the greatest quantity of bisphenol A receptor ERR{gamma} among the human reproductive tissues: Predominant expression of type-1 ERRgamma isoform.
Journal of biochemistry.
2009 Jul; 146(1):113-22. doi:
10.1093/jb/mvp049. [PMID: 19304792] - Marcelo F Montenegro, Lisandra R Pessa, Valéria A Gomes, Zeruesenay Desta, David A Flockhart, Jose E Tanus-Santos. Assessment of vascular effects of tamoxifen and its metabolites on the rat perfused hindquarter vascular bed.
Basic & clinical pharmacology & toxicology.
2009 May; 104(5):400-7. doi:
10.1111/j.1742-7843.2009.00377.x. [PMID: 19413660] - Deo Prakash Pandey, Rosamaria Lappano, Lidia Albanito, Antonio Madeo, Marcello Maggiolini, Didier Picard. Estrogenic GPR30 signalling induces proliferation and migration of breast cancer cells through CTGF.
The EMBO journal.
2009 Mar; 28(5):523-32. doi:
10.1038/emboj.2008.304. [PMID: 19153601] - Sarah A Scott, Paige E Selvy, Jason R Buck, Hyekyung P Cho, Tracy L Criswell, Ashley L Thomas, Michelle D Armstrong, Carlos L Arteaga, Craig W Lindsley, H Alex Brown. Design of isoform-selective phospholipase D inhibitors that modulate cancer cell invasiveness.
Nature chemical biology.
2009 Feb; 5(2):108-17. doi:
10.1038/nchembio.140. [PMID: 19136975] - Jun-Shik Choi, Keon Wook Kang. Enhanced tamoxifen bioavailability after oral administration of tamoxifen in rats pretreated with naringin.
Archives of pharmacal research.
2008 Dec; 31(12):1631-6. doi:
10.1007/s12272-001-2161-7. [PMID: 19099234] - Y Xu, Y Sun, L Yao, L Shi, Y Wu, T Ouyang, J Li, T Wang, Z Fan, T Fan, B Lin, L He, P Li, Y Xie. Association between CYP2D6 *10 genotype and survival of breast cancer patients receiving tamoxifen treatment.
Annals of oncology : official journal of the European Society for Medical Oncology.
2008 Aug; 19(8):1423-1429. doi:
10.1093/annonc/mdn155. [PMID: 18407954] - A Ushmorov, M D Hogarty, X Liu, H Knauss, K M Debatin, C Beltinger. N-myc augments death and attenuates protective effects of Bcl-2 in trophically stressed neuroblastoma cells.
Oncogene.
2008 May; 27(24):3424-34. doi:
10.1038/sj.onc.1211017. [PMID: 18193081] - Sang-Chul Shin, Yong-Ji Piao, Jun-Shik Choi. Effects of morin on the bioavailability of tamoxifen and its main metabolite, 4-hydroxytamoxifen, in rats.
In vivo (Athens, Greece).
2008 May; 22(3):391-5. doi:
NULL. [PMID: 18610753] - Yongji Piao, Sang-Chul Shin, Jun-Shik Choi. Effects of oral kaempferol on the pharmacokinetics of tamoxifen and one of its metabolites, 4-hydroxytamoxifen, after oral administration of tamoxifen to rats.
Biopharmaceutics & drug disposition.
2008 May; 29(4):245-9. doi:
10.1002/bdd.593. [PMID: 18338336] - Tohru Kimura, Maya Tomooka, Noriko Yamano, Kazushige Murayama, Shogo Matoba, Hiroki Umehara, Yoshiakira Kanai, Toru Nakano. AKT signaling promotes derivation of embryonic germ cells from primordial germ cells.
Development (Cambridge, England).
2008 Mar; 135(5):869-79. doi:
10.1242/dev.013474. [PMID: 18216173] - B Pinto, A Bertoli, C Noccioli, S Garritano, D Reali, L Pistelli. Estradiol-antagonistic activity of phenolic compounds from leguminous plants.
Phytotherapy research : PTR.
2008 Mar; 22(3):362-6. doi:
10.1002/ptr.2327. [PMID: 18167044] - Miriam B Buck, Janet K Coller, Thomas E Mürdter, Michel Eichelbaum, Cornelius Knabbe. TGFbeta2 and TbetaRII are valid molecular biomarkers for the antiproliferative effects of tamoxifen and tamoxifen metabolites in breast cancer cells.
Breast cancer research and treatment.
2008 Jan; 107(1):15-24. doi:
10.1007/s10549-007-9526-7. [PMID: 18043895] - J Gjerde, M Hauglid, H Breilid, S Lundgren, J E Varhaug, E R Kisanga, G Mellgren, V M Steen, E A Lien. Effects of CYP2D6 and SULT1A1 genotypes including SULT1A1 gene copy number on tamoxifen metabolism.
Annals of oncology : official journal of the European Society for Medical Oncology.
2008 Jan; 19(1):56-61. doi:
10.1093/annonc/mdm434. [PMID: 17947222] - Robert Mansel, Amit Goyal, Elisabeth Le Nestour, Valérie Masini-Etévé, Katharine O'Connell. A phase II trial of Afimoxifene (4-hydroxytamoxifen gel) for cyclical mastalgia in premenopausal women.
Breast cancer research and treatment.
2007 Dec; 106(3):389-97. doi:
10.1007/s10549-007-9507-x. [PMID: 17351746] - Caroline G Roberts, Ebru Gurisik, Trevor J Biden, Robert L Sutherland, Alison J Butt. Synergistic cytotoxicity between tamoxifen and the plant toxin persin in human breast cancer cells is dependent on Bim expression and mediated by modulation of ceramide metabolism.
Molecular cancer therapeutics.
2007 Oct; 6(10):2777-85. doi:
10.1158/1535-7163.mct-07-0374. [PMID: 17913853] - Kim Leblanc, Emilie Sexton, Sophie Parent, Geoffroy Bélanger, Marie-Claude Déry, Virginie Boucher, Eric Asselin. Effects of 4-hydroxytamoxifen, raloxifene and ICI 182 780 on survival of uterine cancer cell lines in the presence and absence of exogenous estrogens.
International journal of oncology.
2007 Feb; 30(2):477-87. doi:
. [PMID: 17203231] - Sonali Sonnylal, Christopher P Denton, Bing Zheng, Douglas R Keene, Ruming He, Henry P Adams, Carolyn S Vanpelt, Yong J Geng, Jenny M Deng, Richard R Behringer, Benoit de Crombrugghe. Postnatal induction of transforming growth factor beta signaling in fibroblasts of mice recapitulates clinical, histologic, and biochemical features of scleroderma.
Arthritis and rheumatism.
2007 Jan; 56(1):334-44. doi:
10.1002/art.22328. [PMID: 17195237] - Hua-Jun He, Tie-Nian Zhu, Yi Xie, Jinshui Fan, Sutapa Kole, Satya Saxena, Michel Bernier. Pyrrolidine dithiocarbamate inhibits interleukin-6 signaling through impaired STAT3 activation and association with transcriptional coactivators in hepatocytes.
The Journal of biological chemistry.
2006 Oct; 281(42):31369-79. doi:
10.1074/jbc.m603762200. [PMID: 16926159] - Young Chai Lim, Lang Li, Zeruesenay Desta, Qianqian Zhao, James M Rae, David A Flockhart, Todd C Skaar. Endoxifen, a secondary metabolite of tamoxifen, and 4-OH-tamoxifen induce similar changes in global gene expression patterns in MCF-7 breast cancer cells.
The Journal of pharmacology and experimental therapeutics.
2006 Aug; 318(2):503-12. doi:
10.1124/jpet.105.100511. [PMID: 16690721] - Jane L Limer, Alicia T Parkes, Valerie Speirs. Differential response to phytoestrogens in endocrine sensitive and resistant breast cancer cells in vitro.
International journal of cancer.
2006 Aug; 119(3):515-21. doi:
10.1002/ijc.21863. [PMID: 16506217] - Sang-Chul Shin, Jun-Shik Choi, Xiuguo Li. Enhanced bioavailability of tamoxifen after oral administration of tamoxifen with quercetin in rats.
International journal of pharmaceutics.
2006 Apr; 313(1-2):144-9. doi:
10.1016/j.ijpharm.2006.01.028. [PMID: 16516418] - Bo Zhao, Seiji Maruo, Andrew Cooper, Michael R Chase, Eric Johannsen, Elliott Kieff, Ellen Cahir-McFarland. RNAs induced by Epstein-Barr virus nuclear antigen 2 in lymphoblastoid cell lines.
Proceedings of the National Academy of Sciences of the United States of America.
2006 Feb; 103(6):1900-5. doi:
10.1073/pnas.0510612103. [PMID: 16446431] - Daniel R Croft, Michael F Olson. Conditional regulation of a ROCK-estrogen receptor fusion protein.
Methods in enzymology.
2006; 406(?):541-53. doi:
10.1016/s0076-6879(06)06042-3. [PMID: 16472686] - Elton Richard Kisanga, Gunnar Mellgren, Ernst A Lien. Excretion of hydroxylated metabolites of tamoxifen in human bile and urine.
Anticancer research.
2005 Nov; 25(6C):4487-92. doi:
. [PMID: 16334131] - Clara B S Lau, Tony C Y Ho, Terry W L Chan, Stephen C F Kim. Use of dong quai (Angelica sinensis) to treat peri- or postmenopausal symptoms in women with breast cancer: is it appropriate?.
Menopause (New York, N.Y.).
2005 Nov; 12(6):734-40. doi:
10.1097/01.gme.0000184419.65943.01. [PMID: 16278617] - Thomas Porstmann, Beatrice Griffiths, Yuen-Li Chung, Oona Delpuech, John R Griffiths, Julian Downward, Almut Schulze. PKB/Akt induces transcription of enzymes involved in cholesterol and fatty acid biosynthesis via activation of SREBP.
Oncogene.
2005 Sep; 24(43):6465-81. doi:
10.1038/sj.onc.1208802. [PMID: 16007182] - Jing Jin, James R Woodgett. Chronic activation of protein kinase Bbeta/Akt2 leads to multinucleation and cell fusion in human epithelial kidney cells: events associated with tumorigenesis.
Oncogene.
2005 Aug; 24(35):5459-70. doi:
10.1038/sj.onc.1208704. [PMID: 16007218] - J Gjerde, E R Kisanga, M Hauglid, P I Holm, G Mellgren, E A Lien. Identification and quantification of tamoxifen and four metabolites in serum by liquid chromatography-tandem mass spectrometry.
Journal of chromatography. A.
2005 Jul; 1082(1):6-14. doi:
10.1016/j.chroma.2005.01.004. [PMID: 16038189] - J Alejandro Arreguin-Arevalo, Terry M Nett. A nongenomic action of 17beta-estradiol as the mechanism underlying the acute suppression of secretion of luteinizing hormone.
Biology of reproduction.
2005 Jul; 73(1):115-22. doi:
10.1095/biolreprod.105.040329. [PMID: 15772257] - Philippe Rouanet, Gustavo Linares-Cruz, François Dravet, Sylvain Poujol, Sophie Gourgou, Joelle Simony-Lafontaine, Jean Grenier, Andrew Kramar, Jean Girault, Elisabeth Le Nestour, Thierry Maudelonde. Neoadjuvant percutaneous 4-hydroxytamoxifen decreases breast tumoral cell proliferation: a prospective controlled randomized study comparing three doses of 4-hydroxytamoxifen gel to oral tamoxifen.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology.
2005 May; 23(13):2980-7. doi:
10.1200/jco.2005.06.064. [PMID: 15860853] - Young Chai Lim, Zeruesenay Desta, David A Flockhart, Todd C Skaar. Endoxifen (4-hydroxy-N-desmethyl-tamoxifen) has anti-estrogenic effects in breast cancer cells with potency similar to 4-hydroxy-tamoxifen.
Cancer chemotherapy and pharmacology.
2005 May; 55(5):471-8. doi:
10.1007/s00280-004-0926-7. [PMID: 15685451] - Carolyn M Klinge, Kristy A Blankenship, Kelly E Risinger, Shephali Bhatnagar, Edouard L Noisin, Wasana K Sumanasekera, Lei Zhao, Darren M Brey, Robert S Keynton. Resveratrol and estradiol rapidly activate MAPK signaling through estrogen receptors alpha and beta in endothelial cells.
The Journal of biological chemistry.
2005 Mar; 280(9):7460-8. doi:
10.1074/jbc.m411565200. [PMID: 15615701] - Huihui Ye, Hyun-Jung Choi, Jerrod Poe, Thomas E Smithgall. Oligomerization is required for HIV-1 Nef-induced activation of the Src family protein-tyrosine kinase, Hck.
Biochemistry.
2004 Dec; 43(50):15775-84. doi:
10.1021/bi048712f. [PMID: 15595833] - Fabian Köhler, André Zimmermann, Martin Hager, Albrecht E Sippel. A genetic, non-transcriptional assay for nuclear receptor ligand binding in yeast.
Gene.
2004 Aug; 337(?):113-9. doi:
10.1016/j.gene.2004.04.018. [PMID: 15276207] - Paula I Moreira, José B Custódio, Catarina R Oliveira, Maria S Santos. Hydroxytamoxifen protects against oxidative stress in brain mitochondria.
Biochemical pharmacology.
2004 Jul; 68(1):195-204. doi:
10.1016/j.bcp.2004.03.019. [PMID: 15183131]