4-carboxymethylthio-11-deoxycortisol N-hydroxysuccinimidyl ester | 93775-50-9

• 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-carboxymethylthio-11-deoxycortisol N-hydroxysuccinimidyl ester
• 英文别名: 4-carboxymethylthio-11-deoxycortisol N-succinimidyl ester
• CAS: 93775-50-9
• 化学式: C₂₇H₃₅NO₈S
• 分子量: 533.643
• InChiKey: AYRWOXJAZOCQAL-AHIRSVFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.48
• 重原子数：
  37.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  138.28
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  4-carboxymethylthio-11-deoxycortisol N-hydroxysuccinimidyl ester 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 锌 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 生成 4--11-deoxycortisol N-succinimidyl ester
  参考文献：
  名称：

  Bridging phenomena in steroid immunoassays. The effect of bridge length on sensitivity in enzyme immunoassay.

  摘要：

  我们研究了抗血清和酶标记抗原之间的桥异源组合对 11-脱氧皮质醇酶免疫测定灵敏度的影响。为了获得桥长效应的证据，我们比较了使用由 11-脱氧皮质醇衍生物制备的 β-半乳糖苷酶标记抗原与 C-4 位有 N-(羧甲基)氨基甲酰甲硫基的衍生物的检测系统的灵敏度。用 N-琥珀酰亚胺酯法对 11-脱氧皮质醇进行了酶标记。使用三种抗 11-脱氧皮质醇抗血清，通过不同的免疫原免疫兔子。结果发现，使用较短的桥进行酶标记可提高灵敏度。这表明桥长度是影响酶免疫测定灵敏度的一个重要因素。

  DOI：

  10.1248/cpb.34.2105
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 4-(carboxymethylthio)-11-deoxycortisol 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 生成 4-carboxymethylthio-11-deoxycortisol N-hydroxysuccinimidyl ester
  参考文献：
  名称：

  Radioimmunoassay of 11-deoxycortisol. Specificity of antisera raised against 11-deoxycortisol-(C-4)-bovine serum albumin conjugates.

  摘要：

  为了获得用于 11-脱氧皮质醇免疫测定的特异性抗血清，我们用 4-半琥珀酰氧基-11-脱氧皮质醇、4-(羧基甲硫基)-11-脱氧皮质醇、4-(2-羧基乙硫基)-11-脱氧皮质醇和 4-(2-半琥珀酰氧基乙硫基)-11-脱氧皮质醇制备了新的单体-载体共轭物、4-(2-羧基乙硫基)-11-脱氧皮质醇和 4-(2-半琥珀酰氧基乙硫基)-11-脱氧皮质醇采用 N-琥珀酰亚胺酯法与牛血清白蛋白偶联。通过与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血浆标本中 11-脱氧皮质醇的含量，检验了用这些抗原免疫兔子所激发的抗 11-脱氧皮质醇抗血清的特异性。结果表明，获得的抗血清具有相当高的特异性，可用于在甲氧孕酮试验中测定血浆中 11-脱氧皮质醇的水平。该测定可在血浆的二氯甲烷提取物中进行。

  DOI：

  10.1248/cpb.30.2127

文献信息

• Enzyme immunoassay for plasma 11-deoxycortisol. Application to metyrapone test.
  作者：HIROSHI HOSODA、NORIHIRO KOBAYASHI、SHINICHI MIYAIRI、AKEMI KATO、HIROKO KAWAMOTO、TOSHIO NAMBARA

  DOI：10.1248/cpb.32.3594

  日期：——

  A sensitive and relatively specific enzyme immunoassay of 11-deoxycortisol in human plasma has been developed. Enzyme labeling of 11-deoxycortisol was accomplished by the active ester method. The use of 4-carboxymethylthio-11-deoxycortisol N-succinimidyl ester and β-galactosidase in an appropriate molar ratio provided an enzyme-labeled antigen suitable for enzyme immunoassay. The anti-11-deoxycortisol antiserum used was that elicited in the rabbit by immunization with the conjugate of the haptenic derivative with bovine serum albumin. In order to improve the assay specificity, cortisol was used as an agent for the blocking of less specific antibodies present in the antiserum. The specificity of the assay system was assessed by comparing the results of measurement of 11-deoxycortisol in human plasma with those obtained by a radioimmunoassay. The quantitation limit of 11-deoxycortisol was 800 fg per tube. The intra-and inter-assay coefficients of variation for 11-deoxycortisol in human plasma were 3.0-15.8% and 7.6-12.5%, respectively. The present enzyme immunoassay of 11-deoxycortisol was found to be useful in the metyrapone tests for evaluation of pituitary-adrenal function and for differential diagnosis of Cushing's syndrome. The assay can be done on methylene chloride extracts of plasma.

  我们开发出了一种灵敏且相对特异的酶免疫测定法来检测人体血浆中的 11-脱氧皮质醇。11 -脱氧皮质醇的酶标记是通过活性酯法完成的。使用 4-羧甲基硫代-11-脱氧皮质醇 N-琥珀酰亚胺酯和β-半乳糖苷酶以适当的摩尔比提供了适合酶免疫测定的酶标记抗原。所使用的抗-11-脱氧皮质醇抗血清是通过兔用合酶衍生物与牛血清白蛋白的共轭物进行免疫而激发的。为了提高检测的特异性，使用了皮质醇来阻断抗血清中特异性较低的抗体。通过比较人体血浆中 11-脱氧皮质醇的测定结果和放射免疫测定的结果，评估了该测定系统的特异性。11 -脱氧皮质醇的定量限为每管 800 fg。人体血浆中 11-脱氧皮质醇的测定内变异系数为 3.0%-15.8%，测定间变异系数为 7.6%-12.5%。研究发现，11-脱氧皮质醇酶免疫测定法可用于甲氧苄啶试验，以评估垂体-肾上腺功能和鉴别诊断库欣综合征。该测定可在血浆的二氯甲烷提取物中进行。
• Effect of bridge heterologous combination on sensitivity in enzyme immunoassay for 11-deoxycortisol.
  作者：HIROSHI HOSODA、NORIHIRO KOBAYASHI、TOSHIO NAMBARA

  DOI：10.1248/cpb.31.953

  日期：——

  The effect of the bridge heterologous combination between antiserum and enzymelabeled steroid on sensitivity in heterogeneous enzyme immunoassay for 11-deoxycortisol has been investigated. Four 11-deoxycortisol derivatives possessing different bridges at C-4 were employed for the preparation of both antisera and enzyme-labeld antigens. They were 4-(carboxymethylthio)-11-deoxycortisol, 4-(2-carboxyethylthio)-11-deoxycortisol, 4-(2-hemisuccinoyloxyethylthio)-11-deoxycortisol, and 4-hemisuccinoyloxy-11-deoxycortisol. The N-succinimidyl esters of the carboxylated derivatives were reacted with β-galactosidase to give enzyme-labeled antigens. The antisera to 11-deoxycortisol used were those raised against the conjugates of these haptenic derivatives with bovine serum albumin. The sensitivities obtainable with four homologous and twelve heterologous systems were tested. When thioether derivatives were used for enzyme labeling, the effectiveness of heterology on assay sensitivity was dependent upon the length of the bridge. It was found that the heterologous system using the enzyme-labeled steroid obtained from a hapten having a bridge shorter than that used for antibody production resulted in an increase in sensitivity of the assay, whereas the use of a longer bridge was not effective. This finding is in good agreement with that obtained in our previous study on enzyme immunoassay for cortisol.

  抗血清和酶标记类固醇桥异构体组合对11-去氧皮质醇异质酶免疫分析灵敏度的影响已经过研究。四种在C-4处具有不同桥的11-去氧皮质醇衍生物被用于制备抗血清和酶标记抗原。它们分别是4-(羧甲基硫代)-11-去氧皮质醇、4-(2-羧乙基硫代)-11-去氧皮质醇、4-(2-半琥珀酰氧乙基硫代)-11-去氧皮质醇和4-半琥珀酰氧基-11-去氧皮质醇。羧基化衍生物的N-琥珀酰亚胺酯与β-半乳糖苷酶反应，生成酶标记抗原。11-去氧皮质醇抗血清是通过这些半抗原衍生物与牛血清白蛋白的共轭物产生的。四种同源和十二种异源系统的灵敏度进行了测试。当硫醚衍生物用于酶标记时，异源性对检测灵敏度的有效性取决于桥的长度。研究发现，异源系统使用从桥短于用于产生抗体的桥的半抗原获得的酶标记类固醇，可提高检测灵敏度，而使用更长的桥则无效。这一发现与我们之前对皮质醇酶免疫分析的研究结果非常一致