2'-deoxyguanosine | 22837-44-1

• 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: 2'-deoxyguanosine
• 英文别名: 2'-Deoxy-L-guanosine；2-amino-9-[(2S,4R,5S)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
• CAS: 22837-44-1
• 化学式: C₁₀H₁₃N₅O₄
• 分子量: 267.244
• InChiKey: YKBGVTZYEHREMT-SRQIZXRXSA-N

物化性质

• 密度：
  2.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  135
• 氢给体数：
  4
• 氢受体数：
  6

安全信息

• 危险性防范说明：
  P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313
• 危险性描述：
  H315,H319

反应信息

• 作为反应物：
  描述：

  2'-deoxyguanosine 在 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-isobutyryl-β-L-2'-deoxyguanosine
  参考文献：
  名称：

  Enantio- and meso-DNAs: preparation, characterization, and interaction with complementary nucleic acids

  摘要：

  Enantio-DNAs (DNA having 2-deoxy-L-erythro-pentose, the enantiomer of natural 2-deoxy-D-ribose, as the sugar backbone) and meso-DNAs (DNA having an alternating sequence of L-sugars and D-sugars) were prepared by the use of an automated DNA synthesizer. The characteristics of the products were analyzed, focusing on enantio- and meso-dodecadeoxyadenylic acids (designated as L-dA12 and LD-dA12, respectively). Both L-dA12 and LD-dA12 were resistant to the action of phosphodiesterases, though LD-dA12 was decomposed very slowly by snake venom phosphodiesterase. The affinity of these dodecamers for their complementary natural nucleic acids, poly(U) and poly(dT), was analyzed by the UV-mixing curve and melting-temperature measurement methods. Both L-dA12 and LD-dA12 showed affinity for their complementary nucleic acids. L-dA12 showed high selectivity for poly(U) over poly(dT), and a UV-mixing curve analysis suggested that the interaction mode was triplex formation. LD-dA12 showed moderate selectivity for poly(U) over poly(dT). L-dT12, the counterpart of L-dA12, did not show any detectable interaction with its complementary natural nucleic acid.

  DOI：

  10.1021/ja00075a002
• 作为产物：
  描述：

  N²-palmytoylguanine 在 吡啶 、 ammonium hydroxide 、 N,O-双三甲硅基乙酰胺 、 三氟甲磺酸三甲基硅酯 作用下， 反应 28.5h， 生成 2'-deoxyguanosine
  参考文献：
  名称：

  L-Thymidine is phosphorylated by herpes simplex virus type 1 thymidine kinase and inhibits viral growth

  摘要：

  We have demonstrated that herpes simplex 1 (HSV1) thymidine kinase (TK) shows no stereospecificity for D- and L-beta-nucleosides. In vitro, L enantiomers are not recognized by human TK, but function as specific substrates for the viral enzyme in the order: L-thymidine (L-T) much greater than 2'-deoxy-L-guanosine (L-dG) > 2'-deoxy-L-uridine (L-dU) > 2'-deoxy-L-cytidine (L-dC) > 2'-deoxy-L-adenosine (L-dA). HSV1 TK phosphorylates both thymidine enantiomers to their corresponding monophosphates with identical efficiency and the K(i) of L-T (2 muM) is almost identical to the K(m) for the natural substrate D-T (2.8 muM). The L enantiomer reduces the incorporation of exogenous [H-3]T into cellular DNA in HeLa TK-/HSV1 TK+ but not in wild-type HeLa cells, without affecting RNA, protein synthesis, cell growth, and viability. L-T markedly reduces HSV1 multiplication in HeLa cells. Our observations could lead to the development of a novel class of antiviral drugs characterized by low toxicity.

  DOI：

  10.1021/jm00100a029

文献信息

• [EN] NOVEL 3´-DEOXY-3´-METHYLIDENE- -L-NUCLEOSIDES<br/>[FR] NOUVEAUX 3´-DÉSOXY-3´-MÉTHYLIDÈNE- -L-NUCLÉOSIDES
  申请人：NOVADEX PHARMACEUTICALS AB

  公开号：WO2011075052A1

  公开（公告）日：2011-06-23

  The present invention includes novel 3´-deoxy-3´-methylidene-β-L-nucleosides, pharmaceutical composition comprising such compounds, as well as the methods to treat or to prevent viral infections and in particular HBV and/or HIV infections. In accordance with the present invention, there are provided compounds represented by Formula (I), wherein B is selected from A1 and A2;

  本发明包括新颖的3´-去氧-3´-甲基亚-β-L-核苷，包括这些化合物的药物组合物，以及治疗或预防病毒感染，特别是HBV和/或HIV感染的方法。根据本发明，提供了由式（I）表示的化合物，其中B从A1和A2中选择。
• Design and Synthesis of a Trifunctional Molecular System “Programmed” to Block Epidermal Growth Factor Receptor Tyrosine Kinase, Induce High Levels of DNA Damage, and Inhibit the DNA Repair Enzyme (Poly(ADP-ribose) Polymerase) in Prostate Cancer Cells
  作者：Julie Schmitt、Shanlong Huang、Elliot Goodfellow、Christopher Williams、Bertrand J. Jean-Claude

  DOI：10.1021/acs.jmedchem.9b02008

  日期：2020.6.11

  block multiple overlapping effects that characterize chemoresistance. Thus, we designed a new linker that allows assembly of multiple functions (e.g., inhibition of EGFR phosphorylation, induction of DNA lesions, and blockade of their repair) into a single molecule. This led to the successful synthesis of a novel and potent combi-molecule JS230. Here, we demonstrated that in resistant prostate cancer

  晚期癌症对化学疗法的抗性可以由不同的因素介导，例如表皮生长因子受体（EGFR）的过表达和DNA修复酶。因此，当前的护理标准通常涉及多种治疗的组合。在这里，为了减少多种药物组合的不良反应并改善结果，我们提出了一种单一药物的方法来阻断表征化学抗性的多种重叠效应。因此，我们设计了一种新的接头，可以将多个功能（例如，抑制EGFR磷酸化，诱导DNA损伤以及阻断其修复）组装成一个分子。这导致了新型强效组合分子JS230的成功合成。在这里，我们证明了在过表达EGFR的耐药前列腺癌细胞中，它能够（a）以剂量依赖性方式抑制EGFR，（b）破坏DNA，并且（c）通过抑制DNA修复蛋白poly（ ADP-核糖）聚合酶（PARP）。JS230的三重作用机制累积的生长抑制能力优于经典的两种或三种药物组合。
• Photooxidative Damage of Guanine in DG and DNA by the Radicals Derived from the α Cleavage of the Electronically Excited Carbonyl Products Generated in the Thermolysis of Alkoxymethyl-Substituted Dioxetanes and the Photolysis of Alkoxyacetones
  作者：Waldemar Adam、Markus A. Arnold、Chantu R. Saha-Möller

  DOI：10.1021/jo0056491

  日期：2001.1.1

  oxidative reactivity order in the dioxetane thermolysis, as well as in the ketone photolysis, parallels the ability of the excited ketones to release radicals (determined by spin trapping with DMPO and EPR spectroscopy) upon alpha cleavage (Norrish-type-I reaction). In the presence of molecular oxygen, the carbon-centered radicals are scavenged to produce peroxyl radicals, which are proposed as the reactive

  在存在下对3,3,4,4-四甲基-1,2-二氧杂环丁烷（TMD）的甲氧基（MeO-TMD），叔丁氧基（tBuO-TMD）和羟基（HO-TMD）衍生物进行热解与dG和小牛胸腺DNA相比，鸟嘌呤比母TMD的氧化效率更高。对于相应的氧取代的酮相对于丙酮的光解，观察到相同的氧化反应性趋势。二氧杂环丁烷热解以及酮光解中的氧化反应顺序与被激发的酮在α裂解（Norrish-I型反应）时释放自由基的能力（由DMPO和EPR光谱自旋俘获测定）相平行。在分子氧存在下，以碳为中心的自由基被清除以产生过氧自由基，
• NOVEL 3'-DEOXY-3'-METHYLIDENE-BETA-L-NUCLEOSIDES
  申请人：Zhou Xiao Xiong

  公开号：US20120309705A1

  公开（公告）日：2012-12-06

  The present invention includes novel 3′-deoxy-3′-methylidene-β-L-nucleosides, pharmaceutical composition comprising such compounds, as well as the methods to treat or to prevent viral infections and in particular HBV and/or HIV infections. In accordance with the present invention, there are provided compounds represented by Formula (I), wherein B is selected from A1 and A2;

  本发明涉及新型的3'-去氧-3'-甲基亚基-β-L-核苷，包括含有这种化合物的制药组合物，以及治疗或预防病毒感染，特别是乙型肝炎病毒和/或人类免疫缺陷病毒感染的方法。根据本发明，提供了由公式(I)表示的化合物，其中B从A1和A2中选择。
• Gene Therapy of Cancer: Activation of Nucleoside Prodrugs with<i>E. coli</i>Purine Nucleoside Phosphorylase
  作者：John A. Secrist、William B. Parker、Paula W. Allan、L. Lee Bennett、William R. Waud、Jackie W. Truss、Anita T. Fowler、John A. Montgomery、Steven E. Ealick、Alan H. Wells、G. Yancey Gillespie、V. K. Gadi、Eric J. Sorscher

  DOI：10.1080/15257779908041562

  日期：1999.4

  During the last few years, many gene therapy strategies have been developed for various disease targets. The development of anticancer gene therapy strategies to selectively generate cytotoxic nucleoside or nucleotide analogs is an attractive goal. One such approach involves the delivery of herpes simplex virus thymidine kinase followed by the acyclic nucleoside analog ganciclovir. We have developed another gene therapy methodology for the treatment of cancer that has several significant attributes. Specifically, our approach involves the delivery off. coli purine nucleoside phosphorylase, followed by treatment with a relatively non-toxic nucleoside prodrug that is cleaved by the enzyme to a toxic compound. This presentation describes the concept, details our search for suitable prodrugs, and summarizes the current biological data.