dGMP钠盐 | 87713-30-2

• 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
• 中文名称: dGMP钠盐
• 英文名称: 2'-deoxyguanosine-5'-monophosphate sodium salt
• 英文别名: 5'-Guanylic acid, 2'-deoxy-, monosodium salt；sodium;[(2R,3S,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methyl hydrogen phosphate
• CAS: 87713-30-2
• 化学式: C₁₀H₁₃N₅O₇P*Na
• 分子量: 369.206
• InChiKey: WHAXGYYQGCWDBG-FPKZOZHISA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -4.76
• 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：
  189
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  dGMP钠盐 在 三氟乙酸 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.5h， 生成 4-(guanin-8-yl)-7-methoxy-2H-1,4-benzoxazin-3(4H)-one
  参考文献：
  名称：

  由独特的生物活性环状异羟肟酸4-羟基-7-甲氧基-2H-1,4-苯并恶嗪-3（4H）-形成的多中心亲电试剂

  摘要：

  4-羟基-7-甲氧基-2H-1,4-苯并恶嗪-3（4H）-1（HMBOA）由于其药理，农药和抗微生物特性而备受关注。HMBOA的可能的生物活性代谢物是4-乙酰氧基-7-甲氧基-2H-1,4-苯并恶嗪-3（4H）-one（AMBOA）。研究了AMBOA与苯酚，苯胺，硫醇，杂芳族化合物，氨基酸衍生物和核酸的亲电反应，以及该化合物引起的生物学效应的化学机理。结果表明，HMBOA在代谢O-酰化后充当蛋白质和核酸的烷基化剂。

  DOI：

  10.1016/s0040-4020(01)96098-3

文献信息

• [EN] PRODRUG FOR RELEASE OF CISPLATIN AND CYCLOOXYGENASE INHIBITOR<br/>[FR] PRODROGUE POUR LIBÉRATION DE CISPLATINE ET D'UN INHIBITEUR DE CYCLOOXYGÉNASE
  申请人：UNIV GEORGIA

  公开号：WO2015089389A8

  公开（公告）日：2015-08-27
• Relative rates of reaction of Pt(en)Cl (NH2R)+ with guanosine monophosphate as a function of amino group substituent: Toward efficient labeling of DNA for TEM imaging
  作者：Rakesh Kumar、Edward Rosenberg、Miriam Inbar Feske、Antonio G. DiPasquale

  DOI：10.1016/j.jorganchem.2012.11.003

  日期：2013.6

  In an attempt to understand the factors that govern the rates of reaction of the complexes [Pt(en) Cl(NH2R)]+NO3- (en = ethylene diamine) with guanosine monophosphate (dGMP) a series of amine complexes, where R=C8H9NO2 (benzo[d][1,3]dioxol-5-ylmethanamine) (1), C8H11N (phenethylamine) (2), C7H9N (benzylamine) (3), C6H7N (aniline) (4), C6H6IN (p-iodo-aniline) (5) C3H9NO (2-methoxyethylamine) (6) and C6H13N (cyclohexylamine) (7), were synthesized and their reactions with deoxyguanosine monophosphate (dGMP) were followed by H-1 NMR. Compound 1 was initially chosen because it showed significant water solubility. Compound 1 reacted quantitatively but slowly with dGMP and a subsequent Transmission Electron Microscopy (TEM) study of the binding 1 to a GATC DNA repeat gave a TEM micrograph that showed selective labeling of DNA at guanine, using a technique that allowed the laying down of a straight single strand of DNA on a carbon platform. The TEM suggested a possible side reaction with adenine and so a study of the reaction of 1 with adenine was performed and showed slow and what appeared to be non-specific binding to deoxyadenosine monophosphate (dAMP). The reactions of compounds 2-7 with dGMP were then studied by H-1 NMR and it was found that 2 reacted much faster than 1 with dGMP while the remaining complexes reacted more slowly. No reaction of 2 with dAMP was observed in the same time frame. The ultimate goal of the project was to bind a third row transition metal cluster to guanine and given the effective binding of 1 to DNA the synthesis of the complex [Os-3(CO)(11)PPh2(CH2)(2)NH2(en)PtCl]NO3 (9) is also reported that contains Pt as a linker to label guanine. The synthesis was performed by reacting Os-3(CO)(10)(CH3CN)(2) with Ph2PCH2CH2NH2 which gave an eta(2) chelate complex Os-3(CO)(10)PPh2(CH2)(2)NH2 (8). Complex 8 was reacted with [Pt(en)Cl(DMF)]NO3 in a CO atmosphere to give 9. H-1 and Pt-195 NMR indicate formation of an adduct with dGMP but too slowly to be of use in labeling DNA. The solid-state structure of 8 is also reported. (C) 2012 Elsevier B.V. All rights reserved.
• Chemical characterization of DNA adducts derived from the configurationally isomeric benzo[c]phenanthrene-3,4-diol 1,2-epoxides
  作者：Shiv K. Agarwal、Jane M. Sayer、Herman J. C. Yeh、Lewis K. Pannell、Bruce D. Hilton、Margaret A. Pigott、Anthony Dipple、Haruhiko Yagi、Donald M. Jerina

  DOI：10.1021/ja00242a040

  日期：1987.4
• A Carrier-Free Nanostructure Based on Platinum(IV) Prodrug Enhances Cellular Uptake and Cytotoxicity
  作者：Jingjie Tan、Chan Li、Qian Wang、Shuyi Li、Shizhu Chen、Jinchao Zhang、Paul C. Wang、Lei Ren、Xing-Jie Liang

  DOI：10.1021/acs.molpharmaceut.8b00070

  日期：2018.4.2

  Flurbiprofen, a hydrophobic COX inhibitor, was coordinated axially with oxoplatin to form a new conjugate, cis,cis,trans-[Pt(IV)(NH3)(2)Cl-2(flurbiprofen)(2)]. The successful synthesis of this new conjugate was confirmed by H-1, C-13, and Pt-195 NMR. The potential of this conjugate being reduced to cisplatin and subsequently exerting its DNA cross-linking ability was verified using cyclic voltammetry (CV), HPLC, and mass spectrometry (MS). This conjugate showed markedly higher cytotoxicity on many cancer cell lines than cisplatin, flurbiprofen, and their physical mixture (mole ratio, cisplatin:flurbiprofen = 1:2). This is consistent with the result of an apoptosisinducing assay. This conjugate spontaneously assembles carrier-free nanopartides in aqueous solution, which is confirmed by DLS, TEM, SEM, and AFM, and thus facilitates cellular uptake and markedly improves its cytotoxicity and apoptosis-inducing ability in vitro.
• A multi-centered electrophile formed from a unique bioactive cyclic hydroxamic acid, 4-hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one
  作者：Yuichi Hashimoto、Takayoshi Ishizaki、Koichi Shudo

  DOI：10.1016/s0040-4020(01)96098-3

  日期：1991.3

  4-Hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one (HMBOA) is a compound of considerable interest because of its pharmacological, agrochemical, and antimicrobial properties. A plausible bioactive metabolite of HMBOA is 4-acetoxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one (AMBOA). Electrophilic reactions of AMBOA with phenols, anilines, thiols, heteroaromatics, amino acid derivatives and nucleic acids were investigated in relation

  4-羟基-7-甲氧基-2H-1,4-苯并恶嗪-3（4H）-1（HMBOA）由于其药理，农药和抗微生物特性而备受关注。HMBOA的可能的生物活性代谢物是4-乙酰氧基-7-甲氧基-2H-1,4-苯并恶嗪-3（4H）-one（AMBOA）。研究了AMBOA与苯酚，苯胺，硫醇，杂芳族化合物，氨基酸衍生物和核酸的亲电反应，以及该化合物引起的生物学效应的化学机理。结果表明，HMBOA在代谢O-酰化后充当蛋白质和核酸的烷基化剂。