[(2S,3R,4S,5R)-2-[(2S,3R,4S,5S)-3-乙酰氧基-2-[[(3R,8S,9R,10R,13S,14R,16R,17S)-3,17-二羟基-10,13-二甲基-17-[(2S)-6-甲基-3-氧代庚烷-2-基]-1,2,3,4,7,8,9,11,12,14,15,16-十二氢环戊烯并[a]菲-16-基]氧基]-5-羟基四氢吡喃-4-基]氧基-4,5-二羟基四氢吡喃-3-基]4-甲氧基苯甲酸酯 | 145075-81-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 中文名称: [(2S,3R,4S,5R)-2-[(2S,3R,4S,5S)-3-乙酰氧基-2-[[(3R,8S,9R,10R,13S,14R,16R,17S)-3,17-二羟基-10,13-二甲基-17-[(2S)-6-甲基-3-氧代庚烷-2-基]-1,2,3,4,7,8,9,11,12,14,15,16-十二氢环戊烯并[a]菲-16-基]氧基]-5-羟基四氢吡喃-4-基]氧基-4,5-二羟基四氢吡喃-3-基]4-甲氧基苯甲酸酯
• 英文名称: [(2S,3R,4S,5R)-2-[(2S,3R,4S,5S)-3-acetyloxy-2-[[(3R,8S,9R,10R,13S,14R,16R,17S)-3,17-dihydroxy-10,13-dimethyl-17-[(2S)-6-methyl-3-oxoheptan-2-yl]-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-16-yl]oxy]-5-hydroxyoxan-4-yl]oxy-4,5-dihydroxyoxan-3-yl] 4-methoxybenzoate
• CAS: 145075-81-6
• 化学式: C₄₇H₆₈O₁₅
• 分子量: 873.0
• InChiKey: MPXTYZZFIJTPPA-JOQRFCRPSA-N

物化性质

• 沸点：
  932.5±65.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（微量）、甲醇（微量）、吡啶（微量）

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  62
• 可旋转键数：
  15
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  217
• 氢给体数：
  5
• 氢受体数：
  15

制备方法与用途

生物活性

OSW-1 是从虎眼万年青中分离出来的，osterol-binding protein (OSBP) 和 OSBP-elated protein 4 (ORP4) 的特异性拮抗剂，其在人类肿瘤细胞系中的 GI50 值为纳摩尔级别。

靶点

OSBP/ORP4.

体外研究

OSW-1 has a strong inhibitory effect on colon carcinoma cells with low cytotoxicity on normal cells. The anti-proliferative effects of OSW-1 on SW480 and LoVo colon carcinoma cells are characterized by measuring cell viability using the CCK8 assay, and compared the results with other clinical anticancer agents. SW480 and LoVo cell lines are derived from a Dukes' stage B colon carcinoma and a colon carcinoma metastatic nodule, which represent non-metastatic and metastatic carcinomas, respectively. OSW-1 exhibits not only extremely strong anticancer activity in SW480 and LoVo cell lines with an IC ₅₀ of nanomolar concentration, but is also more potent than other anticancer agents by 10-100 times, with a lower cytotoxic effect on normal epithelial cells. These results indicate that OSW-1 has a powerful anticancer effect, but lower cytotoxic effect on normal cells.

体内研究

To ascertain whether or not OSW-1 is as effective in vivo, a nude mouse model inoculated by LoVo cells is adopted, in which OSW-1 treatment is performed when tumors became palpable. The results show that the size of tumors in treated mice is smaller on average than control mice. The significant difference is observed from the 15-17 th day following treatment, and this difference is gradually increased until the animals are sacrificed. Compared with the control group, the tumor weight of the OSW-1-treated group significantly decreases (P<0.05). Additionally, no apparent side effects are observed in OSW-1-treated mice. These results demonstrate that OSW-1 has powerful effects on suppressing colon tumor growth without significant side effects in vivo.