胞苷5-单磷酸水合物 | 104086-76-2

• 物质功能分类: 生物 - 细胞培养 - 添加剂
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 胞苷5-单磷酸水合物
• 中文别名: 2,3-二脱氧-5-胞苷酸
• 英文名称: β-D-2',3'-dideoxycytidine monophosphate
• 英文别名: 2',3'-dideoxycytidine 5'-monophosphate；2',3'-dideoxycytidine-5'-monophosphate；D-2',3'-dideoxy-cytidine monophosphate；D-ddCMP；2',3'-dideoxycitidine-5'-monophosphate；[(2S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl dihydrogen phosphate
• CAS: 104086-76-2
• 化学式: C₉H₁₄N₃O₆P
• 分子量: 291.2
• InChiKey: RAJMXAZJKUGYGW-POYBYMJQSA-N

物化性质

• 熔点：
  ~222 °C (dec.)
• 沸点：
  555.7±60.0 °C(Predicted)
• 密度：
  1.87±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  135
• 氢给体数：
  3
• 氢受体数：
  6

安全信息

• WGK Germany：
  3
• RTECS号：
  HA3980000
• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  胞苷5-单磷酸水合物 在 T₅ bacteriophage deoxynucleoside monophosphate kinase 、 potassium chloride 、 腺苷 5'-三磷酸酯-gamma-32P 、 5’-三磷酸腺苷 、 magnesium chloride 作用下， 生成 [β-(32)P]d2CDP
  参考文献：
  名称：

  T5噬菌体脱氧核糖核苷单磷酸激酶的底物特异性及其在[α-32P]d/rNTP合成中的应用

  摘要：

  噬菌体 T5 脱氧核苷单磷酸激酶（dNMP 激酶，EC 2.7.4.13）显示可催化 d2CMP 和核糖核苷酸 AMP、GMP 和 CMP 的磷酸化，但不磷酸化 UMP。对于磷酰基的天然受体，发现了 km 和 kcat。T5 dNMP 激酶作为能够磷酸化标记的 r/dNMP 的通用酶的适用性已被证明可用于合成 [α-32P]rNTP 和 [α-32P]dNTP。

  DOI：

  10.1134/s1068162009060090
• 作为产物：
  描述：

  2,3-二脱氧胞啶 在 sodium acetate buffer 、 三(4-硝基苯基)磷酸酯 作用下， 反应 12.0h， 以42%的产率得到胞苷5-单磷酸水合物
  参考文献：
  名称：

  Synthesis of conjugates of 2′,3′-dideoxynucleoside-5′-monophosphates with α-amino acids

  摘要：

  先前未被描述的2′,3′-双脱氧尿苷-5′-单磷酸-(L)-甲氧基色氨酰磷酰胺酸酯（5）和2′,3′-双脱氧胞苷-5′-单磷酸-(L)-甲氧基色氨酰磷酰胺酸酯（7）通过化学酶法被分离出来，旨在研究它们的药理学特性并基于它们制备新的药物制剂。

  DOI：

  10.1007/s10600-006-0080-z

文献信息

• Prodrugs Activated by Rna-Dependent Dna-Polymerases
  申请人：Bertini Ivano

  公开号：US20080300215A1

  公开（公告）日：2008-12-04

  Herein described are prodrugs activated by RNA-dependent DNA-polymerases, such as telomerase and retroviral reverse transcriptases, their use for the treatment of haematological tumours and of blood and blood derivatives from patients affected by retroviral infections, and their use for the preparation of pharmaceutical compositions, to be used for the treatment of solid tumours, of precancerous states and of diseases caused by infection with retroviruses.

  本发明描述了由RNA依赖的DNA聚合酶（如端粒酶和逆转录病毒酶）激活的前药，它们用于治疗血液肿瘤以及受逆转录病毒感染的患者的血液和血液衍生物，并用于制备药物组合物，用于治疗实体肿瘤、癌前状态和由逆转录病毒感染引起的疾病。
• Anti-viral compounds, dosage forms and methods
  申请人：BAKER NORTON PHARMACEUTICALS, INC.

  公开号：EP0284405A2

  公开（公告）日：1988-09-28

  Phosphate pharmaceuticals are contemplated, including dosage forms suitable for oral administration. Methods of treating acquired immune deficiency syndrome and Herpes simplex viruses through oral administration of such phosphate derivatives are further contemplated by the present invention.

  本发明考虑使用磷酸盐药物，包括适合口服的剂型。本发明还考虑了通过口服此类磷酸盐衍生物治疗获得性免疫缺陷综合征和单纯疱疹病毒的方法。
• Anti-retroviral agents and delivery systems for the same
  申请人：THE UNITED STATES OF AMERICA as represented by the Secretary United States Department of Commerce

  公开号：EP0286418A1

  公开（公告）日：1988-10-12

  The present invention provides a method for preventing or treating disease caused by retroviruses, particularly human immunodeficiency virus. Liposomes are prepared containing phosphorylated derivatives of nucle­osides which act as chain-terminators of viral DNA. The phosphorylated nucleosides per se, without encapsulation in liposomes, do not readily enter cells. However, they are found to be effective if encapsulated in liposomes because they remain in liposomes longer, they do not escape easily from cells, and they constitute the active form for incorporation in viral DNA chains. When administered to a host, the liposomes are taken up by endocytic and phagocytic cells, which are important reservoirs of HIV infection. If coated with an appro­priate ligand, such as an immunoglobulin molecule, lipo­somes containing the phosphorylated nucleosides can be directed to phagocytic cells, CD4-positive cells, or infected host cells.

  本发明提供了一种预防或治疗由逆转录病毒，特别是人类免疫缺陷病毒引起的疾病的方法。制备的脂质体含有核苷的磷酸化衍生物，这些衍生物是病毒 DNA 的链终止器。磷酸化核苷本身不包裹在脂质体中，不易进入细胞。然而，如果将它们封装在脂质体中，就会发现它们是有效的，因为它们在脂质体中停留的时间更长，不易从细胞中逃逸，而且它们构成了病毒 DNA 链的活性形式。当给宿主用药时，脂质体会被内细胞和吞噬细胞吸收，而内细胞和吞噬细胞是 HIV 感染的重要储存库。如果涂上适当的配体（如免疫球蛋白分子），含有磷酸化核苷的脂质体就能被导向吞噬细胞、CD4 阳性细胞或受感染的宿主细胞。
• Lipid derivatives of antiviral nucleosides, liposomal incorporation and method of use
  申请人：NeXstar Pharmaceuticals, Inc.

  公开号：EP0350287A2

  公开（公告）日：1990-01-10

  Compounds are disclosed for treating AIDS, herpes, and other viral infections by means of lipid derivatives of antiviral agents. The compounds consist of nucleoside analogues having antiviral activity which are linked, commonly through a phosphate group at the 5′ position of the pentose residue, to one of a selected group of lipids. The lipophilic nature of these compounds provide advantages over the use of the nucleoside analogue alone. It also makes it possible to incorporate them into the lamellar structure of liposomes, either alone or combined with similar molecules. In the form of liposomes, these antiviral agents are preferentially taken up by macrophages and monocytes, cells which have been found to harbor the target HIV virus. Additional site specificity may be incorporated into the liposomes with the addition of ligands, such as monoclonal antibodies or other peptides or proteins which bind to viral proteins. Effective nucleoside analogues are dideoxynucleosides, azidothymine (AZT), and acyclovir; lipid groups may be glycolipids, sphingolipids, phospholipids or fatty acids. The compounds persist, after intracellular hydrolysis, as phosphorylated or non-phosphorylated antiviral nucleosides. The compounds are effective in improving the efficacy of antiviral nucleoside analogues by prolonging the antiviral activity after the administration of the drug has ended, and in preventing retroviral replication in HIV infections which have become resistant to therapy with conventional forms of the antiretroviral agents.

  公开了通过抗病毒剂的脂质衍生物治疗艾滋病、疱疹和其他病毒感染的化合物。这些化合物由具有抗病毒活性的核苷类似物组成，核苷类似物通常通过戊糖残基 5′位上的磷酸基团与一组选定的脂质中的一种相连接。与单独使用核苷类似物相比，这些化合物的亲脂性更具优势。这也使得它们可以单独或与类似分子结合，加入脂质体的片层结构中。在脂质体的形式下，这些抗病毒药物会优先被巨噬细胞和单核细胞吸收，而这些细胞已被发现携带目标 HIV 病毒。在脂质体中加入配体，如与病毒蛋白结合的单克隆抗体或其他肽或蛋白质，还可增加作用点的特异性。有效的核苷类似物有双脱氧核苷、叠氮胸苷（AZT）和阿昔洛韦；脂质基团可以是糖脂、鞘磷脂、磷脂或脂肪酸。这些化合物在细胞内水解后，以磷酸化或非磷酸化的抗病毒核苷形式存在。这些化合物可在给药结束后延长抗病毒活性，从而有效改善抗病毒核苷类似物的疗效，并可在对传统形式的抗逆转录病毒药物治疗产生耐药性的艾滋病毒感染中防止逆转录病毒复制。
• Transformed erythrocytes, process for preparing the same, and their use in pharmaceutical compositions
  申请人：COMMUNAUTE ECONOMIQUE EUROPEENNE (CEE)

  公开号：EP0517986A1

  公开（公告）日：1992-12-16

  The invention relates to compositions comprising transformed erythrocytes containing phosphorylated compounds, which do not naturally occur in a human or animal organism, said compounds having the properties of: inhibiting the reverse transcriptase, and being stable in erythrocytes. The compositions of the invention are useful for the treatment of pathologies caused by the infection of a human or an animal by RNA type virus.

  本发明涉及由含有磷酸化化合物的转化红细胞组成的组合物，磷酸化化合物在人类或动物机体中并不自然存在，所述化合物具有以下特性： 抑制逆转录酶，以及 在红细胞中稳定。 本发明的组合物可用于治疗人或动物感染 RNA 型病毒后引起的病症。