8-azidoadenosine-5'-phosphate | 60731-47-7

• 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: 8-azidoadenosine-5'-phosphate
• 英文别名: 8-azidoadenosine-5'-monophosphate；8-azido AMP；8-Azidoadenosin-5'-phosphat；8-azido-[5']adenylic acid；8-Azidoadenosine 5'-monophosphate；[(2R,3S,4R,5R)-5-(6-amino-8-azidopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
• CAS: 60731-47-7
• 化学式: C₁₀H₁₃N₈O₇P
• 分子量: 388.236
• InChiKey: DHPCYOPKNHVUPP-UUOKFMHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  200
• 氢给体数：
  5
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  8-azidoadenosine-5'-phosphate 在 DL-dithiothreitol 作用下， 反应 16.0h， 以65%的产率得到8-amino-5'-AMP
  参考文献：
  名称：

  Synthesis of cyclic adenosine 5′-diphosphate ribose analogues: a C2′ endo/syn “southern” ribose conformation underlies activity at the sea urchin cADPR receptor

  摘要：

  采用化学酶法合成了新型 8 取代碱基和糖修饰的 Ca2+ 调动第二信使环腺苷-5â²-二磷酸核糖（cADPR）类似物，并对其在海胆卵匀浆（SUH）和 Jurkat T 淋巴细胞中的活性进行了评估；通过 1H NMR 光谱进行的构象分析发现，C2â² 内/同步构象是 CADPR 在海胆蛋匀浆（SUH）受体（而不是在 T 细胞-CADPR 受体）中发挥激动剂或拮抗剂活性的关键。

  DOI：

  10.1039/c0ob00396d
• 作为产物：
  描述：

  8-溴膘苷 在 磷酸三甲酯 、 盐酸 、 肼 、 三氯氧磷 、 亚硝酸异戊酯 作用下， 以 乙醇 为溶剂， 生成 8-azidoadenosine-5'-phosphate
  参考文献：
  名称：

  烟酸腺嘌呤二核苷酸磷酸类似物被烟酸和腺嘌呤核苷取代。对受体介导的Ca 2+释放的影响

  摘要：

  烟酸腺嘌呤二核苷酸磷酸酯（NAADP）在哺乳动物和棘皮动物中都是释放Ca 2+的细胞内第二信使。我们报告说，海胆受体可以识别在烟酸5位上引入的大型官能化取代基，尽管其激动剂的效价降低了20-500倍。显示5-（3-叠氮基丙基）-NAADP以31μM的EC 50释放Ca 2+，并与NAADP竞争受体结合，IC 50为56 nM。带电荷的基团与NAADP的烟酸的附着与活性降低有关，这表明烟酸核糖苷部分被认为是中性的两性离子。取代基（Br–和N 3-）可以引入NAADP的8腺苷位置，同时保持高的效力和激动剂效力，尽管激动剂的效力是，但也公认在烟酸的5位和8腺苷位置都取代了NAADP衍生物。大大减少。

  DOI：

  10.1021/acs.jmedchem.5b00279

文献信息

• MODIFIED NUCLEIC ACID MOLECULES AND USES THEREOF
  申请人：MODERNA THERAPEUTICS, INC.

  公开号：US20150307542A1

  公开（公告）日：2015-10-29

  The present disclosure provides modified nucleosides, nucleotides, and nucleic acids, and methods of using them.

  本公开提供了修改的核苷酸，核苷酸和核酸，以及使用它们的方法。
• Complexes of RNA and cationic peptides for transfection and for immunostimulation
  申请人：CureVac GmbH

  公开号：EP2484770A1

  公开（公告）日：2012-08-08

  The present invention relates to a complexed RNA, comprising at least one RNA complexed with one or more oligopeptides, wherein the oligopeptide has a length of 8 to 15 amino acids and has the empirical formula (Arg)l;(;Lys)m;(His)n;(Orn)o;(Xaa)x with the majority of the residues being selected from Arg, Lys, His, Orn. The invention further relates to a method for transfecting a cell or an organism, thereby applying the inventive complexed RNA. Additionally, pharmaceutical compositions and kits comprising the inventive complexed RNA, as well as the use of the inventive complexed RNA for transfecting a cell, tissue or an organism and/or for modulating, preferably inducing or enhancing, an immune response are disclosed herein.

  本发明涉及一种复合 RNA，包括至少一种与一种或多种寡肽复合的 RNA，其中寡肽的长度为 8 至 15 个氨基酸，具有经验式 (Arg)l;(;Lys)m;(His)n;(Orn)o;(Xaa)x，大部分残基选自 Arg、Lys、His、Orn。本发明进一步涉及一种转染细胞或生物体的方法，从而应用本发明的复合 RNA。此外，本文还公开了包含本发明络合 RNA 的药物组合物和试剂盒，以及本发明络合 RNA 用于转染细胞、组织或生物体和/或调节、优选诱导或增强免疫反应的用途。
• Synthesis, Characterization, and Biological Properties of 8-Azido- and 8-Amino-Substituted 2‘,5‘-Oligoadenylates
  作者：Hiroaki Sawai、Atushi Hirano、Hiroyuki Mori、Kazuo Shinozuka、Beihua Dong、Robert H. Silverman

  DOI：10.1021/jm030035k

  日期：2003.11.1

  A series of 8-azido- and 8-amino-substituted 2',5'-oligoadenylatyes was prepared by a uranyl-ion catalyzed polymerization of the corresponding 8-substituted adenosine phosphorimidazolide. Subsequent 5'-dephosphorylation of the resulting 5'-phosphoryl 2',5'-linked oligomers with alkaline phosphatase gave the corresponding core oligomers. The CD spectra indicated that the 8-aminoadenosine analogue of the 2',5'-linked trimer has an anti-orientation as in naturally occurring 2',5'-oligoadenylates, while 8-azido-substituted 2',5'-oligoadenylates have a syn-orientation. The 8-substituted oligomers showed enhanced resistance against digestion by snake venom phosphodiesterase. The 2',5'-linked 8-azidoadenylate trimer and tetramer displayed strong RNase L binding and activating ability, although the corresponding dimer is devoid of such activities. In contrast, very low or no RNase L binding and activating ability were observed in the 8-aminoadenosine analogue of 2',5'-oligoadenylates. Results indicate that the bulkiness and ionic character of the 8-substituting group have significant effects on the ability of these analogues to bind and activate RNase L. Furthermore, the orientation of the glycosidic base in the 2-5A analogues may change from syn to anti during binding to RNase L. The 8-azidoadenosine analogues of 2-5A will be useful tools in the photoaffinity labeling of RNase L, due to their strong RNase L binding ability. In addition, these 8-azidoadenosine compounds may be considered as candidates for experimental therapeutic agents because they have enhanced stability to enzyme degradation while retaining the ability to activate RNase L.
• PRESCOTT, MARK;MCLENNAN, ALEXANDER G., ANAL. BIOCHEM., 184,(1990) N, C. 330-337
  作者：PRESCOTT, MARK、MCLENNAN, ALEXANDER G.

  DOI：——

  日期：——
• CHRONIC FATIGUE SYNDROME DIAGNOSIS
  申请人：Temple University of the Commonwealth System of Higher Education

  公开号：EP0934429B1

  公开（公告）日：2004-05-19