2-amino-5-[(2'-deoxy-β-D-erythro-pentofuranosyl)amino]-4H-imidazol-4-one | 142559-87-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-amino-5-[(2'-deoxy-β-D-erythro-pentofuranosyl)amino]-4H-imidazol-4-one
• 英文别名: 2-amino-5-[(2-deoxy-β-D-erythro-pentofuranosyl)amino]-4H-imidazol-4-one；2'-deoxyimidazolone；dIz；amino-2 [(desoxy-2-β-D-erythropentofurannosyl)amino]-5 imidazole-4；2-Amino-5-[(2-deoxy-beta-erythro-pentofuranosyl)amino]-4h-imidazol-4-one；(4Z)-2-amino-4-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]imino-1H-imidazol-5-one
• CAS: 142559-87-3
• 化学式: C₈H₁₂N₄O₄
• 分子量: 228.208
• InChiKey: JBAFVKWZSLMPDL-VPENINKCSA-N

物化性质

• 沸点：
  495.1±55.0 °C(Predicted)
• 密度：
  2.00±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：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  130
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-amino-5-[(2'-deoxy-β-D-erythro-pentofuranosyl)amino]-4H-imidazol-4-one 在 phosphate buffer 、 水 作用下， 生成 2,2-diamino-4-[(2-deoxy-β-D-erythro-pentafuranosyl)amino]-5-(2H)-oxazolone
  参考文献：
  名称：

  由亚甲基蓝光氧化产生的单重态氧由2'-脱氧鸟苷形成二亚氨基-咪唑核苷。

  摘要：

  单线态氧（（1）O（2））能够诱导遗传毒性，致癌和诱变作用。以前有报道说（1）O（2）与2'-脱氧鸟苷的反应是DNA成分中（1）O（2）的主要靶标，导致形成多种氧化产物，包括8- oxo-7,8-dihydro-2'-deoxyguanosine和spiroiminodihydantoin，氨基咪唑酮和二氨基恶唑酮核苷。除了这些产品之外，我们还报告了一种新型的二亚氨基咪唑核苷，2,5-二亚氨基-4-[（2-脱氧-β-D-赤型戊呋喃糖基）氨基] -2H，5H-咪唑（dD）， 2'-脱氧鸟苷与（1）O（2）的反应是通过在有氧条件下在亚甲基蓝存在下用可见光照射而产生的。它的鉴定是基于与真实化合物相同的色谱和光谱数据，我们最近从2'-脱氧鸟苷与试剂HOCl和髓过氧化物酶-H（2）O（2）-Cl（-）的反应混合物中进行了分离和表征系统。dD的产率由D（2）O增加，而叠氮化物则降低。dD不是由8-oxo-7

  DOI：

  10.1016/s0968-0896(03)00124-x
• 作为产物：
  描述：

  2'-脱氧鸟苷 在 aaph 作用下， 生成 2-amino-5-[(2'-deoxy-β-D-erythro-pentofuranosyl)amino]-4H-imidazol-4-one
  参考文献：
  名称：

  偶氮化合物光解产生的氧基自由基引发鸟嘌呤碱基的氧化改性

  摘要：

  已经通过激光动力学光谱研究了由水溶性自由基产生剂 2,2'-偶氮双（2-脒基丙烷）二盐酸盐（AAPH）的光解引发的鸟嘌呤碱基的氧化损伤。在中性含氧水溶液中，AAPH 的 355 nm 激光闪光光解产生全谱自由基，包括 2-脒基丙-2-过氧自由基 (ROO • )、2-脒基丙-2-氧基 (RO • ) 和超氧化物 (O 2 •- ) 部首。在产生具有特征吸收光谱的产物的反应中监测这些在近紫外-可见光范围内吸收可忽略不计的氧自由基。这种方法表明 RO •自由基诱导 2'-脱氧鸟苷 (dG) 的快速单电子氧化形成鸟嘌呤中性自由基 dG(-H) •。相比之下，ROO •自由基不会以可观察到的速率与 dG 发生反应。使用与四硝基甲烷形成硝基的经典测试反应检测O 2 •-自由基。形成鸟嘌呤氧化终产物的主要途径是 G(-H) •和 O 2 •-自由基结合形成 2,5-二氨基-4 H-咪唑酮(Iz)。这种

  DOI：

  10.1021/jp100686j

文献信息

• DNA Damage by <i>tert</i>-Butoxyl Radicals Generated in the Photolysis of a Water-Soluble, DNA-Binding Peroxyester Acting as a Radical Source
  作者：Waldemar Adam、Günther N. Grimm、Chantu R. Saha-Möller、Francesco Dall'Acqua、Gorgia Miolo、Daniela Vedaldi

  DOI：10.1021/tx980089a

  日期：1998.9.1

  The photolysis of the water-soluble perester 1 leads to tert-butoxyl radicals as confirmed by EPR studies with the spin trap 5, 5-dimethylpyrroline N-oxide (DMPO). In the presence of DNA, oxidative cleavage of the latter was demonstrated by the formation of strand breaks in supercoiled pBR 322 DNA and by a substantial decrease of the melting temperature of salmon testes DNA. Guanidine, released from

  如使用自旋阱5、5-二甲基吡咯啉N-氧化物（DMPO）的EPR研究所证实的，水溶性过酸酯1的光解导致叔丁氧基自由基。在DNA存在下，后者的氧化裂解通过超螺旋pBR 322 DNA中链断裂的形成以及鲑鱼睾丸DNA的解链温度的显着降低来证明。用小牛胸腺DNA和2'-脱氧鸟苷观察到在碱处理下从例如恶唑酮和氧代咪唑烷释放的胍。这些DNA修饰被自由基清除剂二叔丁基甲酚或氢原子供体谷胱甘肽有效地抑制。芳烃生色团的光敏性被排除在外，因为相应的酯2不会引起DNA损伤，而过酯1的光产物也不具有活性。过氧化物1的氧化DNA的功效源于以下事实：通过阳离子过氧化物与DNA的静电结合，叔丁氧基在DNA的紧邻区域中被光解产生，如荧光测量所证实的。这些结果表明，perester 1的光解提供了水性介质中叔丁氧基自由基的合适来源，这是生化研究的必要前提。
• Identification of the α and β Anomers of 1-(2-Deoxy-d-Erythro-Pentofuranosyl)-Oxaluric Acid at the Site of Riboflavin-mediated Photooxidation of Guanine in 2′-Deoxyguanosine and Thymidylyl-(3′-5′)-2′-Deoxyguanosine†
  作者：Garry W. Buchko、Jean Cadet

  DOI：10.1562/2005-06-01-ra-562

  日期：——

  spectroscopy, fast atom bombardment mass spectrometry, and enzymatic analyses. Both alpha-dOx and Tpalpha-dOx slowly convert back into the modified beta-deoxyribonucleoside, indicating that the furanosidic anomers are in dynamic equilibrium. Relative to TpdG, the rate of hydrolysis of Tpbeta-dOx and Tpalpha-dOx by spleen phosphodiesterase is greatly reduced. Hot piperidine (1.0 M, 90 degrees C, 30 min) destroys

  氧饱和水溶液中350nm的光经核黄素介导的2'-脱氧鸟苷（dG）和胸苷基-（3'-5'）-2'-脱氧鸟苷（TpdG）的光敏作用的产物已鉴定为1 -（2-脱氧-β-D-异戊-呋喃糖基）草酸（β-dOx）和胸苷基-（3'-5'）-1-（2-脱氧-β-D-异戊-呋喃糖基）草酸（ Tpbeta-dOx）。在水溶液中，修饰的β-脱氧核糖核苷缓慢转化为α-端基异构体，生成α-dOx和Tpalpha-dOx。这些修饰的核苷和二核苷单磷酸酯已通过HPLC分离，并通过质子和碳NMR光谱，快速原子轰击质谱和酶促分析进行了表征。α-dOx和Tpalpha-dOx都缓慢地转化回修饰的β-脱氧核糖核苷，表明呋喃硅前体处于动态平衡状态。相对于TpdG，脾磷酸二酯酶水解Tpbeta-dOx和Tpalpha-dOx的速率大大降低。热哌啶（1.0 M，90摄氏度，30分钟）会破坏Tpbeta-dOx和Tpalpha-dOx
• DNA damage by the sulfate radical anion: hydrogen abstraction from the sugar moiety versus one-electron oxidation of guanine
  作者：Marina Roginskaya、Reza Mohseni、Derrick Ampadu-Boateng、Yuriy Razskazovskiy

  DOI：10.3109/10715762.2016.1166488

  日期：2016.7.2

  The products of oxidative damage to double-stranded (ds) DNA initiated by photolytically generated sulfate radical anions SO4*- were analyzed using reverse phase (RP) HPLC. Relative efficiencies of two major pathways were compared: production of 8-oxoguanine (8oxoG) and hydrogen abstraction from the DNA 2-deoxyribose moiety (dR) at C1', C4', and C5'-positions. The formation of 8oxoG was found to account

  使用反相（RP）HPLC分析了由光解生成的硫酸根自由基阴离子SO4 *-引发的双链（ds）DNA氧化损伤产物。比较了两种主要途径的相对效率：生成8-​​氧鸟嘌呤（8oxoG）和从C1'，C4'和C5'位置的DNA 2-脱氧核糖部分（dR）提取氢。发现在低照射剂量下8oxoG的形成占所有定量病变的87％。由于其产物的进一步氧化，8oxoG的浓度迅速达到稳定状态，每100个碱基对约有8oxoG。发现另一种鸟嘌呤氧化产物2-氨基-5-（2'-烷基氨基）-4H-咪唑-4-酮（X）从其试探性前体2-氨基-5-[（ 2' 伯胺在中性溶液中处理后，生成[-deoxy-β-D-D-赤-戊呋喃糖基氨基] -4H-咪唑-4-酮（dIz）。X释放的线性剂量依赖性指向直接从鸟嘌呤而不是通过8oxoG氧化形成dIz。发现对dR的损害约占总损害的13％，大多数损害（33％）源自C4′-氧化。尽管与提取C1'氢相关的空
• Photoirradiation products of flavin derivatives, and the effects of photooxidation on guanine
  作者：Katsuhito Kino、Teruhiko Kobayashi、Eiji Arima、Rie Komori、Takanobu Kobayashi、Hiroshi Miyazawa

  DOI：10.1016/j.bmcl.2009.01.112

  日期：2009.4

  Photoirradiation in the presence of riboflavin led to guanine oxidation and the formation of imidazolone. Meanwhile, riboflavin itself was degraded by ultraviolet light A (UV-A) and visible light (VIS) radiation, and the end product was lumichrome. VIS radiation in the presence of riboflavin oxidized guanine similarly to UV-A radiation. Although UV-A radiation with lumichrome oxidized guanine, VIS radiation with lumichrome did not. Thus, UV-A radiation with riboflavin can oxidize guanine even if riboflavin is degraded to lumichrome. In contrast, following VIS radiation degradation of riboflavin to lumichrome, VIS radiation with riboflavin is hardly capable of oxidizing guanine. The consequences of riboflavin degradation and guanine photooxidation can be extended to flavin mononucleotide and flavin adenine dinucleotide. In addition, we report advanced synthesis; carboxymethylflavin was obtained by oxidation of formylmethylflavin with chlorite and hydrogen peroxide; lumichrome was obtained by heating of formylmethylflavin in 50% AcOH; lumiflavin was obtained by incubation of formylmethylflavin in 2 M NaOH, followed by isolation by step-by-step concentration. (C) 2009 Elsevier Ltd. All rights reserved.
• p-Cyano substituted 5-benzoyldeoxyuridine as a novel electron-accepting nucleobase for one-electron oxidation of DNA
  作者：Kazuhiko Nakatani、Kazuhiko Fujisawa、Chikara Dohno、Takashi Nakamura、Isao Saito

  DOI：10.1016/s0040-4039(98)01231-3

  日期：1998.8

  p-Cyano substituted 5-benzoyl-2'-deoxyuridine 1 was synthesized as a novel electron-accepting nucleobase. DNA cleavage by 1 under photoirradiation conditions occurred selectively at the 5'-G of 5'GG3' sequences after hot piperidine treatment. Photoirradiation of 1 in the presence of dG produced imidazolone as a major product. The electron-accepting nucleobase 1 was successfully incorporated into DNA oligomer by automated DNA synthesis using phosporamidite 2. (C) 1998 Elsevier Science Ltd. All rights reserved.