曲奥舒凡 | 299-74-1

• 物质功能分类: 生物化工 - 生化试剂 - 激动剂抑制剂
• 中文名称: 曲奥舒凡
• 英文名称: 1,4-Bis(methylsulfonyloxy)threitol
• 英文别名: DL-Threitol-1,4-bis(methansulfonat)；[(2R,3R)-2,3-dihydroxy-4-methylsulfonyloxybutyl] methanesulfonate；D-Threitol, 1,4-bis(methanesulfonate)；Threitol-1, 4-bismethanesulfonate, meso-；(2S,3S)-Threitol 1,4-bismethanesulfonate；(2S,3S)-Threitol-1,4-bismethansulfonat
• CAS: 299-74-1；299-75-2；1947-62-2；13308-13-9；17088-46-9；21106-06-9
• 化学式: C₆H₁₄O₈S₂
• 分子量: 278.304
• InChiKey: YCPOZVAOBBQLRI-ZBHICJROSA-N

物化性质

• 熔点：
  76-78 °C
• 沸点：
  359.3°C (rough estimate)
• 密度：
  1.305 (estimate)
• 溶解度：
  丙酮（微溶）、DMSO（微溶）、甲醇（微溶）、水（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  -2.34
• 重原子数：
  16.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  127.2
• 氢给体数：
  2.0
• 氢受体数：
  8.0

安全信息

• 危险等级：
  6.1(b)

制备方法与用途

生物活性

Treosulfan (NSC 39069, Treosulphan) 是一种用于常规和大剂量化疗方案的烷基化 alkylating 药剂。Treosulfan 对胰腺癌细胞系具有强大的细胞毒性。

靶点

DNA Alkylator

体外研究

Treosulfan is an alkylating agent. Treosulfan inhibits several cancer cell lines, such as Panc-1, Miapaca-2 and Capan-2 cells, with IC ₅₀ s of 3.6 μg/mL, 1.8 μg/mL and 2.1 μg/mL respectively, and shows nearly 100% cytotoxicity on these cell lines at 100 μg/mL. Treosulfan (0.1-100 μg/mL) in combination with LY 188011 exhibits enhanced activity against cancer cells. However, Treosulfan (1, 2.5, 5 μg/ml) combined with 5-FU (0.1, 0.25, 0.5 μg/ml) has antagonistic effect on Panc-1 cells at intermediate and high concentrations, and on Miapaca-2 cells at all doses. Treosulfan (800 µg/mL) dramatically reduces erythrocyte forward scatter, increases the percentage of annexin-V-binding cells, [Ca ²⁺ ] _i , and ROS. Removal of extracellular Ca ²⁺ abrogates the effect of Treosulfan on annexin-V-binding.

体内研究

Treosulfan (1.5 g/kg/day) induces a rapid myeloablation, depletes the splenic B and T cells in mice. Treosulfan (1.5 g/kg/day) causes olny interleukin-2 production in spleen cells for a short time and without obvious significant effect on synthesis of tumor necrosis factor-α and/or IFN-γ in mice.