3-(2'-deoxy-β-D-erythro-pentafuranosyl)-5,9-dihydro-9-hydroxy-9H-imidazo[2,1-i]purin | 288863-37-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 3-(2'-deoxy-β-D-erythro-pentafuranosyl)-5,9-dihydro-9-hydroxy-9H-imidazo[2,1-i]purin
• 英文别名: 1,N²-etheno-2'-deoxyguanosine
• CAS: 288863-37-6
• 化学式: C₁₂H₁₃N₅O₄
• 分子量: 291.266
• InChiKey: KIKZUHJTWPXRHD-XLPZGREQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.57
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  117.93
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  3-(2'-deoxy-β-D-erythro-pentafuranosyl)-5,9-dihydro-9-hydroxy-9H-imidazo[2,1-i]purin 在 盐酸 作用下， 反应 4.0h， 生成 1,N²-ethenoguanine
  参考文献：
  名称：

  4,5-Epoxy-2(E)-decenal-Induced Formation of 1,N⁶-Etheno-2‘-deoxyadenosine and 1,N²-Etheno-2‘-deoxyguanosine Adducts

  摘要：

  trans-4,5-Epoxy-2(E)-decenal reacted with 2'-deoxyadenosine to give 1,N-6-etheno-2'-deoxyadenosine as well as other 2'-deoxyadenosine adducts. It also reacted with 2'-deoxyguanosine to give 1,N-2-etheno-2'-deoxyguanosine and other 2'-deoxyguanosine adducts. Synthetic trans-4,5-epoxy-2(E)-decenal was quite stable under the reaction conditions that were used. It was not contaminated with 2,3-epoxyoctanal, a potential precursor to the formation of unsubstituted etheno adducts. Furthermore, using a sensitive LC/MS assay, it was possible to show that no 2,3-epoxyoctanal was formed during prolonged incubations of trans-4,5-epoxy-2(E)-decenal. Therefore, trans-4,5-epoxy-2(E)-decenal, a primary product of lipid peroxidation, is a precursor to the formation of 1,1,N-6-etheno-2'-deoxyadenosine and 1,N-2-etheno-2'-deoxyguanosine. There is no need for an additional oxidation step such as would be required if trans,trans-2,4-decadienal or 4-hydroxy-2-nonenal were the lipid hydroperoxide decomposition products that initiated the formation of unsubstituted etheno adducts. These findings provide an important link between a primary product of lipid peroxidation and a mutagenic DNA lesion that has been detected in human tissues.

  DOI：

  10.1021/tx010147j
• 作为产物：
  描述：

  2'-脱氧鸟苷 、 trans-4,5-epoxy-(2E)-dec-2-enal 在 3-吗啉丙磺酸 、 sodium chloride 作用下， 以 乙醇 为溶剂， 反应 48.0h， 生成 3-(2'-deoxy-β-D-erythro-pentafuranosyl)-5,9-dihydro-9-hydroxy-9H-imidazo[2,1-i]purin
  参考文献：
  名称：

  4,5-Epoxy-2(E)-decenal-Induced Formation of 1,N⁶-Etheno-2‘-deoxyadenosine and 1,N²-Etheno-2‘-deoxyguanosine Adducts

  摘要：

  trans-4,5-Epoxy-2(E)-decenal reacted with 2'-deoxyadenosine to give 1,N-6-etheno-2'-deoxyadenosine as well as other 2'-deoxyadenosine adducts. It also reacted with 2'-deoxyguanosine to give 1,N-2-etheno-2'-deoxyguanosine and other 2'-deoxyguanosine adducts. Synthetic trans-4,5-epoxy-2(E)-decenal was quite stable under the reaction conditions that were used. It was not contaminated with 2,3-epoxyoctanal, a potential precursor to the formation of unsubstituted etheno adducts. Furthermore, using a sensitive LC/MS assay, it was possible to show that no 2,3-epoxyoctanal was formed during prolonged incubations of trans-4,5-epoxy-2(E)-decenal. Therefore, trans-4,5-epoxy-2(E)-decenal, a primary product of lipid peroxidation, is a precursor to the formation of 1,1,N-6-etheno-2'-deoxyadenosine and 1,N-2-etheno-2'-deoxyguanosine. There is no need for an additional oxidation step such as would be required if trans,trans-2,4-decadienal or 4-hydroxy-2-nonenal were the lipid hydroperoxide decomposition products that initiated the formation of unsubstituted etheno adducts. These findings provide an important link between a primary product of lipid peroxidation and a mutagenic DNA lesion that has been detected in human tissues.

  DOI：

  10.1021/tx010147j

文献信息

• <i>trans</i>,<i>trans</i>-2,4-Decadienal-Induced 1,<i>N</i>²-Etheno-2‘-deoxyguanosine Adduct Formation
  作者：Ana Paula M. Loureiro、Paolo Di Mascio、Osmar F. Gomes、Marisa H. G. Medeiros

  DOI：10.1021/tx000004h

  日期：2000.7.1

  well-known reaction product of epoxy aldehydes with dGuo. Two new diasteroisomeric products, A2-1 and A2-2, 1-¿[3-(2'-deoxy-beta-D-erythro-pentafuranosyl)-5, 9-dihydro-9H-imidazo[2,1-i]purin-9-hydroxy]-7-yl¿-2-one-3-octanol, were isolated and characterized on the basis of their spectroscopic features as 1,N(2)-etheno adducts possessing a carbon side chain with a carbonyl and a hydroxyl group. The proposed

  近年来，已经表征了许多由α，β-不饱和醛或其环氧化物与DNA碱基反应产生的环延伸的DNA加合物。这些加合物可能导致DNA复制过程中的错误编码，如果不加以修复，则会导致可能导致癌症发展的突变。反式，反式-2、4-癸二醛（DDE）是由脂质过氧化内源性形成的高度细胞毒性醛之一。为了评估其DNA的破坏潜力，我们研究了过氧化物存在下DDE与2'-脱氧鸟苷（dGuo）的反应。通过反相HPLC分离出三种稳定的加合物。加合物A1，3-（2-deoxy-beta-D-erythro-pentafuranosyl）-5,9-dihydro-9H-imidazo [2，1-i] purin-9-hydroxy，是1，N（2的互变异构体）-etheno-2'-deoxyguanosine，一种众所周知的环氧醛与dGuo的反应产物。两个新的非对映异构体产物A2-1和A2-2，1-[[3-（2'-脱氧β-D-赤型五呋喃糖基）-5，9-二氢-9H-咪唑[2