2-(2-氨基-6-氧代-3H-嘌呤-7-基)乙酸 | 73891-84-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 2-(2-氨基-6-氧代-3H-嘌呤-7-基)乙酸
• 中文别名: 二氯(二甲基)硅烷-三氯(苯基)硅烷(1:1)
• 英文名称: 7-carboxymethylguanine
• 英文别名: 7-Carboxymethylguanine；2-(2-amino-6-oxo-1H-purin-7-yl)acetic acid
• CAS: 73891-84-6
• 化学式: C₇H₇N₅O₃
• 分子量: 209.164
• InChiKey: DUXOREVYDYHYSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  2-(2-氨基-6-氧代-3H-嘌呤-7-基)乙酸 在 水 、 sodium carbonate 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Ion Channel-like Crystallographic Signatures in Modified Guanine–Potassium/Sodium Interactions

  摘要：

  This communication describes crystallographic details of structures reminiscent of ion channels, formed from regioisomeric N7 and N9 guanine-carboxylate conjugates with potassium/sodium ions and their subsequent STM observations on Au(111) surface. Ion channel-like crystal structures were obtained with the observation of a notable shift in metal ion coordination from carbonyl to carboxylate oxygen. These results are expected to provide insight into competing sites for modified guanine-metal coordination, an entry into guanine-based ion channels and a route toward guanine-functionalized surfaces.

  DOI：

  10.1021/cg3016518
• 作为产物：
  描述：

  碘乙酸 、 鸟苷 在 lithium hydroxide 作用下， 以 水 为溶剂， 反应 1.17h， 生成 2-(2-氨基-6-氧代-3H-嘌呤-7-基)乙酸
  参考文献：
  名称：

  Detection of 7-(2′-Carboxyethyl)guanine but Not 7-Carboxymethylguanine in Human Liver DNA

  摘要：

  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.

  DOI：

  10.1021/tx100062v

文献信息

• PHOSPHOLIPID ETHER (PLE) CAR T CELL TUMOR TARGETING (CTCT) AGENTS
  申请人：Seattle Children's Hospital (dba Seattle Children's Research Institute)

  公开号：US20200087399A1

  公开（公告）日：2020-03-19

  Aspects of the invention described herein relate to synthetic compounds that are useful for targeting and labeling tumor cells so as to facilitate recognition by binding agents including Chimeric Antigen Receptor T cells (CAR T cells), which are administered to a subject by intravenous or locoregional administration. Several compositions and methods of making and using these compositions to treat or inhibit a disease in a subject are contemplated.
• METHODS AND COMPOSITIONS FOR STIMULATION OF CHIMERIC ANTIGEN RECEPTOR T CELLS WITH HAPTEN LABELLED CELLS
  申请人：Seattle Children's Hospital (dba Seattle Children's Research Institute)

  公开号：US20210317407A1

  公开（公告）日：2021-10-14

  Some embodiments of the methods and compositions provided herein relate to the use of hapten labeled cells to stimulate chimeric antigen receptor (CAR) T cells. In some embodiments, CAR T cells can include a CAR that specifically binds to a hapten. Some embodiments relate to the in vivo or in vitro stimulation CAR T cells by hapten labeled cells.
• [EN] PHOSPHOLIPID ETHER (PLE) CAR T CELL TUMOR TARGETING (CTCT) AGENTS<br/>[FR] AGENTS DE CIBLAGE DE TUMEUR À LYMPHOCYTES T CAR (CTCT) D'ÉTHER DE PHOSPHOLIPIDE (PLE)
  申请人：SEATTLE CHILDRENS HOSPITAL DBA SEATTLE CHILDRENS RES INST

  公开号：WO2018148224A1

  公开（公告）日：2018-08-16

  Aspects of the invention described herein relate to synthetic compounds that are useful for targeting and labeling tumor cells so as to facilitate recognition by binding agents including Chimeric Antigen Receptor T cells (CAR T cells), which are administered to a subject by intravenous or locoregional administration. Several compositions and methods of making and using these compositions to treat or inhibit a disease in a subject are contemplated.
• [EN] ACTIVITY-INDUCIBLE FUSION PROTEINS HAVING A HEAT SHOCK PROTEIN 90 BINDING DOMAIN<br/>[FR] PROTÉINES DE FUSION INDUCTIBLES PAR ACTIVITÉ AYANT UN DOMAINE DE LIAISON À LA PROTÉINE DE CHOC THERMIQUE 90
  申请人：[en]SEATTLE CHILDREN'S HOSPITAL D/B/A SEATTLE CHILDREN'S RESEARCH INSTITUTE

  公开号：WO2022174035A2

  公开（公告）日：2022-08-18

  Activity-inducible fusion proteins whose activity is post-translationally regulated utilizing a hsp90 binding domain and a drug molecule are described. In the absence of the drug molecule, the activity-inducible fusion proteins are inactivated but can be activated by a relevant physiological parameter in the presence of the drug molecule. Examples of the activity-inducible fusion proteins include chimeric antigen receptors (CAR) wherein the relevant physiological parameter is antigen binding.
• 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.