<4-(7-Methoxycoumarinyl)>methyl adenosine cyclic 3',5'-monophosphate

• 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: <4-(7-Methoxycoumarinyl)>methyl adenosine cyclic 3',5'-monophosphate
• 英文别名: 4-[[(4aR,6R,7R,7aS)-6-(6-aminopurin-9-yl)-7-hydroxy-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-2-yl]oxymethyl]-7-methoxychromen-2-one
• 化学式: C₂₁H₂₀N₅O₉P
• 分子量: 517.392
• InChiKey: ABJRXMINLQZBMM-WMTITFOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  179
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  <4-(7-Methoxycoumarinyl)>methyl adenosine cyclic 3',5'-monophosphate 在 水 作用下， 以 1,4-二氧六环 为溶剂， 生成 4-(hydroxymethyl)-7-methoxycoumarin 、 腺苷环磷酸酯
  参考文献：
  名称：

  Photochemical Properties of New Photolabile cAMP Derivatives in a Physiological Saline Solution

  摘要：

  Three new photolabile esters of cAMP (2-anthraquinonyl)methyl (la), (7-methoxycoumarinyl)methyl (2a), and 2-naphthylmethyl (3a), have been developed. The stability and photochemical properties of these derivatives were compared to the previously reported ones in a physiological saline solution (1% DMSO in Ringer's solution, pH 7.4). We found that 2a had satisfactory stability (t(1/2) > 1000 h) in the dark and was photolyzed to release the parent cAMP on 340 nm irradiation (phi(app) = 0.10, epsilon(340) = 6730) more efficiently than previously reported caged cAMPs. A biological test using the melanophores of the medaka (Oryzias latipes) revealed that 2a penetrated into the melanophores, inactive before irradiation and activated to release cAMP upon irradiation. We have developed a new caged cAMP which can be used in the investigation of biological responses regulated by intracellular cAMP concentrations using living cells.

  DOI：

  10.1021/jo00118a008
• 作为产物：
  描述：

  4-溴甲基-7-甲氧基香豆素 、 腺苷环磷酸酯 在 silver(l) oxide 作用下， 以 二甲基亚砜 、 乙腈 为溶剂， 反应 45.0h， 以44%的产率得到<4-(7-Methoxycoumarinyl)>methyl adenosine cyclic 3',5'-monophosphate
  参考文献：
  名称：

  Photochemical Properties of New Photolabile cAMP Derivatives in a Physiological Saline Solution

  摘要：

  Three new photolabile esters of cAMP (2-anthraquinonyl)methyl (la), (7-methoxycoumarinyl)methyl (2a), and 2-naphthylmethyl (3a), have been developed. The stability and photochemical properties of these derivatives were compared to the previously reported ones in a physiological saline solution (1% DMSO in Ringer's solution, pH 7.4). We found that 2a had satisfactory stability (t(1/2) > 1000 h) in the dark and was photolyzed to release the parent cAMP on 340 nm irradiation (phi(app) = 0.10, epsilon(340) = 6730) more efficiently than previously reported caged cAMPs. A biological test using the melanophores of the medaka (Oryzias latipes) revealed that 2a penetrated into the melanophores, inactive before irradiation and activated to release cAMP upon irradiation. We have developed a new caged cAMP which can be used in the investigation of biological responses regulated by intracellular cAMP concentrations using living cells.

  DOI：

  10.1021/jo00118a008

文献信息

• Photochemical Properties of New Photolabile cAMP Derivatives in a Physiological Saline Solution
  作者：Toshiaki Furuta、Hiromi Torigai、Masazumi Sugimoto、Michiko Iwamura

  DOI：10.1021/jo00118a008

  日期：1995.6

  Three new photolabile esters of cAMP (2-anthraquinonyl)methyl (la), (7-methoxycoumarinyl)methyl (2a), and 2-naphthylmethyl (3a), have been developed. The stability and photochemical properties of these derivatives were compared to the previously reported ones in a physiological saline solution (1% DMSO in Ringer's solution, pH 7.4). We found that 2a had satisfactory stability (t(1/2) > 1000 h) in the dark and was photolyzed to release the parent cAMP on 340 nm irradiation (phi(app) = 0.10, epsilon(340) = 6730) more efficiently than previously reported caged cAMPs. A biological test using the melanophores of the medaka (Oryzias latipes) revealed that 2a penetrated into the melanophores, inactive before irradiation and activated to release cAMP upon irradiation. We have developed a new caged cAMP which can be used in the investigation of biological responses regulated by intracellular cAMP concentrations using living cells.