Diethylstilbestrol (BioDeep_00000398402)
Main id: BioDeep_00000002242
Secondary id: BioDeep_00000227695
natural product
代谢物信息卡片
Diethylstilbestrol (Stilbestrol)
化学式: C18H20O2 (268.146322)
中文名称: 己烯雌酚,顺式和反式异构体混合物, 己烯雌酚
谱图信息:
最多检出来源 Danio rerio(blood) 16.67%
分子结构信息
SMILES: C1(=CC=C(C=C1)/C(=C(/C2=CC=C(C=C2)O)CC)CC)O
InChI: InChI=1S/C18H20O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h5-12,19-20H,3-4H2,1-2H3/b18-17+
描述信息
G - Genito urinary system and sex hormones > G03 - Sex hormones and modulators of the genital system > G03C - Estrogens > G03CC - Estrogens, combinations with other drugs
G - Genito urinary system and sex hormones > G03 - Sex hormones and modulators of the genital system > G03C - Estrogens > G03CB - Synthetic estrogens, plain
L - Antineoplastic and immunomodulating agents > L02 - Endocrine therapy > L02A - Hormones and related agents > L02AA - Estrogens
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D004967 - Estrogens
C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C483 - Therapeutic Estrogen
D009676 - Noxae > D002273 - Carcinogens
CONFIDENCE standard compound; INTERNAL_ID 4237
CONFIDENCE standard compound; INTERNAL_ID 4161
同义名列表
数据库引用编号
24 个数据库交叉引用编号
- ChEBI: CHEBI:92795
- ChEBI: CHEBI:41922
- KEGG: C07620
- KEGGdrug: D00577
- KEGGdrug: D81873
- PubChem: 448537
- DrugBank: DB00255
- ChEMBL: CHEMBL411
- MeSH: Diethylstilbestrol
- CAS: 6898-97-1
- CAS: 56-53-1
- MoNA: UF423704
- MoNA: UF423703
- MoNA: UF423702
- MoNA: UF423701
- MoNA: CCMSLIB00000078320
- MoNA: UF416104
- MoNA: UF416103
- MoNA: UF416102
- MoNA: UF416101
- PubChem: 9822
- PDB-CCD: DES
- NIKKAJI: J2.801K
- RefMet: Diethylstilbestrol
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
- Shrishti Madhan, Rajib Dhar, Arikketh Devi. Plant-derived exosomes: a green approach for cancer drug delivery.
Journal of materials chemistry. B.
2024 Feb; 12(9):2236-2252. doi:
10.1039/d3tb02752j. [PMID: 38351750] - V Alampanos, A Kabir, K G Furton, V Samanidou. Rapid exposure monitoring of six bisphenols and diethylstilbestrol in human urine using fabric phase sorptive extraction followed by high performance liquid chromatography - photodiode array analysis.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2021 Jul; 1177(?):122760. doi:
10.1016/j.jchromb.2021.122760. [PMID: 34052754] - Ankur Kumar Tanwar, Neha Dhiman, Amit Kumar, Vikas Jaitak. Engagement of phytoestrogens in breast cancer suppression: Structural classification and mechanistic approach.
European journal of medicinal chemistry.
2021 Mar; 213(?):113037. doi:
10.1016/j.ejmech.2020.113037. [PMID: 33257172] - Alessio Ausili, Inés Rodríguez-González, Alejandro Torrecillas, José A Teruel, Juan C Gómez-Fernández. Diethylstilbestrol Modifies the Structure of Model Membranes and Is Localized Close to the First Carbons of the Fatty Acyl Chains.
Biomolecules.
2021 02; 11(2):. doi:
10.3390/biom11020220. [PMID: 33557377] - Li Zhang, Qiuxia Xu, Yao Li, Hui Zhao, Xingming Shi, Fu Peng, Chenghao Yu. Ameliorative Effects of Component Chinese Medicine From Curcumae Rhizoma and Sparganii Rhizoma, a Traditional Herb Pair, on Uterine Leiomyoma in a Rat Model.
Frontiers in public health.
2021; 9(?):674357. doi:
10.3389/fpubh.2021.674357. [PMID: 34123993] - Julia A Taylor, Maren Bell Jones, Cynthia L Besch-Williford, Ashley F Berendzen, William A Ricke, Frederick S Vom Saal. Interactive Effects of Perinatal BPA or DES and Adult Testosterone and Estradiol Exposure on Adult Urethral Obstruction and Bladder, Kidney, and Prostate Pathology in Male Mice.
International journal of molecular sciences.
2020 May; 21(11):. doi:
10.3390/ijms21113902. [PMID: 32486162] - Xingdong Yang, Yinbiao Wang, Chunmei Song, Xiaofei Hu, Fangyu Wang, Xianyin Zeng. Hapten Synthesis and the Development of an Ultrasensitive Indirect Competitive ELISA for the Determination of Diethylstilbestrol in Food Samples.
Scientific reports.
2020 02; 10(1):3270. doi:
10.1038/s41598-020-59112-1. [PMID: 32094434] - Nikki Brantley, Charles A Lessman. In vivo assessment of gonad status, secondary sex characteristics and spawning in transparent Casper zebrafish.
Mechanisms of development.
2019 12; 160(?):103582. doi:
10.1016/j.mod.2019.103582. [PMID: 31634535] - Dijana Topalović, Dragana Dekanski, Biljana Spremo-Potparević, Andrea Pirković, Sunčica Borozan, Vladan Bajić, Danilo Stojanović, Francesca Giampieri, Massimiliano Gasparrini, Lada Živković. Dry olive leaf extract attenuates DNA damage induced by estradiol and diethylstilbestrol in human peripheral blood cells in vitro.
Mutation research. Genetic toxicology and environmental mutagenesis.
2019 Sep; 845(?):402993. doi:
10.1016/j.mrgentox.2018.12.001. [PMID: 31561897] - Sachiyo Oikawa, Sachiyo Kobayashi, Shinichi Miyagawa, Taisen Iguchi, Tomomi Sato. Diethylstilbestrol Alters the Expression of Activins in the Neonatal Mouse Ovary In Vitro.
In vivo (Athens, Greece).
2019 Jul; 33(4):1095-1102. doi:
10.21873/invivo.11578. [PMID: 31280197] - Weifeng Mao, Yan Song, Haixia Sui, Pei Cao, Zhaoping Liu. Analysis of individual and combined estrogenic effects of bisphenol, nonylphenol and diethylstilbestrol in immature rats with mathematical models.
Environmental health and preventive medicine.
2019 May; 24(1):32. doi:
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Molecules (Basel, Switzerland).
2019 Apr; 24(8):. doi:
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Advances in clinical and experimental medicine : official organ Wroclaw Medical University.
2019 Jan; 28(1):45-50. doi:
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Biosensors & bioelectronics.
2018 Oct; 117(?):575-582. doi:
10.1016/j.bios.2018.06.050. [PMID: 30005376] - Hui Zhao, Yao Li, QiuXia Xu, Fu Peng, JinShuang Zhao, R Clinton Webb, Cheng Peng, ChengHao Yu. Establishment of a rat model for uterine leiomyomas based on Western and traditional Chinese medicine theories.
Brazilian journal of medical and biological research = Revista brasileira de pesquisas medicas e biologicas.
2018 Jul; 51(9):e7627. doi:
10.1590/1414-431x20187627. [PMID: 29972430] - Xue Dong, Guanhui Zhao, Li Liu, Xuan Li, Qin Wei, Wei Cao. Ultrasensitive competitive method-based electrochemiluminescence immunosensor for diethylstilbestrol detection based on Ru(bpy)32+ as luminophor encapsulated in metal-organic frameworks UiO-67.
Biosensors & bioelectronics.
2018 Jul; 110(?):201-206. doi:
10.1016/j.bios.2018.03.066. [PMID: 29625327] - Zhi-Hao Liu, Qi-Liang Chen, Qiang Chen, Fang Li, Ying-Wen Li. Diethylstilbestrol arrested spermatogenesis and somatic growth in the juveniles of yellow catfish (Pelteobagrus fulvidraco), a fish with sexual dimorphic growth.
Fish physiology and biochemistry.
2018 Jun; 44(3):789-803. doi:
10.1007/s10695-018-0469-1. [PMID: 29340879] - Ovokeroye Akpojevwe Abafe, Pumza M Gatyeni, Tlou Chokwe. Development and validation of a confirmatory method for the determination of stilbene estrogens in ostrich serum.
Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment.
2018 Mar; 35(3):458-466. doi:
10.1080/19440049.2017.1411617. [PMID: 29210606] - Yaqin Wang, Yingwen Li, Qiliang Chen, Zhihao Liu. Diethylstilbestrol impaired oogenesis of yellow catfish juveniles through disrupting hypothalamic-pituitary-gonadal axis and germ cell development.
Journal of applied toxicology : JAT.
2018 03; 38(3):308-317. doi:
10.1002/jat.3529. [PMID: 28960386] - Bo Zeng, Gui-Lan Chen, Eliana Garcia-Vaz, Sunil Bhandari, Nikoleta Daskoulidou, Lisa M Berglund, Hongni Jiang, Thomas Hallett, Lu-Ping Zhou, Li Huang, Zi-Hao Xu, Viji Nair, Robert G Nelson, Wenjun Ju, Matthias Kretzler, Stephen L Atkin, Maria F Gomez, Shang-Zhong Xu. ORAI channels are critical for receptor-mediated endocytosis of albumin.
Nature communications.
2017 12; 8(1):1920. doi:
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The Journal of steroid biochemistry and molecular biology.
2017 11; 174(?):265-275. doi:
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Archives of toxicology.
2017 Nov; 91(11):3469-3475. doi:
10.1007/s00204-017-2071-1. [PMID: 28975368] - Olena Shaliutina, Anna Shaliutina-Kolešová, Ievgen Lebeda, Marek Rodina, Ievgeniia Gazo. The in vitro effect of nonylphenol, propranolol, and diethylstilbestrol on quality parameters and oxidative stress in sterlet (Acipenser ruthenus) spermatozoa.
Toxicology in vitro : an international journal published in association with BIBRA.
2017 Sep; 43(?):9-15. doi:
10.1016/j.tiv.2017.05.006. [PMID: 28533019] - Yoshitaka Imamichi, Toshio Sekiguchi, Takeshi Kitano, Takashi Kajitani, Reiko Okada, Yoshihiko Inaoka, Kaoru Miyamoto, Junsuke Uwada, Satoru Takahashi, Takahiro Nemoto, Asuka Mano, Md Rafiqul Islam Khan, Md Tariqul Islam, Koh-Ichi Yuhki, Hitoshi Kashiwagi, Fumitaka Ushikubi, Nobuo Suzuki, Takanobu Taniguchi, Takashi Yazawa. Diethylstilbestrol administration inhibits theca cell androgen and granulosa cell estrogen production in immature rat ovary.
Scientific reports.
2017 08; 7(1):8374. doi:
10.1038/s41598-017-08780-7. [PMID: 28827713] - Freddy O Agoreyo, B Rita Ohimai, Magdalene I Omigie. Effect of Solanum Nigrun on Uterus of Non-gravid Rats.
Ethiopian journal of health sciences.
2017 May; 27(3):239-244. doi:
10.4314/ejhs.v27i3.5. [PMID: 29217922] - Pan Yin, Ying-Wen Li, Qi-Liang Chen, Zhi-Hao Liu. Diethylstilbestrol, flutamide and their combination impaired the spermatogenesis of male adult zebrafish through disrupting HPG axis, meiosis and apoptosis.
Aquatic toxicology (Amsterdam, Netherlands).
2017 Apr; 185(?):129-137. doi:
10.1016/j.aquatox.2017.02.013. [PMID: 28213303] - Dai Zhang, Lifang Zhou, Yajing Lei, Zhan Zhou, Jie Zhou, Shuqing Chen. Investigation of diethylstilbestrol residue level in human urine samples by a specific monoclonal antibody.
Environmental science and pollution research international.
2017 Mar; 24(8):7042-7050. doi:
10.1007/s11356-017-8405-y. [PMID: 28092005] - Qian-Xing Zou, Zhen Peng, Qing Zhao, Hou-Yang Chen, Yi-Min Cheng, Qing Liu, Yuan-Qiao He, Shi-Qi Weng, Hua-Feng Wang, Tao Wang, Li-Ping Zheng, Tao Luo. Diethylstilbestrol activates CatSper and disturbs progesterone actions in human spermatozoa.
Human reproduction (Oxford, England).
2017 02; 32(2):290-298. doi:
10.1093/humrep/dew332. [PMID: 28031325] - V Plesinac-Karapandzic, S Stojanovic Rundic, R Jankovic, M Nadrljanski, Z Milovanovic, A Tomasevic, N Perisie Jeremic. Non-diethylstilbestrol exposed vaginal adenocarcinoma in young patients associated with unilateral renal agenesis: two case reports and literature review.
European journal of gynaecological oncology.
2017; 38(1):157-161. doi:
. [PMID: 29767889] - Liangliang Zhu, Ling Xiao, Wenjuan Li, Yuan Zhang, Wenwen Han, Yu Zhu, Guangbo Ge, Ling Yang. Human UDP-Glucuronosyltransferases 1A1, 1A3, 1A9, 2B4 and 2B7 are Inhibited by Diethylstilbestrol.
Basic & clinical pharmacology & toxicology.
2016 Nov; 119(5):505-511. doi:
10.1111/bcpt.12618. [PMID: 27176228] - Giorgio Biasiotto, Isabella Zanella, Alice Masserdotti, Roberta Pedrazzani, Matteo Papa, Luigi Caimi, Diego Di Lorenzo. Municipal wastewater affects adipose deposition in male mice and increases 3T3-L1 cell differentiation.
Toxicology and applied pharmacology.
2016 Apr; 297(?):32-40. doi:
10.1016/j.taap.2016.02.023. [PMID: 26944108] - Satoko Haeno, Naoyuki Maeda, Kousuke Yamaguchi, Michiko Sato, Aika Uto, Hiroshi Yokota. Adrenal steroidogenesis disruption caused by HDL/cholesterol suppression in diethylstilbestrol-treated adult male rat.
Endocrine.
2016 Apr; 52(1):148-56. doi:
10.1007/s12020-015-0732-5. [PMID: 26349937] - C Yang, W Lim, H Bae, G Song. Aquaporin 3 is regulated by estrogen in the chicken oviduct and is involved in progression of epithelial cell-derived ovarian carcinomas.
Domestic animal endocrinology.
2016 Apr; 55(?):97-106. doi:
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Toxicology and applied pharmacology.
2016 Apr; 296(?):73-84. doi:
10.1016/j.taap.2016.02.001. [PMID: 26853319] - Onat Kadioglu, Yujie Fu, Benjamin Wiench, Yuangang Zu, Thomas Efferth. Synthetic cajanin stilbene acid derivatives inhibit c-MYC in breast cancer cells.
Archives of toxicology.
2016 Mar; 90(3):575-88. doi:
10.1007/s00204-015-1480-2. [PMID: 25716159] - Rachel G Felton, Cynthia C Steiner, Barbara S Durrant, Duane H Keisler, Matthew R Milnes, Christopher W Tubbs. Identification of California Condor Estrogen Receptors 1 and 2 and Their Activation by Endocrine Disrupting Chemicals.
Endocrinology.
2015 Dec; 156(12):4448-57. doi:
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Talanta.
2015 Nov; 144(?):445-50. doi:
10.1016/j.talanta.2015.06.070. [PMID: 26452846] - Bo-wen Weng, Si-chuan Hou, Hai Zhu, Luo Xu, Xiao Luan, Hai-yan Qi, Wei-min Wang, Wei Liu, Li-jiang Sun. [Expression of nNOS and ultrastructural changes in the penile tissue of rats with prolactinoma-induced erectile dysfunction].
Zhonghua nan ke xue = National journal of andrology.
2015 Oct; 21(10):871-6. doi:
. [PMID: 26665672] - J Jeong, H Bae, W Lim, F W Bazer, G Song. Diethylstilbestrol regulates expression of avian apolipoprotein D during regression and recrudescence of the oviduct and epithelial-derived ovarian carcinogenesis.
Domestic animal endocrinology.
2015 Jul; 52(?):82-9. doi:
10.1016/j.domaniend.2015.03.005. [PMID: 25929245] - Pei-Shan Cai, Dan Li, Jing Chen, Chao-Mei Xiong, Jin-Lan Ruan. Comparison of two thin-film microextractions for the analysis of estrogens in aqueous tea extract and environmental water samples by high performance liquid chromatography-ultraviolet detection.
Food chemistry.
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Toxicology and applied pharmacology.
2015 Mar; 283(2):109-16. doi:
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Molecular and cellular endocrinology.
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Toxicological sciences : an official journal of the Society of Toxicology.
2015 Feb; 143(2):333-48. doi:
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Neuro endocrinology letters.
2015; 36 Suppl 1(?):88-94. doi:
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Steroids.
2014 Dec; 92(?):96-100. doi:
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Prikladnaia biokhimiia i mikrobiologiia.
2014 Nov; 50(6):604-11. doi:
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Toxicology and applied pharmacology.
2014 Oct; 280(2):224-35. doi:
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Huan jing ke xue= Huanjing kexue.
2014 Aug; 35(8):3169-74. doi:
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Indian journal of pharmacology.
2014 Jul; 46(4):416-9. doi:
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Saudi medical journal.
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Experimental and toxicologic pathology : official journal of the Gesellschaft fur Toxikologische Pathologie.
2013 Nov; 65(7-8):1083-9. doi:
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Biomedical chromatography : BMC.
2013 Jul; 27(7):825-30. doi:
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Biomedical and environmental sciences : BES.
2013 Apr; 26(4):249-57. doi:
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Journal of medical microbiology.
2013 Feb; 62(Pt 2):232-240. doi:
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Experimental and clinical endocrinology & diabetes : official journal, German Society of Endocrinology [and] German Diabetes Association.
2013 Feb; 121(2):94-101. doi:
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PloS one.
2013; 8(4):e61726. doi:
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PloS one.
2013; 8(7):e65935. doi:
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Chemical research in toxicology.
2012 Nov; 25(11):2553-66. doi:
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Disease models & mechanisms.
2012 Nov; 5(6):870-80. doi:
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Toxicology and applied pharmacology.
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Talanta.
2012 Aug; 97(?):222-8. doi:
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Endocrinology.
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Environmental science & technology.
2012 Jul; 46(14):7826-35. doi:
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Biochemical and biophysical research communications.
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2012 Jun; 1241(?):13-20. doi:
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2012 Jun; 47(3):355-64. doi:
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BMC complementary and alternative medicine.
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Journal of bioinformatics and computational biology.
2012 Apr; 10(2):1241012. doi:
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American journal of physiology. Endocrinology and metabolism.
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Reproductive toxicology (Elmsford, N.Y.).
2012 Jan; 33(1):35-44. doi:
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Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica.
2011 Oct; 36(19):2680-3. doi:
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Archives of environmental contamination and toxicology.
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Journal of environmental monitoring : JEM.
2011 May; 13(5):1366-73. doi:
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Human reproduction (Oxford, England).
2011 Apr; 26(4):920-6. doi:
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The Journal of biological chemistry.
2011 Feb; 286(7):5078-86. doi:
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International journal of molecular sciences.
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Free radical research.
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IUBMB life.
2010 Oct; 62(10):746-51. doi:
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Andrologia.
2010 Oct; 42(5):285-90. doi:
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Frontiers in neuroendocrinology.
2010 Oct; 31(4):400-19. doi:
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Experimental and toxicologic pathology : official journal of the Gesellschaft fur Toxikologische Pathologie.
2010 Sep; 62(5):461-9. doi:
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Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment.
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Hormones (Athens, Greece).
2010 Jul; 9(3):191-205. doi:
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Toxicological sciences : an official journal of the Society of Toxicology.
2010 Jun; 115(2):462-74. doi:
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Endocrine.
2010 Jun; 37(3):396-402. doi:
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Toxicology mechanisms and methods.
2010 Mar; 20(3):105-11. doi:
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Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials.
2010 Feb; 33(2):243-5. doi:
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Neuroscience letters.
2009 Dec; 467(2):159-63. doi:
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The Journal of reproduction and development.
2009 Dec; 55(6):629-37. doi:
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Nigerian journal of physiological sciences : official publication of the Physiological Society of Nigeria.
2009 Dec; 24(2):187-94. doi:
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Poultry science.
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The Journal of reproduction and development.
2009 Oct; 55(5):461-6. doi:
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JPMA. The Journal of the Pakistan Medical Association.
2009 Aug; 59(8):568-70. doi:
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International journal of gynecological cancer : official journal of the International Gynecological Cancer Society.
2009 Aug; 19(6):1004-10. doi:
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Molecular and cellular endocrinology.
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Aquatic toxicology (Amsterdam, Netherlands).
2009 May; 92(4):271-80. doi:
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