5'-phosphatidyl-2'-deoxy-2'-methylenecytidine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: 5'-phosphatidyl-2'-deoxy-2'-methylenecytidine
• 英文别名: sodium;[(2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3-hydroxy-4-methylideneoxolan-2-yl]methyl [(2S)-2,3-di(hexadecanoyloxy)propyl] phosphate
• 化学式: C₄₅H₇₉N₃O₁₁P*Na
• 分子量: 892.099
• InChiKey: MESJKEUPNOOTJU-YMTXBLIMSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  6.56
• 重原子数：
  61
• 可旋转键数：
  40
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  199
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  5'-phosphatidyl-2'-deoxy-2'-methylenecytidine 在 phospholipase A2 、 sodium salt of choleic acid 、 3,3-dimethylglutarate-NaOH buffer 、 calcium chloride 作用下， 生成
  参考文献：
  名称：

  Nucleosides and nucleotides. 155. synthesis, antitumor effects, and possible enzymatic activation mechanism of 5′-phosphatidyl-2′-deoxy-2′-methylenecytidine (DMDC)

  摘要：

  2'-Deoxy-2'-methylenecytidine (DMDC, 1) and its 5-fluoro congener (5-F-DMDC, 2), potent antitumor nucleosides developed by us, were efficiently converted to their 5'-phosphatidyl derivatives bearing palmitoyl residues (3 and 4, respectively) as novel antitumor phospholipids by phospholipase D-catalyzed trans-phosphatidylation. These phospholipids 3 and 4, administered i.p., remarkably prolonged the life-span of mice which were i.p.-inoculated with M5076 sarcoma, and the effects were clearly superior to that of DMDC. Compound 3 was a good substrate for phospholipase A(2) from bovine pancreas as well as phospholipase D from Streptomyces, while it was slightly hydrolyzed by phospholipase C from Bacillus cereus. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00389-7
• 作为产物：
  描述：

  2,3-二棕榈酰-Sn-甘油-1-磷酰胆碱 、 2'-甲基-2'-脱氧亚基胞苷 在 sodium acetate buffer 、 Dianion WK-20 resin (Na⁽¹⁺⁾ form) 、 phospholipase D 作用下， 生成 5'-phosphatidyl-2'-deoxy-2'-methylenecytidine
  参考文献：
  名称：

  Nucleosides and nucleotides. 155. synthesis, antitumor effects, and possible enzymatic activation mechanism of 5′-phosphatidyl-2′-deoxy-2′-methylenecytidine (DMDC)

  摘要：

  2'-Deoxy-2'-methylenecytidine (DMDC, 1) and its 5-fluoro congener (5-F-DMDC, 2), potent antitumor nucleosides developed by us, were efficiently converted to their 5'-phosphatidyl derivatives bearing palmitoyl residues (3 and 4, respectively) as novel antitumor phospholipids by phospholipase D-catalyzed trans-phosphatidylation. These phospholipids 3 and 4, administered i.p., remarkably prolonged the life-span of mice which were i.p.-inoculated with M5076 sarcoma, and the effects were clearly superior to that of DMDC. Compound 3 was a good substrate for phospholipase A(2) from bovine pancreas as well as phospholipase D from Streptomyces, while it was slightly hydrolyzed by phospholipase C from Bacillus cereus. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00389-7

文献信息

• Nucleosides and nucleotides. 155. synthesis, antitumor effects, and possible enzymatic activation mechanism of 5′-phosphatidyl-2′-deoxy-2′-methylenecytidine (DMDC)
  作者：Satoshi Shuto、Hirokazu Awano、Akihiro Fujii、Keiji Yamagami、Akira Matsuda

  DOI：10.1016/0960-894x(96)00389-7

  日期：1996.9

  2'-Deoxy-2'-methylenecytidine (DMDC, 1) and its 5-fluoro congener (5-F-DMDC, 2), potent antitumor nucleosides developed by us, were efficiently converted to their 5'-phosphatidyl derivatives bearing palmitoyl residues (3 and 4, respectively) as novel antitumor phospholipids by phospholipase D-catalyzed trans-phosphatidylation. These phospholipids 3 and 4, administered i.p., remarkably prolonged the life-span of mice which were i.p.-inoculated with M5076 sarcoma, and the effects were clearly superior to that of DMDC. Compound 3 was a good substrate for phospholipase A(2) from bovine pancreas as well as phospholipase D from Streptomyces, while it was slightly hydrolyzed by phospholipase C from Bacillus cereus. Copyright (C) 1996 Elsevier Science Ltd