16-Ketoestradiol
(Synonyms: 16-keto E2, NSC 51169, 16-Oxoestradiol) 目录号 : GC49848
An active metabolite of estrone
Cas No.:566-75-6
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
16-Ketoestradiol is an active metabolite of the endogenous estrogen estrone .1 It is formed from estrone via an estriol or a 16-epiestriol intermediate by oxidation of the C-16 hydroxyl. 16-Ketoestradiol binds to estrogen receptor α (ERα) and ERβ with IC50 values of 112.2 and 50.1 nM for the human receptors, respectively.2 Intravaginal administration of 16-ketoestradiol increases vaginal epithelial thickness, stratification, and cornification in mice, indicating antiestrogenic activity.3
1.Brinton, L.A., Trabert, B., Anderson, G.L., et al.Serum estrogens and estrogen metabolites and endometrial cancer risk among postmenopausal womenCancer Epidemiol. Biomarkers Prev.25(7)1081-1089(2016) 2.Zhu, B.T., Han, G.-Z., Shim, J.-Y., et al.Quantitative structure-activity relationship of various endogenous estrogen metabolites for human estrogen receptor α and β subtypes: Insights into the structural determinants favoring a differential subtype bindingEndocrinology147(9)4132-4150(2006) 3.Martin, L.Dimethylstilbestrol and 16-oxo-estradiol: Anti-estrogens or estrogens•Steroids13(1)1-10(1969)
| Cas No. | 566-75-6 | SDF | Download SDF |
| 别名 | 16-keto E2, NSC 51169, 16-Oxoestradiol | ||
| Canonical SMILES | C[C@@]12[C@](CC([C@@H]2O)=O)([H])[C@@]3([H])[C@@](CC1)([H])C4=CC=C(O)C=C4CC3 | ||
| 分子式 | C18H22O3 | 分子量 | 286.4 |
| 溶解度 | DMSO: slightly soluble,Ethanol: slightly soluble,Methanol: slightly soluble | 储存条件 | -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 | 3.4916 mL | 17.4581 mL | 34.9162 mL |
| 5 mM | 0.6983 mL | 3.4916 mL | 6.9832 mL |
| 10 mM | 0.3492 mL | 1.7458 mL | 3.4916 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 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % 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。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
ESTROGEN-INDUCED 16-HYDROXYSTEROID DEHYDROGENASE ACTIVITY IN RAT KIDNEY
Science 1963 Oct 11;142(3589):243-4.PMID:14057375DOI:10.1126/science.142.3589.243.
The activity of an enzyme system which readily converts estriol to 16-Ketoestradiol is present only in the kidneys of mature female rats and is absent in the kidneys of male rats and immature rats of either sex. The full enzyme activity occurs in kidneys of rats of either sex at any stage of maturity after administration of estradiol for 2 weeks. The time course of the appearance and disappearance of the enzyme, the absence of detectable inhibitors and activators, and evaluation of cofactor requirements suggest that this may be an example of enzyme induction by the hormone. Furthermore, the enzyme activity itself represents a metabolic pathway for estriol metabolism whose potential quantitative significance has not heretofore been recognized.
Estrogen metabolites in human corpus luteum physiology: differential effects on angiogenic activity
Fertil Steril 2016 Jul;106(1):230-237.e1.PMID:26994433DOI:10.1016/j.fertnstert.2016.03.003.
Objective: To determine tissue concentrations of E2, estrone, P, and estrogens metabolites (EMs) 2-methoxyestradiol, 2-methoxyestrone, 4-hydroxyestrone, and 16-Ketoestradiol in corpus luteum (CL) of different ages, and after hCG administration; and to examine the effects of EMs on vascular endothelial growth factor (VEGF) secretion and angiogenic activity released by cultured luteinizing granulosa cells in the presence and absence of hCG. Design: Experimental study. Setting: University. Patient(s): Thirty-two healthy women of reproductive age. Intervention(s): Corpus luteum was collected at the time of minilaparotomy for tubal sterilization, at varying stages of the luteal phase (LP). Late-LP CL was collected 24 hours after IM administration of 10,000 IU hCG. Granulosa cells were isolated from follicular aspirates obtained from healthy women participating in our IVF program for male factor infertility. Main outcomes measure(s): Estrogen metabolite concentrations were determined in CL tissue, and VEGF was assessed in conditioned medium. The angiogenic activity was analyzed by bioassay. Result(s): Concentrations of EMs with proangiogenic activity (16-Ketoestradiol and 4-hydroxyestrone) were higher in early and mid-LP CL vs. late-LP CL. These EMs and hCG increased VEGF production and angiogenic activity. Conversely, late-LP CL had significantly higher levels of 2-methoxyestrone and 2-methoxyestradiol, which have antiangiogenic activity. Administration of hCG reduced the production of these EMs. Conclusion(s): Our findings suggest that the EMs are important paracrine modulators of CL function. Administration of hCG increases the production of EMs with proangiogenic activity and reduces the secretion of those EMs with antiangiogenic action, suggesting a novel mechanism by which the late-LP CL is rescued in conception cycles.
[Excretion of estriol, estetrol, 16-epi-estriol, 16-keto-estradiol and 16-hydroxyestrone in the 24-hour urine of pregnant women in the last trimester]
Endokrinologie 1975 Aug;65(3):254-65.PMID:1222727doi
In this publication a method is given which allows simultaneous estimation of estriol, estetrol, 16-epiestriol, 16-Ketoestradiol and 16-hydroxyestrone in urine of pregnant women. First conjugates are precipitated with ammoniumsulfate and hydrolyzed. Then the steroids are extracted and converted to azodyes by reacting with the diazonium salt dark blue r. After separation by thin layer chromatography the azodyes are measured by remission analysis with a chromatogramm spectrophotometer. From the data obtained from 66 cases norm groups were set up for the excretion of the steroids in the 3rd trimester of pregnancy. In the last month of pregnancy the average excretion, expressed in % of excreted estriol, is as follows: estetrol 5,7%, 16-epiestriol 3,1%, 16-Ketoestradiol 7,0%, 16-hydroxyestrone 5,3%.
Urinary oestrogen steroidome as an indicator of the risk of localised prostate cancer progression
Br J Cancer 2021 Jul;125(1):78-84.PMID:33828256DOI:10.1038/s41416-021-01376-z.
Background: Prostate cancer (PCa) is the most common cancer in North American men. Beyond the established contribution of androgens to disease progression, growing evidence suggest that oestrogen-related pathways might also be of clinical importance. The aim of this study was to explore the association of urinary oestrogen levels with clinical outcomes. Methods: Urine samples from the prospective multi-institutional PROCURE cohort were collected before RP for discovery (n = 259) and validation (n = 253). Urinary total oestrogens (unconjugated + conjugated), including oestrone and oestradiol, their bioactive and inactive catechol and methyl derivatives (n = 15), were measured using mass spectrometry (MS). Results: The median follow-up time for the discovery and replication cohorts was 7.6 and 6.5 years, respectively. Highly significant correlations between urinary oestrogens were observed; however, correlations with circulating oestrogens were modest. Our findings indicate that higher levels of urinary oestriol and 16-Ketoestradiol were associated with lower risk of BCR. In contrast, higher levels of 2-methoxyestrone were associated with an increased risk of development of metastasis/deaths. Conclusions: Our data suggest that urinary levels of oestriol and 16-Ketoestradiol metabolites are associated with a more favourable outcome, whereas those of 2-methoxyestrone are associated with an elevated risk of metastasis after RP. Further studies are required to better understand the impact of oestrogens on disease biology and as easily accessible urine-based risk-stratification markers.
Twelve natural estrogens in urines of swine and cattle: Concentration profiles and importance of eight less-studied
Sci Total Environ 2022 Jan 10;803:150042.PMID:34525709DOI:10.1016/j.scitotenv.2021.150042.
Although four major natural estrogens (i.e., estrone (E1), 17β-estradiol (E2), estriol (E3) and 17α-estradiol (αE2)) have been commonly found in livestock urine, this study reports the occurrence of eight other less-studied natural estrogens in urine of swine and cattle, i.e. 2-hydroxyestone (2OHE1), 4-hydroxyestrone (4OHE1), 2-hydroxyestradiol (2OHE2), 4-hydroxyestradiol (4OHE2), 16-epiestriol (16epiE3), 16α-hydroxyestrone (16αE1), 16-Ketoestradiol (16ketoE2), and 17epiestriol (17epiE3). Results showed that each estrogen was found in at least one urine sample, and 6 of 8 the less-studied estrogens were present at frequencies of ≥90% in boars, ≥70% in sows, and ≥50% in dairy cattle. Five of eight the less-studied estrogens were present at frequencies of ≥33.3% in four beef cattle and one bull. On a concentration basis, the 8 less-studied natural estrogens represented 73.2%, 85.2%, 39.9%, 47.7%, 26.9%, 56.0% and 44.1% of total concentrations of the twelve natural estrogens when combining data from all animals. Similar results were observed based on estrogen equivalence, which indicated these newly detected eight less-studied natural estrogens were not negligible. This work is the first to figure out the importance of these less-studied natural estrogens in livestock urine, and their potential environmental risks associated with discharge of livestock wastewater should be urgently assessed in a holistic manner.