2-Methoxyestrone
(Synonyms: 2-甲基雌酮) 目录号 : GC33810
An active metabolite of estrone
Cas No.:362-08-3
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
2-methoxy Estrone is an active metabolite of the endogenous estrogen estrone .1 It is formed from estrone by catechol-O-methyltransferase (COMT). 2-methoxy Estrone inhibits the proliferation of isolated bovine brain-derived capillary endothelial cells (IC50 = 11.5 ?M).2 It increases the levels of 6-keto prostaglandin F1α in human umbilical vein endothelial cells (HUVECs) when used at concentrations of 0.001, 0.01, and 0.1 ?M.3 2-methoxy Estrone (0.5 mg/kg) reduces ovariectomy-induced increases in serum cholesterol in rats.4
1.Dawling, S., Roodi, N., Mernaugh, R.L., et al.Catechol-O-methyltransferase (COMT)-mediated metabolism of catechol estrogens: Comparison of wild-type and variant COMT isoformsCancer Res.61(18)6716-6722(2001) 2.Fotsis, T., Zhang, Y., Pepper, M.S., et al.The endogenous oestrogen metabolite 2-methoxyoestradiol inhibits angiogenesis and suppresses tumour growthNature368(6468)237-239(1994) 3.Seeger, H., Mueck, A.O., and Lippert, T.H.Effect of estradiol metabolites on prostacyclin synthesis in human endothelial cell culturesLife Sci.65(13)PL167-PL170(1999) 4.Liu, D., and Bachmann, K.A.An investigation of the relationship between estrogen, estrogen metabolites and blood cholesterol levels in ovariectomized ratsJ. Pharmacol. Exp. Ther.286(1)561-568(1998)
| Cas No. | 362-08-3 | SDF | |
| 别名 | 2-甲基雌酮 | ||
| Canonical SMILES | C[C@]1([C@](CC2)([H])[C@]3([H])CCC4=C(C=C(OC)C(O)=C4)[C@@]3([H])CC1)C2=O | ||
| 分子式 | C19H24O3 | 分子量 | 300.39 |
| 溶解度 | DMSO : 50 mg/mL (166.45 mM; Need ultrasonic) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.329 mL | 16.645 mL | 33.2901 mL |
| 5 mM | 0.6658 mL | 3.329 mL | 6.658 mL |
| 10 mM | 0.3329 mL | 1.6645 mL | 3.329 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
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| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
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Inhibition of deoxyglucose uptake in MCF-7 breast cancer cells by 2-Methoxyestrone and 2-methoxyestrone-3-O-sulfamate
Mol Cell Endocrinol 2000 Feb 25;160(1-2):61-6.PMID:10715539DOI:10.1016/s0303-7207(99)00256-7.
Most cancer cells are dependent on glucose uptake to fulfil their energy requirements. In the present investigation we have examined the ability of 2-Methoxyestrone (2-MeOE1), 2-methoxyestradiol (2-MeOE2), 2-methoxyestrone-3-O-sulfamate (2-MeOEMATE), and a number of related compounds, to inhibit 2-deoxy-D-[1-(3)H]-glucose uptake in MCF-7 breast cancer cells. Glucose uptake was shown to be linear with respect to cell number and time over a 5-35min period. 2-MeOE2, 2-MeOE1 and 2-MeOEMATE inhibited glucose uptake by 25-49% at 10 microM. 2-Hydroxyestradiol and estrone sulfate had little effect on glucose uptake, whereas estrone glucuronide inhibited uptake by 29%. There is evidence that 2-methoxyestrogens may exert an anti-mitotic effect on cells by stabilizing microtubules in a similar manner to that of paclitaxel. We therefore examined the effect of exposing cells to 2-MeOEMATE or paclitaxel for 24 h on basal or insulin stimulated glucose uptake. Using these conditions, 2-MeOEMATE and paclitaxel inhibited basal glucose uptake by 50 and 22%, respectively, and insulin stimulated uptake by 36 and 51%, respectively. The development of drugs that can inhibit glucose uptake could have therapeutic potential for the treatment of breast cancer.
Radioimmunoassay of 2-hydroxyesterone and 2-Methoxyestrone in human urine
Steroids 1979 May;33(5):563-76.PMID:462497DOI:10.1016/0039-128x(79)90036-9.
An assay for the quantitative determination of 2-hydroxyestrone and 2-Methoxyestrone in human urine is described. The analytical procedure involves several purification steps: XAD-2 column chromatography of urine (1 ml), hot acid hydrolysis under reducing conditions, extraction with benzene/ethyl acetate, separation of monophenolic steroids from catecholestrogens by the formation of borate complexes, and partition between different solvents. Quantitation is achieved by radioimmunoassay using highly specific antibodies. For correction of procedural losses [6, 7-3H2] 2-hydroxyestrone and [6, 7-3H2] 2-Methoxyestrone are used as internal standards. The method is highly specific as checked by comparison to a double-isotope-derivative method and a newly developed gas chromatography-mass spectrometry procedure. Using this method the urinary excretion of 2-hydroxyestrone and 2-Methoxyestrone was studied in children, men, cycling, pregnant and postmenopausal women. Special interest was focussed on the molar ratios of 2-hydroxyestrone to 2-Methoxyestrone and the so called "total estrogens" which vary markedly within the different groups investigated. The excretion of 2-hydroxyestrone is especially favoured in women during the menstrual cycle and pregnancy.
2-Hydroxyestrone suppresses and 2-Methoxyestrone augments the preovulatory prolactin surge in the cycling rat
Endocrinology 1982 Apr;110(4):1448-50.PMID:7199421DOI:10.1210/endo-110-4-1448.
The nonuterotropic metabolite of estradiol, 2-hydroxyestrone, administered at noon of proestrus to four-day cycling rats, abolishes the preovulatory prolactin rise in a large percentage of animals tested. In animals synchronized with exogenous estradiol, 2-hydroxyestrone universally induced a long delay in the prolactin surge. The principal metabolite of 2-hydroxyestrone, 2-Methoxyestrone, given at noon of proestrus, significantly augments the magnitude of the preovulatory prolactin rise possibly by inhibiting the formation of endogenous 2-hydroxyestrogens in the brain. The results obtained are consistent with the concept of a physiological function for 2-hydroxyestrogens as estrogen antagonists in the CNS.
Metabolism of 2-Methoxyestrone in normal men
J Clin Endocrinol Metab 1983 Aug;57(2):277-82.PMID:6863476DOI:10.1210/jcem-57-2-277.
We studied, in four normal men, the metabolism of 2-Methoxyestrone (2-MeOE1) using pulse injections of either [3H]2MeOE1 (two men) or [14C]methoxy-2-MeOE1 plus [3H]2-MeOE1 (two men) by analysis of blood samples drawn at increasing time intervals after the pulse and of urine collected for 5 days. The disappearance from the blood of radioactivity as 2-MeOE1 could be characterized as a function that was the sum of three exponentials. The mean +/- SE value for the initial volume of distribution was 32 +/- 9 liters, and the mean MCR was 2470 +/- 770 liters/day. The disappearance of total 3H radioactivity from the blood was considerably slower, with a mean MCR of 290 +/- 30 liters/day, indicating the presence of a slowly turning over pool of 2-MeOE1 metabolites, probably including the 2-MeOE1 3-sulfate conjugate. The disappearance of total 14C radioactivity was slower than that of total 3H, indicating considerable demethylation of 2-MeOE1 with a very slow excretion of 14C from the released methyl group. In none of the subjects could we find in the blood radioactivity as unconjugated [3H]2-hydroxyestrone ( [3H]2-OHE1). However, examination of the urine indicated that considerable demethylation of [3H]2-MeOE1 had occurred. At least 64% of the urinary 3H-containing metabolites from the mixed dose had lost the 14C-bearing methoxylcarbon atom. The fractionated metabolites were qualitatively and quantitatively similar to those found earlier for [3H]2-OHE1. We conclude that 2-MeOE1, which of itself has little biological activity, can act as a pool of potentially active 2-OHE1 in the tissues.
The role of 2-Methoxyestrone in estrogen action
J Steroid Biochem 1983 Jul;19(1B):635-8.PMID:6310247DOI:10.1016/0022-4731(83)90229-7.
The plasma and tissue concentrations of 2-Methoxyestrone (2-MeOE1) and 2-hydroxyestrone (2-OHE1) were measured in immature rats. The plasma levels of 2-MeOE1 were found to be high at birth and to decrease through puberty, when the low levels found in the adult rats were achieved. 2-OHE1 was undetectable in the plasma and brain, and barely detectable in the uterus and liver. 2-MeOE1 was undetectable in the brain and uterus, but high in the liver. The affinity of 2-MeOE1 and 2-OHE1 for rat alpha-fetoprotein was found to be low, while the affinity of estradiol, estrone, 4-hydroxyestrone, and 4-fluoroestradiol was high. This data suggests that 2-OHE1 and 2-MeOE1 would be available to estrogen target tissues in the fetal and neonatal rat. Although these metabolites lack uterotropic activity they are capable of acting in the liver. It is suggested that the plasma 2-MeOE1 of neonatal rats acts as a prohormone capable of stimulating the liver and other estrogen target tissues which possess demethylating enzymes. It is pointed out that unlike estradiol the non-steroidal estrogens such as diethylstibestrol (DES) lack the ability to form two sets of catechol and guaicol metabolites, i.e. "C-2" and "C-4" metabolites with their different biological characteristics are not formed by DES.