3-(3-hydroxyestra-1,3,5(10)-trien-17-on-4-yl)thiopropanoic acid | 848186-33-4

• 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-(3-hydroxyestra-1,3,5(10)-trien-17-on-4-yl)thiopropanoic acid
• CAS: 848186-33-4
• 化学式: C₂₁H₂₆O₄S
• 分子量: 374.501
• InChiKey: HAXMSSXOMKSUSK-PBOVLVJJSA-N

物化性质

• 熔点：
  108-112 °C
• 沸点：
  560.2±50.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.38
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  74.6
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-(3-hydroxyestra-1,3,5(10)-trien-17-on-4-yl)thiopropanoic acid 在 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 60.0h， 生成 N-(13-(t-butoxycarbonylamino)-4,7,10-trioxatridecanyl)-3-(3-hydroxyestra-1,3,5(10)-trien-17-on-4-yl)thiopropanamide
  参考文献：
  名称：

  Estrogen conjugation and antibody binding interactions in surface plasmon resonance biosensing

  摘要：

  Thioether-linked 3-mercaptopropionic acid derivatives of 17 beta-estradiol and estrone were formed at the A-ring 4-position of the steroids by substitution of their 4-bromo analogues. The carboxylic acid terminal was used to link to an oligoethylene glycol (OEG) chain of 15-atoms in length. The OEG derivative of 17 beta-estradiol was then in situ immobilized on a carboxymethylated dextran-coated gold sensor surface used to detect refractive index changes upon protein binding to the surface by surface plasmon propagation in a BIAcore surface plasmon resonance (SPR) instrument. TWO other estradiol-OEG derivatives with Mannich reaction linkage at the 2-position and hemisuccinate linkage at the 3-position were also immobilized on the sensor surfaces for comparison. Binding performance between these immobilized different positional conjugates and monoclonal anti-estradiol antibody, raised from a G-position conjugate, clearly demonstrated that both 2- and 4-conjugates, not conjugated through existing functional groups, gave strong antibody bindings, whereas the 3-conjugate through an existing functional group (3-OH) gave very little binding (2% compared to the 2-conjugate). Both 2- and 4-position conjugates were then applied in a highly sensitive estradiol SPR immunoassay with secondary antibody mediated signal enhancement that gave up to a 9.5-fold signal enhancement of primary antibody binding, and a detection limit of 25 pg/mL was achieved for a rapid and convenient flow-through immunoassay of estradiol. (c) 2006 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2006.03.004
• 作为产物：
  描述：

  雌酚酮 在 氢氧化钾 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 甲醇 、 乙醇 、 丙酮 为溶剂， 反应 48.0h， 生成 3-(3-hydroxyestra-1,3,5(10)-trien-17-on-4-yl)thiopropanoic acid
  参考文献：
  名称：

  Estrogen conjugation and antibody binding interactions in surface plasmon resonance biosensing

  摘要：

  Thioether-linked 3-mercaptopropionic acid derivatives of 17 beta-estradiol and estrone were formed at the A-ring 4-position of the steroids by substitution of their 4-bromo analogues. The carboxylic acid terminal was used to link to an oligoethylene glycol (OEG) chain of 15-atoms in length. The OEG derivative of 17 beta-estradiol was then in situ immobilized on a carboxymethylated dextran-coated gold sensor surface used to detect refractive index changes upon protein binding to the surface by surface plasmon propagation in a BIAcore surface plasmon resonance (SPR) instrument. TWO other estradiol-OEG derivatives with Mannich reaction linkage at the 2-position and hemisuccinate linkage at the 3-position were also immobilized on the sensor surfaces for comparison. Binding performance between these immobilized different positional conjugates and monoclonal anti-estradiol antibody, raised from a G-position conjugate, clearly demonstrated that both 2- and 4-conjugates, not conjugated through existing functional groups, gave strong antibody bindings, whereas the 3-conjugate through an existing functional group (3-OH) gave very little binding (2% compared to the 2-conjugate). Both 2- and 4-position conjugates were then applied in a highly sensitive estradiol SPR immunoassay with secondary antibody mediated signal enhancement that gave up to a 9.5-fold signal enhancement of primary antibody binding, and a detection limit of 25 pg/mL was achieved for a rapid and convenient flow-through immunoassay of estradiol. (c) 2006 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2006.03.004