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582-46-7

中文名稱 土曲霉酮
英文名稱 TERREIN
CAS 582-46-7
分子式 C8H10O3
分子量 154.164
MOL 文件 582-46-7.mol
更新日期 2023/12/28 17:18:54
582-46-7 結(jié)構(gòu)式 582-46-7 結(jié)構(gòu)式

基本信息

中文別名
土曲霉素
土曲霉酮
英文別名
TERREIN
Terrain
NSC 29130
(+)Terrein
NSC-291308
(+) Terrein, NSC 291308
(4S,5R)-4,5-Dihydroxy-3-[(E)-1-propenyl]-2-cyclopenten-1-one
(4S,5R)-4,5-Dihydroxy-3-(1E)-1-propen-1-yl-2-cyclopenten-1-one
2-Cyclopenten-1-one, 4,5-dihydroxy-3-(1E)-1-propen-1-yl-, (4S,5R)-
所屬類別
生物:菌種與培養(yǎng)

物理化學(xué)性質(zhì)

熔點(diǎn)125-127℃
沸點(diǎn)327.2±42.0 °C(Predicted)
密度1.449±0.06 g/cm3(Predicted)
儲存條件?20°C
溶解度H2O:可溶 1-1.10 mg/mL,透明,無色
酸度系數(shù)(pKa)11.77±0.60(Predicted)
形態(tài)固體

安全數(shù)據(jù)

危險(xiǎn)性符號(GHS)GHS hazard pictograms
GHS07
警示詞警告
危險(xiǎn)性描述H302-H315-H319-H335
WGK Germany3
海關(guān)編碼29419000

常見問題列表

概述
土曲霉酮(terrein)是從曲霉菌特雷斯中提取的一種生物活性代謝產(chǎn)物,可以抑制黑色素的生成。同時(shí),由于土曲霉酮的結(jié)構(gòu)相對簡單,容易體外合成。目前,已有多篇文章報(bào)道土曲霉酮可以在體外抑制多種腫瘤細(xì)胞的增殖。
應(yīng)用
土曲霉酮化合物具有黑色素生物合成抑制作用。如同常規(guī)黑色素生物合成抑制劑曲酸一樣,土曲霉酮化合物以劑量依賴的方式抑制黑色素生物合成,抑制作用是曲酸的10倍。土曲霉酮對乳腺癌、卵巢癌、肝癌等多種腫瘤細(xì)胞有抑制增殖的作用。
生物活性
Terrein 是一種黑色素生成抑制劑。Terrein 誘導(dǎo)乳腺癌細(xì)胞凋亡 (apoptosis)。Terrein是銅綠假單胞菌 (Pseudomonas aeruginosa) 中的群體感應(yīng)和 c-di-GMP 抑制劑。
體外研究

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.
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