土曲霉酮
概述应用生物活性体外研究 专题
| 中文名称 | 土曲霉酮 |
|---|---|
| 中文同义词 | 土曲霉酮;土曲霉素 |
| 英文名称 | TERREIN |
| 英文同义词 | TERREIN;(4S,5R)-4,5-Dihydroxy-3-[(E)-1-propenyl]-2-cyclopenten-1-one;NSC-291308;(+) Terrein, NSC 291308;(4S,5R)-4,5-Dihydroxy-3-(1E)-1-propen-1-yl-2-cyclopenten-1-one;NSC 29130;Terrain;2-Cyclopenten-1-one, 4,5-dihydroxy-3-(1E)-1-propen-1-yl-, (4S,5R)- |
| CAS号 | 582-46-7 |
| 分子式 | C8H10O3 |
| 分子量 | 154.16 |
| EINECS号 | |
| 相关类别 | 微生物代谢物;Antibiotic |
| Mol文件 | 582-46-7.mol |
| 结构式 |  |
土曲霉酮 性质
| 熔点 | 125-127℃ |
|---|---|
| 沸点 | 327.2±42.0 °C(Predicted) |
| 密度 | 1.449±0.06 g/cm3(Predicted) |
| 储存条件 | -20°C |
| 溶解度 | H2O：可溶 1-1.10 mg/mL，透明，无色 |
| 形态 | 固体 |
| 酸度系数(pKa) | 11.77±0.60(Predicted) |
土曲霉酮 用途与合成方法
概述
土曲霉酮(terrein)是从曲霉菌特雷斯中提取的一种生物活性代谢产物，可以抑制黑色素的生成。同时，由于土曲霉酮的结构相对简单，容易体外合成。目前，已有多篇文章报道土曲霉酮可以在体外抑制多种肿瘤细胞的增殖。
应用
土曲霉酮化合物具有黑色素生物合成抑制作用。如同常规黑色素生物合成抑制剂曲酸一样，土曲霉酮化合物以剂量依赖的方式抑制黑色素生物合成，抑制作用是曲酸的10倍。土曲霉酮对乳腺癌、卵巢癌、肝癌等多种肿瘤细胞有抑制增殖的作用。
生物活性
Terrein 是一种黑色素生成抑制剂。Terrein 诱导乳腺癌细胞凋亡 (apoptosis)。Terrein是铜绿假单胞菌 (Pseudomonas aeruginosa) 中的群体感应和 c-di-GMP 抑制剂。
体外研究
Treatment of Mel-Ab cells with Terrein (10-100 µM) for 4 days significantly reduces melanin levels in a dose-dependent manner. Terrein reduces melanin synthesis by reducing tyrosinase production via ERK activation.
Terrein (5-500 µM; 24 and 48 hours) reduces the viability of these cells in concentration- and time-dependent manners.
Terrein (150, 250, 500µM; 24 hours) induces programmed cell death in both invasive and non-invasive breast cancer cell lines. Thus, the optimal non-toxic concentrations of Terrein (25 and 75 µM) were used for subsequent experiments.
Terrein (25 and 75 µM) significantly decrease the mRNA levels of both MMP-2 and MMP-9 in MDA-MB-231 cells. Terrein (75 µM) significantly decrease the mRNA levels of both MMP-2 and MMP-9 in MCF-7 cells.
Terrein (75 µM) inhibits the expression of RhoA, RhoB, p-Rac1 in MCF-7 cells. Terrein (75 µM) inhibits the expression of RhoB, p-Rac1 in MDA-MB-231 cells.
Terrein (10, 30, and 100 μM) inhibits the production of virulence factors such as elastase, pyocyanin, and rhamnolipid, as well as biofilm formation in P. aeruginosa PAO1 and PA14 strains.
Cell Viability Assay
| Cell Line: | MCF-7 and MDA-MB-231 cells |
| Concentration: | 5, 25, 50, 75, 100, 150, 250, 500 µM |
| Incubation Time: | 24 and 48 hours |
| Result: | The IC 50 s for MCF-7 and MDA-MB-231 cells after 24 h of incubation were 2.34 mM and 700 µM, respectively. After 48 h of incubation, the IC 50 s are 244.3 µM for MCF-7 and 244.5 µM for MDA-MB-231 cells. |
Apoptosis Analysis
| Cell Line: | MCF-7 and MDA-MB-231 cells |
| Concentration: | 25, 75, 150, 250, 500 µM |
| Incubation Time: | 24 hours |
| Result: | The percentages of apoptotic cells after 25 and 75 µM treatment were 7.52 and 5.82%, respectively for MCF-7 cells (9.94% for the control), and 15.77 and 15.82%, respectively for MDA-MB-231 cells (8.79% for the control). |
RT-PCR
| Cell Line: | MCF-7 and MDA-MB-231 cells |
| Concentration: | 25, 75 µM |
| Incubation Time: | |
| Result: | Decreased the mRNA levels of both MMP-2 and MMP-9 in a concentration-dependent manner. |
Western Blot Analysis
| Cell Line: | MCF-7 and MDA-MB-231 cells |
| Concentration: | 75 µM |
| Incubation Time: | 6, 12 and 24 hours |
| Result: | RhoA and RhoB protein levels were significantly decreased after 6 h of 75 µM treatment in MCF-7 cells. Phosphorylated (p)-Rac1 was also slightly decreased at 12 h. However, RhoC and Cdc42 levels remained unchanged. RhoB protein levels and Rac1 phosphorylation were also decreased in MDA-MB-231 cells at 12 and 24 h, respectively. |
安全信息
| WGK Germany | 3 |
|---|---|
| 海关编码 | 29419000 |
