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16-Ketoestradiol Sale

(Synonyms: 16-keto E2, NSC 51169, 16-Oxoestradiol) 目录号 : GC49848

An active metabolite of estrone

16-Ketoestradiol Chemical Structure

Cas No.:566-75-6

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产品描述

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)

Chemical Properties

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
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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
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Research Update

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.