(R)-N-Acetyl-S-<(7S,8S)-2-carboxy-7,8-dihydro-8-hydroxy-7-naphthyl>cysteine

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-N-Acetyl-S-<(7S,8S)-2-carboxy-7,8-dihydro-8-hydroxy-7-naphthyl>cysteine
• 英文别名: (7S,8S)-7-[(2R)-2-acetamido-2-carboxyethyl]sulfanyl-8-hydroxy-7,8-dihydronaphthalene-2-carboxylic acid
• 化学式: C₁₆H₁₇NO₆S
• 分子量: 351.38
• InChiKey: NCCUMPSLNZNVOD-IHRRRGAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  149
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  5,6-dihydro-naphthalene-2-carboxylic acid methyl ester 在 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile 、 sodium methylate 、 N-溴代乙酰胺 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 溶剂黄146 为溶剂， 反应 8.0h， 生成 (R)-N-Acetyl-S-<(7S,8S)-2-carboxy-7,8-dihydro-8-hydroxy-7-naphthyl>cysteine
  参考文献：
  名称：

  Hapten design and development of an ELISA (enzyme-linked immunosorbent assay) for the detection of the mercapturic acid conjugates of naphthalene

  摘要：

  Measurement of urinary metabolites constitutes a noninvasive method to assess toxic exposure. Naphthalene is a common environmental contaminant showing selective pulmonary toxicity in mice and presumably is involved in development of lung disease in man (Buckpitt, A.R.; Franklin, R.B. Pharmacol. Ther. 1989, 41, 339). A glutathione-based detoxification pathway leads to the formation of the mercapturic acid conjugates [NaphMA 1, (R)-N-acetyl-S-[(1R*,2R*)-1,2-dihydro-1-hydroxy-2-naphthyl]cysteine] and (R)-N-acetyl-S-[(1R*,2R*)-1,2-dihydro-2-hydroxy-1-naphthyl]cysteine] which are excreted in urine. Herein we report the development of an immunoassay for the specific detection of these urinary metabolites. This study confirms the importance of appropriate hapten design and synthesis in controlling the specificity and sensitivity of the immunoassay. Our strategy was to prepare haptens that allow covalent attachment to a carrier protein at a site opposite to the N-acetylcysteine moiety. The antibodies obtained by immunizing six rabbits with these NaphMA derivatives (haptens 13 and 14) have been used for the development of an ELISA (enzyme-linked immunosorbent assay) which detects NaphMA 1 in the range between 100 and 6 pg/mL with an I50 of 29 pg/mL. Its ability to detect these important naphthalene metabolites in human urine is demonstrated.

  DOI：

  10.1021/jo00078a039

文献信息

• Hapten design and development of an ELISA (enzyme-linked immunosorbent assay) for the detection of the mercapturic acid conjugates of naphthalene
  作者：Maria Pilar Marco、Bruce D. Hammock、Mark J. Kurth

  DOI：10.1021/jo00078a039

  日期：1993.12

  Measurement of urinary metabolites constitutes a noninvasive method to assess toxic exposure. Naphthalene is a common environmental contaminant showing selective pulmonary toxicity in mice and presumably is involved in development of lung disease in man (Buckpitt, A.R.; Franklin, R.B. Pharmacol. Ther. 1989, 41, 339). A glutathione-based detoxification pathway leads to the formation of the mercapturic acid conjugates [NaphMA 1, (R)-N-acetyl-S-[(1R*,2R*)-1,2-dihydro-1-hydroxy-2-naphthyl]cysteine] and (R)-N-acetyl-S-[(1R*,2R*)-1,2-dihydro-2-hydroxy-1-naphthyl]cysteine] which are excreted in urine. Herein we report the development of an immunoassay for the specific detection of these urinary metabolites. This study confirms the importance of appropriate hapten design and synthesis in controlling the specificity and sensitivity of the immunoassay. Our strategy was to prepare haptens that allow covalent attachment to a carrier protein at a site opposite to the N-acetylcysteine moiety. The antibodies obtained by immunizing six rabbits with these NaphMA derivatives (haptens 13 and 14) have been used for the development of an ELISA (enzyme-linked immunosorbent assay) which detects NaphMA 1 in the range between 100 and 6 pg/mL with an I50 of 29 pg/mL. Its ability to detect these important naphthalene metabolites in human urine is demonstrated.