3-[(methoxycarbonyl)dithio]-L-alanine

• 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: 3-[(methoxycarbonyl)dithio]-L-alanine
• 英文别名: (2R)-2-amino-3-(methoxycarbonyldisulfanyl)propanoic acid
• 化学式: C₅H₉NO₄S₂
• 分子量: 211.263
• InChiKey: KDQDZFGDLYPQON-VKHMYHEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  140
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-[(methoxycarbonyl)dithio]-L-alanine 在 potassium hydrosulfide 作用下， 以 甲醇 为溶剂， 反应 1.5h， 生成 L-thiocysteine potassium salt
  参考文献：
  名称：

  Iterative synthetic strategies and gene deletant experiments enable the first identification of polysulfides in Saccharomyces cerevisiae

  摘要：

  聚硫化物，潜在的信号分子，首次在酵母中被合成、发现并探索。

  DOI：

  10.1039/c9cc03020d
• 作为产物：
  描述：

  氯化甲氧羰基硫 、 L-半胱氨酸盐酸盐无水物 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 1.3h， 生成 3-[(methoxycarbonyl)dithio]-L-alanine
  参考文献：
  名称：

  S-allylmercaptocysteine suppresses the growth of human gastric cancer xenografts through induction of apoptosis and regulation of MAPK and PI3K/Akt signaling pathways

  摘要：

  Gastric cancer remains as a common lethal malignancy worldwide. Developing novel anti-gastric cancer drugs with minimal side effects is necessary to address this public health issue. S-allylmercaptocysteine (SAMC), one of the water-soluble organosulfur garlic derivatives, has been demonstrated as a suppressive agent against tumors. In this study, we examined the effect of SAMC on human gastric carcinoma growth in vivo and explored the underlying mechanism. Human gastric cancer SGC-7901 cells were inoculated subcutaneously in BALB/c nude mice. When xenograft tumors reached about 100 mm(3), mice were treated with SAMC for 30 days. We observed that SAMC administration in mice effectively delayed the growth of SGC-7901 xenografts without signs of toxicity. TUNEL staining confirmed that the tumors from SAMC-treated mice exhibited a markedly higher apoptotic index. Mechanistic studies suggested that this activity may arise from its effects on the caspase activation and modulation of MAPK and PI3K/Akt signaling pathways. Taken together, these data support development of SAMC as a potential agent for gastric cancer therapy. (C) 2017 Published by Elsevier Inc.

  DOI：

  10.1016/j.bbrc.2017.06.107

文献信息

• S-allylmercaptocysteine suppresses the growth of human gastric cancer xenografts through induction of apoptosis and regulation of MAPK and PI3K/Akt signaling pathways
  作者：Xiaosong Zhu、Xiaoyan Jiang、Ang Li、Yueyue Sun、Yan Liu、Xiao Sun、Xiuli Feng、Siying Li、Zhongxi Zhao

  DOI：10.1016/j.bbrc.2017.06.107

  日期：2017.9

  Gastric cancer remains as a common lethal malignancy worldwide. Developing novel anti-gastric cancer drugs with minimal side effects is necessary to address this public health issue. S-allylmercaptocysteine (SAMC), one of the water-soluble organosulfur garlic derivatives, has been demonstrated as a suppressive agent against tumors. In this study, we examined the effect of SAMC on human gastric carcinoma growth in vivo and explored the underlying mechanism. Human gastric cancer SGC-7901 cells were inoculated subcutaneously in BALB/c nude mice. When xenograft tumors reached about 100 mm(3), mice were treated with SAMC for 30 days. We observed that SAMC administration in mice effectively delayed the growth of SGC-7901 xenografts without signs of toxicity. TUNEL staining confirmed that the tumors from SAMC-treated mice exhibited a markedly higher apoptotic index. Mechanistic studies suggested that this activity may arise from its effects on the caspase activation and modulation of MAPK and PI3K/Akt signaling pathways. Taken together, these data support development of SAMC as a potential agent for gastric cancer therapy. (C) 2017 Published by Elsevier Inc.
• Iterative synthetic strategies and gene deletant experiments enable the first identification of polysulfides in <i>Saccharomyces cerevisiae</i>
  作者：Lisa I. Pilkington、Rebecca C. Deed、Katie Parish-Virtue、Chien-Wei Huang、Michelle E. Walker、Vladimir Jiranek、David Barker、Bruno Fedrizzi

  DOI：10.1039/c9cc03020d

  日期：——

  Polysulfides, potential signalling molecules, were synthesised and then found and explored for the first time in yeast.

  聚硫化物，潜在的信号分子，首次在酵母中被合成、发现并探索。