2-Methoxyestradiol (BioDeep_00000001217)

Main id: BioDeep_00000016574

Secondary id: BioDeep_00000398848

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite Chemicals and Drugs natural product BioNovoGene_Lab2019 Volatile Flavor Compounds


代谢物信息卡片


(1S,10R,11S,14S,15S)-4-methoxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol

化学式: C19H26O3 (302.1881846)
中文名称: 2-甲氧雌二醇, 2-甲氧基雌二醇
谱图信息: 最多检出来源 Homo sapiens(blood) 0.3%

分子结构信息

SMILES: CC12CCC3C(C1CCC2O)CCC4=CC(=C(C=C34)OC)O
InChI: InChI=1S/C19H26O3/c1-19-8-7-12-13(15(19)5-6-18(19)21)4-3-11-9-16(20)17(22-2)10-14(11)12/h9-10,12-13,15,18,20-21H,3-8H2,1-2H3

描述信息

2-Methoxyestradiol (2ME2) is a drug that prevents the formation of new blood vessels that tumors need in order to grow (angiogenesis). It is derived from estrogen, although it binds poorly to known estrogen receptors, and belongs to the family of drugs called angiogenesis inhibitors. It has undergone Phase 1 clinical trials against breast cancers. Preclinical models also suggest that 2ME2 could also be effective against inflammatory diseases such as rheumatoid arthritis. The CAS name for 2ME2 is (17 beta)-2-methoxyestra-1,3,5(10)-triene-3,17-diol. It also acts as a vasodilator. [HMDB]
2-Methoxyestradiol (2ME2) is a drug that prevents the formation of new blood vessels that tumours need in order to grow (angiogenesis). It is derived from estrogen, although it binds poorly to known estrogen receptors, and belongs to the family of drugs called angiogenesis inhibitors. It has undergone phase 1 clinical trials against breast cancers. Preclinical models also suggest that 2ME2 could also be effective against inflammatory diseases such as rheumatoid arthritis. 2ME2 also acts as a vasodilator.
C274 - Antineoplastic Agent > C163758 - Targeted Therapy Agent > C1821 - Selective Estrogen Receptor Modulator
C274 - Antineoplastic Agent > C129818 - Antineoplastic Hormonal/Endocrine Agent > C481 - Antiestrogen
C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C483 - Therapeutic Estrogen
D050258 - Mitosis Modulators > D050256 - Antimitotic Agents > D050257 - Tubulin Modulators
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones
D000970 - Antineoplastic Agents > D050256 - Antimitotic Agents
C147908 - Hormone Therapy Agent > C547 - Hormone Antagonist
C1892 - Chemopreventive Agent
2-Methoxyestradiol (2-ME2), an orally active endogenous metabolite of 17β-estradiol (E2), is an apoptosis inducer and an angiogenesis inhibitor with potent antineoplastic activity. 2-Methoxyestradiol also destablize microtubules. 2-Methoxyestradio, also a potent superoxide dismutase (SOD) inhibitor and a ROS-generating agent, induces autophagy in the transformed cell line HEK293 and the cancer cell lines U87 and HeLa[1][2][3][4][5][6].

同义名列表

32 个代谢物同义名

(1S,10R,11S,14S,15S)-4-methoxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol; 2-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol; 2,3,17β-Trihydroxy-1,3,5(10)-estratriene 2-methyl ether; 1,3,5(10)-ESTRATRIEN-2,3,17-BETA-triol 2-methyl ether; 3,17β-Dihydroxy-2-methoxy-1,3,5(10)-estratriene; (17 beta)-2-Methoxyestra-1,3,5(10)-triene-3,17-diol; 1,3,5(10)-ESTRATRIEN-2,3,17-b-triol 2-methyl ether; (17beta)-2-Methoxyestra-1,3,5(10)-triene-3,17-diol; 1,3,5(10)-ESTRATRIEN-2,3,17-β-triol 2-methyl ether; 1,3,5(10)-Estratriene-2,3,17-triol 2-methyl ether; (17Β)-2-methoxyestra-1,3,5(10)-triene-3,17-diol; 2-Methoxyestra-1,3,5(10)-triene-3,17beta-diol; 2-Methoxyestra-1,3,5(10)-triene-3,17β-diol; 2-Methoxyestradiol, (17alpha)-isomer; 2-Hydroxyestradiol 2-methyl ether; 2-Hydroxyestradol 2-methyl ether; 2-(Methyl-11C)methoxyestradiol; 2 Methoxyestradiol 17 beta; 2-Methoxyestradiol-17 beta; 2-Methoxyestradiol-17beta; 2-Methoxyestradiol-17b; 2-Methoxyestradiol-17β; 2-Methoxyoestradiol; 2 Methoxyoestradiol; 2 Methoxyestradiol; 2-Methoxyestradiol; 2-Methoxy-e2; Panzem; 2ME2; 2-ME2; NSC-659853; 2-Methoxy-17beta-estradiol



数据库引用编号

27 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

3 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(2)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(1)

PathBank(0)

PharmGKB(0)

14 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

  • Yifan Ding, Na Guo, Yuhan Jiang, Sihan Liu, Tongpei Zhou, Haoyun Bai, Yanni Lv, Shengli Han, Langchong He. Establishment of cluster of differentiation 20 immobilized cell membrane chromatography for the screening of active antitumor components in traditional Chinese medicine. Journal of chromatography. A. 2024 Apr; 1721(?):464845. doi: 10.1016/j.chroma.2024.464845. [PMID: 38552371]
  • Qin Li, Peng Zhao, Yu Wen, Zhimin Zou, Xihe Qin, Hongping Tan, Jian Gong, Qihua Wu, Chen Zheng, Kun Zhang, Qiaobing Huang, Marc Maegele, Zhengtao Gu, Li Li. Polydatin ameliorates TBI induced secondary brain injury by inhibiting NLRP3-induced neuroinflammation associated with SOD2 acetylation. Shock (Augusta, Ga.). 2022 Dec; ?(?):. doi: 10.1097/shk.0000000000002066. [PMID: 36477654]
  • Marta Waszkiewicz, Anna Choromanska, Julita Kulbacka, Jolanta Saczko. The photodynamic reaction with IR-775 cyanine combined with 2-methoxyestradiol in ovarian (SKOV-3) and human breast adenocarcinoma (MDA MB-231) cell lines. Photodiagnosis and photodynamic therapy. 2022 Jun; 38(?):102766. doi: 10.1016/j.pdpdt.2022.102766. [PMID: 35182779]
  • Eslam Hassan, Shady Allam, Ahmed M Mansour, Aya Shaheen, Salama A Salama. The potential protective effects of estradiol and 2-methoxyestradiol in ischemia reperfusion-induced kidney injury in ovariectomized female rats. Life sciences. 2022 May; 296(?):120441. doi: 10.1016/j.lfs.2022.120441. [PMID: 35240160]
  • Tomohiro Ibata, Jingya Lyu, Hitomi Imachi, Kensaku Fukunaga, Seisuke Sato, Toshihiro Kobayashi, Takanobu Saheki, Takafumi Yoshimura, Koji Murao. Effects of 2-Methoxyestradiol, a Main Metabolite of Estradiol on Hepatic ABCA1 Expression in HepG2 Cells. Nutrients. 2022 Jan; 14(2):. doi: 10.3390/nu14020288. [PMID: 35057469]
  • Asako Kumagai, Satoru Takeda, Eisei Sohara, Shinichi Uchida, Hiroshi Iijima, Astuo Itakura, Daisuke Koya, Keizo Kanasaki. Dietary Magnesium Insufficiency Induces Salt-Sensitive Hypertension in Mice Associated With Reduced Kidney Catechol-O-Methyl Transferase Activity. Hypertension (Dallas, Tex. : 1979). 2021 07; 78(1):138-150. doi: 10.1161/hypertensionaha.120.16377. [PMID: 33840199]
  • Xinyang Liu, Taoqian Zhao, Yue Xu, Pengchao Huo, Xia Xu, Zhenzhong Zhang, Qingfeng Tian, Nan Zhang. Co-administration of paclitaxel and 2-methoxyestradiol using folate-conjugated human serum albumin nanoparticles for improving drug resistance and antitumor efficacy. Pharmaceutical development and technology. 2021 Jan; 26(1):1-10. doi: 10.1080/10837450.2020.1829640. [PMID: 32985928]
  • Ahmad S Azhar, Zaher F Zaher, Osama M Ashour, Ashraf B Abdel-Naim. 2-Methoxyestradiol ameliorates metabolic syndrome-induced hypertension and catechol-O-methyltransferase inhibited expression and activity in rats. European journal of pharmacology. 2020 Sep; 882(?):173278. doi: 10.1016/j.ejphar.2020.173278. [PMID: 32544503]
  • Marwa S Hamza, Moustafa Sayed, Salama Salama. 2-Methoxyestradiol inhibits high fat diet-induced obesity in rats through modulation of adipose tissue macrophage infiltration and immunophenotype. European journal of pharmacology. 2020 Jul; 878(?):173106. doi: 10.1016/j.ejphar.2020.173106. [PMID: 32283059]
  • Lamei Yu, Weijian Li, Byung Mun Park, Gi-Ja Lee, Suhn Hee Kim. Hypoxia augments NaHS-induced ANP secretion via KATP channel, HIF-1α and PPAR-γ pathway. Peptides. 2019 11; 121(?):170123. doi: 10.1016/j.peptides.2019.170123. [PMID: 31386893]
  • Sahand Sadeghi, Amirhossein Davoodvandi, Mohammad Hossein Pourhanifeh, Nasrin Sharifi, Reza ArefNezhad, Roxana Sahebnasagh, Shirin Amiri Moghadam, Amirhossein Sahebkar, Hamed Mirzaei. Anti-cancer effects of cinnamon: Insights into its apoptosis effects. European journal of medicinal chemistry. 2019 Sep; 178(?):131-140. doi: 10.1016/j.ejmech.2019.05.067. [PMID: 31195168]
  • YaBing Xing, Xin Liu, Xiao Li, Fang Ding, JunYa Zhang, XinHong Guo. PEG-PCL modification and intestinal sustained-release of solid lipid nanoparticles for improving oral bioavailability of 2-methoxyestradiol. Journal of liposome research. 2019 Sep; 29(3):207-214. doi: 10.1080/08982104.2018.1529792. [PMID: 30280943]
  • Hai Tao, Juanjuan Mei, Xiaoyan Tang. The anticancer effects of 2-methoxyestradiol on human huh7 cells in vitro and in vivo. Biochemical and biophysical research communications. 2019 05; 512(3):635-640. doi: 10.1016/j.bbrc.2019.02.068. [PMID: 30914193]
  • Emanuel Guajardo-Correa, Denisse Mena-Silva, Patricia Diaz, Carlos Godoy-Guzmán, Hugo Cardenas, Pedro A Orihuela. 2-Methoxyoestradiol impairs mouse embryo implantation via F-spondin. Reproduction, fertility, and development. 2019 Apr; 31(4):689-697. doi: 10.1071/rd18114. [PMID: 30449298]
  • Cong Wang, Bo Zuo, Xiaofan Wu. The Role of Macrophage Migration Inhibitory Factor in Remote Ischemic Postconditioning. The Canadian journal of cardiology. 2019 04; 35(4):501-510. doi: 10.1016/j.cjca.2018.12.040. [PMID: 30935641]
  • Khadidja Aya Beladjila, Djemaa Berrehal, Zahia Kabouche, Maria Paola Germanò, Valeria D'Angelo, Nunziatina De Tommasi, Felicia D'Andrea, Alessandra Braca, Marinella De Leo. Antiangiogenic Activity of Compounds Isolated from Anarrhinum pedatum. Journal of natural products. 2019 03; 82(3):510-519. doi: 10.1021/acs.jnatprod.8b00893. [PMID: 30835462]
  • Eman Salah, Sheldon I Bastacky, Edwin K Jackson, Stevan P Tofovic. 2-Methoxyestradiol Attenuates Angiotensin II-Induced Hypertension, Cardiovascular Remodeling, and Renal Injury. Journal of cardiovascular pharmacology. 2019 03; 73(3):165-177. doi: 10.1097/fjc.0000000000000649. [PMID: 30839510]
  • Thikryat Neamatallah, Ashraf B Abdel-Naim, Basma G Eid, Atif Hasan. 2-Methoxyestradiol attenuates liver fibrosis in mice: implications for M2 macrophages. Naunyn-Schmiedeberg's archives of pharmacology. 2019 03; 392(3):381-391. doi: 10.1007/s00210-018-1577-2. [PMID: 30535572]
  • Nan Zhang, Jiangnan Zhang, Pei Wang, Xinyang Liu, Pengchao Huo, Yue Xu, Wenjie Chen, Hongying Xu, Qingfeng Tian. Investigation of an antitumor drug-delivery system based on anti-HER2 antibody-conjugated BSA nanoparticles. Anti-cancer drugs. 2018 04; 29(4):307-322. doi: 10.1097/cad.0000000000000586. [PMID: 29381491]
  • Danling Liu, Jiadong Wang, Yanan Xu. Clinical Significance of Low 2-Methoxyestradiol Levels in Serum and Tissue of Recurrent Juvenile-Onset Laryngeal Papillomatosis. Otolaryngology--head and neck surgery : official journal of American Academy of Otolaryngology-Head and Neck Surgery. 2018 03; 158(3):566-570. doi: 10.1177/0194599817740578. [PMID: 29110580]
  • Irene B Sørvik, Eirik Johansson Solum, Nils A Labba, Trond Vidar Hansen, Ragnhild E Paulsen. Differential effects of some novel synthetic oestrogen analogs on oxidative PC12 cell death caused by serum deprivation. Free radical research. 2018 Feb; 52(2):273-287. doi: 10.1080/10715762.2018.1430363. [PMID: 29405079]
  • Chao He, Wei Zhang, Suobei Li, Wei Ruan, Junmei Xu, Feng Xiao. Edaravone Improves Septic Cardiac Function by Inducing an HIF-1α/HO-1 Pathway. Oxidative medicine and cellular longevity. 2018; 2018(?):5216383. doi: 10.1155/2018/5216383. [PMID: 29765498]
  • Ashraf B Abdel-Naim, Thikryat Neamatallah, Basma G Eid, Ahmed Esmat, Abdulmohsin J Alamoudi, Gamal S Abd El-Aziz, Osama M Ashour. 2-Methoxyestradiol Attenuates Testosterone-Induced Benign Prostate Hyperplasia in Rats through Inhibition of HIF-1α/TGF-β/Smad2 Axis. Oxidative medicine and cellular longevity. 2018; 2018(?):4389484. doi: 10.1155/2018/4389484. [PMID: 30154949]
  • Jiayi Wan, Zheng Hu, Ke Zeng, Yongxiang Yin, Min Zhao, Miaoxin Chen, Qi Chen. The reduction in circulating levels of estrogen and progesterone in women with preeclampsia. Pregnancy hypertension. 2018 Jan; 11(?):18-25. doi: 10.1016/j.preghy.2017.12.003. [PMID: 29523268]
  • Hannah Oh, Hannah Arem, Charles E Matthews, Nicolas Wentzensen, Kerryn W Reding, Louise A Brinton, Garnet L Anderson, Sally B Coburn, Jane A Cauley, Chu Chen, Deborah Goodman, Ruth M Pfeiffer, Roni T Falk, Xia Xu, Britton Trabert. Sitting, physical activity, and serum oestrogen metabolism in postmenopausal women: the Women's Health Initiative Observational Study. British journal of cancer. 2017 Sep; 117(7):1070-1078. doi: 10.1038/bjc.2017.268. [PMID: 28817836]
  • Yuming Liang, Xiaozhou Zhen, Kaiwen Wang, Jing Ma. Folic acid attenuates cobalt chloride-induced PGE2 production in HUVECs via the NO/HIF-1alpha/COX-2 pathway. Biochemical and biophysical research communications. 2017 08; 490(2):567-573. doi: 10.1016/j.bbrc.2017.06.079. [PMID: 28624453]
  • Ajeeth K Pingili, Karen N Davidge, Shyamala Thirunavukkarasu, Nayaab S Khan, Akemi Katsurada, Dewan S A Majid, Frank J Gonzalez, L Gabriel Navar, Kafait U Malik. 2-Methoxyestradiol Reduces Angiotensin II-Induced Hypertension and Renal Dysfunction in Ovariectomized Female and Intact Male Mice. Hypertension (Dallas, Tex. : 1979). 2017 06; 69(6):1104-1112. doi: 10.1161/hypertensionaha.117.09175. [PMID: 28416584]
  • T Toimela, O Huttala, E Sabell, M Mannerström, J R Sarkanen, T Ylikomi, T Heinonen. Intra-laboratory validated human cell-based in vitro vasculogenesis/angiogenesis test with serum-free medium. Reproductive toxicology (Elmsford, N.Y.). 2017 06; 70(?):116-125. doi: 10.1016/j.reprotox.2016.11.015. [PMID: 27915012]
  • Hong-Ik Cho, Min-Jong Seo, Sun-Mee Lee. 2-Methoxyestradiol protects against ischemia/reperfusion injury in alcoholic fatty liver by enhancing sirtuin 1-mediated autophagy. Biochemical pharmacology. 2017 05; 131(?):40-51. doi: 10.1016/j.bcp.2017.02.008. [PMID: 28213273]
  • Anushka Dikshit, Karen Hales, Dale Buchanan Hales. Whole flaxseed diet alters estrogen metabolism to promote 2-methoxtestradiol-induced apoptosis in hen ovarian cancer. The Journal of nutritional biochemistry. 2017 04; 42(?):117-125. doi: 10.1016/j.jnutbio.2017.01.002. [PMID: 28178600]
  • Gopikrishna J Pillai, Bindhu Paul-Prasanth, Shantikumar V Nair, Deepthy Menon. Influence of surface passivation of 2-Methoxyestradiol loaded PLGA nanoparticles on cellular interactions, pharmacokinetics and tumour accumulation. Colloids and surfaces. B, Biointerfaces. 2017 Feb; 150(?):242-249. doi: 10.1016/j.colsurfb.2016.11.040. [PMID: 27923186]
  • Shun-Long Wu, Ya-Jun Li, Kui Liao, Lei Shi, Na Zhang, Shuang Liu, Yao-Yao Hu, Shao-Lin Li, Ying Wang. 2-Methoxyestradiol inhibits the proliferation and migration and reduces the radioresistance of nasopharyngeal carcinoma CNE-2 stem cells via NF-κB/HIF-1 signaling pathway inactivation and EMT reversal. Oncology reports. 2017 Feb; 37(2):793-802. doi: 10.3892/or.2016.5319. [PMID: 28000883]
  • Anna L Eriksson, Anna S Wilhelmson, Johan B Fagman, Henrik Ryberg, Antti Koskela, Juha Tuukkanen, Åsa Tivesten, Claes Ohlsson. The Bone Sparing Effects of 2-Methoxyestradiol Are Mediated via Estrogen Receptor-α in Male Mice. Endocrinology. 2016 Nov; 157(11):4200-4205. doi: 10.1210/en.2016-1402. [PMID: 27631553]
  • P Díaz, H Cardenas, P A Orihuela. Red Maca (Lepidium meyenii) did not affect cell viability despite increased androgen receptor and prostate-specific antigen gene expression in the human prostate cancer cell line LNCaP. Andrologia. 2016 Oct; 48(8):922-6. doi: 10.1111/and.12681. [PMID: 27681649]
  • Cher M Dallal, Louise A Brinton, Charles E Matthews, Ruth M Pfeiffer, Terryl J Hartman, Jolanta Lissowska, Roni T Falk, Montserrat Garcia-Closas, Xia Xu, Timothy D Veenstra, Gretchen L Gierach. Association of Active and Sedentary Behaviors with Postmenopausal Estrogen Metabolism. Medicine and science in sports and exercise. 2016 Mar; 48(3):439-48. doi: 10.1249/mss.0000000000000790. [PMID: 26460631]
  • Miriam Pertegal, Francisco J Fenoy, Moisés Hernández, Jaime Mendiola, Juan L Delgado, Bárbara Bonacasa, Andrés Corno, Bernardo López, Vicente Bosch, Isabel Hernández. Fetal Val108/158Met catechol-O-methyltransferase (COMT) polymorphism and placental COMT activity are associated with the development of preeclampsia. Fertility and sterility. 2016 Jan; 105(1):134-43.e1. doi: 10.1016/j.fertnstert.2015.09.019. [PMID: 26450530]
  • Thomas Thekkumkara, Russell Snyder, Vardan T Karamyan. Competitive Binding Assay for the G-Protein-Coupled Receptor 30 (GPR30) or G-Protein-Coupled Estrogen Receptor (GPER). Methods in molecular biology (Clifton, N.J.). 2016; 1366(?):11-17. doi: 10.1007/978-1-4939-3127-9_2. [PMID: 26585123]
  • Yuli Qian, Ahmad Sherbini, Bahar Matin, Yanli Zhao, John Castellot, David J Greenblatt. Inhibition of 2-methoxyestradiol glucuronidation by probenecid. The Journal of pharmacy and pharmacology. 2015 Nov; 67(11):1585-92. doi: 10.1111/jphp.12462. [PMID: 26272356]
  • Jolanta Saczko, Anna Choromańska, Nina Rembiałkowska, Magda Dubińska-Magiera, Iwona Bednarz-Misa, Julia Bar, Anna Marcinkowska, Julita Kulbacka. Oxidative modification induced by photodynamic therapy with Photofrin®II and 2-methoxyestradiol in human ovarian clear carcinoma (OvBH-1) and human breast adenocarcinoma (MCF-7) cells. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2015 Apr; 71(?):30-6. doi: 10.1016/j.biopha.2015.02.008. [PMID: 25960212]
  • Bin Du, Tiantian Wang, Shuping Han, Xiaohui Cao, Tiantian Qu, Feifei Zhao, Xinhong Guo, Hanchun Yao. Determination of 2-methoxyestradiol by chemiluminescence based on luminol-KMnO4-CdTe quantum dots system. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. 2015 Feb; 136 Pt B(?):149-54. doi: 10.1016/j.saa.2014.08.032. [PMID: 25439823]
  • Miriam Pertegal, Francisco J Fenoy, Barbara Bonacasa, Jaime Mendiola, Juan L Delgado, Moises Hernández, Miguel G Salom, Vicente Bosch, Isabel Hernández. 2-methoxyestradiol plasma levels are associated with clinical severity indices and biomarkers of preeclampsia. Reproductive sciences (Thousand Oaks, Calif.). 2015 Feb; 22(2):198-206. doi: 10.1177/1933719114537716. [PMID: 24899468]
  • Bin Du, Tiantian Qu, Zheng Chen, Xiaohui Cao, Shuping Han, Guopeng Shen, Lei Wang. A novel restricted access material combined to molecularly imprinted polymers for selective solid-phase extraction and high performance liquid chromatography determination of 2-methoxyestradiol in plasma samples. Talanta. 2014 Nov; 129(?):465-72. doi: 10.1016/j.talanta.2014.05.005. [PMID: 25127620]
  • María L Oróstica, John López, Lidia M Zuñiga, Daniella Utz, Patricia Díaz, Patricia Reuquen, Alexis Parada-Bustamante, Hugo Cardenas, Pedro A Orihuela. Mating decreases plasma levels of TGFβ1 and regulates myosalpinx expression of TGFβ1/TGFBR3 in the rat. Molecular reproduction and development. 2014 Nov; 81(11):1053-61. doi: 10.1002/mrd.22427. [PMID: 25359088]
  • Hanchun Yao, Min Zhang, Wenyuan Zeng, Xiaoying Zeng, Zhenzhong Zhang. Sensitive determination of 2-methoxyestradiol in pharmaceutical preparations and serum samples using flow injection chemiluminescence. Luminescence : the journal of biological and chemical luminescence. 2014 May; 29(3):261-5. doi: 10.1002/bio.2538. [PMID: 23836511]
  • Min Zhang, Xiangqin Xiao, Wenyuan Zeng, Xiaoying Zeng, Hanchun Yao. Determination of 2-methoxyestradiol in serum samples and pharmaceutical preparations by silver nanoparticles-enhanced chemiluminescence. Talanta. 2014 Mar; 120(?):331-5. doi: 10.1016/j.talanta.2013.11.048. [PMID: 24468378]
  • Hui-Hui Li, Ying-Jie Zhao, Yan Li, Cai-Feng Dai, Sheikh O Jobe, Xing-Sheng Yang, Xing-Fu Li, Manish S Patankar, Ronald R Magness, Jing Zheng. Estradiol 17β and its metabolites stimulate cell proliferation and antagonize ascorbic acid-suppressed cell proliferation in human ovarian cancer cells. Reproductive sciences (Thousand Oaks, Calif.). 2014 Jan; 21(1):102-11. doi: 10.1177/1933719113492211. [PMID: 23757313]
  • Ying-Yin Chen, Ching-Hua Yeh, Edmund Cheung So, Ding-Ping Sun, Li-Yun Wang, Chung-Hsi Hsing. Anticancer drug 2-methoxyestradiol protects against renal ischemia/reperfusion injury by reducing inflammatory cytokines expression. BioMed research international. 2014; 2014(?):431524. doi: 10.1155/2014/431524. [PMID: 25229058]
  • Jingwen Si, Ning Wang, Huan Wang, Juan Xie, Jian Yang, Hui Yi, Zixuan Shi, Jing Ma, Wen Wang, Lifang Yang, Shiqiang Yu, Junchang Li. HIF-1α signaling activation by post-ischemia treatment with astragaloside IV attenuates myocardial ischemia-reperfusion injury. PloS one. 2014; 9(9):e107832. doi: 10.1371/journal.pone.0107832. [PMID: 25238237]
  • Zhijun Shen, Yanming Wu, Xiao Chen, Xinwen Chang, Qian Zhou, Jian Zhou, Hao Ying, Jing Zheng, Tao Duan, Kai Wang. Decreased maternal serum 2-methoxyestradiol levels are associated with the development of preeclampsia. Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology. 2014; 34(6):2189-99. doi: 10.1159/000369662. [PMID: 25562165]
  • Paulina Kohen, Soledad Henríquez, Candy Rojas, Phillip M Gerk, Wilder A Palomino, Jerome F Strauss, Luigi Devoto. 2-Methoxyestradiol in the human corpus luteum throughout the luteal phase and its influence on lutein cell steroidogenesis and angiogenic activity. Fertility and sterility. 2013 Nov; 100(5):1397-404. doi: 10.1016/j.fertnstert.2013.07.1980. [PMID: 23954354]
  • Ravi Shankar, Abhilash Samykutty, Corinne Riggin, Sneha Kannan, Ursula Wenzel, Rohit Kolhatkar. Cathepsin B degradable star-shaped peptidic macromolecules for delivery of 2-methoxyestradiol. Molecular pharmaceutics. 2013 Oct; 10(10):3776-88. doi: 10.1021/mp400261h. [PMID: 23971990]
  • Alejandra Perez-Sepulveda, Pedro P España-Perrot, Errol R Norwitz, Sebastián E Illanes. Metabolic pathways involved in 2-methoxyestradiol synthesis and their role in preeclampsia. Reproductive sciences (Thousand Oaks, Calif.). 2013 Sep; 20(9):1020-9. doi: 10.1177/1933719113477483. [PMID: 23456663]
  • Guodong Wang, Liming Song, Huiping Wang, Nianzeng Xing. Quercetin synergizes with 2-methoxyestradiol inhibiting cell growth and inducing apoptosis in human prostate cancer cells. Oncology reports. 2013 Jul; 30(1):357-63. doi: 10.3892/or.2013.2469. [PMID: 23673431]
  • Jianwen Jin, Hanchun Yao, Zheng Chen, Li Pang, Bin Du. Flow injection chemiluminescence determination of 2-methoxyestradiol based on inhibition of luminol-potassium ferricyanide reaction. Luminescence : the journal of biological and chemical luminescence. 2013 May; 28(3):270-4. doi: 10.1002/bio.2376. [PMID: 22522659]
  • Hyun-Joo Seol, Geum-Joon Cho, Min-Jeong Oh, Hai-Joong Kim. 2-methoxyoestradiol levels and placental catechol-O-methyltransferase expression in patients with late-onset preeclampsia. Archives of gynecology and obstetrics. 2013 May; 287(5):881-6. doi: 10.1007/s00404-012-2663-1. [PMID: 23233290]
  • Xiaowen Mao, Tingting Wang, Yanan Liu, Michael G Irwin, Jing-song Ou, Xiao-long Liao, Xia Gao, Yuan Xu, Kwok F J Ng, Paul M Vanhoutte, Zhengyuan Xia. N-acetylcysteine and allopurinol confer synergy in attenuating myocardial ischemia injury via restoring HIF-1α/HO-1 signaling in diabetic rats. PloS one. 2013; 8(7):e68949. doi: 10.1371/journal.pone.0068949. [PMID: 23874823]
  • Alejandra Pérez-Sepúlveda, María José Torres, Francisco J Valenzuela, Raimundo Larraín, Horacio Figueroa-Diesel, José Galaz, Jyh Kae Nien, Ramón Serra, Luis Michea, Sebastián E Illanes. Low 2-methoxyestradiol levels at the first trimester of pregnancy are associated with the development of pre-eclampsia. Prenatal diagnosis. 2012 Nov; 32(11):1053-8. doi: 10.1002/pd.3954. [PMID: 22886584]
  • Seoung Ju Park, Kyung Sun Lee, So Ri Kim, Han Jung Chae, Wan Hee Yoo, Dong Im Kim, Myoung Shin Jeon, Yong Chul Lee. AMPK activation reduces vascular permeability and airway inflammation by regulating HIF/VEGFA pathway in a murine model of toluene diisocyanate-induced asthma. Inflammation research : official journal of the European Histamine Research Society ... [et al.]. 2012 Oct; 61(10):1069-83. doi: 10.1007/s00011-012-0499-6. [PMID: 22692279]
  • Aster Legesse-Miller, Irene Raitman, Erin M Haley, Albert Liao, Lova L Sun, David J Wang, Nithya Krishnan, Johanna M S Lemons, Eric J Suh, Elizabeth L Johnson, Benjamin A Lund, Hilary A Coller. Quiescent fibroblasts are protected from proteasome inhibition-mediated toxicity. Molecular biology of the cell. 2012 Sep; 23(18):3566-81. doi: 10.1091/mbc.e12-03-0192. [PMID: 22875985]
  • XinHong Guo, YaBing Xing, XinXin Zhang, JunMei Li, Qian Mei, HongLing Zhang, ChengQun Chen, ZhenZhong Zhang, FuDe Cui. In vivo controlled release and prolonged antitumor effects of 2-methoxyestradiol solid lipid nanoparticles incorporated into a thermosensitive hydrogel. Drug delivery. 2012 May; 19(4):188-93. doi: 10.3109/10717544.2012.690002. [PMID: 22643052]
  • Shuzhang Du, Ling Zhu, Bin Du, Xiufang Shi, Zhenzhong Zhang, Shuyu Wang, Chaofeng Zhang. Pharmacokinetic evaluation and antitumor activity of 2-methoxyestradiol nanosuspension. Drug development and industrial pharmacy. 2012 Apr; 38(4):431-8. doi: 10.3109/03639045.2011.609560. [PMID: 21951208]
  • Justine Yang Bruce, Jens Eickhoff, Roberto Pili, Theodore Logan, Michael Carducci, Jamie Arnott, Anthony Treston, George Wilding, Glenn Liu. A phase II study of 2-methoxyestradiol nanocrystal colloidal dispersion alone and in combination with sunitinib malate in patients with metastatic renal cell carcinoma progressing on sunitinib malate. Investigational new drugs. 2012 Apr; 30(2):794-802. doi: 10.1007/s10637-010-9618-9. [PMID: 21174224]
  • Sharon Anderson, Terry T Oyama, Jessie N Lindsley, William E Schutzer, Douglas R Beard, Vincent H Gattone, Radko Komers. 2-Hydroxyestradiol slows progression of experimental polycystic kidney disease. American journal of physiology. Renal physiology. 2012 Mar; 302(5):F636-45. doi: 10.1152/ajprenal.00265.2011. [PMID: 22160773]
  • Xinhong Guo, Yabing Xing, Qian Mei, Hongling Zhang, Zhenzhong Zhang, Fude Cui. Preparation and cytotoxicity of 2-methoxyestradiol-loaded solid lipid nanoparticles. Anti-cancer drugs. 2012 Feb; 23(2):185-90. doi: 10.1097/cad.0b013e32834cf8d0. [PMID: 22027535]
  • Jiang Huang, Jianghao Sun, Yanhua Chen, Yongmei Song, Lijia Dong, Qinmin Zhan, Ruiping Zhang, Zeper Abliz. Analysis of multiplex endogenous estrogen metabolites in human urine using ultra-fast liquid chromatography-tandem mass spectrometry: a case study for breast cancer. Analytica chimica acta. 2012 Jan; 711(?):60-8. doi: 10.1016/j.aca.2011.10.058. [PMID: 22152797]
  • Jiping Wang, Hongxia Liu, Bo Chen, Qiang Li, Xuliang Huang, Liqun Wang, Xiaohua Guo, Qiaobing Huang. RhoA/ROCK-dependent moesin phosphorylation regulates AGE-induced endothelial cellular response. Cardiovascular diabetology. 2012 Jan; 11(?):7. doi: 10.1186/1475-2840-11-7. [PMID: 22251897]
  • A K Tsakalof, D C Gkagtzis, G N Koukoulis, C S Hadjichristodoulou. Development of GC-MS/MS method with programmable temperature vaporization large volume injection for monitoring of 17β-estradiol and 2-methoxyestradiol in plasma. Analytica chimica acta. 2012 Jan; 709(?):73-80. doi: 10.1016/j.aca.2011.09.043. [PMID: 22122934]
  • Tal Hirschhorn, Lior Barizilay, Nechama I Smorodinsky, Marcelo Ehrlich. Differential regulation of Smad3 and of the type II transforming growth factor-β receptor in mitosis: implications for signaling. PloS one. 2012; 7(8):e43459. doi: 10.1371/journal.pone.0043459. [PMID: 22927969]
  • Christopher M Masi, Louise C Hawkley, John T Cacioppo. Serum 2-methoxyestradiol, an estrogen metabolite, is positively associated with serum HDL-C in a population-based sample. Lipids. 2012 Jan; 47(1):35-8. doi: 10.1007/s11745-011-3600-y. [PMID: 21809102]
  • Han Zhou, Xi Chen, Wei-Ming Zhang, Lu-Ping Zhu, Lei Cheng. HIF-1α inhibition reduces nasal inflammation in a murine allergic rhinitis model. PloS one. 2012; 7(11):e48618. doi: 10.1371/journal.pone.0048618. [PMID: 23133644]
  • Lei Wang, Haijun Zhang, Baoan Chen, Guohua Xia, Shuai Wang, Jian Cheng, Zeye Shao, Chong Gao, Wen Bao, Liang Tian, Yanyan Ren, Peipei Xu, Xiaohui Cai, Ran Liu, Xuemei Wang. Effect of magnetic nanoparticles on apoptosis and cell cycle induced by wogonin in Raji cells. International journal of nanomedicine. 2012; 7(?):789-98. doi: 10.2147/ijn.s28089. [PMID: 22359456]
  • Jennifer S Carew, Juan A Esquivel, Claudia M Espitia, Christoph M Schultes, Marcel Mülbaier, Joe D Lewis, Bernd Janssen, Francis J Giles, Steffan T Nawrocki. ELR510444 inhibits tumor growth and angiogenesis by abrogating HIF activity and disrupting microtubules in renal cell carcinoma. PloS one. 2012; 7(1):e31120. doi: 10.1371/journal.pone.0031120. [PMID: 22295124]
  • Kathleen A Pennington, Jessica M Schlitt, Daniel L Jackson, Laura C Schulz, Danny J Schust. Preeclampsia: multiple approaches for a multifactorial disease. Disease models & mechanisms. 2012 Jan; 5(1):9-18. doi: 10.1242/dmm.008516. [PMID: 22228789]
  • Xinhong Guo, Fude Cui, Yabing Xing, Qian Mei, Zhenzhong Zhang. Investigation of a new injectable thermosensitive hydrogel loading solid lipid nanoparticles. Die Pharmazie. 2011 Dec; 66(12):948-52. doi: ". [PMID: 22312700]
  • Ching-Hua Yeh, Willy Chou, Chin-Chen Chu, Edmund Cheung So, Huai-Chia Chang, Jhi-Joung Wang, Chung-Hsi Hsing. Anticancer agent 2-methoxyestradiol improves survival in septic mice by reducing the production of cytokines and nitric oxide. Shock (Augusta, Ga.). 2011 Nov; 36(5):510-6. doi: 10.1097/shk.0b013e318231866f. [PMID: 21841536]
  • Franck Belibi, Iram Zafar, Kameswaran Ravichandran, Anamarija Bauer Segvic, Alkesh Jani, Danica Galesic Ljubanovic, Charles L Edelstein. Hypoxia-inducible factor-1α (HIF-1α) and autophagy in polycystic kidney disease (PKD). American journal of physiology. Renal physiology. 2011 May; 300(5):F1235-43. doi: 10.1152/ajprenal.00348.2010. [PMID: 21270095]
  • Violeta Ristoiu, Koji Shibasaki, Kunitoshi Uchida, Yiming Zhou, Bich-Hoai Thi Ton, Maria-Luiza Flonta, Makoto Tominaga. Hypoxia-induced sensitization of transient receptor potential vanilloid 1 involves activation of hypoxia-inducible factor-1 alpha and PKC. Pain. 2011 Apr; 152(4):936-945. doi: 10.1016/j.pain.2011.02.024. [PMID: 21376466]
  • Irene Abreu-Rodríguez, Rocío Sánchez Silva, Ana Paula Martins, Graça Soveral, Juan José Toledo-Aral, José López-Barneo, Miriam Echevarría. Functional and transcriptional induction of aquaporin-1 gene by hypoxia; analysis of promoter and role of Hif-1α. PloS one. 2011; 6(12):e28385. doi: 10.1371/journal.pone.0028385. [PMID: 22174795]
  • Maggie Laidlaw, Carla A Cockerline, Daniel W Sepkovic. Effects of a breast-health herbal formula supplement on estrogen metabolism in pre- and post-menopausal women not taking hormonal contraceptives or supplements: a randomized controlled trial. Breast cancer : basic and clinical research. 2010 Dec; 4(?):85-95. doi: 10.4137/bcbcr.s6505. [PMID: 21234288]
  • Raghvendra K Dubey, Edwin K Jackson, Delbert G Gillespie, Lefteris C Zacharia, Bruno Imthurn, Marinella Rosselli. Resveratrol, a red wine constituent, blocks the antimitogenic effects of estradiol on human female coronary artery smooth muscle cells. The Journal of clinical endocrinology and metabolism. 2010 Sep; 95(9):E9-17. doi: 10.1210/jc.2010-0460. [PMID: 20534756]
  • Bhupendra Singh, Sarah M Mense, Nimee K Bhat, Sandeep Putty, William A Guthiel, Fabrizio Remotti, Hari K Bhat. Dietary quercetin exacerbates the development of estrogen-induced breast tumors in female ACI rats. Toxicology and applied pharmacology. 2010 Sep; 247(2):83-90. doi: 10.1016/j.taap.2010.06.011. [PMID: 20600213]
  • Intawat Nookaew, Britt G Gabrielsson, Agneta Holmäng, Ann-Sofie Sandberg, Jens Nielsen. Identifying molecular effects of diet through systems biology: influence of herring diet on sterol metabolism and protein turnover in mice. PloS one. 2010 Aug; 5(8):e12361. doi: 10.1371/journal.pone.0012361. [PMID: 20808764]
  • Emanuela Taioli, Annie Im, Xia Xu, Timothy D Veenstra, Gretchen Ahrendt, Seymour Garte. Comparison of estrogens and estrogen metabolites in human breast tissue and urine. Reproductive biology and endocrinology : RB&E. 2010 Aug; 8(?):93. doi: 10.1186/1477-7827-8-93. [PMID: 20678202]
  • Shi-Jin Zhang, Marie Sandström, Maria Ahlsén, Niklas Ivarsson, Hua Zhu, Jianjie Ma, Jian-Ming Ren, Håkan Westerblad, Abram Katz. 2-Methoxyoestradiol inhibits glucose transport in rodent skeletal muscle. Experimental physiology. 2010 Aug; 95(8):892-8. doi: 10.1113/expphysiol.2010.053405. [PMID: 20472648]
  • Carmen M Barnes, Thomas F McElrath, Judah Folkman, Anne R Hansen. Correlation of 2-methoxyestradiol levels in cord blood and complications of prematurity. Pediatric research. 2010 May; 67(5):545-50. doi: 10.1203/pdr.0b013e3181d4efef. [PMID: 20098341]
  • Marie-Pierre Cayer, Mathieu Drouin, Maryse Proulx, Daniel Jung. 2-Methoxyestradiol induce the conversion of human peripheral blood memory B lymphocytes into plasma cells. Journal of immunological methods. 2010 Apr; 355(1-2):29-39. doi: 10.1016/j.jim.2010.02.012. [PMID: 20202470]
  • Jadwiga Piwowarska, Stanisław Radowicki, Jan Pachecka. Simultaneous determination of eight estrogens and their metabolites in serum using liquid chromatography with electrochemical detection. Talanta. 2010 Apr; 81(1-2):275-80. doi: 10.1016/j.talanta.2009.11.069. [PMID: 20188920]
  • Xiahui Tan, Hayat Dagher, Craig A Hutton, Jane E Bourke. Effects of PPAR gamma ligands on TGF-beta1-induced epithelial-mesenchymal transition in alveolar epithelial cells. Respiratory research. 2010 Feb; 11(?):21. doi: 10.1186/1465-9921-11-21. [PMID: 20178607]
  • S P Tofovic, T Jones, G Petrusevska. Dose-dependent therapeutic effects of 2-Methoxyestradiol on Monocrotaline-Induced pulmonary hypertension and vascular remodelling. Prilozi. 2010; 31(1):279-95. doi: . [PMID: 20693947]
  • Susan R Sturgeon, Stella L Volpe, Elaine Puleo, Elizabeth R Bertone-Johnson, Joanna Heersink, Sara Sabelawski, Kristina Wahala, Carol Bigelow, Mindy S Kurzer. Effect of flaxseed consumption on urinary levels of estrogen metabolites in postmenopausal women. Nutrition and cancer. 2010; 62(2):175-80. doi: 10.1080/01635580903305342. [PMID: 20099191]
  • Pedro A Orihuela, Lidia M Zuñiga, Mariana Rios, Alexis Parada-Bustamante, Walter D Sierralta, Luis A Velásquez, Horacio B Croxatto. Mating changes the subcellular distribution and the functionality of estrogen receptors in the rat oviduct. Reproductive biology and endocrinology : RB&E. 2009 Nov; 7(?):139. doi: 10.1186/1477-7827-7-139. [PMID: 19948032]
  • Daniela Matei, Jeanne Schilder, Gregory Sutton, Susan Perkins, Tim Breen, Check Quon, Carolyn Sidor. Activity of 2 methoxyestradiol (Panzem NCD) in advanced, platinum-resistant ovarian cancer and primary peritoneal carcinomatosis: a Hoosier Oncology Group trial. Gynecologic oncology. 2009 Oct; 115(1):90-96. doi: 10.1016/j.ygyno.2009.05.042. [PMID: 19577796]
  • P S Tofovic, B M Rosado, K R Dubey, Z Mi, Edwin K Jackson. Effects of estradiol metabolites on cAMP production and degradation. Prilozi. 2009 Jul; 30(1):5-24. doi: . [PMID: 19736528]
  • Y Chen, M B Azad, S B Gibson. Superoxide is the major reactive oxygen species regulating autophagy. Cell death and differentiation. 2009 Jul; 16(7):1040-52. doi: 10.1038/cdd.2009.49. [PMID: 19407826]
  • Jinping Zhang, Anheng Liu, Rongrong Hou, Juan Zhang, Xin Jia, Weifeng Jiang, Jianzong Chen. Salidroside protects cardiomyocyte against hypoxia-induced death: a HIF-1alpha-activated and VEGF-mediated pathway. European journal of pharmacology. 2009 Apr; 607(1-3):6-14. doi: 10.1016/j.ejphar.2009.01.046. [PMID: 19326475]
  • Amye J Tevaarwerk, Kyle D Holen, Dona B Alberti, Carolyn Sidor, Jamie Arnott, Check Quon, George Wilding, Glenn Liu. Phase I trial of 2-methoxyestradiol NanoCrystal dispersion in advanced solid malignancies. Clinical cancer research : an official journal of the American Association for Cancer Research. 2009 Feb; 15(4):1460-5. doi: 10.1158/1078-0432.ccr-08-1599. [PMID: 19228747]
  • E Kirches, M Warich-Kirches. 2-methoxyestradiol as a potential cytostatic drug in gliomas?. Anti-cancer agents in medicinal chemistry. 2009 Jan; 9(1):55-65. doi: 10.2174/187152009787047725. [PMID: 19149482]
  • Ernest Brahn, Mona L Banquerigo, John K Lee, Eun J Park, William E Fogler, Stacy M Plum. An angiogenesis inhibitor, 2-methoxyestradiol, involutes rat collagen-induced arthritis and suppresses gene expression of synovial vascular endothelial growth factor and basic fibroblast growth factor. The Journal of rheumatology. 2008 Nov; 35(11):2119-28. doi: 10.3899/jrheum.080302. [PMID: 18792999]
  • Keizo Kanasaki, Kristin Palmsten, Hikaru Sugimoto, Shakil Ahmad, Yuki Hamano, Liang Xie, Samuel Parry, Hellmut G Augustin, Vincent H Gattone, Judah Folkman, Jerome F Strauss, Raghu Kalluri. Deficiency in catechol-O-methyltransferase and 2-methoxyoestradiol is associated with pre-eclampsia. Nature. 2008 Jun; 453(7198):1117-21. doi: 10.1038/nature06951. [PMID: 18469803]