adenosine 5'-monophosphate monosodium salt | 132-00-3

• 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: adenosine 5'-monophosphate monosodium salt
• 英文别名: adenosine 5'-monophosphate sodium salt；AMP sodium salt；sodium;[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl hydrogen phosphate
• CAS: 132-00-3
• 化学式: C₁₀H₁₃N₅O₇P*Na
• 分子量: 369.206
• InChiKey: FYWLYWMEGHCZAX-MCDZGGTQSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -5.49
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  189
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  adenosine 5'-monophosphate monosodium salt 在 Dowex D₅₀ (H⁺) 作用下， 以 水 为溶剂， 生成 5'-腺嘌呤核苷酸
  参考文献：
  名称：

  合成5'-二磷酸腺苷核糖末端核糖类似物作为瞬时受体电位阳离子通道TRPM2的探针。

  摘要：

  TRPM2（瞬态受体潜在阳离子通道，M亚家族，成员2）是一种非选择性阳离子通道，参与对氧化应激的反应和炎症。它在自身免疫和神经退行性疾病中的作用使其成为有吸引力的药理靶标。核苷酸5'-二磷酸核糖核苷（ADPR）与胞质NUDT9同源性（NUDT9 H的结合））域激活频道。尚缺乏对ADPR如何与TRPM2配体结合域相互作用的详细理解，这妨碍了调节剂的合理设计，但已知ADPR的末端核糖对于激活至关重要。为了更详细地研究其作用，我们设计了合成途径以合成ADPR和2'-deoxy-ADPR的新型类似物，这些类似物仅通过从末端核糖上除去单个羟基进行修饰。ADPR类似物是通过将核苷磷咪唑盐与脱氧糖磷酸酯偶联而获得的。相应的基于C2''的类似物被证明是不稳定的。通过膜片钳在表达TRPM2的HEK293细胞中对C1”-和C3” -ADPR类似物进行电生理学评估。此外，末端核糖的所有羟基均被封闭的化合物为其1”-β-

  DOI：

  10.1021/acs.joc.9b00338
• 作为产物：
  描述：

  腺苷 在 disodium hydrogenphosphate 、 magnesium chloride 作用下， 以 水 为溶剂， 反应 72.0h， 生成 adenosine 5'-monophosphate monosodium salt
  参考文献：
  名称：

  腺苷、腺苷 5'-单磷酸、肌苷和肌苷 5'-单磷酸之间反应的热化学；d-组氨酸转化为（尿刊酸+氨）

  摘要：

  摘要 报道了一系列酶催化反应的平衡和量热测量结果，这些反应涉及腺苷 5'-单磷酸 (AMP)、腺苷和 d-组氨酸的脱氨基，以及 AMP 和 5'-单磷酸 (IMP) 的脱磷酸。这些测量值已使用描述溶液中复杂平衡的模型进行了分析。获得的结果是： Δ r H om = -(49.6±0.5) kJ·mol -1 对于 AMP 2- (aq) + H 2 O(l) + H + (aq) = HIMP 2- (aq) + NH + 4 (水溶液); Δ r H om = -(49.4±0.7) kJ·mol -1 腺苷(aq) + H 2 O(l) + H + (aq) = 肌苷(aq) + NH + 4 (aq)；Δ r G om = -(13.0±0.4) kJ·mol -1 ，Δ r H om = (0.9±0.4) kJ·mol -1 ，以及Δ r S om = (47±2) J·K -1

  DOI：

  10.1006/jcht.1993.1009

文献信息

• Synthesis, Biological Activity, and Molecular Modeling of Ribose-Modified Deoxyadenosine Bisphosphate Analogues as P2Y₁ Receptor Ligands
  作者：Erathodiyil Nandanan、Soo-Yeon Jang、Stefano Moro、Hea Ok Kim、Maqbool A. Siddiqui、Pamela Russ、Victor E. Marquez、Roger Busson、Piet Herdewijn、T. Kendall Harden、José L. Boyer、Kenneth A. Jacobson

  DOI：10.1021/jm990249v

  日期：2000.3.1

  than the corresponding (S)-isomer. The 2-chloro-N(6)-methyl-(N)-methanocarba analogue was an antagonist of IC(50) 51.6 nM. Thus, the ribose ring (N)-conformation appeared to be favored in recognition at P2Y(1) receptors. A cyclobutyl analogue was an antagonist with IC(50) of 805 nM, while morpholine ring-containing analogues were nearly inactive. Anhydrohexitol ring-modified bisphosphate derivatives

  已经探索了腺苷 3', 5'-二磷酸作为 P2Y(1) 受体拮抗剂的构效关系，揭示了 N(6)-甲基基团的效力增强作用和取代核糖部分的能力。 Nandanan et al. J. Med. Chem. 1999, 42, 1625-1638)。我们引入了受约束的碳环（以探索糖褶皱的作用）、与腺嘌呤部分的非糖基键以及磷酸基团移位。每种类似物对 P2Y(1) 受体的生物学活性的特点是测量其刺激火鸡红细胞膜中的磷脂酶 C（激动剂作用）和抑制其由 30 nM 2-甲基硫腺苷-5'-二磷酸（拮抗剂作用）引起的刺激的能力）。N(6)-甲基在几个案例中的加入将纯激动剂转化为拮抗剂。碳环 N(6)-methyl-2'-deoxyadenosine bisphosphate 类似物是纯 P2Y(1) 受体拮抗剂，与核糖类似物 (MRS 2179) 等效。在一系列环约束的甲卡巴衍生物中，稠合环丙烷部分将核苷的假糖环约束为北
• Sulfonyl Imidazolium Salts as Reagents for the Rapid and Efficient Synthesis of Nucleoside Polyphosphates and Their Conjugates
  作者：Samy Mohamady、Ahmed Desoky、Scott D. Taylor

  DOI：10.1021/ol203178k

  日期：2012.1.6

  A procedure for the synthesis of nucleoside polyphosphates and their conjugates using sulfonylimidazolium salts as key reagents is described. The procedure is rapid and high yielding, does not require prior protection and subsequent deprotection of the donors or acceptors, and can be used to activate nucleoside mono-, di- and triphosphates, and a wide variety of acceptors and donors can be used.

  描述了使用磺酰亚胺咪唑鎓盐作为关键试剂合成核苷多磷酸盐及其缀合物的方法。该方法是快速且高产率的，不需要供体或受体的事先保护和随后的脱保护，并且可以用于活化核苷单，二和三磷酸，并且可以使用各种各样的受体和供体。
• Enzyme Kinetics and Pharmacological Characterization of Nucleotidases Released from the Guinea Pig Isolated Vas Deferens during Nerve Stimulation: Evidence for a Soluble Ecto-Nucleoside Triphosphate Diphosphohydrolase-Like ATPase and a Soluble Ecto-5′-Nucleotidase-Like AMPase
  作者：Svetlana T. Mihaylova-Todorova、Latchezar D. Todorov、David P. Westfall

  DOI：10.1124/jpet.102.033332

  日期：2002.9.1

  Previously, we have demonstrated that stimulation of the sympathetic nerves of the guinea pig vas deferens evokes release not only of the cotransmitters ATP and norepinephrine but also of soluble nucleotidases that break down extracellular ATP, ADP, and AMP into adenosine. In this study we show that the apparent K m values of the releasable enzyme activity vary depending on which of these adenine nucleotides is used as initial substrate. The K m value for ATP was 33.6 ± 2.3 μM, 21.0 ± 2.3 μM for ADP, and 10.0 ± 1.1 μM for AMP. The ratios of the V maxvalues for each enzyme reaction were 4:2:3. We have also found a different sensitivity of the metabolism of ATP and AMP by releasable nucleotidases to known nucleotidase inhibitors. Suramin inhibited the breakdown of ATP by releasable nucleotidases in a noncompetitive manner and with a K i value of 53 μM, but had no effect on the breakdown of AMP. The 5′-nucleotidase inhibitor α,β-methylene ADP inhibited the breakdown of AMP but not that of ATP. Concanavalin A inhibited the breakdown of AMP but had neither inhibitory nor facilitatory effects on the breakdown of ATP. 6- N , N -Diethyl-β,γ-dibromomethylene-d-ATP (ARL67156), an ecto-ATPase inhibitor, suppressed ATPase and AMPase activities, whereas NaN3 (10 mM) affected neither reaction, but inhibited the ADP metabolism. Phosphatase- and phosphodiesterase inhibitors did not affect the activity of the releasable nucleotidases. This evidence suggests that the soluble nucleotidases released during neurogenic stimulation of the guinea pig vas deferens combine an ecto-5′-nucleotidase-like and an ecto-nucleoside triphosphate diphosphohydrolase-like activity.

  之前，我们已经证明刺激豚鼠输精管的交感神经不仅引发ATP和去甲肾上腺素等共同传递物质的释放，还引发可溶性核苷酸酶的释放，这些酶将细胞外ATP、ADP和AMP分解为腺苷。在本研究中，我们展示了可释放酶活性的表观K_m值取决于所用的腺苷酸作为起始底物。ATP的K_m值为33.6 ± 2.3 μM，ADP为21.0 ± 2.3 μM，AMP为10.0 ± 1.1 μM。每种酶反应的V_max值比率为4:2:3。我们还发现可释放核苷酸酶对已知核苷酸酶抑制剂的ATP和AMP代谢有不同的敏感性。苏黎世抑制了可释放核苷酸酶对ATP的分解，属于非竞争性抑制，K_i值为53 μM，但对AMP的分解没有影响。5′-核苷酸酶抑制剂α,β-亚甲基ADP抑制了AMP的分解，但对ATP则没有影响。刀豆凝集素A抑制了AMP的分解，但对ATP的分解既没有抑制作用也没有促进作用。6-N,N-二乙基-β,γ-双溴亚甲基-d-ATP（ARL67156），一种外源ATP酶抑制剂，抑制了ATP酶和AMP酶活性，而NaN3（10 mM）对两种反应均没有影响，但抑制了ADP的代谢。磷酸酶和磷酸二酯酶抑制剂对可释放核苷酸酶的活性没有影响。这些证据表明，在豚鼠输精管的神经刺激过程中释放的可溶性核苷酸酶结合了类似外源5′-核苷酸酶和外源核苷三磷酸二磷酸水解酶的活性。
• COMPOSITION FOR CELL PROLIFERATION
  申请人：Otsuka Pharmaceutical Company, Limited

  公开号：EP1498101A1

  公开（公告）日：2005-01-19

  The present invention provides a method for effectively exerting a cell proliferation promoting effect of a purine nucleic acid-related substance. The present invention provides a composition for cell proliferation containing a purine nucleic acid-related substance and a pyrimidine nucleic acid-related substance. Further, the present invention provides a method for potentiating the cell proliferation promoting effect of the purine nucleic acid-related substance by using the purine nucleic acid-related substance in combination with the pyrimidine nucleic acid-related substance. Still further, the present invention provides a method for promoting cell proliferation, where the method comprising applying purine nucleic acid-related substance in combination with the pyrimidine nucleic acid-related substance to the skin or mucosa.

  本发明提供了一种有效发挥嘌呤核酸相关物质促进细胞增殖作用的方法。本发明提供了一种含有嘌呤核酸相关物质和嘧啶核酸相关物质的细胞增殖组合物。此外，本发明还提供了一种通过将嘌呤核酸相关物质与嘧啶核酸相关物质结合使用来增强嘌呤核酸相关物质促进细胞增殖效果的方法。更进一步，本发明提供了一种促进细胞增殖的方法，该方法包括将嘌呤核酸相关物质与嘧啶核酸相关物质结合应用于皮肤或粘膜。
• CHLOASMA AMELIORATION COMPOSITION AND DULLNESS AMELIORATION COMPOSITION
  申请人：OTSUKA PHARMACEUTICAL CO., LTD.

  公开号：EP1512405A1

  公开（公告）日：2005-03-09

  The present invention provides a composition that can effectively improve melasma and a composition that can effectively reduce skin dullness. The composition for improving melasma comprises a purine nucleic acid-related substance and a pharmaceutically or cosmetically acceptable carrier, and exhibits an excellent melasma improving effect due to the action of the purine nucleic acid-related substance contained. The composition for reducing skin dullness comprises a purine nucleic acid-related substance and a pharmaceutically or cosmetically acceptable carrier, and exhibits an excellent effect of reducing skin dullness due to the action of the purine nucleic acid-related substance contained.

  本发明提供了一种可有效改善黄褐斑的组合物和一种可有效减轻皮肤暗沉的组合物。 用于改善黄褐斑的组合物包括一种嘌呤核酸相关物质和一种药学上或化妆品上可接受的载体，由于所含嘌呤核酸相关物质的作用，该组合物具有极佳的改善黄褐斑的效果。 减少皮肤暗沉的组合物包含一种嘌呤核酸相关物质和一种药学上或化妆品上可接受的载体，由于所含嘌呤核酸相关物质的作用，该组合物具有极佳的减少皮肤暗沉的效果。