p-NBTGR | 13153-27-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: p-NBTGR
• 英文别名: 2-[2-amino-6-[(4-nitrophenyl)methylsulfanyl]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 13153-27-0
• 化学式: C17H18N6O6S
• 分子量: 434.4
• InChiKey: BRSNNJIJEZWSBU-UHFFFAOYSA-N

物化性质

• 熔点：
  203-205 °C
• 沸点：
  858.3±75.0 °C(Predicted)
• 密度：
  1.3888 (rough estimate)
• 溶解度：
  溶于二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  211
• 氢给体数：
  4
• 氢受体数：
  11

安全信息

• 安全说明：
  S24/25

制备方法与用途

生物活性

NBTGR (对硝基苯硫鸟苷) 是核苷转运的有效抑制剂；其抑制腺苷摄取的 Ki 值为 70 nM。

靶点

• Ki: 70 nM (腺苷摄取)

体外研究

一系列含有烷芳巯基取代基团的嘌呤核糖核苷在嘌呤6位上具有较强的多种核苷代谢方面（涉及核糖基转移）的抑制作用。NBTGR 是一种能有效抑制人体红细胞核苷转运的化合物；当细胞暴露于 1 μM NBTGR 后，尿苷摄取的初始速率会降至零。该抑制剂与细胞结合牢固，多次洗涤也不能恢复被 NBTGR 处理过的细胞的尿苷运输能力。NBTGR 抑制尿苷、肌苷和胞苷的流入，而不影响相应的碱基或 D-葡萄糖及 L-亮氨酸的摄取。尿苷能以浓度依赖的方式对抗 NBTGR 对尿苷转运的抑制作用。NBTGR 及其类似物似乎与核苷的易化转运机制相互作用。

文献信息

• Method for Increasing Plant Stress Tolerance and Seed Dormancy
  申请人：The Australian National University

  公开号：US20180355369A1

  公开（公告）日：2018-12-13

  The present invention provides a method for increasing the levels of 3′-phosphoadenosine-5′-phosphate (PAP) or a derivative or analogue thereof in cells of said plant compared to an untreated or wild-type plant grown under the same stress conditions. The methods may comprise administration to the plant and/or the soil it is growing in of: PAP or a derivative or analogue thereof, a substance that enhances or promotes synthesis or accumulation of PAP or said derivative or analogue thereof; or a substance that inhibits or compromises an activity metabolising or removing PAP or said derivative or analogue thereof. Alternatively, the methods may comprise genetic modification of cells of said plant which modifications allow for increased accumulation of PAP or a derivative or analogue thereof in cells of said plant (or in seeds thereof) at least under stress conditions compared to a wild-type plant. The methods find particular application in increasing the tolerance of plants to abiotic stress conditions, which may be selected from increased salinity, increased sodium levels, drought, light stress and pH stress. The present invention also provides a method for extending the dormancy of a seed, as compared to an untreated seed, said method comprising accumulating in cells within said seed an increased level of PAP or a derivative or analogue thereof compared to an untreated or wild-type seed.