雌三醇-16beta-D-葡糖苷酸 | 1852-50-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 中文名称: 雌三醇-16beta-D-葡糖苷酸
• 中文别名: 雌三醇-16alfa-(beta-D-葡糖苷酸)；3,17b-二羟基-1,3,5(10)-雌甾三烯-16a-基-beta-D-葡糖苷酸
• 英文名称: estriol-16α-D-glucoronide
• 英文别名: Estriol O16-glucuronide；3,17β-dihydroxy-1,3,5(10)-estratrien-16α-yl-β-D-glucopyranosiduronic acid；estriol 16α-β-D-glucuronide；estriol 16-(β-glucuronide)；estriol-16α-glucuronide；estriol 16 glucuronide；16-Glucuronide-estriol；(2S,3S,4S,5R,6R)-6-[[(8R,9S,13S,14S,16R,17R)-3,17-dihydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-16-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• CAS: 1852-50-2
• 化学式: C₂₄H₃₂O₉
• 分子量: 464.513
• InChiKey: FQYGGFDZJFIDPU-JRSYHJKYSA-N

物化性质

• 沸点：
  738.3±60.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  33
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.708
• 拓扑面积：
  157
• 氢给体数：
  6
• 氢受体数：
  9

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S36/37
• 危险类别码：
  R40
• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  雌三醇-16beta-D-葡糖苷酸 在 palladium on activated charcoal N-羟基丁二酰亚胺 、 氢气 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 为溶剂， 反应 16.0h， 生成 N-(6-aminohexyl)-(3,17β-hydroxy-1,3,5(10)-estratrien-16α-yl-β-D-glucopyranosid)uronamide
  参考文献：
  名称：

  Studies on immunological assay of urinary estrogens. III. A new latex agglutination inhibition reaction method.

  摘要：

  本文描述了一种简单、快速的新方法，用于检测妊娠尿液中的雌激素。该方法的原理基于固-固体系中的乳胶凝集抑制反应。通过用山羊产生的抗雌三醇16-葡萄糖醛酸苷抗体使乳胶颗粒敏感化，获得抗体乳胶试剂（Ab-Latex）。通过缩聚聚丙烯酸与雌三醇16-葡萄糖醛酸苷（E3-16-G）和赖氨酸-乳胶（由羧酸改性乳胶制备）的缩聚反应，制备出雌三醇16-葡萄糖醛酸苷结合乳胶试剂（E3-16-G-Latex）。六亚甲基二胺用于将E3-16-G与聚丙烯酸结合。乳胶凝集抑制试验在不透明的玻璃载玻片上进行。将一滴（30μl）Ab-Latex悬浮液和一滴E3-16-G-Latex悬浮液滴加到一滴稀释的尿液样本中，并充分混合。轻轻旋转载玻片2分钟，在雌激素浓度为0.1μg/ml（作为雌三醇）或更高时，观察到肉眼可见的凝集抑制模式。尿液中的雌激素值可通过将灵敏度乘以能够产生阳性反应的最高稀释因子来获得。该试验不仅与游离雌三醇发生交叉反应，还与所有在类固醇环中第3位具有游离

  DOI：

  10.1248/cpb.29.1335
• 作为产物：
  描述：

  雌三醇 在 吡啶 、 sodium hydroxide 、 无水碳酸镉 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 106.5h， 生成 雌三醇-16beta-D-葡糖苷酸
  参考文献：
  名称：

  The synthesis of estriol 16- and 17-monoglucuronide from estriol

  摘要：

  An efficient and convenient procedure for the synthesis of estriol 16- and 17-monoglucuronides from estriol is described. This is achieved by the selective protection and deprotection of the hydroxy groups in estriol, Koenigs-Knorr reactions with methyl 1-bromo-1-deoxy-2,3,4-tri-O-acetyl-alpha-D-glucopyranuronate and subsequent hydrolysis. The products have been characterized by proton nuclear magnetic resonance (1H NMR), two-dimensional 1H homonuclear shift-correlated spectra (2D-COSY) and mass spectra. The selective Koenigs-Knorr reaction of the alcoholic hydroxyl group in the presence of a phenolic hydroxyl group is also reported.

  DOI：

  10.1016/0039-128x(93)90001-4

文献信息

• Regiospecificity and Stereospecificity of Human UDP-Glucuronosyltransferases in the Glucuronidation of Estriol, 16-Epiestriol, 17-Epiestriol, and 13-Epiestradiol
  作者：Nina Sneitz、Mikko Vahermo、Johanna Mosorin、Liisa Laakkonen、Donald Poirier、Moshe Finel

  DOI：10.1124/dmd.112.049072

  日期：2013.3

  The glucuronidation of estriol, 16-epiestriol, and 17-epiestriol by the human UDP-glucuronosyltransferases (UGTs) of subfamilies 1A, 2A, and 2B was examined. UGT1A10 is highly active in the conjugation of the 3-OH in all these estriols, whereas UGT2B7 is the most active UGT toward one of the ring D hydroxyls, the 16-OH in estriol and 16-epiestriol, but the 17-OH in 17-epiestriol. Kinetic analyses indicated that the 17-OH configuration plays a major role in the affinity of UGT2B7 for estrogens. The glucuronidation of the different estriols by the human liver and intestine microsomes reflects the activity of UGT1A10 and UGT2B7 in combination with the tissues’ difference in UGT1A10 expression. The UGT1A10 mutant 1A10-F93G exhibited much higher V max values than UGT1A10 in estriol and 17-epiestriol glucuronidation, but a significantly lower value in 16-epiestriol glucuronidation. To this study on estriol glucuronidation we have added experiments with 13-epiestradiol, a synthetic estradiol in which the spatial arrangement of the methyl on C18 and the hydroxyl on C17 is significantly different than in other estrogens. In comparison with estradiol glucuronidation, the C13 configuration change decreases the turnover of UGTs that conjugate the 3-OH, but increases it in UGTs that primarily conjugate the 17-OH. Unexpectedly, UGT2B17 exhibited similar conjugation rates of both the 17-OH and 3-OH of 13-espiestradiol. The combined results reveal the strong preference of UGT1A10 for the 3-OH of physiologic estrogens and the equivalently strong preference of UGT2B7 and UGT2B17 for the hydroxyls on ring D of such steroid hormones.

  检查了亚家族 1A、2A 和 2B 的人 UDP-葡萄糖醛酸基转移酶 (UGT) 对雌三醇、16-表三醇和 17-表三醇的葡萄糖醛酸化。 UGT1A10 在所有这些雌三醇中的 3-OH 缀合中具有高度活性，而 UGT2B7 是对 D 环羟基之一（雌三醇和 16-表三醇中的 16-OH）最活跃的 UGT，但 17 中的 17-OH -表三醇。动力学分析表明，17-OH构型在UGT2B7与雌激素的亲和力中起主要作用。人肝和肠微粒体对不同雌三醇的葡萄糖醛酸化反映了UGT1A10和UGT2B7的活性以及组织中UGT1A10表达的差异。 UGT1A10突变体1A10-F93G在雌三醇和17-表三醇葡萄糖醛酸化中表现出比UGT1A10高得多的V max 值，但在16-表三醇葡萄糖醛酸化中表现出显着较低的值。在这项关于雌三醇葡萄糖醛酸化的研究中，我们添加了 13-表雌二醇的实验，这是一种合成雌二醇，其中 C18 上的甲基和 C17 上的羟基的空间排列与其他雌激素显着不同。与雌二醇葡萄糖醛酸化相比，C13构型变化降低了缀合3-OH的UGT的周转率，但增加了主要缀合17-OH的UGT的周转率。出乎意料的是，UGT2B17 表现出与 13-espiestradiol 的 17-OH 和 3-OH 相似的缀合率。综合结果揭示了UGT1A10对生理雌激素的3-OH的强烈偏好，以及UGT2B7和UGT2B17对此类类固醇激素的环D上的羟基的同样强烈的偏好。
• Functional associative coatings for nanoparticles
  申请人：Hainfeld James F.

  公开号：US20080089836A1

  公开（公告）日：2008-04-17

  Described herein are nanoparticles that are coated with a bilayer of molecules formed from surface binding molecules and amphiphatic molecules. The bilayer coating self assembles on the nanoparticles from readily available materials/molecules. The modular design of the bilayer coated nanoparticles provides a means for readily and efficiently optimizing the properties of the bilayer coated nanoparticle compositions. Also described herein are uses of such nanoparticles in medicine, laboratory techniques, industrial and commerical applications.

  本文描述了一种纳米颗粒，其表面涂覆有由表面结合分子和两亲分子形成的双层分子层。该双层涂层可以自组装在纳米颗粒上，使用易得的材料/分子。双层涂层纳米颗粒的模块化设计提供了一种方便和高效地优化其性质的方法。此外，本文还描述了这种纳米颗粒在医学、实验室技术、工业和商业应用中的用途。
• ISOLATION MATERIAL FOR HORMONE DISRUPTING SUBSTANCE, METHOD OF CONCENTRATING AND METHOD OF CLEAN-UP
  申请人：Japan Envirochemicals, Ltd.

  公开号：EP1514597A1

  公开（公告）日：2005-03-16

  The present invention relates to an isolation material for an endocrine disruptor, which is prepared by immobilizing an anti-endocrine disruptor antibody to a graft-chain-containing carrier made of a polymeric material via covalent binding. According to the present invention, an isolation material for an endocrine disruptor, which is capable of specific and efficient isolation of an endocrine disruptor, and an endocrine disruptor concentration and a clean-up method capable of specific and efficient concentration or clean-up of an endocrine disruptor at a high rate can be afforded.

  本发明涉及一种内分泌干扰物的分离材料，其制备方法是通过共价结合将抗内分泌干扰物抗体固定在聚合物材料制成的含接枝链载体上。根据本发明，可以提供一种用于内分泌干扰物的分离材料，该材料能够特异、高效地分离内分泌干扰物，还可以提供一种内分泌干扰物浓缩和净化方法，该方法能够特异、高效地浓缩或高速净化内分泌干扰物。
• Ogushi, Susumu; Koga, Satoshi; Ito, Kiyoshi, Agricultural and Biological Chemistry, 1986, vol. 50, # 12, p. 3093 - 3100
  作者：Ogushi, Susumu、Koga, Satoshi、Ito, Kiyoshi、Makino, Yasutaka、Ando, Makoto、Tsuru, Daisuke

  DOI：——

  日期：——
• An assay for urinary estriol-16α-glucuronide based on antibody-enhanced chemiluminescence
  作者：F. Kohen、J.B. Kim、G. Barnard、H.R. Lindner

  DOI：10.1016/0039-128x(80)90029-x

  日期：1980.10

  An immunoassay for estriol-16 alpha-glucuronide in pregnancy urine is described that utilizes antibody-enhanced chemiluminescence. The steroid glucuronide was covalently conjugated with the chemiluminescent marker aminobutyl-ethyl-isoluminol. The light yield of this conjugate upon oxidation was augmented by specific antibody, and this effect was inhibited by addition of the homologous steroid glucuronide (10-100 pg) in a dose-dependent manner. The assay does not require separation of bound and free ligand and proved satisfactory with respect to sensitivity, precision and accuracy. Assay results obtained by radioimmunoassay and chemiluminescence immunoassay were in good agreement (r = 0.98; n = 25).