({[3-hydroxyestra-1(10),2,4-trien-17-ylidene]amino}oxy)acetic acid | 16218-61-4

• 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-hydroxyestra-1(10),2,4-trien-17-ylidene]amino}oxy)acetic acid
• 英文别名: estrone 17-(O-carboxymethyl)oxime；2-({(E)-[(8R,9S,13S,14S)-3-hydroxy-13-methyl-7,8,9,11,12,13,15,16-octahydro-6H-cyclopenta[a]phenanthren-17(14H)-ylidene]amino}oxy)acetic acid；3-Hydroxyestra-1,3,5(10)-trien-17-one O-(carboxymethyl)oxime；2-[(E)-[(8R,9S,13S,14S)-3-hydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ylidene]amino]oxyacetic acid
• CAS: 16218-61-4
• 化学式: C₂₀H₂₅NO₄
• 分子量: 343.423
• InChiKey: UZKYYNQEKCAXLJ-YBFXVWRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 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：
  79.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ({[3-hydroxyestra-1(10),2,4-trien-17-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-hydroxyestra-1(10),2,4-trien-17-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：

  雌酚酮 、 2-(氨基氧基)乙酸 在 吡啶 作用下， 反应 17.0h， 以100%的产率得到({[3-hydroxyestra-1(10),2,4-trien-17-ylidene]amino}oxy)acetic acid
  参考文献：
  名称：

  Design, synthesis and biological evaluation of nuclear receptor-degradation inducers

  摘要：

  Compounds that regulate the function(s) of nuclear receptors (NRs) are useful for biological studies and as candidate therapeutic agents. Most such compounds are agonists or antagonists. On the other hand, we have developed specific protein degradation inducers, which we designated as SNIPERs (Specific and Nongenetic IAPs-dependent Protein ERasers), for selective degradation of target proteins. SNIPERs are hybrid molecules consisting of an appropriate ligand for the protein of interest, coupled to a ligand for inhibitor of apoptosis proteins (IAPs), which target the bound protein for polyubiquitination and proteasomal degradation. We considered that protein knockdown with SNIPERs would be a promising alternative approach for modulating NR function. In this study, we designed and synthesized degradation inducers targeting retinoic acid receptor (RAR), estrogen receptor (ER), and androgen receptor (AR). These newly synthesized RAR, ER, and AR SNIPERs, 9, 11, and 13, respectively, were confirmed to significantly reduce the levels of the corresponding NRs in live cells. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.09.041

文献信息

• Reagent for immunoassay, and kit containing the same
  申请人：MOCHIDA PHARMACEUTICAL CO., LTD.

  公开号：EP0383313A2

  公开（公告）日：1990-08-22

  A reagent for use in an immunoassay for measuring haptens, antigens or antibodies by means of a competitive binding method, which comprises a combination of an antibody and a labelled hapten or a labelled antigen or a combination of a hapten or an antigen and a labelled antibody, wherein the antibody and the labelled hapten or the labelled antigen in one combination or the hapten or the antigen and the labelled antibody in another combination are capable of undergoing reversible binding, and a device for use in an immunoassay wherein the reagent of the present invention is included in a single container. An immunoassay can be performed in a short time by the use of the immunoassay device of the present invention.

  一种用于免疫测定的试剂，通过竞争结合的方法来测量杂合体、抗原或抗体，该试剂 包括抗体与标记的杂合体或标记的抗原的组合，或杂合体或抗原与标记的抗体的组合、其中一种组合中的抗体和标记的合蛋白或标记的抗原，或另一种组合中的合蛋白或抗原和标记的抗体能够进行可逆结合，以及一种用于免疫测定的装置，其中本发明的试剂包含在一个容器中。 使用本发明的免疫测定装置可在短时间内完成免疫测定。
• 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.
• US3966744A
  申请人：——

  公开号：US3966744A

  公开（公告）日：1976-06-29
• US3966764A
  申请人：——

  公开号：US3966764A

  公开（公告）日：1976-06-29
• US5283176A
  申请人：——

  公开号：US5283176A

  公开（公告）日：1994-02-01