N²-(1-carboxyethyl)-2'-deoxyguanosine | 252039-58-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: N²-(1-carboxyethyl)-2'-deoxyguanosine
• 英文别名: n2-(1-Carboxyethyl)-2'-deoxyguanosine；2-[[9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-oxo-1H-purin-2-yl]amino]propanoic acid
• CAS: 252039-58-0
• 化学式: C₁₃H₁₇N₅O₆
• 分子量: 339.308
• InChiKey: MXNKUBJIXVVNPY-UNYLCCJPSA-N

物化性质

• 密度：
  1.90±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  158
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  DL-甘油醛 生成 N²-(1-carboxyethyl)-2'-deoxyguanosine
  参考文献：
  名称：

  METHODS OF QUANTIFYING N2-(1-CARBOXYETHYL)-2'-DEOXY-GUANOSINE (CEdG) AND SYNTHESIS OF OLIGONUCLEOTIDES CONTAINING CEdG

  摘要：

  通过测量生物样本中N2-羧乙基-2'-脱氧鸟苷（CEdG）水平的方法，以及将这些水平与已知的正常水平进行比较，可以诊断多种疾病，包括糖尿病和癌症。方法还可以通过在治疗前后测量CEdG水平来确定治疗疾病的疗效。测量CEdG水平使用液相色谱电喷雾离子化串联质谱。

  公开号：

  US20120071559A1

文献信息

• [EN] METHODS OF QUANTIFYING METHYLGLYOXAL-INDUCED NUCLEIC ACID ADDUCTS<br/>[FR] PROCÉDÉS DE QUANTIFICATION D'ADDUITS À L'ACIDE NUCLÉIQUE INDUITS PAR LE MÉTHYLGLYOXAL
  申请人：HOPE CITY

  公开号：WO2019152728A1

  公开（公告）日：2019-08-08

  Methods of quantifying a N 2 -(1-carboxyethyl)-2'-deoxyguanosine (CEdG) and N 2 -(1-carboxyethyl)-guanosine (CEG) levels in biological samples and comparing those levels to known normal levels can diagnose a number of metabolic disorders or complications associated therewith, including diabetes, its associated complications, and cancer. Methods can also determine whether therapies for disorders are effective by measuring CEdG and CEG levels before and after treatment. Measurement of CEdG and CEG levels is achieved by using liquid chromatography electrospray ionization tandem mass spectrometry.

  测量生物样本中N2-(1-羧基乙基)-2'-脱氧鸟苷（CEdG）和N2-(1-羧基乙基)-鸟苷（CEG）水平的方法，并将这些水平与已知的正常水平进行比较，可以诊断出许多代谢性疾病或相关并发症，包括糖尿病、其相关并发症和癌症。该方法还可以通过在治疗前后测量CEdG和CEG水平来确定治疗疾病的疗效。使用液相色谱电喷雾离子化串联质谱技术可实现CEdG和CEG水平的测量。
• <scp>DJ</scp> ‐1 is not a deglycase and makes a modest contribution to cellular defense against methylglyoxal damage in neurons
  作者：Melissa Conti Mazza、Sarah C. Shuck、Jiusheng Lin、Michael A. Moxley、John Termini、Mark R. Cookson、Mark A. Wilson

  DOI：10.1111/jnc.15656

  日期：2022.8

  Human DJ-1 is a cytoprotective protein whose absence causes Parkinson's disease and is also associated with other diseases. DJ-1 has an established role as a redox-regulated protein that defends against oxidative stress and mitochondrial dysfunction. Multiple studies have suggested that DJ-1 is also a protein/nucleic acid deglycase that plays a key role in the repair of glycation damage caused by methylglyoxal

  人 DJ-1 是一种细胞保护蛋白，其缺失会导致帕金森病，并且还与其他疾病有关。DJ-1 作为一种氧化还原调节蛋白具有既定的作用，可抵御氧化应激和线粒体功能障碍。多项研究表明，DJ-1 还是一种蛋白质/核酸去糖酶，在修复由中枢代谢形成的反应性α-酮醛甲基乙二醛 (MG) 引起的糖基化损伤中起关键作用。相互矛盾的报道表明，DJ-1 是一种乙二醛酶，但不是一种去糖酶，并且在糖化防御中不起主要作用。解决这个问题对于了解 DJ-1 如何保护细胞免受可能导致疾病的损伤非常重要。我们发现 DJ-1 在体外降低了 MG 与鸟嘌呤和半胱氨酸的可逆加合物的水平。DJ-1 作用于可逆半硫缩醛底物的稳态动力学与计算动力学模型充分拟合，该模型仅需要 DJ-1 乙二醛酶活性，支持去糖化是 DJ-1 表面活性而非真实活性的结论。灵敏和定量的同位素稀释质谱表明，DJ-1 适度降低了原代和培养的神经元细胞系和整个小鼠大脑中
• Methods of quantifying N2-(1-carboxyethyl)-2′-deoxy-guanosine (CEdG) and synthesis of oligonucleotides containing CEdG
  申请人：CITY OF HOPE

  公开号：US11179361B2

  公开（公告）日：2021-11-23

  Methods of quantifying a N2-(1-carboxyethyl)-2′-deoxyguanosine (CEdG) levels in biological samples and comparing those levels to known normal levels can diagnose a number of metabolic disorders or complications associated therewith, including diabetes, its associated complications, and cancer. Methods can also determine whether therapies for disorders are effective by measuring CEdG levels before and after treatment. Measurement of CEdG levels is achieved by using liquid chromatography electrospray ionization tandem mass spectrometry.

  对生物样本中的 N2-（1-羧乙基）-2′-脱氧鸟苷（CEdG）水平进行量化并将这些水平与已知的正常水平进行比较的方法，可以诊断一些代谢紊乱或与之相关的并发症，包括糖尿病、其相关并发症和癌症。通过测量治疗前后的 CEdG 水平，还可以确定治疗疾病的方法是否有效。CEdG 水平的测量是通过液相色谱电喷雾离子化串联质谱法实现的。
• Mutagenic Potential of DNA Glycation: Miscoding by (<i>R</i>)- and (<i>S</i>)-<i>N</i>²-(1-Carboxyethyl)-2′-deoxyguanosine
  作者：Gerald E. Wuenschell、Daniel Tamae、Angelique Cercillieux、Rio Yamanaka、Calvin Yu、John Termini

  DOI：10.1021/bi901924b

  日期：2010.3.9

  Elevated circulating glucose resulting from complications of obesity and metabolic disease can result ill the accumulation of advanced glycation end products (AGES) of proteins, lipids, and DNA. The formation of DNA-AGEs assumes particular importance as these adducts may contribute to genetic instability and elevated cancer risk associated with metabolic disease, The principal DNA-AGE, N-2-(1-carboxyethyl)-2'-deoxyguanosine (CEdG), is formed as I Mixture of R and S isomers at both the polymer and monomer levels. Ill order to examine the miscoding potential of this adduct, oligonucleotides Substituted with (R)- and (S)-CEdG and the corresponding triphosphates (R)- and (S)-CEdGTP were synthesized, and base-pairing preferences For each stereoisomer were examined using steady-state kinetic approaches. Purine dNTPs were preferentially incorporated opposite template CEdG when either the Klenow (Kf(-)) or Thermus aquaticus (Taq) polymerases were used. The Kf(-) polymerase preferentially incorporated dGTP, whereas Taq demonstrated a bias for dATP. Kf(-) Incorporated purines opposite the R isomer with greater efficiency, but Taq favored the S isomer. Incorporation of (R)- and (S)-CEdGTP only Occurred opposite dC and was catalyzed by Kf(-) with equal efficiencies. Primer extension from a 3'-terminal CEdG was observed only for the R isomer. These data Suggest CEdG is the likely adduct responsible for the observed pattern of G transversions induced by exposure to elevated glucose or its alpha-oxoaldehyde decomposition product methylglyoxal. The results Imply that CEdG within template DNA and the corresponding triphosphate possess different syn/anti conformations during replication which influence base-pairing preferences. The Implications for CEdG-induced mutagenesis in vivo are discussed.
• METHODS OF QUANTIFYING N2-(1-CARBOXYETHYL)-2'-DEOXY-GUANOSINE (CEDG) AND SYNTHESIS OF OLIGONUCLEOTIDES CONTAINING CEDG
  申请人：CITY OF HOPE

  公开号：US20150290156A1

  公开（公告）日：2015-10-15

  Methods of quantifying a N 2 -carboxyethyl-2′-deoxyguanosine (CEdG) levels in biological samples and comparing those levels to known normal levels can diagnose a number of disorders, including diabetes and cancer. Methods can also determine whether therapies for disorders are effective by measuring CEdG levels before and after treatment. Measurement of CEdG levels occurs using liquid chromatography electrospray ionization tandem mass spectrometry.