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γ-Tocotrienol

(Synonyms: γ-生育三烯酚) 目录号 : GD23102

γ-Tocotrienol(γ-T3)是生育三烯醇的一个亚型,是维生素E的主要类型,具有两个取代甲基。

γ-Tocotrienol Chemical Structure

Cas No.:14101-61-2

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10mM (in 1mL DMSO)
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1mg
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5mg
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10mg
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25mg
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Sample solution is provided at 25 µL, 10mM.

Description

γ-Tocotrienol (γ-T3) is a subtype of tocotrienol and a major type of vitamin E with two substituted methyl groups[1]. γ-Tocotrienol has effects on anti-inflammation, anti-oxidation, chemoprevention against malignancies (verified in vitro), acute radiation syndrome, and house dust mite-induced asthma [2,3,4].

In vitro studies show that γ-Tocotrienol (0-90μmol/L) inhibited the proliferation of gastric cancer MKN45 cells and AGS cells, and arrested the cell cycle at the G0/G1 phase in a dose-dependent manner. Moreover, autophagy was increased in MKN45 cells treated with γ-Tocotrienol (0-45μmol/L)[2]. γ-Tocotrienol (30μmol/L; 24h) also regulates gastric cancer by targeting notch signaling pathway[5]. And γ-Tocotrienol (PC-3 cells; 10μg/mL; 72h) induces apoptosis in prostate cancer cells by targeting the Ang-1/Tie-2 signaling pathway[6].

In vivo experiments show that γ-Tocotrienol ([18F]F-γ-T-3; 14.8MBq; administration by injection) has upper abdominal accumulation with evidence of renal clearance, only low concentrations in the thorax (lung/heart) and head, and rapid clearance from blood[7]. γ-Tocotrienol also protects mice from targeted thoracic radiation injury(100 or 200mg/kg; 14 or 16Gy/min; SC administration)[8].

References:
[1] Komiyama, K et al. “Studies on the biological activity of tocotrienols.” *Chemical & pharmaceutical bulletin*vol. 37,5 (1989): 1369-71. doi:10.1248/cpb.37.1369
[2] Zhu, Hao et al. “γ-Tocotrienol enhances autophagy of gastric cancer cells by the regulation of GSK3β/β-Catenin pathway.” *Molecular carcinogenesis* vol. 63,10 (2024): 2013-2025. doi:10.1002/mc.23790
[3] Peh, Hong Yong et al. “Vitamin E Isoform γ-Tocotrienol Downregulates House Dust Mite-Induced Asthma.” *Journal of immunology (Baltimore, Md. : 1950)* vol. 195,2 (2015): 437-44. doi:10.4049/jimmunol.1500362
[4] Singh, Vijay K, and Martin Hauer-Jensen. “γ-Tocotrienol as a Promising Countermeasure for Acute Radiation Syndrome: Current Status.” *International journal of molecular sciences* vol. 17,5 663. 3 May. 2016, doi:10.3390/ijms17050663
[5] Xie, Ling, and Juan Yan. “γ-tocotrienol regulates gastric cancer by targeting notch signaling pathway.” *Hereditas* vol. 160,1 15. 13 Apr. 2023, doi:10.1186/s41065-023-00277-w
[6] Tang, Kai Dun et al. “Gamma-Tocotrienol Induces Apoptosis in Prostate Cancer Cells by Targeting the Ang-1/Tie-2 Signalling Pathway.” *International journal of molecular sciences* vol. 20,5 1164. 7 Mar. 2019, doi:10.3390/ijms20051164
[7] Roselt, Peter et al. “Synthesis of [18F]F-γ-T-3, a Redox-Silent γ-Tocotrienol (γ-T-3) Vitamin E Analogue for Image-Based In Vivo Studies of Vitamin E Biodistribution and Dynamics.” *Molecules (Basel, Switzerland)* vol. 25,23 5700. 3 Dec. 2020, doi:10.3390/molecules25235700
[8]Kumar, Vidya P et al. “Gamma Tocotrienol Protects Mice From Targeted Thoracic Radiation Injury.” *Frontiers in pharmacology* vol. 11 587970. 12 Nov. 2020, doi:10.3389/fphar.2020.587970

γ-Tocotrienol(γ-T3)是生育三烯醇的一个亚型,是维生素E的主要类型,具有两个取代甲基[1]。γ-T3具有抗炎、抗氧化、化学预防恶性肿瘤(体外实验验证)、急性辐射综合征和尘螨诱发的哮喘等作用[2,3,4]

体外实验表明,γ-Tocotrienol (0~90μmol/L)能抑制胃癌MKN45细胞和AGS细胞的增殖,并使细胞周期阻滞在G0/G1期,且呈剂量依赖性[2]。此外,γ-Tocotrienol (0-45μmol/L)处理后,MKN45细胞的自噬增强[2]。γ-Tocotrienol(30μmol/L; 24h)也通过靶向notch信号通路调控胃癌[5]。γ-Tocotrienol (10μg/mL; 72h)通过靶向Ang-1/Tie-2信号通路诱导前列腺癌细胞凋亡[6]

体内实验表明,γ-Tocotrienol ([18F]F-γ-T-3; 14.8 MBq; 体内注射)具有上腹部蓄积和肾脏清除的特点,仅在胸部(肺/心)和头部有低浓度,并且从血脑屏障中迅速清除[7]。γ-Tocotrienol还能保护小鼠免受胸部靶向辐射损伤(100或200mg/kg; 14 or 16Gy/min; S.C)[8]

实验参考方法

Cell experiment [1]:

Cell lines

human gastric cancer cell line MKN-45

Preparation Method

MKN-45 cells were seeded into 96-well plates at 5,000 cells per well and allowed to adhere overnight. MKN-45 cells were treated with γ-Tocotrienol (30μmol/L) or not for 24h. Cells were collected and total cellular RNA was isolated using TRIzol reagent.

Reaction Conditions

30μmol/L; 24h

Applications

Significantly altered signaling pathways after γ-Tocotrienol treatment were enriched for human papillomavirus infection (HPV) pathway and notch signaling pathway. The same significantly down-regulated genes notch1 and notch2 were present in both pathways in γ-Tocotrienol-treated gastric cancer cells compared to controls.

Animal experiment [2]:

Animal models

C3H/HeN male mice, irradiated with 14 or 16Gy/min

Preparation Method

For lung-PBI, C3H/HeN male mice were exposed to 14 or 16Gy doses of radiation to the lung area (below the neck to diaphragm). Irradiated mice were administered either saline or γ-Tocotrienol (200mg/kg; SC) 24h prior to PBI. γ-Tocotrienol (200mg/kg) or saline (n=12 per group) were administered SC 24h prior to irradiation. In addition to the irradiated groups of animals, blood and tissues from an age-matched naïve group (n=12) was collected at each time point.

Dosage form

100 or 200mg/kg; SC administration

Applications

Regeneration and increase of cellularity and megakaryocytes on γ-Tocotrienol treatment was compared to significant loss of cellularity in saline group. Peak alveolitis was observed on day 14 post-PBI and protection from alveolitis by γ-Tocotrienol was noted. In irradiated lung tissue, thirty proteins were found to be differentially expressed but modulated by γ-Tocotrienol to reverse the effects of irradiation.

References:
[1]Xie, Ling, and Juan Yan. “?-tocotrienol regulates gastric cancer by targeting notch signaling pathway.” *Hereditas* vol. 160,1 15. 13 Apr. 2023, doi:10.1186/s41065-023-00277-w
[2]. Kumar, Vidya P et al. “Gamma Tocotrienol Protects Mice From Targeted Thoracic Radiation Injury.” *Frontiers in pharmacology* vol. 11 587970. 12 Nov. 2020, doi:10.3389/fphar.2020.587970

化学性质

Cas No. 14101-61-2 SDF
别名 γ-生育三烯酚
分子式 C28H42O2 分子量 410.63
溶解度 DMSO : 100 mg/mL (243.53 mM; Need ultrasonic) 储存条件 Store at -20°C
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1 mM 2.4353 mL 12.1764 mL 24.3528 mL
5 mM 487.1 μL 2.4353 mL 4.8706 mL
10 mM 243.5 μL 1.2176 mL 2.4353 mL
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