Adenosine, 3-deaza- | 6736-58-9

• 物质功能分类: 生物化工 - 核苷类药物 - 核苷中间体
• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 咪唑[4，5-c]吡啶核糖核苷和核糖核苷酸
• 英文名称: Adenosine, 3-deaza-
• 英文别名: 2-(4-aminoimidazo[4,5-c]pyridin-1-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 6736-58-9
• 化学式: C₁₁H₁₄N₄O₄
• 分子量: 266.25
• InChiKey: DBZQFUNLCALWDY-UHFFFAOYSA-N

物化性质

• 熔点：
  228-229°C
• 沸点：
  665.7±65.0 °C(Predicted)
• 密度：
  1.90±0.1 g/cm3 (20 ºC 760 Torr)
• 溶解度：
  H2O：10 mg/mL 加热至 60°C

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  127
• 氢给体数：
  4
• 氢受体数：
  7

安全信息

• 危险等级：
  6.1(a)
• 安全说明：
  S24/25
• WGK Germany：
  3
• 海关编码：
  29419090
• 包装等级：
  II
• 危险类别：
  6.1(a)
• 危险品运输编号：
  UN 2811

制备方法与用途

生物活性

3-Deazaadenosine 是一种 S-腺苷高半胱氨酸水解酶 (S-adenosylhomocysteine hydrolase) 抑制剂，其 Ki 值为 3.9 µM；该化合物具有抗炎、抗增殖及抗 HIV 等活性。

靶点

• IC50: 0.15 (HIV-1, A012 病毒株), 0.20 µM (HIV-1, A018 病毒株)
• Ki: 3.9 µM (S-腺苷高半胱氨酸水解酶)

体外研究

3-Deazaadenosine 是 S-腺苷高半胱氨酸水解酶的抑制剂，Ki 值为 3.9 µM。该化合物表现出抗 HIV 的活性，并能抑制由 HIV-1 (A012 和 A018 病毒株) 感染的外周血单核细胞（PBMCs）中的 p24 抗原，其 IC50 值分别为 0.15 µM 和 0.20 µM。在 RAW 264.7 细胞中，3-Deazaadenosine (1-100 µM) 能抑制 LPS 引起的 TNF-α mRNA 表达、增加 NF-κB 的 DNA 结合活性，并导致 IκBα 的蛋白酶降解（而非 IκBβ）。在 100 µM 浓度下，3-Deazaadenosine 增强了 NF-κB 的核转位，但阻断了 LPS 引起的 NF-κB 转录活性；这种抑制作用可通过添加高半胱氨酸而增强。在 50 和 100 µM 浓度下，3-Deazaadenosine 剂量依赖性地抑制 RAf、ERK（蛋白依赖性激酶 1）、Akt 和 FoxO1a 的磷酸化。此外，50 µM 浓度的 3-Deazaadenosine 能通过干扰 RAs 信号通路抑制血管平滑肌细胞 (VSMC) 的增殖。

文献信息

• 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.
• ADENOSINE ANALOG AND ITS USE IN REGULATING THE CIRCADIAN CLOCK
  申请人：NATIONAL INSTITUTE OF BIOLOGICAL SCIENCES, BEIJING

  公开号：US20210338706A1

  公开（公告）日：2021-11-04

  The present invention provides a kind of nucleoside analogue compounds, and a composition comprising the compound and pentostatin, their use for modulating circadian rhythm, preferably, for shifting circadian phase, and methods for modulating circadian rhythm, preferably, for shifting circadian phase via the compound or the composition.
• 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.
• US9982237B2
  申请人：——

  公开号：US9982237B2

  公开（公告）日：2018-05-29