GS-sHep

• 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: GS-sHep
• 英文别名: (2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-3-heptan-2-ylsulfanyl-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
• 化学式: C₁₇H₃₁N₃O₆S
• 分子量: 405.516
• InChiKey: GELUFAOMDCVNMM-SPOOISQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  27
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  184
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  乙醇 、 GS-sHep 在 三甲基氯硅烷 作用下， 反应 16.0h， 以85%的产率得到Et-GS-sHep
  参考文献：
  名称：

  Inhibition of glutathione S-transferase in rat hepatocytes by a glycine-tetrazole modified S-alkyl–GSH analogue

  摘要：

  Glutathione (GSH) conjugates inhibit enzymes that are involved in drug metabolism and drug resistance, but their cellular uptake is very low. To improve membrane-permeability, we synthesized a novel GSH-conjugate analogue with a tetrazole carboxylate isostere at the glycine position. Introduction of the tetrazole decreases inhibitory potency towards CDNB conjugation by glutathione S-transferase. However, the tetrazole derivative inhibited 2-bromoisovalerylurea conjugation in rat liver cytosol, as well as in hepatocytes. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00247-0
• 作为产物：
  描述：

  谷胱甘肽 、 2-溴庚烷 在 12-冠醚-4 、 potassium iodide 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 以65%的产率得到GS-sHep
  参考文献：
  名称：

  Inhibition of glutathione S-transferase in rat hepatocytes by a glycine-tetrazole modified S-alkyl–GSH analogue

  摘要：

  Glutathione (GSH) conjugates inhibit enzymes that are involved in drug metabolism and drug resistance, but their cellular uptake is very low. To improve membrane-permeability, we synthesized a novel GSH-conjugate analogue with a tetrazole carboxylate isostere at the glycine position. Introduction of the tetrazole decreases inhibitory potency towards CDNB conjugation by glutathione S-transferase. However, the tetrazole derivative inhibited 2-bromoisovalerylurea conjugation in rat liver cytosol, as well as in hepatocytes. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00247-0

文献信息

• Inhibition of glutathione S-transferase in rat hepatocytes by a glycine-tetrazole modified S-alkyl–GSH analogue
  作者：Danny Burg、Liesbeth Hameetman、Dmitri V Filippov、Gijs A van der Marel、Gerard J Mulder

  DOI：10.1016/s0960-894x(02)00247-0

  日期：2002.6

  Glutathione (GSH) conjugates inhibit enzymes that are involved in drug metabolism and drug resistance, but their cellular uptake is very low. To improve membrane-permeability, we synthesized a novel GSH-conjugate analogue with a tetrazole carboxylate isostere at the glycine position. Introduction of the tetrazole decreases inhibitory potency towards CDNB conjugation by glutathione S-transferase. However, the tetrazole derivative inhibited 2-bromoisovalerylurea conjugation in rat liver cytosol, as well as in hepatocytes. (C) 2002 Elsevier Science Ltd. All rights reserved.