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Oxidation of estrone by permanganate: Reaction kinetics and estrogenicity removal

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Chinese Science Bulletin 2010年第9期55卷 802-808页

作者： XiaoLing Shao Jun Ma Gang Wen JingJing Yang Harbin Inst Technol Sch Municipal & Environm Engn Harbin 150090 Peoples R China

Permanganate was used as an oxidant to control estrone in the present study. Kinetics was determined at pH 2.5-9.4 and temperature 15–40°C for the reaction of estrone with potassium permanganate. It was found that the reaction is second-order overall and first-order with respect to both estrone and permanganate. The second-order rate constant for the reaction at pH 5.8 and 25°C is 44.45 L mol-1 s-1. The reaction rate first decreased with the increase of pH in the range of 2.5-6.6 and then increased greatly with the increase of pH in the range of 6.6-9.4. In addition, the rate constant exponentially increased with the increase of reaction temperature. Removal of estrogenicity was also investigated during the degradation of estrone using yeast estrogen screen (YES). Results show that the estrogenicity increased in the initial 15 min of reaction and then decreased fast, with a removal rate of 73.8% within the 30 min of reaction. Results also demonstrate that the reaction rate between estrone and permanganate is faster in natural water background than in the ultra-pure water system. Permanganate oxidation is therefore a feasible option for removal of estrone in drinking water treatment processes. However, the contact time must be enough in order to remove estrone without causing the increase of estrogenicity.

关键词： estrone permanganate rate constants estrogenicity

Molecular Docking Studies of estrone-Coumarin Derivatives as Aromatase and 17β-HSD1 Inhibitors Related to Hormone Receptor Positive (HR+) Breast Cancer

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Advances in Enzyme Research 2022年第4期10卷 83-100页

作者： Silvia Alejandra Meza-Ireta Blanca Colin-Lozano Penélope Merino-Montiel José Luis Vega-Báez Sara Montiel-Smith Facultad de Ciencias Químicas Ciudad Universitaria Benemérita Universidad Autónoma de Puebla Puebla México

Hormone Receptor positive (HR+) breast cancer is the most common malignancy in women. New strategies in the treatments have targeted the estrogen biosynthesis pathways including the inhibition of the aromatase and 17β-HSD1 enzymes. The present work, describes the study of a new family of 9 hybrid compounds derived from estrone attached to a coumarin fragment, linked through different lengths of hydrocarbon chains. The activity of these compounds was evaluated by molecular docking with two relevant enzymes in breast cancer (HR+). It has been proposed nine compounds as 17β-HSD1 inhibitors and six as aromatase inhibitors. We found important interactions with key amino acids at the orthosteric site of each enzyme and their score values compared to the crystallographic ligand. The in silico analysis showed good score values in the proposed compounds, where the steroidal portion presented important interactions with Met374 and Tyr155 in aromatase and in 17β-HSD1 respectively. Highlighting Compounds 2, 5 and 8 with an aromatic ring at the C4 position of the coumarin moiety, which favored arene-H type interactions essential for protein-ligand recognition. In addition, the results related to the 17β-HSD1 enzyme demonstrated how the length of the linker influences the interaction;the best score was found for derivative 8 with a chain of 8 methylenes.

关键词： estrone Coumarins Aromatase Inhibitors 17β-HSD1 Inhibitors Molecular Docking

Simultaneous Determination of Hexoestrol, Diethylstilbestrol, estrone and 17-Beta-estradiol in Feed by Gas Chromatography-mass Spectrometry

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Journal of Northeast Agricultural University(English Edition) 2016年第1期23卷 44-49页

作者： Huo Feng Li Ning Lin Xiao-Li Institute of Veterinary Drug and Food Control Harbin 150010 China

A method was developed for the simultaneous determination of four kinds of estrogens （hexoestrol, diethylstilbestrol, estrone, and 17-beta-estradiol） in feed by gas chromatography-mass spectrometry （GC-MS）. After the sample was extracted by ethyl ether and cleaned-up on HLB phase extraction column, four kinds of estrogens were derived and quantified in gas chromatographymass spectrometry. The results showed that the linear detectable ranged from 2.5 ng· mL-1 to 250 ng· mL-1for hexoestrol and from 5 ng· mL-1 to 500 ng· mL-1 for three other estrogens with the correlation coefficients （R2） were no less than 0.990. The recoveries were in the range of 76.34%-96.33% and the relative standard deviation was no more than 22.7%. The limits of quantitation （LOQ） for all analytics were between 10 ug· kg^-1 and 20 ug· kg^-1. The method was accurate and sensitive and could meet the actual requirements for the analyses of feed samples.

关键词： gas chromatography-mass spectrometry hexoestrol diethylstilbestrol estrone 17-beta-estradiol feed

A SIMPLE TWO-STEP SYNTHESIS OF Δ^(6(7))-estrone

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Chinese Science Bulletin 1983年第8期28卷 1112-1114页

作者：陆海珍范仲文蒋洪德 Shanghai Institute of Biochemistry Academia Sinica No.12 Pharmaceutical Factory of Shanghaiith the continuous developments in labeling techniques assay methods of radioisotopes and their increasing applications in physiological and biochemical research it has become both possible and necessary to supply highly active labeled estrogens. 6 7-~3H_(2-)estrone and 6 7-~3H_(2-)estradiol are the more widely used commercial products of

With the continuous developments in labeling techniques, assay methods of radioisotopes and their increasing applications in physiological and biochemical research, it has become both possible and necessary to supply highly active labeled estrogens. 6, 7-3H2-estrone and 6, 7-3H2-estradiol are the more widely used commercial products

关键词： labeled physiological labeling estradiol biochemical SIMPLE estrone andro ultraviolet estrogen

Enzymatic treatment of estrogens and estrogen glucuronide

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Journal of Environmental Sciences 2009年第6期21卷 731-735页

作者： Takaaki Tanaka Toshiyuki Tamura Yuuichi Ishizaki Akito Kawasaki Tomokazu Kawase Masahiro Teraguchi Masayuki Taniguchi Department of Materials Science and Technology Niigata University Venture Business Laboratory Niigata University Department of Chemistry and Chemical Engineering Niigata University

Natural and synthetic estrogens from sewage treatment systems are suspected to influence the reproductive health of the animals in the rivers. In this article, we investigated the enzymatic treatment of three estrogens （estrone, 17β-estradiol, and 17α-ethynyletstradiol） by a fungal laccase which oxidize phenolic compounds with dissolved oxygen. The elimination of the estrogenic activities by enzymatic oxidation was demonstrated by medaka vitellogenin assay. In addition, we developed an enzymatic treatment system comprised of β-D-glucuronidase and the laccase for 17β-estradiol 3-（β-D-glucuronide） degradation. The two enzymes eliminated 17β-estradiol 3-（β- D-glucuronide） and the intermediate, 17β-estradiol, efficiently.

关键词： enzymatic treatment laccase estrone estradiol ethynylestradiol glucuronidase glucuronide

Rapid Microwave Assisted Synthesis and Antiproliferative Evaluation of Novel Steroidal Thiazole Derivatives

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Chemical Research in Chinese Universities 2017年第2期33卷 206-212页

作者： HUANG Yanmin ZHAO Dandan LIU Chang GAN Chunfang ZHAN Junyan LIN Qifu SHI Haixin CUI Jianguo College of Chemistry and Material Science Guangxi Teachers Education University Nanning 530001 P. R. China Guangxi Colleges and University Key Laboratory of Beibu Gulf Oil and Natural Gas Resource Effectfve Utffizat~'on Qizhou University Qizhou 535011 P. R. China

Three series of novel steroidal thiazole derivatives were synthesized by microwave assisted one-potreaction from pregnenolone, testosterone and estrone, respectively. Their structures were characterized by IR, NMRand HRMS, and the antiproliferative activities of all the synthesized compounds against human cervical carcinoma（HeLa）, human liver carcinoma（HepG2）, human lung carcinoma（A549）, nasopharyngeal carcinoma（CNE2） andnormal kidney epithelial cells（HEK293T） were screened. Among the compounds, 1-estron-17＇-ylidene-2-[4＇-（p-bromophenyl）-2＇-thiazol]hydrazone（12） displayed distinct antiproliferative activity against all the tested cancercell lines and was almost inactive to normal kidney epithelial cells.

关键词： Microwave assisted synthesis Pregnenolone Testosterone estrone Steroidal thiazole derivative

Effect of Irradiation Wavelength on Kinetics of Direct Photodegradation of estrone

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Effect of Irradiation Wavelength on Kinetics of Direct Photo...

Drinking water safety： science, technology, engineering and policy

作者： Yiwei Deng Paul Diven Padma Kadiyala the Department of Natural Sciences University of Michigan-Dearborn

Natural and synthetic estrogens present a potential threat to aquatic life.This is due to their alarming effects on reproduction and developmental processes of aquatic organisms.These estrogens disrupt the organisms’ endocrine systems and decreased their fertility.The estrogens reach the aquatic environment through urban and industrial waste discharges.Irradiation of the wastewater under ultra-violet light showed that these estrogens could be degraded.In this study, estrone(E1) was chosen as a representative of the estrogens.The photochemical behavior of E1 was investigated under ultra-violet irradiation at 254 nm and 350 nm.The photodegradation of E1 yielded several intermediates.The concentrations of estrone and the intermediates were monitored during photodegradation using a high performance liquid chromatography(HPLC) method.The photodegradation of E1 at both wavelengths followed pseudo-first-order kinetics with respect to E1 concentration.The HPLC chromatograms indicated that three peaks were sequentially formed with time through plausible consecutive reactions.Further study is needed to identify the reaction intermediates/products in order to propose the detailed reaction mechanisms.

关键词： estrone photodegradation steriod estrogens

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Frontiers of Environmental Science & Engineering 2015年第1期9卷 2-2页

作者： Jun MA David RECKHOW Yuefeng XIE School of Environmental and Municipal Engineering Harbin Institute of Technology Harbin 150090 China Department of Civil and Environmental Engineering University of Massachusetts at Amherst Amherst MA 01003 USA Environmental Engineering Programs The Pennsylvania State University Middletown PA 17057 USA

Safe drinking water is crucial for protecting public health, a top-priority of environmental professionals. In order to prevent or remediate the numerous environmental problems that exist in current drinking water systems, there is an urgent need to develop innovative and efficient science, technology, engineering and policy as a means to reduce potential risks. Emerging contaminants, including pharmaceuticals and personal care products, have gained great attention in water treatment. The removal of estrone, bisphenol A, nitrofurazone and oxytetracycline was investigated in three studies. Chlorinated aromatics, as pollutants from chemical spills, were also investigated. Ultrafiltration, in combination with ozonation and enhanced coagulation, was investigated for its removal of organic matters and fouling mechanisms, respectively. The occurrence and control of manganese and aggregation kinetics of manganese dioxide colloids were topics of two other papers.

关键词： Drinking Water Analytic Hierarchy Process estrone Natural Organic Matter Oxytetracycline

11β-【4-(N,N-二甲氨基)苯基】-17α-(丙炔-1)Δ-4.9一雌甾二烯-17β-羟-3-酮(RU-486)的合成

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中国药科大学学报 1986年第4期 282-285页

作者：陈连植盛时方秀如杨晓陈蓓宁施菊芳刘才夏彭司勋南京药学院药物化学教研室南京药学院药物化学教研室研究生

抗旱孕药物的研究对计划生育具有重要意义。Jean G T等合成了系列11-β取代19去甲基孕激素类化合物,发现11β-[4-(N,N—二甲氨基)苯基]-17α-(丙炔-1)-Δ-雌甾二烯-17β-羟-3-酮具有抗旱孕的活性(简称RU-486)。它是一种结构新型的抗早孕... 详细信息

抗旱孕药物的研究对计划生育具有重要意义。Jean G T等合成了系列11-β取代19去甲基孕激素类化合物,发现11β-[4-(N,N—二甲氨基)苯基]-17α-(丙炔-1)-Δ-雌甾二烯-17β-羟-3-酮具有抗旱孕的活性(简称RU-486)。它是一种结构新型的抗早孕药,具有终止娠妊的作用。药理学研究表明RU-486与孕激素受体有较强的亲和力,能阻

关键词： RU-486 Antiprogestone agent estrone 11β-(4-dimethyl-aminophenyl)-17β-hydroxy-17(?)-(1-propynyl)-estra-4 9-dien-3-one.