| 1193686-95-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• CAS: 1193686-95-1
• 化学式: C₁₄H₁₉N₅O₅
• 分子量: 342.302
• InChiKey: DKBDYPZFCQIHPX-MOEULSKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.07
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  134.66
• 氢给体数：
  4.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  ¹⁵N₅-2′-deoxyguanosine 、 丁烯-2-醛 在 D-赖氨酸 作用下， 反应 12.0h， 生成
  参考文献：
  名称：

  在线液相色谱-电喷雾串联质谱法同时测定DNA中1，N 2 -Etheno-2'-deoxyguanosine和1，N 2 -Propano-2'-deoxyguanosine的超灵敏定量方法

  摘要：

  由外源性和内源性化合物产生的环外DNA加合物正在成为研究各种人类疾病和空气污染暴露的潜在工具。建立了一种高灵敏度的方法，该方法涉及在线反相高效液相色谱和多反应监测模式下电喷雾串联质谱检测，并采用稳定同位素标记的内标物同时定量1，N 2 -etheno-2'-脱氧鸟苷（1，ñ 2 -εdGuo）和1，ñ 2 -propano -2'-脱氧鸟苷（1，ñ 2-propanodGuo）中的DNA。这种方法可以直接在线定量2'-deoxyguanosine和ca。在同一分析中，在100μg水解的DNA中有500 amol加合物。使用新开发的技术，1，的准确确定Ñ 2 -etheno -2'-脱氧鸟苷和1，Ñ 2在人培养细胞的DNA提取物-propano -2'-脱氧鸟苷的水平（4.01±0.32 1，Ñ 2 -εdGuo / 10 8 dGuo和3.43±0.33 1，N 2 -propanodGuo

  DOI：

  10.1021/tx1001018

文献信息

• [¹³C₂]- Acetaldehyde Promotes Unequivocal Formation of 1,<i>N</i>²-Propano-2′-deoxyguanosine in Human Cells
  作者：Camila Carrião M. Garcia、José Pedro F. Angeli、Florêncio P. Freitas、Osmar F. Gomes、Tiago F. de Oliveira、Ana Paula M. Loureiro、Paolo Di Mascio、Marisa H. G. Medeiros

  DOI：10.1021/ja2004686

  日期：2011.6.22

  Acetaldehyde is an environmentally widespread genotoxic aldehyde present in tobacco smoke, vehicle exhaust and several food products. Endogenously, acetaldehyde is produced by the metabolic oxidation of ethanol by hepatic NAD-dependent alcohol dehydrogenase and during threonine catabolism. The formation of DNA adducts has been regarded as a critical factor in the mechanisms of acetaldehyde mutagenicity and carcinogenesis. Acetaldehyde reacts with 2'-deoxyguanosine in DNA to form primarily N-2-ethylidene-2'-deoxyguanosine. The subsequent reaction of N-2-ethylidenedGuo with another molecule of acetaldehyde gives rise to 1,N-2-propano-2'-deoxyguanosine (1,N-2-propanodGuo), an adduct also found as a product of the crotonaldehyde reaction with dGuo. However, adducts resulting from the reaction of more than one molecule of acetaldehyde in vivo are still controversial. In this study, the unequivocal formation of 1,N-2-propanodGuo by acetaldehyde was assessed in human cells via treatment with [C-13(2)]-acetaldehyde. Detection of labeled 1,N-2-propanodGuo was performed by HPLC/MS/MS. Upon acetaldehyde exposure (703 mu M), increased levels of both 1,N-2-etheno-2'-deoxyguanosine (1,N-2-epsilon dGuo), which is produced from alpha,beta-unsaturated aldehydes formed during the lipid peroxidation process, and 1,N-2-propanodGuo were observed. The unequivocal formation of 1,N-2-propanodGuo in cells exposed to this aldehyde can be used to elucidate the mechanisms associated with acetaldehyde exposure and cancer risk.