N(7)-羟基乙基鸟嘌呤 | 53498-52-5

• 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: N(7)-羟基乙基鸟嘌呤
• 英文名称: N-7-(2-Hydroxyethyl)guanine
• 英文别名: N(7)-Hydroxyethylguanine；2-amino-7-(2-hydroxyethyl)-1H-purin-6-one
• CAS: 53498-52-5
• 化学式: C₇H₉N₅O₂
• 分子量: 195.181
• InChiKey: OCAWYYAMQRJCOY-UHFFFAOYSA-N

物化性质

• 熔点：
  >300°C
• 溶解度：
  碱性溶液（微溶），DMSO（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  106
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N(7)-羟基乙基鸟嘌呤 在 盐酸 、 亚硝酸特丁酯 作用下， 反应 4.0h， 生成 N7-(2-羟乙基)黄嘌呤
  参考文献：
  名称：

  A Gas Chromatography/Electron Capture/Negative Chemical Ionization High-Resolution Mass Spectrometry Method for Analysis of Endogenous and Exogenous N7-(2-Hydroxyethyl)guanine in Rodents and Its Potential for Human Biological Monitoring

  摘要：

  A gas chromatography/electron capture/negative chemical ionization high-resolution mass spectrometry (GC/EC/NCI-HRMS) method was developed for quantitating N7-(2-hydroxyethyl)guanine (N7-HEG) with excellent sensitivity and specificity. [4,5,6,8-C-13(4)]-N7-HEG was synthesized, characterized and quantitated using HPLC/electrospray ionization mass spectrometry (HPLC/ESI-MS) so it could serve as an internal standard. After being converted to its corresponding xanthine and derivatized with pentafluorobenzyl (PFB) bromide twice, the PFB derivative of N7-HEG was characterized using GC/EC/NCI-HRMS carried out at full scan mode. The most abundant fragment was at m/z 555, with a molecular formula of C21H9N4O3F10, resulting from the loss of one PFB group. By monitoring m/z 555.0515 (analyte) and m/z 559.0649 (internal standard), this assay demonstrated a linear relationship over a range of I fmol to 1 pmol of N7-HEG versus 20 fmol of [C-13(4)]-N7-HEG on column. The limit of detection (LOD) for the complete assay was 600 amol (S/N = 5) injected on column. The variation of this assay was within 15% from 1 to 20 fmol of N7-HEG versus 2 fmol of [C-13(4)]-N7-HEG; with four replications for each calibration standard. Two hundred to three hundred micrograms of spleen DNA of control rats and mice and 100 mu g of spleen DNA of rats and mice exposed to 3000 ppm ethylene far 6 h/day for 5 days were analyzed using GC/EC/NCI-HRMS. The amounts of N7-HEG varied from 0.2 to 0.3 pmol/mu mol of guanine in tissues of control rats. Ethylene-exposed animals had 5-15-fold higher N7-HEG levels than controls. This assay was able to quantitate N7-HEG in 25-30 mu g of DNA from human lymphocytes with excellent specificity. This was due in part to human tissues having 10-15-fold higher amounts of endogenous N7-HEG than rodents. These results show that this GC/EC/NCI-HRMS method is highly sensitive and specific and can be used in biological monitoring and molecular dosimetry and molecular epidemiology studies.

  DOI：

  10.1021/tx990059n
• 作为产物：
  描述：

  环氧乙烷 、 鸟苷 在 溶剂黄146 、 盐酸 作用下， 反应 5.5h， 生成 N(7)-羟基乙基鸟嘌呤
  参考文献：
  名称：

  比较人血红蛋白的N末端缬氨酸和人DNA的N-7鸟嘌呤在体外形成乙烯，丙烯和苯乙烯7,8-氧化物的加合物。

  摘要：

  环氧化合物在大分子的各种亲核位点（如血红蛋白和DNA）反应。为了研究环氧乙烷（EO），环氧丙烷（PO）和苯乙烯7,8-氧化物（SO）在其中两个位置上的反应速率常数，即血红蛋白中的N末端缬氨酸和N-7鸟嘌呤中的DNA是这项研究的主要目标。这两个反应性位点分别是研究最多的血红蛋白和DNA加合物。因此，还进一步关注了体外测定的反应常数在体内的适用性。Hb [分别为2.7 l（mol Hb h）-1和1.0 l（mol Hb h）-1]中EO和PO与N末端缬氨酸之间的二级速率常数的测定与文献值一致。与N-7-鸟嘌呤[16x10（-3）l（mol DNA核苷酸h）-1和7的反应常数。[分别为7x10（-3）l（mol DNA核苷酸h）-1]低于以前发表的值，可能是由于所使用的方法不同。使用体外获得的值对体内情况进行建模可得到EO和PO的一致图片。相反，对于SO，N末端缬氨酸[1.5 l（mol Hb

  DOI：

  10.1016/s1383-5718(98)00106-5

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
• Products of the Direct Reaction of the Diazonium Ion of a Metabolite of the Carcinogen <i>N</i>-Nitrosomorpholine with Purines of Nucleosides and DNA
  作者：Charles N. Zink、Nicolas Soissons、James C. Fishbein

  DOI：10.1021/tx100093a

  日期：2010.7.19

  major products in the cases of both the nucleoside and DNA adducts. The rates of formation of HE adducts are accelerated in DNA, relative to the nucleosides in the cases of the N7-EA-Ade, N7-EA-Gua, and O6-EA-Gua adducts by factors of 7, 14, and 54, respectively. The initial rates of depurination of the N3-EA-Ade, N7-EA-Gua, and N7-EA-Gua adducts have also been quantified, and they are unexceptional in

  已合成了许多衍生自3-羟基-N-亚硝基吗啉的重氮离子的嘌呤核苷和核碱基加合物作为二甲基缩醛。在大多数情况下，将它们转化为醛，或者在两种情况下，将其转化为醛，用温和的酸处理，以生成标准品，用于定量研究上述强力致癌物N的代谢产物对嘌呤核苷和DNA的烷基化作用。-亚硝基吗啉。在许多条件下，就其分解倾向而言，已表征了所得核碱基乙氧基乙醛（EA）加合物的稳定性。与苯并咪唑模型的先前表征的加合物相比，该稳定性通常是无例外的。嘌呤核苷和DNA上加合物的沉积在反应中进行了定量，在该反应中，3-膦基过氧化氢-N-亚硝基吗啉在21±2°C下被水溶性膦还原为羟基代谢物。加合物的谱图与从无环二烷基亚硝胺的简单α-羟基代谢产物观察到的高度相似，双链DNA反应中三种最丰富的乙氧基乙醛（EA）加合物为N7-EA-Gua〜O 6-EA-Gua> N3-EA-Ade。对于主要产物，对于核苷和DNA加合物，已经确定了由最初形
• Method for the production of nucleic acids consisting of stochastically combined parts of source nucleic acids
  申请人：Direvo Biotech AG

  公开号：EP1281757A1

  公开（公告）日：2003-02-05

  Methods and kit for producing recombinant chimeric polynucleotides comprising: forming heteroduplices with single-stranded, partially heterologous source nucleic acids which contain at least one marker nucleotide, introducing single-stranded nicks at sites of the marker nucleotides, and starting synthesis of single-stranded nucleic acids at the nick sites, the non-nicked strand serving as template.

  用于生产重组嵌合多核苷酸的方法和试剂盒，包括：与含有至少一个标记核苷酸的单链部分异源核酸形成异源复合物，在标记核苷酸位点引入单链缺口，并在缺口位点开始合成单链核酸，非缺口链作为模板。
• METHOD OF MODIFYING NUCLEOTIDE CHAIN
  申请人：MATSUSHITA ELECTRIC INDUSTRIAL CO., LTD.

  公开号：EP1647592A1

  公开（公告）日：2006-04-19

  A method for modifying a nucleotide chain, which includes: allowing a catabolic enzyme specific to a nucleotide sequence containing a specific base such as hypoxanthine (Hx) to act on a nucleotide chain (I) to be modified having the above described nucleotide sequence containing a specific base on the 3'-terminal side thereof; and forming a functional group (for example, an aldehyde group) capable of binding to a desired modifier (for example, NH2R having an amino group) on the 3'-terminus of the nucleotide chain (I); so as to bind the above described modifier to the 3'-terminus of the nucleotide chain. Using a nucleotide chain as a modification target which has a nucleotide sequence containing a specific base acting as an enzyme substrate on its 3'-terminal side, this method enables decomposition of only the above described nucleotide sequence portion, thereby forming a functional group that reacts with a desired modifier and binds thereto. By this method, a nucleotide chain can directly be modified with a modifier, thereby easily labeling or conjugating the nucleotide chain. Further, when immobilization of a nucleotide chain is intended, stable and strong immobilization can be attained using a modifier as a linker.

  一种修饰核苷酸链的方法，包括让对含有特定碱基（如次黄嘌呤（Hx））的核苷酸序列具有特异性的分解酶作用于待修饰的核苷酸链（I），该核苷酸链具有在其 3'- 末端侧含有特定碱基的上述核苷酸序列；并在核苷酸链（I）的 3'末端形成能够与所需修饰剂（例如具有氨基的 NH2R）结合的官能团（例如醛基），从而将上述修饰剂结合到核苷酸链的 3'末端。使用核苷酸链作为修饰靶，该核苷酸链的 3'- 末端含有作为酶底物的特定碱基的核苷酸序列，这种方法可以只分解上述核苷酸序列部分，从而形成与所需修饰剂反应并结合的官能团。通过这种方法，核苷酸链可以直接被修饰剂修饰，从而方便地标记或连接核苷酸链。此外，当需要固定核苷酸链时，使用修饰剂作为连接剂可以实现稳定而牢固的固定。
• NEGATIVE PHOTOSENSITIVE RESIN COMPOSITION, PRODUCTION METHOD FOR POLYIMIDE, PRODUCTION METHOD FOR CURED RELIEF PATTERN, AND SEMICONDUCTOR DEVICE
  申请人：Asahi Kasei Kabushiki Kaisha

  公开号：EP4006073A1

  公开（公告）日：2022-06-01

  To provide a negative photosensitive resin composition which exhibits satisfactory resolution even when shifts occur in focus depth, and which has satisfactory adhesion to a mold resin and exhibits a low dielectric constant; a method for producing a polyimide using the photosensitive resin composition; a method for producing a cured relief pattern; and a semiconductor device including the cured relief pattern. Disclosed is a negative photosensitive resin composition including a polyimide precursor having a structure represented by general formula (A1), (B) a photopolymerization initiator, and (C) a solvent.

  提供一种负感光树脂组合物，该组合物即使在聚焦深度发生偏移时也能表现出令人满意的分辨率，并且与模具树脂具有令人满意的粘附性，并表现出较低的介电常数；提供一种使用该感光树脂组合物生产聚酰亚胺的方法；提供一种生产固化浮雕图案的方法；以及提供一种包括固化浮雕图案的半导体器件。 本发明公开了一种阴性光敏树脂组合物，该组合物包括具有通式(A1)表示的结构的聚酰亚胺前体、(B)光聚合引发剂和(C)溶剂。