2-(2-氨基-6-氧代-3H-嘌呤-7-基)乙醛 | 73100-87-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 2-(2-氨基-6-氧代-3H-嘌呤-7-基)乙醛
• 中文别名: 1,5-二羟基-3-甲基-8-(2,6,7,7a-四氢-4H-呋喃并[3,2-c]吡喃-4-氧基)蒽-9,10-二酮
• 英文名称: N-7-(2-Oxoethyl)guanine
• 英文别名: 7-(2-oxoethyl)guanine；7-N-(2-Oxoethyl)guanine；2-(2-amino-6-oxo-1H-purin-7-yl)acetaldehyde
• CAS: 73100-87-5
• 化学式: C₇H₇N₅O₂
• 分子量: 193.165
• InChiKey: GWIQUBKMOOZLKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-氨基-6-氧代-3H-嘌呤-7-基)乙醛 在 硼氘化钠 作用下， 以42%的产率得到N-7-(2-d1-2-Hydroxyethyl)guanine
  参考文献：
  名称：

  Tandem mass spectrometric approaches for the analysis of alkylguanines in human urine

  摘要：

  AbstractHuman exposure to carcinogenic alkylating agents can lead to the formation of covalently bound adducts in DNA, some of which are excreted in urine as alkylated purines following DNA degradation and repair. Tandem mass spectrometric methods have been developed for the qualitative and quantitative determination of such alkylpurines in human urine. Short‐chain alkyl‐ and hydroxyalkylguanines have been synthesized with the substituents at theN‐7‐,O6‐ andN2‐positions of guanine. Examination of the product ion scans of their molecular ions (electron impact (EI) ionization) revealed that the ion atm/z151, [guanine]+, was common to all of the alkylguanines studied, with the exception of the methylated analogues. Precursor ion scans of this ion on partially purified human urine extracts showed the presence of several ions (e.g.m/z179, 195) which were consistent with molecular ions for alkylguanines. The presence of these and other constituents was confirmed by product ion spectra of molecular ions (EI and fast atom bombardment), and by high‐performance liquid chromatographic separation prior to tandem mass spectrometry (MS/MS). Evidence was obtained for the presence ofN‐7‐methyl‐,N2‐dimethyl‐,N2‐dimethyl‐,N2‐ethyl‐ andN‐7‐(2‐hydroxyethyl)guanine. Quantitative methods were established for these five alkyl guanines using gas chromatography mass spectrometry (GC/MS) and GC/MS/MS. Deuterated internal standards were synthesized and added to the urine prior to extraction of alkylpurines by Sep‐Pak cartridge chromatography. The products were converted into theirtert‐butyldimethylsilyl derivatives and analysed by selected ion monitoring (SIM) of [M – 57]+or by multiple reaction monitoring (MRM) of the fragmentation M+˙→ [M – 57]+. The MRM method yielded values forN‐7‐methylguanine of 2.57 ± S.D. 1.32 mg day−1(n= 6),N2‐methylguanine of 0.31 ± 0.10 mg day−1(n= 10) andN2‐dimethylguanine of 0.21 ± 0.23 mg day−1(n= 10).N2‐Ethyl‐ andN‐7‐(2‐hydroxyethyl)guanine could only be detected by SIM at levels of ∼0.5 and 2 μg day−1, respectively. The MRM analyses, although inherently less sensitive than the SIM analyses, exhibit greater selectivity and consequently fewer contaminant ions.

  DOI：

  10.1002/oms.1210280514
• 作为产物：
  描述：

  鸟苷 在 sodium periodate 作用下， 生成 2-(2-氨基-6-氧代-3H-嘌呤-7-基)乙醛
  参考文献：
  名称：

  Tandem mass spectrometric approaches for the analysis of alkylguanines in human urine

  摘要：

  AbstractHuman exposure to carcinogenic alkylating agents can lead to the formation of covalently bound adducts in DNA, some of which are excreted in urine as alkylated purines following DNA degradation and repair. Tandem mass spectrometric methods have been developed for the qualitative and quantitative determination of such alkylpurines in human urine. Short‐chain alkyl‐ and hydroxyalkylguanines have been synthesized with the substituents at theN‐7‐,O6‐ andN2‐positions of guanine. Examination of the product ion scans of their molecular ions (electron impact (EI) ionization) revealed that the ion atm/z151, [guanine]+, was common to all of the alkylguanines studied, with the exception of the methylated analogues. Precursor ion scans of this ion on partially purified human urine extracts showed the presence of several ions (e.g.m/z179, 195) which were consistent with molecular ions for alkylguanines. The presence of these and other constituents was confirmed by product ion spectra of molecular ions (EI and fast atom bombardment), and by high‐performance liquid chromatographic separation prior to tandem mass spectrometry (MS/MS). Evidence was obtained for the presence ofN‐7‐methyl‐,N2‐dimethyl‐,N2‐dimethyl‐,N2‐ethyl‐ andN‐7‐(2‐hydroxyethyl)guanine. Quantitative methods were established for these five alkyl guanines using gas chromatography mass spectrometry (GC/MS) and GC/MS/MS. Deuterated internal standards were synthesized and added to the urine prior to extraction of alkylpurines by Sep‐Pak cartridge chromatography. The products were converted into theirtert‐butyldimethylsilyl derivatives and analysed by selected ion monitoring (SIM) of [M – 57]+or by multiple reaction monitoring (MRM) of the fragmentation M+˙→ [M – 57]+. The MRM method yielded values forN‐7‐methylguanine of 2.57 ± S.D. 1.32 mg day−1(n= 6),N2‐methylguanine of 0.31 ± 0.10 mg day−1(n= 10) andN2‐dimethylguanine of 0.21 ± 0.23 mg day−1(n= 10).N2‐Ethyl‐ andN‐7‐(2‐hydroxyethyl)guanine could only be detected by SIM at levels of ∼0.5 and 2 μg day−1, respectively. The MRM analyses, although inherently less sensitive than the SIM analyses, exhibit greater selectivity and consequently fewer contaminant ions.

  DOI：

  10.1002/oms.1210280514

文献信息

• Synthesis of potential inhibitors of hypoxanthine-guanine phosphoribosyltransferase for testing as antiprotozoal agents. 1. 7-Substituted 6-oxopurines
  作者：James R. Piper、Anne G. Laseter、John A. Montgomery

  DOI：10.1021/jm00178a002

  日期：1980.4

  bromoacetate) and 3- and 4-(fluorosulfonyl)benzoyl chlorides afforded derivatives bearing functional groups capable of forming covalent bonds with enzymes through displacement reactions. 4-Chlorobenzyl derivatives were similarly prepared as potential inhibitors that might act through hydrophobic bonding. Three 7-substituted guanines whose side chains bear other functions (7-guanine-3-propranesulfonic acid, guanine-7-acetaldehyde

  生物学证据表明，次黄嘌呤-鸟嘌呤磷酸核糖基转移酶（EC 2.4.2.8）对于疟疾寄生虫中的细胞增殖至关重要，而对哺乳动物细胞则无关紧要。制备其中7个取代基带有官能团或疏水基团的7位取代的鸟嘌呤和次黄嘌呤，其目的是找到合适构成的化合物，其类似于正常底物，使其能够竞争HGRPTase的可逆嘌呤结合位点，同时允许取代基抑制剂分子与酶上合适的位点形成共价键或强疏水键。从羟烷基化和鸟苷烷基化开始的多步合成导致在7位上被以下链取代的四个关键鸟嘌呤：2-氨基乙基，3-氨基-2-羟丙基，3-氨基苄基，和4-氨基苄基。类似地，制备了7-（4-氨基苄基）次黄嘌呤。在侧链氨基上与溴乙酸酐（或4-硝基苯基溴乙酸酯）和3-和4-（氟磺酰基）苯甲酰氯的反应提供了带有能够通过置换反应与酶形成共价键的官能团的衍生物。类似地，将4-氯苄基衍生物制备为可能通过疏水键起作用的潜在抑制剂。制备了三个侧链还具有其他功能的7-取代的
• Methods and products for analyzing polymers
  申请人：——

  公开号：US20020119455A1

  公开（公告）日：2002-08-29

  Methods and products for analyzing polymers are provided. The methods include methods for determining various other structural properties of the polymers.

  提供了分析聚合物的方法和产品。这些方法包括确定聚合物各种其他结构特性的方法。
• A New LC-MS/MS Method for the Quantification of Endogenous and Vinyl Chloride-Induced 7-(2-Oxoethyl)Guanine in Sprague–Dawley Rats
  作者：Esra Mutlu、Yo-Chan Jeong、Leonard B. Collins、Amy-Joan L. Ham、Patricia B. Upton、Gary Hatch、Darrell Winsett、Paul Evansky、James A. Swenberg

  DOI：10.1021/tx200447w

  日期：2012.2.20

  Vinyl chloride (VC) is an industrial chemical that is known to be carcinogenic to animals and humans. VC primarily induces hepatic angiosarcomas following high exposures (>= 50 ppm). VC is also found in Superfund sites at ppb concentrations as a result of microbial metabolism of trichloroethylene and perchloroethylene. Here, we report a new sensitive LC-MS/MS method to analyze the major DNA adduct formed by VC, 7-(2-oxoethylguanine) (7-OEG). We used this method to analyze tissue DNA from both adult and weanling rats exposed to 1100 ppm [C-13(2)]-VC for 5 days. After neutral thermal hydrolysis, 7-OEG was derivatized with O-t-butyl hydroxylamine to an oxime adduct, followed by LC-MS/MS analysis. The limit of detection was 1 fmol, and the limit of quantitation was 1.5 fmol on the column. The use of stable isotope VC allowed us to demonstrate for the first time that endogenous 7-OEG was present in tissue DNA. We hypothesized that endogenous 7-OEG was formed from lipid peroxidation and demonstrated the formation of [C-13(2)]-7-OEG from the reaction of calf thymus DNA with [C-13(18)]-ethyl linoleate (EtLa) under peroxidizing conditions. The concentrations of endogenous 7-OEG in liver, lung, kidney, spleen, testis, and brain DNA from adult and weanling rats typically ranged from 1.0 to 10.0 adducts per 10(6) guanine. The exogenous 7-OEG in liver DNA from adult rats exposed to 1100 ppm [C-13(2)]-VC for 5 days was 104.0 +/- 23.0 adducts per 10(6) guanine (n = 4), while concentrations in other tissues ranged from 1.0 to 39.0 adducts per 10(6) guanine (n = 4). Although endogenous concentrations of 7-OEG in tissues in weanling rats were similar to those of adult rats, exogenous [C-13(2)]-7-OEG concentrations were higher in weanlings, averaging 300 adducts per 10(6) guanine in liver. Studies on the persistence of [C-13(2)]-7-OEG in adult rats sacrificed 2, 4, and 8 weeks postexposure to [C-13(2)]-VC demonstrated a half-life of 7-OEG of 4 days in both liver and lung.
• FOST, U.;MARCZYNSKI, B.;KASEMANN, R.;OTTENWALDER, H.;PETER, H., FRESENIUS Z. ANAL CHEM., 334,(1989) N, C. 701-702
  作者：FOST, U.、MARCZYNSKI, B.、KASEMANN, R.、OTTENWALDER, H.、PETER, H.

  DOI：——

  日期：——
• METHODS AND PRODUCTS FOR ANALYZING POLYMERS
  申请人：Chan, Eugene Y.

  公开号：EP1009802A2

  公开（公告）日：2000-06-21