[35S]glutathione | 35430-77-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [35S]glutathione
• 英文别名: 35S-glutathione；[35S]-GSH；[35S]GSH；PSG；(2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-1-oxo-3-(35S)sulfanylpropan-2-yl]amino]-5-oxopentanoic acid
• CAS: 35430-77-4
• 化学式: C₁₀H₁₇N₃O₆S
• 分子量: 310.261
• InChiKey: RWSXRVCMGQZWBV-DMPAQHNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.5
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  160
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-叠氮苯甲酰甲基溴 、 [35S]glutathione 在 还原型辅酶II(NADPH)四钠盐 作用下， 以 phosphate buffer 为溶剂， 反应 1.0h， 生成 [35S]-(p-azidophenacyl)glutathione
  参考文献：
  名称：

  Shen, Hongxie; Schultz, Mary P.; Tew, Kenneth D., Journal of Pharmacology and Experimental Therapeutics, 1999, vol. 290, # 3, p. 1101 - 1106

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 sodium 35S-sulphate 、 YEPD liquid broth 作用下， 以 水 为溶剂， 生成 [35S]glutathione
  参考文献：
  名称：

  Biosynthesis of high specific activity35S-glutathione

  摘要：

  The biosynthesis of high specific activity S-35- glutathione was carried out using a diploid strain of baker's yeast -'Saccharomyces cerevisiae'. Yeast cells were grown in a synthetic medium in which sodium S-35- sulphate was supplemented as sole sulphur source. During growth, a major fraction of the radioactivity was incorporated into the protein as S-35-methionine and S-35-cysteine. After the growth of yeast, the cell wall was broken using a cell disrupter and the free S-35-glutathione present was separated from protein and other sulphur containing compounds by chromatographic procedures. The specific activity of the S-35- glutathione was determined by Hydrolysing into its constituent amino acids and quantifying them using an amino acid analyser employing a post-column orthophthaldehyde derivatization method, followed by radioactivity assay of S-35-cysteine. The overall radiochemical yield of S-35-glutathione was 5 %, The radiochemical purity of the product was found to be greater than 95 % and its specific activity, greater than 1000 Ci/mmol when sodium S-35-sulphate having a specific activity of 1200 Ci/mmol was used as the starting material.

  DOI：

  10.1002/1099-1344(200009)43:10<971::aid-jlcr380>3.0.co;2-q

文献信息

• A novel noninvasive method for assessing glutathione-conjugate efflux systems in the brain
  作者：Toshimitsu Okamura、Tatsuya Kikuchi、Kiyoshi Fukushi、Yasushi Arano、Toshiaki Irie

  DOI：10.1016/j.bmc.2007.02.045

  日期：2007.5

  Brain efflux systems export such conjugated metabolites as glutathione (GSH) and glucuronate conjugates, generated by the detoxification process, from the brain and serve to protect the brain from harmful metabolites. The intracerebral. injection of a radiolabeled conjugate is a useful technique to assess brain efflux systems; however, this technique is not applicable to humans. Hence, we devised a novel noninvasive approach for assessing GSH-conjugate efflux systems using positron emission tomography. Here, we investigated whether or not a designed proprobe can deliver its GSH conjugate into the brain. Radiolabeled 6-chloro-7-methylpurine (7m6CP) was designed as the proprobe, and [C-14]7m6CP was prepared by the reaction of 6-chloropurine with [C-14]CH3I as a model of [C-11]CH3I. The radiochemical yield and purity of [C-14]7m6CP were 10-20% and greater than 99%, respectively. High brain uptake (0.8% ID/g) at 1 min was observed, followed by gradual radioactivity clearance from the brain for 5-60 min after the injection of [C-14]7m6CP into rats. Analysis of metabolites confirmed confirmed that the presence of [C-14]7m6CP was hardly observed, and 80% of the radioactivity was identical to its GSH conjugate for 15-60 min. The brain radioactivity was single-exponentially decreased during the period of 15-60 min post-injection of [C-14]7m6CP, and the first-order efflux rate constant of the conjugate, estimated from the slope, was 0.0253 min(-1). These results showed that (1) [C-14]7m6CP readily entered the brain, (2) it efficiently and specifically transformed to the GSH conjugate within the brain, and (3) after [C-14]7m6CP disappearance, the clearance of radioactivity represented the only efflux of GSH conjugate. We conclude that 7m6CP can deliver the GSH conjugate into the brain and would be useful for assessing GSH-conjugate efflux systems noninvasively. (c) 2007 Elsevier Ltd. All rights reserved.
• Reactivity of 6-Halopurine Analogs with Glutathione as a Radiotracer for Assessing Function of Multidrug Resistance-Associated Protein 1
  作者：Toshimitsu Okamura、Tatsuya Kikuchi、Kiyoshi Fukushi、Toshiaki Irie

  DOI：10.1021/jm901332c

  日期：2009.11.26

  6-Bromo-7-[C-11]methylpurine is reported to react with glutathione via glutathione S-transferases in the brain and to be converted into a substrate for multidrug resistance-associated protein 1 (MRP1), an efflux pump. The compound with a rapid conversion rate allows quantitative assessment of MRP1 function, but this rate is probably susceptible to interspecies differences. Hence, for application to different species, including humans, it is necessary to adjust the conversion rate by modifying the chemical structure. We therefore designed 6-Halo-9-(or 7)-[C-14]methylpurine (halogen: F, Cl, Br, or I), and evaluated them in vitro with respect to enzymatic reactivity with glutathione using brain homogenates from the mouse, rat, or monkey. There was a marked difference in reactivity between these species. Changes in the position of the methyl group and halogen on N-methyl-6-halopurine provided various compounds possessing wide-ranging reactivity with glutathione. In conclusion, the adjustment of reactivity of 6-bromo-7-[C-11]methylpurine may allow assessment of MRP1 function in the brain in various species.
• Biosynthesis of high specific activity35S-glutathione
  作者：N. Jayachandran、K. P. Asokan、V. K. P. Unny

  DOI：10.1002/1099-1344(200009)43:10<971::aid-jlcr380>3.0.co;2-q

  日期：2000.9

  The biosynthesis of high specific activity S-35- glutathione was carried out using a diploid strain of baker's yeast -'Saccharomyces cerevisiae'. Yeast cells were grown in a synthetic medium in which sodium S-35- sulphate was supplemented as sole sulphur source. During growth, a major fraction of the radioactivity was incorporated into the protein as S-35-methionine and S-35-cysteine. After the growth of yeast, the cell wall was broken using a cell disrupter and the free S-35-glutathione present was separated from protein and other sulphur containing compounds by chromatographic procedures. The specific activity of the S-35- glutathione was determined by Hydrolysing into its constituent amino acids and quantifying them using an amino acid analyser employing a post-column orthophthaldehyde derivatization method, followed by radioactivity assay of S-35-cysteine. The overall radiochemical yield of S-35-glutathione was 5 %, The radiochemical purity of the product was found to be greater than 95 % and its specific activity, greater than 1000 Ci/mmol when sodium S-35-sulphate having a specific activity of 1200 Ci/mmol was used as the starting material.
• Shen, Hongxie; Schultz, Mary P.; Tew, Kenneth D., Journal of Pharmacology and Experimental Therapeutics, 1999, vol. 290, # 3, p. 1101 - 1106
  作者：Shen, Hongxie、Schultz, Mary P.、Tew, Kenneth D.

  DOI：——

  日期：——