[1-¹³C]dehydroascorbic acid | 1159923-26-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: [1-¹³C]dehydroascorbic acid
• 英文别名: (5R)-5-[(1S)-1,2-dihydroxyethyl](213C)oxolane-2,3,4-trione
• CAS: 1159923-26-8
• 化学式: C₆H₆O₆
• 分子量: 175.099
• InChiKey: SBJKKFFYIZUCET-HYAXHRHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [1-¹³C]dehydroascorbic acid 在 iron(III) sulfate 、 水 作用下， 生成 L-苏糖酸 、 oxalic acid
  参考文献：
  名称：

  的C铁介导的裂解？水中三羰基化合物中的C键

  摘要：

  一种三邻位三羰基化合物经历C： Ç裂解通过三价铁离子（参见方案）介导的。观察到的茚三酮和脱氢抗坏血酸的裂解与氨基酸检测和维生素C的代谢有关。

  DOI：

  10.1002/anie.200806296
• 作为产物：
  描述：

  [1-¹³C]ascorbic acid 在 iron(III) sulfate 、 水 作用下， 生成 [1-¹³C]dehydroascorbic acid
  参考文献：
  名称：

  的C铁介导的裂解？水中三羰基化合物中的C键

  摘要：

  一种三邻位三羰基化合物经历C： Ç裂解通过三价铁离子（参见方案）介导的。观察到的茚三酮和脱氢抗坏血酸的裂解与氨基酸检测和维生素C的代谢有关。

  DOI：

  10.1002/anie.200806296

文献信息

• Hyperpolarized [1-¹³C]-Ascorbic and Dehydroascorbic Acid: Vitamin C as a Probe for Imaging Redox Status in Vivo
  作者：Sarah E. Bohndiek、Mikko I. Kettunen、De-en Hu、Brett W. C. Kennedy、Joan Boren、Ferdia A. Gallagher、Kevin M. Brindle

  DOI：10.1021/ja2045925

  日期：2011.8.3

  Dynamic nuclear polarization (DNP) of C-13-labeled metabolic substrates in vitro and their subsequent intravenous administration allow both the location of the hyperpolarized substrate and the dynamics of its subsequent conversion into other metabolic products to be detected in vivo. We report here the hyperpolarization of [1-C-13]-ascorbic acid (AA) and [1-C-13]-dehydroascorbic acid (DMA), the reduced and oxidized forms of vitamin C, respectively, and evaluate their performance as probes of tumor redox state. Solution-state polarization of 10.5 +/- 1.3% was achieved for both forms at pH 3.2, whereas at pH 7.0, [1-C-13]-AA retained polarization of 5.1 +/- 0.6% and 1-C-13]-DHA retained 8.2 +/- 1.1%. The spin-lattice relaxation times (T-1's) for these labeled nuclei are long at 9.4 T: 15.9 +/- 0.7 s for AA and 20.5 +/- 0.9 s for DMA. Extracellular oxidation of [1-C-13]-AA and intracellular reduction of [1-C-13]-DHA were observed in suspensions of murine lymphoma cells. The spontaneous reaction of DHA with the cellular antioxidant glutathione was monitored in vitro and was approximately 100-fold lower than the rate observed in cell suspensions, indicating enzymatic involvement in the intracellular reduction. [1-C-13]-DHA reduction was also detected in lymphoma tumors in vivo. In contrast, no detectable oxidation of [1-C-13]-AA was measured in the same tumors, consistent with the notion that tumors maintain a reduced micro environment. This study demonstrates that hyperpolarized C-13-labeled vitamin C could be used as a noninvasive biomarker of redox status in vivo, which has the potential to translate to the clinic.