冈田酸甲酯 | 78111-14-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 冈田酸甲酯
• 英文名称: okadaic acid methyl ester
• 英文别名: methyl okadaate；methyl (2R)-3-[(2S,6R,8S,11R)-2-[(E,2R)-4-[(2S,2'R,4R,4aS,6R,8aR)-4-hydroxy-2-[(1S,3S)-1-hydroxy-3-[(2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl]butyl]-3-methylidenespiro[4a,7,8,8a-tetrahydro-4H-pyrano[3,2-b]pyran-6,5'-oxolane]-2'-yl]but-3-en-2-yl]-11-hydroxy-4-methyl-1,7-dioxaspiro[5.5]undec-4-en-8-yl]-2-hydroxy-2-methylpropanoate
• CAS: 78111-14-5
• 化学式: C₄₅H₇₀O₁₃
• 分子量: 819.043
• InChiKey: BVEXVMARIREFTJ-TXMWGMRISA-N

物化性质

• 沸点：
  898.7±65.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  58
• 可旋转键数：
  11
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  172
• 氢给体数：
  4
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  冈田酸甲酯 在 咪唑 、 氢氟酸 、 碳酸氢钠 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 9.75h， 生成 methyl 27-deoxy-27-oxookadaate
  参考文献：
  名称：

  Selective Elimination of Human Pluripotent Stem Cells by a Marine Natural Product Derivative

  摘要：

  One of the current obstacles to stem cell therapy is the tumorigenic potential of residual undifferentiated stem cells. The present study reports rediscovery of a synthetic derivative of okadaic acid, a marine polyether toxin, as a reagent that selectively induces the death of human pluripotent stem cells. Cell-based screening of 333 cytotoxic compounds identified methyl 27-deoxy-27-oxookadaate (molecule 1) as a substrate of two ATP-binding cassette (ABC) transporters, ABCB1 (MDR1) and ABCG2 (BCRP), whose expression is repressed in human embryonic stem cells and induced pluripotent stem cells. The results demonstrate that selective elimination of human pluripotent stern cells can be achieved by designing cytotoxic small molecules with appropriate ABC-transporter selectivity.

  DOI：

  10.1021/ja501795c
• 作为产物：
  描述：

  重氮甲烷 、 冈田(软海绵)酸 以 甲醇 为溶剂， 以98%的产率得到冈田酸甲酯
  参考文献：
  名称：

  Structure-Activity Relationship of Okadaic Acid, a Potent Protein Phosphatases PP1 and PP2A Inhibitor: 24-epi-Okadaic Acid and a 18-Membered Lactone Analog

  摘要：

  DOI：

  10.3987/com-08-s(n)88

文献信息

• Okadaic acid, a cytotoxic polyether from two marine sponges of the genus Halichondria
  作者：Kazuo Tachibana、Paul J. Scheuer、Yasumasa Tsukitani、Hiroyuki Kikuchi、Donna Van Engen、Jon Clardy、Yalamanchili Gopichand、Francis J. Schmitz

  DOI：10.1021/ja00399a082

  日期：1981.5
• Arteche, Elena; Strippoli, Giuseppe; Loirand, Gervaise, Journal of Pharmacology and Experimental Therapeutics, 1997, vol. 282, # 1, p. 201 - 207
  作者：Arteche, Elena、Strippoli, Giuseppe、Loirand, Gervaise、Pacaud, Pierre、Candenas, Luz、Molto, Juan-Carlos、Souto, Luisa、Fernandez, Javier、Norte, Manuel、Martin, Julio D.、Savineau, Jean-Pierre

  DOI：——

  日期：——
• ICHIKAWA, YOSHIYASU;ISOBE, MINORU;GOTO, TOSHIO, AGR. AND BIOL. CHEM., 52,(1988) N 4, C. 975-981
  作者：ICHIKAWA, YOSHIYASU、ISOBE, MINORU、GOTO, TOSHIO

  DOI：——

  日期：——
• Structure-Activity Relationship of Okadaic Acid, a Potent Protein Phosphatases PP1 and PP2A Inhibitor: 24-epi-Okadaic Acid and a 18-Membered Lactone Analog
  作者：Daisuke Uemura、Masaki Kita、Makoto Kuramoto、Tatsuhiko Chiba、Akihiro Yamada、Nobuko Yamada、Takako Ishida、Takeharu Haino、Kaoru Yamada、Yasuharu Ijuin、Osamu Ohno

  DOI：10.3987/com-08-s(n)88

  日期：——
• Selective Elimination of Human Pluripotent Stem Cells by a Marine Natural Product Derivative
  作者：Ting-Fang Kuo、Di Mao、Nao Hirata、Bilon Khambu、Yasuhisa Kimura、Eihachiro Kawase、Hiroki Shimogawa、Makoto Ojika、Norio Nakatsuji、Kazumitsu Ueda、Motonari Uesugi

  DOI：10.1021/ja501795c

  日期：2014.7.16

  One of the current obstacles to stem cell therapy is the tumorigenic potential of residual undifferentiated stem cells. The present study reports rediscovery of a synthetic derivative of okadaic acid, a marine polyether toxin, as a reagent that selectively induces the death of human pluripotent stem cells. Cell-based screening of 333 cytotoxic compounds identified methyl 27-deoxy-27-oxookadaate (molecule 1) as a substrate of two ATP-binding cassette (ABC) transporters, ABCB1 (MDR1) and ABCG2 (BCRP), whose expression is repressed in human embryonic stem cells and induced pluripotent stem cells. The results demonstrate that selective elimination of human pluripotent stern cells can be achieved by designing cytotoxic small molecules with appropriate ABC-transporter selectivity.