4-(2-carboxyethylthio)cortisol | 74997-23-2

• 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
• 英文名称: 4-(2-carboxyethylthio)cortisol
• 英文别名: 4-(2-Carboxyethylthio)cortisol；3-[[(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-4-yl]sulfanyl]propanoic acid
• CAS: 74997-23-2
• 化学式: C₂₄H₃₄O₇S
• 分子量: 466.596
• InChiKey: XUXUPWQOVRFGOR-MZCPSODSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  157
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-羟基丁二酰亚胺 、 4-(2-carboxyethylthio)cortisol 在 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 生成 (2,5-dioxopyrrolidin-1-yl) 3-[[(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-4-yl]sulfanyl]propanoate
  参考文献：
  名称：

  The specificity in enzyme immunoassay for plasma and urine cortisol.

  摘要：

  研究了皮质醇异构酶免疫测定的特异性。通过 N-琥珀酰亚胺酯法以适当的类固醇与酶的摩尔比对皮质醇进行酶标记。三种皮质醇衍生物在 C-4 上具有不同的桥，并与β-半乳糖苷酶共价连接。所使用的抗皮质醇抗血清是通过用这些合酶衍生物与牛血清白蛋白的共轭物对兔子进行免疫而激发的。为了获得高灵敏度，在抗血清和酶标记皮质醇的桥异源组合中进行了酶免疫测定。通过测量生物液体中的皮质醇含量，并将结果与放射免疫测定法的结果进行比较，评估了这些测定系统的特异性。此外，还对 15 种密切相关的类固醇进行了交叉反应测试。结果发现，使用针对 4-（2-羧基乙硫基）皮质醇-蛋白共轭物的抗血清进行的检测具有较高的特异性，适用于测定人体血浆和尿液中的皮质醇。

  DOI：

  10.1248/cpb.29.3606
• 作为产物：
  描述：

  氢化可的松 在 4-甲基苯磺酸吡啶 氢氧化钾 、 sodium hydroxide 、 双氧水 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 4-(2-carboxyethylthio)cortisol
  参考文献：
  名称：

  Synthesis of corticosteroid haptens possessing the bridge at the C-4 position.

  摘要：

  为了获得用于放射免疫测定和酶免疫测定的特定抗血清，制备了新的氢化可的松、11-去氧氢化可的松和可的松的半抗原。通过使用适当保护的21-单叔丁基二甲基硅醚（即4-羟基类固醇的关键中间体）合成了4-羟基可的松和4-羟基-11-去氧可的松的4-半琥珀酸酯。另外，通过以巯基乙酸作为催化剂，催化开环4,5-环氧化物合成了类固醇的4-羧基-甲基硫衍生物。除此之外，相关半抗原的制备也进行了描述。

  DOI：

  10.1248/cpb.28.1294

文献信息

• Specificity of antisera raised against cortisol-4-bovine serum albumin conjugates in radioimmunoassay.
  作者：HIROSHI HOSODA、SHINICHI MIYAIRI、NORIHIRO KOBAYASHI、TOSHIO NAMBARA

  DOI：10.1248/cpb.28.3369

  日期：——

  In order to obtain specific antisera for use in radioimmunoassay and enzyme immunoassay of cortisol, new hapten-carrier conjugates were prepared from 4-hemisuccinoyloxycortisol, 4-(carboxymethylthio) cortisol, 4-(2-carboxyethylthio) cortisol and 4-(2-hemisuccinoyloxyethylthio) cortisol by coupling with bovine serum albumin (BSA) employing the N-hydroxysuccinimide ester method or mixed anhydride method. The specificity of anti-cortisol antisera elicited in rabbits by immunization with these antigens was tested by cross-reaction studies with closely related steroids and by measuring the amount of cortisol in urine specimens by means of radioimmunoassay. Comparison of the specificity of these antisera with that of other antisera prepared with BSA conjugates of cortisol 3-(O-carboxymethyl) oxime and 21-hemisuccinoylcortisol was also carried out. The results showed that the antisera obtained were sufficiently specific and thus that the C-4 position was suitable for the attachment of a carrier protein for use in the production of antibodies.

  为了获得用于皮质醇放射免疫测定和酶免疫测定中的特异性抗血清，我们采用N-羟基琥珀酰亚胺酯法或混合酸酐法，通过将4-半琥珀酰氧基皮质醇、4-(羧甲基硫代)皮质醇、4-(2-羧乙基硫代)皮质醇和4-(2-半琥珀酰氧乙基硫代)皮质醇与牛血清白蛋白（BSA）偶联，制备了新的半抗原载体偶联物。通过用这些抗原对家兔进行免疫，我们测试了抗皮质醇抗血清的特异性，具体方法是采用密切相关的类固醇进行交叉反应研究，以及通过放射免疫测定法测量尿液样本中的皮质醇含量。我们还对这些抗血清的特异性与皮质醇3-(O-羧甲基)肟和21-半琥珀酰氧皮质醇的BSA偶联物制备的其他抗血清的特异性进行了比较。结果表明，所获得的抗血清具有足够的特异性，因此C-4位适合连接载体蛋白用于生产抗体。
• Synthesis of corticosteroid haptens possessing the bridge at the C-4 position.
  作者：HIROSHI HOSODA、SHINICHI MIYAIRI、TOSHIO NAMBARA

  DOI：10.1248/cpb.28.1294

  日期：——

  In order to obtain specific antisera for use in radioimmunoassay and enzyme immunoassay, new haptens of cortisol, 11-deoxycortisol and cortisone were prepared. The synthesis of the 4-hemisuccinates of 4-hydroxycortisol and 4-hydroxy-11-deoxycortisol was accomplished by employing suitably protected 21-mono-tert-butyldimethylsilyl ethers of the 4-hydroxysteroids as key intermediates. As another type of hapten, the 4-carboxy-methylthio derivatives of corticosteroids were prepared by base-catalyzed ring opening of the 4, 5-epoxide with mercaptoacetic acid. In addition, the preparation of related haptens is described.

  为了获得用于放射免疫测定和酶免疫测定的特定抗血清，制备了新的氢化可的松、11-去氧氢化可的松和可的松的半抗原。通过使用适当保护的21-单叔丁基二甲基硅醚（即4-羟基类固醇的关键中间体）合成了4-羟基可的松和4-羟基-11-去氧可的松的4-半琥珀酸酯。另外，通过以巯基乙酸作为催化剂，催化开环4,5-环氧化物合成了类固醇的4-羧基-甲基硫衍生物。除此之外，相关半抗原的制备也进行了描述。
• The specificity in enzyme immunoassay for plasma and urine cortisol.
  作者：HIROSHI HOSODA、NORIHIRO KOBAYASHI、SHINICHI MIYAIRI、TOSHIO NAMBARA

  DOI：10.1248/cpb.29.3606

  日期：——

  The specificity in heterogeneous enzyme immunoassays for cortisol has been investigated. Enzyme labeling of cortisol was accomplished by the N-succinimidyl ester method at an appropriate molar ratio of steroid to enzyme. Three cortisol derivatives possessing different bridges at C-4 were covalently linked to β-galactosidase. The anticortisol antisera used were those elicited in rabbits by immunization with the conjugates of these haptenic derivatives with bovine serum albumin. With the aim of obtaining high sensitivity, enzyme immunoassays were carried out in the bridge heterologous combinations of antiserum and enzyme-labeled cortisol. The specificity of these assay systems was assessed by measuring the amount of cortisol in biological fluids, and by comparison of the results with those of radioimmunoassays. The cross-reactivities were also tested with fifteen kinds of closely related steroids. The assay using the antiserum raised against the 4-(2-carboxyethylthio) cortisol-protein conjugate was found to be relatively specific and applicable to the determination of cortisol in human plasma and urine.

  研究了皮质醇异构酶免疫测定的特异性。通过 N-琥珀酰亚胺酯法以适当的类固醇与酶的摩尔比对皮质醇进行酶标记。三种皮质醇衍生物在 C-4 上具有不同的桥，并与β-半乳糖苷酶共价连接。所使用的抗皮质醇抗血清是通过用这些合酶衍生物与牛血清白蛋白的共轭物对兔子进行免疫而激发的。为了获得高灵敏度，在抗血清和酶标记皮质醇的桥异源组合中进行了酶免疫测定。通过测量生物液体中的皮质醇含量，并将结果与放射免疫测定法的结果进行比较，评估了这些测定系统的特异性。此外，还对 15 种密切相关的类固醇进行了交叉反应测试。结果发现，使用针对 4-（2-羧基乙硫基）皮质醇-蛋白共轭物的抗血清进行的检测具有较高的特异性，适用于测定人体血浆和尿液中的皮质醇。