3',3'-cyclic-di-inosine monophospate | 79940-41-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - （3'->5'）-二核苷酸和类似物
• 英文名称: 3',3'-cyclic-di-inosine monophospate
• 英文别名: 3',3'-cdIMP；c-di-IMP；C-di-IMP；9-[(1S,6R,8R,9R,10S,15R,17R,18R)-3,9,12,18-tetrahydroxy-3,12-dioxo-17-(6-oxo-1H-purin-9-yl)-2,4,7,11,13,16-hexaoxa-3λ5,12λ5-diphosphatricyclo[13.3.0.06,10]octadecan-8-yl]-1H-purin-6-one
• CAS: 79940-41-3
• 化学式: C₂₀H₂₂N₈O₁₄P₂
• 分子量: 660.387
• InChiKey: VFTRASQVWRBMKD-XPWFQUROSA-N

物化性质

• 密度：
  2.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -5.6
• 重原子数：
  44
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  289
• 氢给体数：
  6
• 氢受体数：
  18

制备方法与用途

C-di-IMP（环二 IMP）是一种STING激动剂，可应用于肿瘤研究领域。

反应信息

• 作为反应物：
  描述：

  3',3'-cyclic-di-inosine monophospate 在 ammonium acetate 作用下， 生成
  参考文献：
  名称：

  Synthesis of cyclic di-nucleotidic acids as potential inhibitors targeting diguanylate cyclase

  摘要：

  Five analogs of cyclic di-nucleotidic acid including c-di-GMP were synthesized and evaluated for their biological activities on Slr1143, a diguanylate cyclase of Synechocystis sp. Slr1143 was overexpressed from the recombinant plasmid which contained the gene of interest and subsequently purified by affinity chromatography. A new HPLC method capable of separating the compound and product peaks with good resolution was optimized and applied to the analysis of the compounds. Results obtained show that cyclic di-inosinylic acid 1b demonstrates a stronger inhibition on Slr1143 than c-di-GMP and is a potential inhibitor for biofilm formation. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.07.068
• 作为产物：
  描述：

  在 triethylamine tris(hydrogen fluoride) 作用下， 反应 12.0h， 生成 3',3'-cyclic-di-inosine monophospate
  参考文献：
  名称：

  Synthesis of cyclic di-nucleotidic acids as potential inhibitors targeting diguanylate cyclase

  摘要：

  Five analogs of cyclic di-nucleotidic acid including c-di-GMP were synthesized and evaluated for their biological activities on Slr1143, a diguanylate cyclase of Synechocystis sp. Slr1143 was overexpressed from the recombinant plasmid which contained the gene of interest and subsequently purified by affinity chromatography. A new HPLC method capable of separating the compound and product peaks with good resolution was optimized and applied to the analysis of the compounds. Results obtained show that cyclic di-inosinylic acid 1b demonstrates a stronger inhibition on Slr1143 than c-di-GMP and is a potential inhibitor for biofilm formation. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.07.068

文献信息

• Synthesis of Oligoinosinates with 2′–5′ Internucleotide Linkage in Aqueous Solution Using Pb²⁺Ion
  作者：Hiroaki Sawai、Masaji Ohno

  DOI：10.1246/bcsj.54.2759

  日期：1981.9

  the polymerization of inosine-5′-phosphorimidazolide in aqueous solution using Pb2+ ion. 2′–5′ Internucleotide linkage was preferentially formed. The yields of the 2′–5′ linked dimer, trimer, and tetramer were 14.8, 4.5, and 1.6%, respectively. A small amount of linkage isomers of oligoinosinates with 3′–5′ linkage was obtained. The products were characterized by sequential enzyme tests.

  通过使用 Pb2+ 离子在水溶液中聚合肌苷-5'-磷咪唑啉，合成高达五聚体的低聚肌苷酸。优先形成 2'–5' 核苷酸间连接。2'-5' 连接的二聚体、三聚体和四聚体的产率分别为 14.8、4.5 和 1.6%。获得了少量具有3'-5'连接的低聚肌苷酸的连接异构体。产品通过连续酶试验表征。
• DC-SIGN ANTIBODY CONJUGATES COMPRISING STING AGONISTS
  申请人：NOVARTIS AG

  公开号：US20210170043A1

  公开（公告）日：2021-06-10

  Provided herein are immunoconjugates comprising an anti-DC-SIGN antibody conjugated to a STING agonist. Also disclosed are methods of making the immunoconjugates and methods of treating cancer using the immunoconjugates.
• Synthesis of cyclic di-nucleotidic acids as potential inhibitors targeting diguanylate cyclase
  作者：Shi Min Ching、Wan Jun Tan、Kim Lee Chua、Yulin Lam

  DOI：10.1016/j.bmc.2010.07.068

  日期：2010.9

  Five analogs of cyclic di-nucleotidic acid including c-di-GMP were synthesized and evaluated for their biological activities on Slr1143, a diguanylate cyclase of Synechocystis sp. Slr1143 was overexpressed from the recombinant plasmid which contained the gene of interest and subsequently purified by affinity chromatography. A new HPLC method capable of separating the compound and product peaks with good resolution was optimized and applied to the analysis of the compounds. Results obtained show that cyclic di-inosinylic acid 1b demonstrates a stronger inhibition on Slr1143 than c-di-GMP and is a potential inhibitor for biofilm formation. (c) 2010 Elsevier Ltd. All rights reserved.