8-((1,1'-联苯)-4-基氨基)-2'-脱氧鸟苷 | 84283-08-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 中文名称: 8-((1,1'-联苯)-4-基氨基)-2'-脱氧鸟苷
• 中文别名: 3(2H)-异噻唑酮,5-(3-吡咯烷基)-
• 英文名称: N-(2′-deoxyguanosin-8-yl)-4-aminobiphenyl
• 英文别名: 8-[(1,1'-biphenyl)-4-ylamino]-2'-deoxyguanosine；N-(2'-deoxyguanosin-8-yl)-4-aminobiphenyl；N-(2-deoxyguanosine-8-yl)-4-aminobiphenyl；N-(deoxyguanosine-8-yl)-4-aminobiphenyl；N-(deoxyguanosin-8-yl)-4-aminobiphenyl；dG-4-ABP；N-(2'-Deoxyguanosin-8-yl)-4-aminobiphenyl；2-amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-8-(4-phenylanilino)-1H-purin-6-one
• CAS: 84283-08-9
• 化学式: C₂₂H₂₂N₆O₄
• 分子量: 434.454
• InChiKey: JPQHAFBEGLGQRF-GVDBMIGSSA-N

物化性质

• 熔点：
  278°C dec.
• 密度：
  1.61±0.1 g/cm3(Predicted)
• 溶解度：
  溶于二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  147
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  8-((1,1'-联苯)-4-基氨基)-2'-脱氧鸟苷 在 sodium hexachloroiridate 作用下， 以 甲醇 、 phosphate buffer 为溶剂， 以3 mg的产率得到
  参考文献：
  名称：

  Chemical and Electrochemical Oxidation of C8-Arylamine Adducts of 2‘-Deoxyguanosine

  摘要：

  The electrochemical and chemical oxidation of a series of C8-arylamine adducts of 2'-deoxyguanosine has been examined. The oxidations were found to be reversible by cyclic and square-wave voltammetry in both aqueous buffer and aprotic organic solvent. The mechanism of the oxidation in protic media was either one- or two-electron, depending on the aryl group. The chemical oxidation resulted in guanidinohydantoin and spiroiminodihydantoin rearrangement products similar to those observed for 8-oxo-7,8-dihydro-2'-deoxyguanosine.

  DOI：

  10.1021/ja066404u
• 作为产物：
  描述：

  N-羟基-4-氨基联苯 生成 8-((1,1'-联苯)-4-基氨基)-2'-脱氧鸟苷
  参考文献：
  名称：

  定量的人淋巴母细胞TK6细胞中N-（脱氧鸟苷-8-基）-4-氨基联苯加合物的定量及其与突变，毒性和基因表达谱的关系。

  摘要：

  锚定在表型端点的基因表达谱可能导致识别预测致突变性或致癌性的特征。此处进行的研究描述了暴露于N-羟基-4-氨基联苯（一种4-氨基联苯的诱变产物）后，人TK6淋巴母细胞系中DNA加合物的分析。据报道，一种经验证的纳米级LC微电喷雾质谱分析法可用于检测和定量N-（脱氧鸟苷-8-基）-4-氨基联苯（dG-C8-ABP），这是4-氨基联苯的主要DNA加合物。基于10：1的信噪比，确定的定量限对应于大约27 fg的dG-C8-ABP柱上注射。该测定法已用于测量人TK6淋巴母细胞系中加合物的稳态水平与剂量的关系（0.5、1。0和10.0 microM）和暴露于N-羟基-4-氨基联苯后的时间（2、6和27小时）。然后将细胞中dG-C8-ABP加合物的水平（在10（9）个核苷酸中为18至500个加合物）与细胞毒性，TK（胸苷激酶）和HPRT基因座的诱导突变以及基因表达谱相关联通过微阵列分析。通过生长曲线外

  DOI：

  10.1021/ac0607360

文献信息

• Synthesis of DNA Strands Site-Specifically Damaged by C8-Arylamine Purine Adducts and Effects on Various DNA Polymerases
  作者：Nicolas Böge、Maike I. Jacobsen、Zita Szombati、Sabrina Baerns、Francesca Di Pasquale、Andreas Marx、Chris Meier

  DOI：10.1002/chem.200800979

  日期：2008.12.8

  C8-Arylamine-dG and C8-arylamine-dA adducts have been prepared using palladium cross-coupling chemistry. These adducts were subsequently converted into the corresponding 5'-O-DMTr-C8-arylamine-3'-O-phosphoramidites and then used for the automated synthesis of different site-specifically modified oligonucleotides. These "damaged" oligonucleotides have been characterized by ESI-MS, UV thermal stability

  使用钯交叉偶联化学已经制备了C8-芳胺-dG和C8-芳基胺-dA加合物。随后将这些加合物转化为相应的5'-O-DMTr-C8-芳基胺-3'-O-亚磷酰胺，然后用于自动合成不同的位点特异性修饰的寡核苷酸。这些“损坏”的寡核苷酸已通过ESI-MS，UV热稳定性测定和圆二色性进行了表征，它们已用于EcoRI测定以及使用各种DNA聚合酶的引物延伸研究中。
• Site-Specific Synthesis and Properties of Oligonucleotides Containing C8-Deoxyguanosine Adducts of the Dietary Mutagen IQ
  作者：C. Eric Elmquist、James S. Stover、Zhiwei Wang、Carmelo J. Rizzo

  DOI：10.1021/ja0487022

  日期：2004.9.1

  The site-specific synthesis of oligonucleotides containing the C8-deoxyguanosine adduct of the highly mutagenic heterocyclic amine 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) has been achieved, and the oligonucleotides were characterized by UV melting temperature analysis, circular dichroism, and UV absorption spectroscopy. Examination of these data indicated that the IQ-adduct is accommodated in

  已实现含有高致突变杂环胺2-氨基-3-甲基咪唑并[4,5-f]喹啉(IQ)的C8-脱氧鸟苷加合物的寡核苷酸的定点合成，并通过UV熔解温度表征寡核苷酸分析、圆二色性和紫外吸收光谱。对这些数据的检查表明 IQ 加合物适应于截然不同的环境。这种依赖于序列的构象偏好可能在 IQ 修饰的寡核苷酸的致突变性和修复中发挥关键作用。
• A practical approach for the chemical synthesis of 2′-deoxyguanosine-C8 adducts with mutagenic/carcinogenic amino- or nitro-arenes
  作者：Takeji Takamura-Enya、Satoko Ishikawa、Masataka Mochizuki、Keiji Wakabayashi

  DOI：10.1016/s0040-4039(03)01484-9

  日期：2003.8

  of 2′-deoxyguanosine-C8 (dG-C8) adducts with several mutagenic and carcinogenic amino- or nitro-arenes were developed using the palladium-mediated cross-coupling reaction of protected 8-amino-dG with bromoarenes in around 80% yields, followed by conventional deprotection procedures. This approach can be applied to preparation of a variety of authentic dG-C8 adducts with amino or nitro-arenes.

  利用钯介导的受保护的8-氨基-dG与溴代芳烃的交叉偶联反应，开发了合成具有几种致突变和致癌的氨基或硝基芳烃的2'-脱氧鸟苷-C8（dG-C8）加合物的合成方法。大约80％的收率，然后进行常规的脱保护程序。该方法可用于制备各种带有氨基或硝基芳烃的可靠的dG-C8加合物。
• Kinetics of Hydrolysis of 8-(Arylamino)-2‘-deoxyguanosines
  作者：Michael Novak、Megan Ruenz、Shahrokh Kazerani、Krisztina Toth、Thach-Mien Nguyen、Brian Heinrich

  DOI：10.1021/jo0163492

  日期：2002.4.1

  the C-N bond of the neutral nucleoside, 1, occurs that has not been previously reported for simple purine nucleosides. Finally, under mildly alkaline conditions a process consistent with spontaneous decomposition of the anion 1(-) or OH(-)-induced decomposition of 1 is observed. The latter process has been observed for other purine nucleosides, including the closely related 1d, and involves nucleophilic

  8-（芳基氨基）-2'-脱氧鸟苷或C-8加合物是由衍生自致癌胺和诱变胺的N-芳基氮鎓离子与DNA的2'-脱氧鸟苷（dG）和鸟苷残基反应形成的主要加合物。通过UV和HPLC方法在20℃在酸性，中性和弱碱性条件下测定三种C-8加合物1a-c的水解动力学。在pH <2时，主要的水解过程是双质子化底物1H（2）（+ 2）的CN键的自发裂解（方案2）。在这些条件下，C-8加合物的反应活性比dG高2至5倍。在3
• Identification of Carcinogen DNA Adducts in Human Saliva by Linear Quadrupole Ion Trap/Multistage Tandem Mass Spectrometry
  作者：Erin E. Bessette、Simon D. Spivack、Angela K. Goodenough、Tao Wang、Shailesh Pinto、Fred F. Kadlubar、Robert J. Turesky

  DOI：10.1021/tx100098f

  日期：2010.7.19

  DNA adducts of carcinogens derived from tobacco smoke and cooked meat were identified by liquid chromatography−electrospray ionization/multistage tandem mass spectrometry (LC-ESI/MS/MSn) in saliva samples from 37 human volunteers on unrestricted diets. The N-(deoxyguanosin-8-yl) (dG-C8) adducts of the heterocyclic aromatic amines 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP), 2-amino-9H-pyrido[2

  通过液相色谱-电喷雾电离/多级串联质谱 (LC-ESI/MS/MS n ) 在来自 37 名无限制饮食的人类志愿者的唾液样本中鉴定了源自烟草烟雾和熟肉的致癌物的 DNA 加合物。杂环芳香胺 2-amino-1-methyl-6-phenylimidazo[4,5- b ]pyridine (PhIP), 2-amino-9 H的N -(deoxyguanosin-8-yl) (dG-C8) 加合物-吡啶并[2,3- b ]吲哚(AαC)、2-氨基-3,8-二甲基咪唑[4,5- f ]喹喔啉(MeIQx)和芳香胺4-氨基联苯(4-ABP)是通过 LC-ESI/MS/MS n 进行表征和定量，在 MS 3处采用连续反应监测使用线性四极杆离子阱 (LIT) 质谱仪 (MS) 的扫描阶段模式。PhIP 的 DNA 加合物最常被发现：dG-C8-PhIP 在 29 名曾经吸烟者中有 13 名的唾液样本和