[{[3,17-dihydroxyestra-1(10),2,4-trien-6-ylidene]amino}oxy]acetic acid | 35048-47-6

• 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
• 英文名称: [{[3,17-dihydroxyestra-1(10),2,4-trien-6-ylidene]amino}oxy]acetic acid
• 英文别名: 17β-estradiol 6-carboxymethyloxime；6-ketoestradiol-17β 6-(O-carboxymethyl)oxime；Estradiol-6-cmo；2-[(E)-[(8R,9S,13S,14S,17S)-3,17-dihydroxy-13-methyl-8,9,11,12,14,15,16,17-octahydro-7H-cyclopenta[a]phenanthren-6-ylidene]amino]oxyacetic acid
• CAS: 35048-47-6
• 化学式: C₂₀H₂₅NO₅
• 分子量: 359.422
• InChiKey: AWARIMYXKAIIGO-FIIMHDCBSA-N

物化性质

• 熔点：
  195-197 °C (decomp)
• 沸点：
  572.6±60.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)
• 溶解度：
  DMSO（轻微）、甲醇（轻微、加热、超声处理）

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  99.4
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

• 安全说明：
  S22,S24/25

反应信息

• 作为反应物：
  描述：

  [{[3,17-dihydroxyestra-1(10),2,4-trien-6-ylidene]amino}oxy]acetic acid 在 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 N-{6-[[({[3,17-dihydroxyestra-1(10),2,4-trien-6-ylidene]amino}oxy)acetyl](methyl)amino]hexyl}-N-methyl-6-{[5-(2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoyl]amino}hexanamide
  参考文献：
  名称：

  Facile Synthesis of CIDs:  Biotinylated Estrone Oximes Efficiently Heterodimerize Estrogen Receptor and Streptavidin Proteins in Yeast Three Hybrid Systems

  摘要：

  We synthesized estrone oximes as chemical inducers of protein heterodimerization (CIDs). Estrone-17-(O-carboxymethyl)oxime coupled to biotinamidocaproic acid via N,N'-dimethylhexane-1,6-diamine efficiently heterodimerizes estrogen receptors (ERs) and streptavidin Y43A in yeast three hybrid systems, activating gene expression over 100-fold at 10 muM. Related hexane-1,6-diamine and estradiol-6-(O-carboxymethyl)oxime derivatives were ineffective CIDs due to low affinity for ERs when bound to streptavidin. Estrone oximes bind ERs with submicromolar affinity and effectively display small molecules to target proteins expressed in yeast.

  DOI：

  10.1021/ol0497537
• 作为产物：
  描述：

  [(8R,9S,13S,14S,17S)-3-乙酰氧基-13-甲基-6-氧代-8,9,11,12,14,15,16,17-八氢-7H-环戊二烯并[a]菲-17-基]乙酸酯 、 羧甲基羟胺半盐酸盐 在 potassium carbonate 作用下， 生成 [{[3,17-dihydroxyestra-1(10),2,4-trien-6-ylidene]amino}oxy]acetic acid
  参考文献：
  名称：

  An Efficient Synthesis of 6-Oxo-17-β-Estradiol and itsO-Carboxymethyl Oxime

  摘要：

  Estradiol was efficiently oxidized into 6-oxo estradiol using pyridinium chlorochromate. Previously reported yields were considerably increased by the use of oxidizing agent adsorbed onto celite. The oxo compound was then transformed into the corresponding O-carboxymethyl oxime derivative in quantitative yield.

  DOI：

  10.1080/00397919808005713

文献信息

• An easy preparation of hapten active esters via solid supported EDAC
  作者：Maciej Adamczyk、Jeffrey R. Fishpaugh、Phillip G. Mattingly

  DOI：10.1016/0040-4039(95)01761-6

  日期：1995.11

  Bioconjugates are preferably prepared by reacting an active ester of the hapten of interest to the protein. Preparation of active esters with solid supported EDAC and N-hydroxysuccinunide or pentafluorophenol affords active esters in excellent yield and purity

  生物缀合物优选地通过使感兴趣的半抗原的活性酯与蛋白质反应来制备。用固体负载的EDAC和N-羟基琥珀酰亚胺或五氟苯酚制备活性酯可提供具有优异收率和纯度的活性酯
• Improved method of determining the amount of estradiol in a fluid sample and a respective kit therefor
  申请人：ABBOTT LABORATORIES

  公开号：EP0982592A2

  公开（公告）日：2000-03-01

  An improved method of determining the amount of estradiol in a fluid sample and a respective kit therefore is disclosed. In particular, the invention discloses specific pretreatment conditions improving the accuracy of estradiol assays carried out on fluid samples. Likewise, appropriate pretreatment solutions to be incorporated into an improved assay kit are disclosed.

  本发明公开了一种测定流体样品中雌二醇含量的改进方法和相应的试剂盒。特别是，本发明公开了特定的预处理条件，可提高对流体样本进行雌二醇检测的准确性。同样，本发明还公开了可用于改进检测试剂盒的适当预处理溶液。
• The synthesis and study of some potential affinity labeling reagents for estrogen receptors
  作者：Thomas Ratajczak、Peter N. Sheppard、Robert J. Capon、Roland Hähnel

  DOI：10.1016/0039-128x(81)90053-2

  日期：1981.11

  The influence of the following affinity labeling reagents on the binding of tritiated estradiol-17 beta (E) by human and calf uterine cytosols was studied: 11 beta-chloromethylestradiol (ORG4333), 2-azidoestradiol (2A-E), 4-azidoestradiol (4A-E), 3-azidohexestrol (3A-H), estradiol-17 beta 17-bromoacetate (E-17BrAc), 6-[O-carbo-(2'-chloroethoxy)methyl] oximinoestradiol (6-CMOEtC1), 17-[O-carbo-(2'-chloroethoxy) methyl] oximinoestrone (17-CMOEtCl), 2-di (2'-hydroxy-3'-chloropropyl)aminoestradiol (E-Mustard). For the human uterine estrogen receptor the relative binding affinity decreased in the order E greater than ORG 4333 greater than E-17BrAc greater than 3A-H greater than 2A-E greater than 4A-E greater than 6-CMOEtCl greater than E-Mustard greater than 17-CMOEtCl. The binding characteristics of the calf uterine estrogen receptor were qualitatively similar, but quantitatively different. ORG 4333 appeared to form a highly stable association with the receptors, but alkylation of the protein could not be conclusively demonstrated.
• Evaluation of chemiluminescent estradiol conjugates by using a surface plasmon resonance detector
  作者：Maciej Adamczyk、Yon-Yih Chen、John C Gebler、Donald D Johnson、Phillip G Mattingly、Jeffrey A Moore、Rajarathnam E Reddy、Jiang Wu、Zhiguang Yu

  DOI：10.1016/s0039-128x(00)00091-x

  日期：2000.6

  A series of chemiluminescent 17 beta-estradiol probes were synthesized. Relative equilibrium dissociation constants (K-D) for the interaction of an anti-E-2 Fab fragment for the probes in solution were evaluated using a single E-2-analog biosensor surface on a BIAcore surface plasmon resonance instrument. The results show the antibody fragment binds all chemiluminescent conjugates tested with high affinity showing only minor preferences for site of substitution (C6 versus C7), stereochemistry (alpha versus beta), or linker moiety. (C) 2000 Elsevier Science Inc. All rights reserved.
• DETERMINATION OF ESTRADIOL BY COMPETITIVE IMMUNOASSAY
  申请人：ABBOTT LABORATORIES

  公开号：EP0650521B1

  公开（公告）日：2001-03-07