8-oxo-2'-deoxyguanosine-5'-monophosphate | 127027-50-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: 8-oxo-2'-deoxyguanosine-5'-monophosphate
• 英文别名: 8-Oxo-dGMP；[(2R,3S,5R)-5-(2-amino-6,8-dioxo-1,7-dihydropurin-9-yl)-3-hydroxyoxolan-2-yl]methyl dihydrogen phosphate
• CAS: 127027-50-3
• 化学式: C₁₀H₁₄N₅O₈P
• 分子量: 363.224
• InChiKey: AQIVLFLYHYFRKU-VPENINKCSA-N

物化性质

• 密度：
  2.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  196
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2ˊ-脱氧鸟苷-5ˊ-一磷酸 在 trans-1,2-diaminocyclohexanetetrachloroplatinum(IV) 、 水 、 sodium chloride 作用下， 生成 8-oxo-2'-deoxyguanosine-5'-monophosphate
  参考文献：
  名称：

  铂（IV）配合物氧化5'-dGMP，5'-dGDP和5'-dGTP。

  摘要：

  我们之前曾报道过，Pt（IV）复合物[Pt（IV）（dach）Cl4] [反式-d，1-1,2-二氨基环己烷四氯铂（IV）]与5'-dGMP的N7（脱氧鸟苷-5 '-单磷酸酯）以相对较快的速度氧化为8-oxo-5'-dGMP。在这里，我们进一步研究了Pt（IV）配合物氧化5'-dGMP的动力学。[H8-5'-dGMP-Pt（IV）]和[D8-5'-dGMP-Pt（IV）]中5'-dGMP和Pt（IV）之间的电子传输速率常数相似，给出的值很小动力学同位素效应（KIE：1.2±0.2）。这个小的KIE表示[H8-5'-dGMP-Pt（IV）]中H8的去质子化不参与鸟嘌呤（G）和Pt（IV）之间电子转移的速率确定步骤。我们还研究了5'-dGDP（脱氧鸟苷-5'-二磷酸）和5'-dGTP（脱氧鸟苷-5'）的反应 （三磷酸）与Pt（IV）配合物。我们的结果表明，[Pt（IV）（dach）Cl4]通过

  DOI：

  10.1007/s00775-015-1312-0

文献信息

• Fe(II) phthalocyanine catalyzed oxidation of dGMP by molecular oxygen
  作者：Aleksandra A. Kuznetsova、Lyudmila I. Solovyeva、Oleg L. Kaliya、Evgeniy A. Lukyanets、Dmitri G. Knorre、Olga S. Fedorova

  DOI：10.1016/j.bmcl.2009.05.088

  日期：2009.8

  We show that iron(II)-phthalocyanines are able to catalyze guanosine oxidation by molecular oxygen in the presence of reducing agents such as ascorbic acid and 2-mercaptoethanol. The products of 5′-monophosphate-2′-deoxyguanosine (dGMP) oxidation were directly analyzed using the HPLC-ESI/MS method. The main oxidation products were 5′-phospho-2′-deoxy-8-oxo-7,8-dihydroguanine and the 1,N2-glyoxal adduct

  我们表明，铁（II）-酞菁能够在还原剂如抗坏血酸和2-巯基乙醇的存在下通过分子氧催化鸟嘌呤氧化。使用HPLC-ESI / MS方法直接分析5'-单磷酸-2'-脱氧鸟苷（dGMP）氧化的产物。主要的氧化产物是5'-单磷酸-2'-脱氧鸟苷的5'-磷酸-2'-脱氧-8-氧代7,8-二氢鸟嘌呤和1，N2-乙二醛加合物。
• [EN] PYRIMIDINE DERIVATIVES FOR USE IN THE TREATMENT OF CANCER<br/>[FR] DÉRIVÉS DE PYRIMIDINE UTILISÉS DANS LE TRAITEMENT DU CANCER
  申请人：MERCK PATENT GMBH

  公开号：WO2016128140A1

  公开（公告）日：2016-08-18

  Compounds of Formula I or II in which R1, X1 and X2 have the meanings indicated in claim 1, are MTH1 inhibitors and can be employed, inter alia, in the treatment of cancer.

  具有公式I或II的化合物，其中R1、X1和X2具有权利要求1中所示的含义，是MTH1抑制剂，可以用于治疗癌症。
• Solution structure, mutagenesis, and NH exchange studies of the MutT enzyme–Mg2+-8-oxo-dGMP complex
  作者：M.A. Massiah、V. Saraswat、H.F. Azurmendi、A.S. Mildvan

  DOI：10.1016/j.molstruc.2003.12.060

  日期：2004.8

  (37-fold), suggesting that Asn-119 functioned both as a hydrogen bond donor to C8O, and a hydrogen bond acceptor from N7H of 8-oxo-dGMP, while aspartate at position −119 functioned as an acceptor of a single hydrogen bond. Much smaller weakening effects (0.3–0.4 kcal/mol) on the binding of dGMP and dAMP were found, indicating specific hydrogen bonding of Asn-119 to 8-oxo-dGMP. While formation of the wild

  摘要 来自大肠杆菌的 MutT 焦磷酸水解酶（129 个残基）催化三磷酸核苷 (NTP) 的水解，包括 8-oxo-dGTP，通过在 Pβ 上的取代，产生 NMP 和焦磷酸。产物 8-oxo-dGMP 是一种异常紧密结合的缓慢交换抑制剂，KD=52 nM，（ΔG°=−9.8 kcal/mol），比 dGMP 的结合（ΔG°= −3.7 kcal/mol)。尽管不利的 -TΔS°结合（+22 kcal/mol），但对 8-oxo-dGMP 的更高亲和力源于更有利的 ΔH 结合（-32 kcal/mol）。MutT-Mg2+-8-oxo-dGMP 复合物的溶液结构显示出狭窄的疏水性核苷酸结合裂缝，在少数极性残基中具有 Asn-119 和 Arg-78。N119A、N119D、R78K 和 R78A 单突变，以及 R78K+N119A 双突变都显示出基本完整的活性位点，基于 dGTP 水解动力学参数和
• Advanced drug development and manufacturing
  申请人：Los Alamos National Security, LLC

  公开号：EP2511844A2

  公开（公告）日：2012-10-17

  There is described an apparatus for measuring protein characteristics comprising an X-ray fluorescence (XRF) spectrometer comprising a source of polychromatic X-rays, an X-ray detector, a protein, a molecule that has been exposed to and at least weakly binds to the protein, a plurality of X-ray fluorescence signal data obtained by irradiating chemical elements in the protein and molecule with the polychromatic X-rays and a security system for maintaining records for the data from the plurality of X-ray fluorescence signal measurements. There is also described an x-ray microscope for measuring a sample.

  描述了一种测量蛋白质特性的仪器，该仪器包括一个 X 射线荧光 (XRF) 光谱仪，其中包括一个多色 X 射线源、一个 X 射线探测器、一个蛋白质、一个已暴露于该蛋白质并至少与该蛋白质弱结合的分子、通过用多色 X 射线照射蛋白质和分子中的化学元素而获得的多个 X 射线荧光信号数据，以及一个用于维护多个 X 射线荧光信号测量数据记录的安全系统。此外，还介绍了一种用于测量样品的 X 射线显微镜。
• Induction of 8-oxo-dGTPase activity in human lymphoid cells and normal fibroblasts by oxidative stress
  作者：Frauke Meyer、Emerich Fiala、Johannes Westendorf

  DOI：10.1016/s0300-483x(00)00140-2

  日期：2000.5

  The pre-mutagen 8-Oxo-2'-deoxyguanosine-5'-triphosphate (8-oxo-dGTP) is formed during normal cellular metabolism and its incorporation into DNA leads to transversion mutations. Human cells possess the hMTH-1 gene encoding the enzyme 8-oxo-dGTPase, which catalyzes the hydrolysis of 8-oxo-dGTP to the corresponding 8-oxo-dGMP, preventing mutations. To elucidate the involvement of 8-oxo-dGTPase in carcinogenesis, we studied hMTH-1 gene expression and enzyme activity in response to oxidative stress to human skin fibroblasts and Jurkat cells. In fibroblasts, ranges from 0 to 100 mu M H2O2 caused a 2-fold induction of hMTH-1-mRNA expression and a 3-fold induction of enzyme activity. A 1.7-fold induction of mRNA expression and a 3.5-fold induction of enzyme activity was obtained in Jurkat cells after treatment ranging from 0 to 300 mu M H2O2. Cytotoxic concentrations of hydrogen peroxide lead to an almost complete loss of enzyme activity and an inhibition of hMTH-1 mRNA expression. Induction of hMTH-1 gene expression was prevented by addition of actinomycin D and cycloheximide. These data indicate the inducibility of the hMTH-1 gene expression and enzyme activity by prooxidative molecules, such,Is hydrogen peroxide. These parameters can thus be used as a marker of oxidative stress. (C) 2000 Elsevier Science Ireland Ltd. All rights reserved.