8-(methylamino)adenosine 5'-diphosphate trisodium salt | 100044-57-3

• 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: 8-(methylamino)adenosine 5'-diphosphate trisodium salt
• CAS: 100044-57-3
• 化学式: C₁₁H₁₅N₆O₁₀P₂*3Na
• 分子量: 522.191
• InChiKey: AWEXQAWIYVDAOL-MCDZGGTQSA-K

计算性质

• 辛醇/水分配系数(LogP)：
  -6.6
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  253.12
• 氢给体数：
  4.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  8-(methylamino)adenosine 5'-diphosphate trisodium salt 在 磷酸烯醇丙酮酸单环己胺盐 作用下， 以 水 为溶剂， 反应 16.0h， 以70%的产率得到8-(methylamino)adenosine 5'-triphosphate tetrasodium salt
  参考文献：
  名称：

  Isozyme-specific enzyme inhibitors. 10. Adenosine 5'-triphosphate derivatives as substrates or inhibitors of methionine adenosyltransferases of rat normal and hepatoma tissues

  摘要：

  Monosubstituted adenosine 5'-triphosphate (ATP) derivatives with a substituent of up to four atoms at any of eight positions in the adenosine moiety, or with an isosteric group replacement at O5' or in the triphosphate moiety, have been evaluated kinetically as substrates and inhibitors of liver (I), kidney (II), and Novikoff hepatoma (T) variants of rat methionine adenosyltransferase. Inhibitory potencies were expressed as KM(ATP)/Ki (for competitive inhibition vs. ATP) or as KM(ATP)/KM when no Ki value was available. Variant I was inhibited more powerfully than II or T by all of four ATP derivatives for which comparative data were obtained. Among 15 ATP derivatives, four were substrates of II or T and the remainder inhibited II and T competitively with respect to ATP; most derivatives exhibited at least moderate (greater than 0.5) inhibitory potency. Differential inhibition of II and T was shown by 11 of 14 ATP derivatives; relative inhibitory potencies (T:II) ranged from 5.5 with 2-SCH3-ATP [KM(ATP)/Ki = 1.3 with T] to 0.24 with the ATP isostere with a C5'-CH2-P alpha system [KM(ATP)/Ki = 1.9 with II]. The most effective inhibitor was the P beta, P gamma imido isostere of ATP with inhibitory potencies of 25 and 35 for II and T, respectively. The findings provide further evidence that substrate derivatives with single short groups attached at various positions, or with single isosteric group replacements, are frequently useful probes in the design of isozyme-selective inhibitors.

  DOI：

  10.1021/jm00153a003
• 作为产物：
  描述：

  monolithium mono(((2R,3S,4R,5R)-5-(6-amino-8-bromo-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl diphosphate) 、 甲胺 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.83h， 以70%的产率得到8-(methylamino)adenosine 5'-diphosphate trisodium salt
  参考文献：
  名称：

  物种或同工酶特异性酶抑制剂。9.腺苷5′-二磷酸衍生物抑制大鼠丙酮酸激酶同工酶的选择性作用。

  摘要：

  已合成了在8个位置中的任何一个位置具有1-4个原子的取代基的5'-二磷酸腺苷衍生物（ADP），并被评估为肝脏（L），肌肉（M）和肾脏（K）同功酶的底物和抑制剂大鼠丙酮酸激酶（PK）的作用。当没有Ki值可用时，化合物的抑制能力表示为KM（ADP）/ Ki或KM（ADP）/ KM。14种ADP衍生物中有9种表现出不同的抑制作用。14种衍生物中的5种对M和K同工酶进行免疫交叉反应，但不与L形式交叉反应。PK-K被两种衍生物优先抑制，PK-L被三种衍生物抑制，PK-M被两种衍生物抑制。在最有选择性和/或最有效的抑制剂中，有3'-OMe-ADP [KM（ADP）/ Ki = 0.07，PK-K；抑制力，K / M / L，7.6：6.0：1]，N6-Me，N6-（CH2）4N（Me）COMe-ADP（预先制备）[KM（ADP）/ KM = 0.43（PK-L; 抑制力，L / K / M，3：2：1]和8-NHEt-ADP

  DOI：

  10.1021/jm00352a017