7-(2'-carboxyethyl)guanine | 1082-07-1

• 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: 7-(2'-carboxyethyl)guanine
• 英文别名: 7-(2-Carboxyethyl)guanine；3-(2-amino-6-oxo-1H-purin-7-yl)propanoic acid
• CAS: 1082-07-1
• 化学式: C₈H₉N₅O₃
• 分子量: 223.191
• InChiKey: ZGZWMFXNXFNBOT-UHFFFAOYSA-N

物化性质

• 密度：
  1.89±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  三甲基氯化锡 、 7-(2'-carboxyethyl)guanine 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以86%的产率得到
  参考文献：
  名称：

  有机锡氧烷支持的核碱基阵列：含有鸟嘌呤，尿嘧啶和2-氨基嘌呤的聚合物和分子有机锡复合物的合成和超分子结构†

  摘要：

  L1H {L1H = 3-（N9-胍基）丙酸}与Me 3 SnCl或（n -Bu 3 Sn）2 O的反应得到一维配位聚合物[Me 3 Sn（L1）] n（1）和[ n -Bu 3 Sn（L1）] n（2）。L 2 H {L 2 H ＝ 3-（N7-胍基）丙酸}与Me 3 SnCl之间的反应也得到一维配位聚合物[Me 3 Sn（L2）] n（3）。L3H [尿嘧啶-6-羧酸]与（Ph 3 Sn）2的相似反应O以2∶1的比例得到二聚体[（n- Bu 3 SnL3）2 ·H 2 O]（4）。在3- {N9-（2-氨基嘌呤基）}丙酸（L4H）与Me 3 SnCl的1：1反应中获得单核化合物[Me 3 Sn（L4）·H 2 O]（5）。配合物1-5由于多种分子间的相互作用，在固态下显示出丰富的超分子结构。因此，在一维配位聚合物3中，已观察到链间鸟嘌呤单元之间的三氢键（G G）。类似地，在4中观察到了同位四重奏

  DOI：

  10.1039/c6ce00719h
• 作为产物：
  描述：

  鸟嘌呤 在 乙醇 、 sodium hydride 、 三乙胺 作用下， 以 水 、 二甲胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 3-(2-氨基-6-氧代-3H-嘌呤-9-基)丙酸 、 7-(2'-carboxyethyl)guanine
  参考文献：
  名称：

  Small Molecules in the Cone Snail Arsenal

  摘要：

  Cone snails are renowned for producing peptide-based venom, containing conopeptides and conotoxins, to capture their prey. A novel small-molecule guanine derivative with unprecedented features, genuanine, was isolated from the venom of two cone snail species. Genuanine causes paralysis in mice, indicating that small molecules and not just polypeptides may contribute to the activity of cone snail venom.

  DOI：

  10.1021/acs.orglett.5b02389

文献信息

• Quantitation by liquid chromatography-nanoelectrospray ionization-high resolution tandem mass spectrometry of DNA adducts derived from methyl glyoxal and carboxyethylating agents in leukocytes of smokers and non-smokers
  作者：Guang Cheng、Sarah A. Reisinger、Peter G. Shields、Dorothy K. Hatsukami、Silvia Balbo、Stephen S. Hecht

  DOI：10.1016/j.cbi.2020.109140

  日期：2020.8

  The method was applied for the analysis of these two DNA adducts in leukocyte DNA from 20 smokers and 20 non-smokers, in part to test the hypothesis that 7-2′-CEG could be formed by endogenous nitrosation, as previously observed in rats treated with nitrosodihydrouracil and nitrite. Levels of 7-2′-CEG (mean ± S.D.) were 0.6 ± 0.2 pmol/μmol dG in smokers and 0.5 ± 0.2 pmol/μmol dG in non-smokers, while

  建立了液相色谱-纳米电喷雾电离高分辨率串联质谱（LC-NSI-HRMS / MS）方法用于定量DNA加合物7-（2'-羧乙基）鸟嘌呤（7-2'-CEG）和N 2的方法-（1'-羧乙基）鸟嘌呤（N 2 -1'-CEG），作为它们的甲酯，存在于吸烟者和非吸烟者的人白细胞DNA中。先前已在所有分析的人类肝脏样品中鉴定出7-2'-CEG，它由未知的羧乙基化剂形成，而N 2-1'-CEG由晚期糖基化终产物甲基乙二醛形成。该方法用于分析来自20位吸烟者和20位非吸烟者的白细胞DNA中的这两种DNA加合物，部分目的是为了验证以下假设：如先前在治疗的大鼠中观察到的，内源性亚硝化可形成7-2'-CEG与亚硝基二氢尿嘧啶和亚硝酸盐。吸烟者的7-2'-CEG水平（平均值±SD）为0.6±0.2 pmol /μmoldG，非吸烟者为0.5±0.2 pmol /μmoldG，而N 2-1'-CEG在吸烟者中为4.5±1
• METHOD OF MODIFYING NUCLEOTIDE CHAIN
  申请人：MATSUSHITA ELECTRIC INDUSTRIAL CO., LTD.

  公开号：EP1647592A1

  公开（公告）日：2006-04-19

  A method for modifying a nucleotide chain, which includes: allowing a catabolic enzyme specific to a nucleotide sequence containing a specific base such as hypoxanthine (Hx) to act on a nucleotide chain (I) to be modified having the above described nucleotide sequence containing a specific base on the 3'-terminal side thereof; and forming a functional group (for example, an aldehyde group) capable of binding to a desired modifier (for example, NH2R having an amino group) on the 3'-terminus of the nucleotide chain (I); so as to bind the above described modifier to the 3'-terminus of the nucleotide chain. Using a nucleotide chain as a modification target which has a nucleotide sequence containing a specific base acting as an enzyme substrate on its 3'-terminal side, this method enables decomposition of only the above described nucleotide sequence portion, thereby forming a functional group that reacts with a desired modifier and binds thereto. By this method, a nucleotide chain can directly be modified with a modifier, thereby easily labeling or conjugating the nucleotide chain. Further, when immobilization of a nucleotide chain is intended, stable and strong immobilization can be attained using a modifier as a linker.

  一种修饰核苷酸链的方法，包括让对含有特定碱基（如次黄嘌呤（Hx））的核苷酸序列具有特异性的分解酶作用于待修饰的核苷酸链（I），该核苷酸链具有在其 3'- 末端侧含有特定碱基的上述核苷酸序列；并在核苷酸链（I）的 3'末端形成能够与所需修饰剂（例如具有氨基的 NH2R）结合的官能团（例如醛基），从而将上述修饰剂结合到核苷酸链的 3'末端。使用核苷酸链作为修饰靶，该核苷酸链的 3'- 末端含有作为酶底物的特定碱基的核苷酸序列，这种方法可以只分解上述核苷酸序列部分，从而形成与所需修饰剂反应并结合的官能团。通过这种方法，核苷酸链可以直接被修饰剂修饰，从而方便地标记或连接核苷酸链。此外，当需要固定核苷酸链时，使用修饰剂作为连接剂可以实现稳定而牢固的固定。
• Cell-derived viral vaccines with low levels of residual cell DNA
  申请人：Novartis Vaccines and Diagnostics GmbH

  公开号：EP2301572A1

  公开（公告）日：2011-03-30

  The present invention relates to vaccine products for the treatment or prevention of viral infections. Further provided are methods of reducing contaminants associated with the preparation of cell culture vaccines. Residual functional cell culture DNA is degraded by treatment with a DNA alkylating agent, such as β-propiolactone (BPL), thereby providing a vaccine comprising immunogenic proteins derived from a virus propagated on cell culture, substantially free of residual functional cell culture DNA.

  本发明涉及用于治疗或预防病毒感染的疫苗产品。本发明还提供了减少与制备细胞培养疫苗相关的污染物的方法。残留的功能性细胞培养 DNA 可通过 DNA 烷化剂（如 β-丙内酯 (BPL)）降解，从而提供一种由免疫原蛋白组成的疫苗，免疫原蛋白来源于在细胞培养物上繁殖的病毒，基本上不含残留的功能性细胞培养 DNA。
• Cell-derived viral vaccines with low levels of residual cell dna
  申请人：Novartis Vaccines and Diagnostics GmbH

  公开号：EP2842572A1

  公开（公告）日：2015-03-04

  The present invention relates to vaccine products for the treatment or prevention of viral infections. Further provided are methods of reducing contaminants associated with the preparation of cell culture vaccines. Residual functional cell culture DNA is degraded by treatment with a DNA alkylating agent, such as β-propiolactone (BPL), thereby providing a vaccine comprising immunogenic proteins derived from a virus propagated on cell culture, substantially free of residual functional cell culture DNA.

  本发明涉及用于治疗或预防病毒感染的疫苗产品。本发明还提供了减少与制备细胞培养疫苗相关的污染物的方法。残留的功能性细胞培养 DNA 可通过 DNA 烷化剂（如 β-丙内酯 (BPL)）降解，从而提供一种由免疫原蛋白组成的疫苗，免疫原蛋白来源于在细胞培养物上繁殖的病毒，基本上不含残留的功能性细胞培养 DNA。
• Detection of 7-(2′-Carboxyethyl)guanine but Not 7-Carboxymethylguanine in Human Liver DNA
  作者：Guang Cheng、Mingyao Wang、Peter W. Villalta、Stephen S. Hecht

  DOI：10.1021/tx100062v

  日期：2010.6.21

  7-Carboxymethylguanine (7-CMGua) and 7-(2'-carboxyethyl)guanine (7-CEGua) are DNA adducts that potentially could be formed upon the metabolism of the carcinogenic nitrosamines N-nitrososarcosine (NSAR) and 3-(methylnitrosamino)propionic acid (MNPA), respectively, or from other sources such as nitrosation of glycine (7-CMGua) or reaction of DNA with acrylic acid (7-CEGua). Since both NSAR and MNPA have been detected in human urine and there are plausible sources of exposure to other precursors to these adducts, we analyzed human liver DNA for 7-CMGua and 7-CEGua, using liquid chromatography-electrospray ionization-tandem mass spectrometry-selected reaction monitoring (LC-ESI-MS/MS-SRM). Human hepatic DNA was mixed with [N-15(5)]7-CMGua and [N-15(5)]7-CEGua as internal standards and enzymatically hydrolyzed. The hydrolysate was partially purified by solid-phase extraction, and the resulting fraction was treated with acetyl chloride in methanol to convert 7-CMGua and 7-CEGua to their methyl esters. After a second solid-phase extraction, LC-ESI-MS/MS-SRM analysis was carried out using the transitions m/z 224 [M + H](+) -> m/z 164 [(M + H) - HCOOCH3](+) and m/z 238 [M + H](+) -> m/z 152 [BH](+) for the methyl esters of 7-CMGua and 7-CEGua, respectively. The method was sensitive, accurate, precise, and apparently free from artifact formation. 7-CEGua, as its methyl ester, was detected in all 24 human liver samples analyzed, mean +/- SD, 373 +/- 320 fmol/mu mol Gua (74.6 adducts per 10(9) nucleotides), range 17-1189 fmol/mu mol Gua, but the methyl ester of 7-CMGua was not detected in any sample. These results demonstrate the ubiquitous presence of 7-CEGua in human liver DNA. Acrylic acid may be a likely endogenous precursor to 7-CEGua.