腺苷高碘酸氧化物 | 34240-05-6

• 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: 腺苷高碘酸氧化物
• 英文名称: α-adenosine 2',3'-dialdehyde
• 英文别名: adenosine-2',3'-dialdehyde；adenosine dialdehyde；Adox；α-Hydroxymethyl-α'-adeninyl-diglykolaldehyd；2-[1-(6-amino-purin-9-yl)-2-oxo-ethoxy]-3-hydroxy-propionaldehyde；2-[1-(6-aminopurin-9-yl)-2-oxoethoxy]-3-hydroxypropanal
• CAS: 34240-05-6
• 化学式: C₁₀H₁₁N₅O₄
• 分子量: 265.228
• InChiKey: ILMNSCQOSGKTNZ-UHFFFAOYSA-N

物化性质

• 沸点：
  532.9±60.0 °C(Predicted)
• 密度：
  1.69±0.1 g/cm3(Predicted)
• 溶解度：
  溶于二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  133
• 氢给体数：
  2
• 氢受体数：
  8

安全信息

• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• 海关编码：
  2933990090

制备方法与用途

生物活性

腺苷类似物Adenosine Dialdehyde (ADOX)也是S-adenosylmethionine-dependent methyltransferase抑制剂，其IC50值为40 nM。

靶点

Target	Value
AdoHcy hydrolase (Cell-free)	40 nM

体外研究

Adenosine dialdehyde (AdOx) 是一种间接抑制剂，能够进入细胞内。它会抑制S-adenosyl-L-homocystein hydrolase，导致S-adenosyl-L-homo cystein (Adoicy)的积累。S-adenosyl-L-homo cystein (Adoicy) 又是甲基转移酶的抑制剂。AdOx能够抑制Tax激活的NF-κB通路，促进p53重新激活并诱导p53靶向基因表达。它还能引起IκB激酶复合体降解并通过稳定IκBα抑制NF-kB信号传导。在HTLV-1转化淋巴细胞中，AdOx能够诱导G2/M期细胞周期阻滞和细胞死亡，但对正常细胞无此作用。

体内研究

AdOx 对小鼠神经母细胞瘤的原位生长具有有效的抑制作用，并能延长携瘤小鼠的生命周期。然而，在通过稳态输液途径给药时，AdOx 并不抑制造血功能。当腹腔注射剂量为20 mg/kg/day的AdOx 时，能够延长约40%的小鼠寿命。

反应信息

• 作为反应物：
  描述：

  腺苷高碘酸氧化物 、 在 sodium hydroxide 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 反应 3.0h， 生成 2-[2-[[2-[2-[[2-[2-[[2-[2-[[2-[2-[2-[[2-[2-[2-[2-(6-Aminopurin-9-yl)-6-(hydroxymethyl)morpholin-4-yl]ethoxy]ethoxy]-1-hydroxyethylidene]amino]ethoxy]ethoxy]-1-hydroxyethylidene]amino]ethyl-[2-(4-hydroxy-5-methyl-2-oxopyrimidin-1-yl)acetyl]amino]-1-hydroxyethylidene]amino]ethyl-[2-(4-hydroxy-5-methyl-2-oxopyrimidin-1-yl)acetyl]amino]-1-hydroxyethylidene]amino]ethyl-[2-(4-hydroxy-5-methyl-2-oxopyrimidin-1-yl)acetyl]amino]-1-hydroxyethylidene]amino]ethyl-[2-(4-hydroxy-5-methyl-2-oxopyrimidin-1-yl)acetyl]amino]ethanimidic acid
  参考文献：
  名称：

  核糖核酸酶L-活性2'，5'-寡腺苷酸-肽核酸的融合合成。

  摘要：

  通过高碘酸盐氧化将2-5A缀合至N-（2-氨基乙基）-甘氨酰PNA，然后与氨基衍生的PNA偶联并最终还原氰基硼氢化物。2-5A五聚体与四聚胸腺嘧啶PNA的加合物激活了RNase L，其效力与早期版本的2-5A-PNA或2-5A-DNA相同。

  DOI：

  10.1016/s0960-894x(00)00240-7
• 作为产物：
  描述：

  N6-苯甲酰基腺嘌呤 在 sodium periodate 、 四氧化锇 、 硫化氢 、 氨 、 四氯化锡 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 51.0h， 生成 腺苷高碘酸氧化物
  参考文献：
  名称：

  Nucleosides and nucleotides. LXII. Synthesis and optical properties of 2,3-dideoxy-D-erythro-hex-2-enopyranosyl nucleosides.

  摘要：

  在氯化锡或三甲基硅基三氟甲烷磺酸盐存在下，3, 4, 6-三-O-乙酰基-D-葡萄糖醇与三甲基硅基化的核苷碱基的缩合反应生成了2, 3-二脱氧-D-红糖-hex-2-烯吡喃糖核苷的异构体混合物。这些异构体的2-己烯吡喃糖核苷的圆二色性（CD）光谱符号与通常的核苷或葡萄糖吡喃糖核苷的符号相反。文中还展示了其他例子，说明核苷糖部分的不饱和键对CD光谱的贡献。

  DOI：

  10.1248/cpb.33.3689

文献信息

• Treatment System and Method for Preserving Fresh Produce
  申请人：Kravitz Howard

  公开号：US20080085346A1

  公开（公告）日：2008-04-10

  A treatment system and method for preserving fresh produce is disclosed. The method includes providing fresh produce to be preserved, washing the fresh produce in an aqueous solution of hydrogen peroxide having a pH greater than about 9.0, and washing the fresh produce in a mixture of a anti-microbial agent and an acid activator. The system includes tanks containing the wash solutions and conveyor system to transfer fresh produce to and from the tanks.

  公开了一种保鲜新鲜农产品的处理系统和方法。该方法包括提供要保鲜的新鲜农产品，在pH大于约9.0的过氧化氢水溶液中清洗新鲜农产品，并在抗微生物剂和酸活化剂混合物中清洗新鲜农产品。该系统包括含有洗涤溶液的水槽和传送带系统，用于将新鲜农产品从水槽中转移出来。
• FULVENE AND FULVALENE ANALOGS AND THEIR USE IN TREATING CANCERS
  申请人：Arbiser Jack L.

  公开号：US20080275016A1

  公开（公告）日：2008-11-06

  Compounds, pharmaceutical compositions including the compounds, and methods of preparation and use thereof are disclosed. The compounds are fulvene and/or fulvalene analogs. The compounds and compositions can be used to treat and/or prevent a wide variety of cancers, including drug resistant cancers, as well as numerous inflammatory, degenerative and vascular diseases, including various ocular diseases. Representative fulvene and/or fulvalene analogs include fulvene and fulvalene analogues of various dyes, hormones, sugars, peptides, oligonucleotides, amino acids, nucleotides, nucleosides, and polyols. The compounds are believed to function, at least, by inhibiting Nox or ROS. In some embodiments, the Nox is one that is selectively expressed in cancer cells over normal cells, or one that is expressed in higher amounts in cancer cells over normal cells. Thus, the compounds are novel therapeutic agents for a variety of cancers and other diseases.
• COMPOSITIONS AND METHODS FOR REPROGRAMING NON-PLURIPOTENT CELLS INTO PLURIPOTENT STEM CELLS
  申请人：HONG GUAN LTD.

  公开号：US20160145581A1

  公开（公告）日：2016-05-26

  The invention provides a composition and a method for inducing pluripotency in non-pluripotent eukaryotic cells. The composition comprises chemical inducers of pluripotency (CIPs) including glycogen synthase kinase (GSK) inhibitors, TGFp receptor inhibitors, cyclic AMP agonists, S-adenosylhomocysteine hydrolase (SAH) inhibitors, and optionally an agent that promotes histone acetylation. The method comprises contacting a cell with the CIPs for a sufficient period of time to reprogram the cell into a pluripotent stem cell.
• IMPROVED METHODS FOR REPROGRAMING NON-PLURIPOTENT CELLS INTO PLURIPOTENT STEM CELLS
  申请人：Beihao Stem Cell and Regenerative Medicine Research Institute Co., Ltd.

  公开号：US20190282624A1

  公开（公告）日：2019-09-19

  Provided are chemical inducers of pluripotency (CIP) which include glycogen synthase kinase inhibitors, TGFβ receptor inhibitors, cyclic AMP agonists and S-adenosylhomocysteine hydrolase (SAH) inhibitors or histone acetylators. A method of inducing pluripotency in a partially or completely differentiated cell by using such chemical inducers of pluripotency is also provided. The method includes: (i) contacting a cell with the CIPs for a sufficient period of time to result in reprogramming the cell into a pluripotent stem cell having ESC-like characteristics (CiPSC). Isolated chemically induced pluripotent stem cells (CiPSCs) and their progeny, produced by inducing differentiation of the CiPSCs, can be used in a number of applications, including but not limited to cell therapy and tissue engineering.
• METHODS FOR REPROGRAMING NON-PLURIPOTENT CELLS INTO PLURIPOTENT STEM CELLS
  申请人：Beihao Stem Cell and Regenerative Medicine Research Institute Co., Ltd.

  公开号：US20220025321A1

  公开（公告）日：2022-01-27

  Provided are chemical inducers of pluripotency (CIP) which include glycogen synthase kinase inhibitors, TGFβ receptor inhibitors, cyclic AMP agonists and S-adenosylhomocysteine hydrolase (SAH) inhibitors or histone acetylators. A method of inducing pluripotency in a partially or completely differentiated cell by using such chemical inducers of pluripotency is also provided. The method includes: (i) contacting a cell with the CIPs for a sufficient period of time to result in reprograming the cell into a pluripotent stem cell having ESC-like characteristics (CiPSC). Isolated chemically induced pluripotent stem cells (CiPSCs) and their progeny, produced by inducing differentiation of the CiPSCs, can be used in a number of applications, including but not limited to cell therapy and tissue engineering.