肌苷肟 | 3414-62-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 中文名称: 肌苷肟
• 英文名称: N⁶-hydroxyadenosine
• 英文别名: 6-Hydroxyadenosine；(2R,3R,4S,5R)-2-[6-(hydroxyamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 3414-62-8
• 化学式: C₁₀H₁₃N₅O₅
• 分子量: 283.244
• InChiKey: QROZCFCNYCVEDO-KQYNXXCUSA-N

物化性质

• 熔点：
  195 °C (decomp)(Solv: ethanol (64-17-5))
• 沸点：
  425.8°C (rough estimate)
• 密度：
  1.3790 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  146
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  肌苷肟 在 还原型辅酶Ⅰ 作用下， 以 aq. phosphate buffer 为溶剂， 反应 0.38h， 生成 腺苷
  参考文献：
  名称：

  The Mitochondrial Amidoxime Reducing Component (mARC) Is Involved in Detoxification of N-Hydroxylated Base Analogues

  摘要：

  The "mitochondrial Amidoxime Reducing Component" (mARC) is the newly discovered fourth molybdenum enzyme in mammals. All hitherto analyzed mammals express two mARC proteins, referred to as mARC1 and mARC2. Together with their electron transport proteins cytochrome b(5) and NADH cytochrome b(5) reductase, they form a three-component enzyme system and catalyze the reduction of N-hydroxylated prodrugs. Here, we demonstrate the reductive detoxification of toxic and mutagenic N-hydroxylated nucleobases and their corresponding nucleosides by the mammalian mARC-containing enzyme system. The N-reductive activity was found in all tested tissues with the highest detectable conversion rates in liver, kidney, thyroid, and pancreas. According to the presumed localization, the N-reductive activity is most pronounced in enriched mitochondrial fractions. In vitro assays with the respective recombinant three-component enzyme system show that both mARC isoforms are able to reduce N-hydroxylated base analogues, with mARC1 representing the more efficient isoform. On the basis of the high specific activities with N-hydroxylated base analogues relative to other N-hydroxylated substrates, our data suggest that mARC proteins might be involved in protecting cellular DNA from misincorporation of toxic N-hydroxylated base analogues during replication by converting them to the correct purine or pyrimidine bases, respectively.

  DOI：

  10.1021/tx300298m
• 作为产物：
  描述：

  6-氯嘌呤核苷 在 羟胺 作用下， 以 乙醇 、 水 为溶剂， 以77%的产率得到肌苷肟
  参考文献：
  名称：

  Anti-malarial activity of N6-modified purine analogues

  摘要：

  Plasmodium falciparum causes one of the deadliest forms of malaria and resistance to the currently available drugs makes it imperative to develop new, safe and potent drugs. Parasites such as P. falciparum are unable to synthesise purines de novo and to this end often have multiple purine uptake and salvage systems. With this in mind, we have designed and synthesised libraries of purine analogues as potential anti-malarial agents. Herein, we report three compounds with promising activity against the highly chloroquine-resistant VS1 P. falciparum namely: N-6-hydroxyadenine (1c), 2-amino-N-6-aminoadenosine (2b) and 2-amino-N-6-amino-N-6-methyladenosine (4b). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.05.038

文献信息

• [EN] CATIONIC LIPIDS AND USES THEREOF<br/>[FR] LIPIDES CATIONIQUES ET LEURS UTILISATIONS
  申请人：FACTOR BIOSCIENCE INC

  公开号：WO2021003462A1

  公开（公告）日：2021-01-07

  The present invention relates to novel cationic lipids of formula I, and more specifically formula IV. These are used, for example, in liposomes for the delivery of nucleic acids to cells.

  本发明涉及新型公式I的阳离子脂质，更具体地是公式IV。例如，这些脂质可用于脂质体中将核酸传递给细胞。
• [EN] NOVEL N-ALKOXYADENINE DERIVATIVES ACTING AS CYTOKINE INHIBITORS<br/>[FR] NOUVEAUX DERIVES DE N-ALCOXYADENINE INHIBANT LA CYTOKINE
  申请人：NOVO NORDISK A/S

  公开号：WO1998001459A1

  公开（公告）日：1998-01-15

  (EN) The present invention relates to novel $i(N),9-disubstituted adenine derivatives and novel aristeromycin analogues which are further substituted at the adenine 2-position, and which have a hydroxymethyl group, or an ester or ester isostere at a position corresponding to the ribose 4-position, and pharmaceutically acceptable addition salts thereof. The compounds act as cytokine inhibitors. Also covered are processes for preparation of the above derivatives and their pharmaceutical compositions as well as methods for using the compounds and compositions as drugs for the treatment of disorders involving cytokines in humans.(FR) L'invention concerne des nouveaux dérivés d'adénine $i(N),9-disubstitués et de nouveaux analogues d'aristéromycine substitués en outre à la position 2 de l'adénine, et ayant un groupe hydroxyméthyle ou un ester ou un ester isostère à une position qui correspond à la position 4 de la ribose, et les sels d'addition pharmaceutiquement acceptable de ces substances. De tels composés inhibent la cytokine. On décrit des procédés relatifs à l'élaboration des dérivés et de leurs compositions pharmaceutiques ainsi que des procédés relatifs à l'utilisation des composés et des compositions comme médicaments pour traiter les affections impliquant la cytokine chez l'homme.

  本发明涉及新型$i(N),9-二取代腺嘌呤衍生物和新型阿里斯特霉素类似物，后者在腺嘌呤2位进一步取代，并在相应于核糖4位的位置具有羟甲基基团、酯或酯类似物，以及其药学上可接受的加合物盐。这些化合物作为细胞因子抑制剂。还涵盖了制备上述衍生物及其药物组成物的过程，以及将这些化合物和组合物作为治疗人类细胞因子相关疾病的药物的方法。
• Nucleoside derivatives for treating hepatitis C virus infection
  申请人：Genelabs Technologies, Inc.

  公开号：US20040147464A1

  公开（公告）日：2004-07-29

  Disclosed are compounds, compositions and methods for treating hepatitis C virus infections.

  本文揭示了用于治疗丙型肝炎病毒感染的化合物、组合物和方法。
• NUCLEOSIDE DERIVATIVES FOR TREATING HEPATITIS C VIRUS INFECTION
  申请人：Roberts Christopher Don

  公开号：US20080249060A1

  公开（公告）日：2008-10-09

  Disclosed are compounds, compositions and methods for treating hepatitis C virus infections.

  本发明涉及用于治疗丙型肝炎病毒感染的化合物、组合物和方法。
• METHODS AND PRODUCTS FOR TRANSFECTING CELLS
  申请人：FACTOR BIOSCIENCE INC.

  公开号：US20140356906A1

  公开（公告）日：2014-12-04

  The present invention relates in part to nucleic acids encoding proteins, nucleic acids containing non-canonical nucleotides, therapeutics comprising nucleic acids, methods, kits, and devices for inducing cells to express proteins, methods, kits, and devices for transfecting, gene editing, and reprogramming cells, and cells, organisms, and therapeutics produced using these methods, kits, and devices. Methods for inducing cells to express proteins and for reprogramming and gene-editing cells using RNA are disclosed. Methods for producing cells from patient samples, cells produced using these methods, and therapeutics comprising cells produced using these methods are also disclosed.

  本发明部分涉及编码蛋白质的核酸、含非规范核苷酸的核酸、包含核酸的治疗剂、诱导细胞表达蛋白质的方法、试剂盒和装置、转染、基因编辑和重编程细胞的方法、试剂盒和装置，以及使用这些方法、试剂盒和装置生产的细胞、生物体和治疗剂。公开了使用RNA诱导细胞表达蛋白质、重编程和基因编辑细胞的方法。还公开了从患者样本中制备细胞的方法、使用这些方法制备的细胞以及包含使用这些方法制备的细胞的治疗剂。