P¹-2-(methylthio)adenosyl-P²-(RS)-1-(4,5-dimethoxy-2-nitrophenyl)ethyl pyrophosphate | 1019307-51-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: P¹-2-(methylthio)adenosyl-P²-(RS)-1-(4,5-dimethoxy-2-nitrophenyl)ethyl pyrophosphate
• 英文别名: MRS2703；[[(2R,3S,4R,5R)-5-(6-amino-2-methylsulfanylpurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] 1-(4,5-dimethoxy-2-nitrophenyl)ethyl hydrogen phosphate
• CAS: 1019307-51-7
• 化学式: C₂₁H₂₈N₆O₁₄P₂S
• 分子量: 682.499
• InChiKey: UQHRJVYVEWLTQB-MXOUNDOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  44
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  311
• 氢给体数：
  5
• 氢受体数：
  19

反应信息

• 作为产物：
  描述：

  2-甲基硫代二磷酸腺苷 、 1-(4,5-dimethoxy-2-nitrophenyl)diazoethane 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以66%的产率得到P¹-2-(methylthio)adenosyl-P²-(RS)-1-(4,5-dimethoxy-2-nitrophenyl)ethyl pyrophosphate
  参考文献：
  名称：

  Caged agonist of P2Y1 and P2Y12 receptors for light-directed facilitation of platelet aggregation

  摘要：

  We have prepared a caged form (MRS2703) of a potent dual agonist of the P2Y(1) and P2Y(12) nucleotide receptors, 2-MeSADP, by blocking the p-phosphate group with a 1-(3,4-dimethyloxyphenyl)eth-1-yl phosphoester. Although MRS2703 is itself inactive at human P2Y(1) and P2Y(12) receptors expressed heterologously in 1321N1 astrocytoma cells or in washed human platelets, this derivative readily regenerates the parent agonist upon mild irradiation with long-wave UV light (360 nm). The functional effect of the regenerated agonist was demonstrated by a rise in intracellular calcium mediated by either P2Y(1) or P2Y(12) receptors in transfected cells. Washed human platelets exposed to a solution of MRS2703 were induced to aggregate upon UV irradiation. At 1.0 mu M MRS2703, full aggregation was achieved within 1 min of irradiation. Thus, this caged nucleotide promises to be a useful probe for potent P2Y receptor activation with light-directed spatial and temporal control. Published by Elsevier Inc.

  DOI：

  10.1016/j.bcp.2007.10.037

文献信息

• Caged agonist of P2Y1 and P2Y12 receptors for light-directed facilitation of platelet aggregation
  作者：Zhan-Guo Gao、Béatrice Hechler、Pedro Besada、Christian Gachet、Kenneth A. Jacobson

  DOI：10.1016/j.bcp.2007.10.037

  日期：2008.3

  We have prepared a caged form (MRS2703) of a potent dual agonist of the P2Y(1) and P2Y(12) nucleotide receptors, 2-MeSADP, by blocking the p-phosphate group with a 1-(3,4-dimethyloxyphenyl)eth-1-yl phosphoester. Although MRS2703 is itself inactive at human P2Y(1) and P2Y(12) receptors expressed heterologously in 1321N1 astrocytoma cells or in washed human platelets, this derivative readily regenerates the parent agonist upon mild irradiation with long-wave UV light (360 nm). The functional effect of the regenerated agonist was demonstrated by a rise in intracellular calcium mediated by either P2Y(1) or P2Y(12) receptors in transfected cells. Washed human platelets exposed to a solution of MRS2703 were induced to aggregate upon UV irradiation. At 1.0 mu M MRS2703, full aggregation was achieved within 1 min of irradiation. Thus, this caged nucleotide promises to be a useful probe for potent P2Y receptor activation with light-directed spatial and temporal control. Published by Elsevier Inc.