TMS
(Synonyms: 2,3',4,5'-四甲氧基二苯乙烯,(E)-2,3',4,5'-tetramethoxystilbene) 目录号 : GC15445
TMS（2,3',4,5'-tetramethoxystilbene）是一种特异性强效的CYP1B1抑制剂，IC50值为6±2nmol/L。
Cas No.:24144-92-1
Sample solution is provided at 25 µL, 10mM.
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TMS (2,3′,4,5′-tetramethoxystilbene) is a specific and powerful CYP1B1 inhibitor, with an IC50 value of 6±2nmol/L[1]. TMS has been used in CYP1B1 enzyme activity studies and in screening and comparative studies of TMS analogues[2].
In vitro, TMS(0-20μmol/L) significantly inhibited 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD)-stimulated CYP1B1 protein and mRNA expression in a concentration-dependent manner in MCF-7, MCF-10A and HL-60 cells after 24 hours of incubation[3]. TMS (10μmol/L) treatment for 72 hours significantly inhibited the viability of MDA-MB-231 cells and induced cell apoptosis[4]. TMS (20μmol/L) treatment for 48 hours caused an increase in the level of cell cycle inhibitor p27kip1 and promoted the apoptosis of PC-3 prostate cancer cells[5].
In vivo, TMS, intraperitoneal injection of 300μg/kg every 3 days, normalized blood pressure in a rat model of hypertension, reduced CYP1B1 activity, inhibited cardiovascular and renal hypertrophy, and prevented increased vascular reactivity and endothelial dysfunction[6]. Daily treatment with TMS (600μg/kg; i.p.) for 6 weeks reduced the production of reactive oxygen species (ROS) and the increase in NADPH oxidase activity, and inhibited the increase in proinflammatory cytokines and catecholamines in spontaneously hypertensive rats (SHR), accompanied by the decreased plasma levels of inflammatory cytokines[7].
References:
[1]Kim S, Ko H, Park J E, et al. Design, synthesis, and discovery of novel trans-stilbene analogues as potent and selective human cytochrome P450 1B1 inhibitors[J]. Journal of medicinal chemistry, 2002, 45(1): 160-164.
[2]Chun Y J, Oh Y K, Kim B J, et al. Potent inhibition of human cytochrome P450 1B1 by tetramethoxystilbene[J]. Toxicology letters, 2009, 189(1): 84-89.
[3]Chun Y J, Lee S K, Kim M Y. Modulation of human cytochrome P450 1B1 expression by 2, 4, 3′, 5′-tetramethoxystilbene[J]. Drug metabolism and disposition, 2005, 33(12): 1771-1776.
[4]Chae Y S, Kim J G, Jung H J, et al. Anticancer effect of (E)-2-hydroxy-3′, 4, 5′-trimethoxystilbene on breast cancer cells by mitochondrial depolarization[J]. Cancer chemotherapy and pharmacology, 2011, 68: 349-358.
[5]Kim S W, Jung H K, Kim M Y. Induction of p27 kip1 by 2, 4, 3′, 5′-tetramethoxystilbene is regulated by protein phosphatase 2A-dependent Akt dephosphorylation in PC-3 prostate cancer cells[J]. Archives of pharmacal research, 2008, 31: 1187-1194.
[6]Sahan-Firat S, Jennings B L, Yaghini F A, et al. 2, 3′, 4, 5′-Tetramethoxystilbene prevents deoxycorticosterone-salt-induced hypertension: contribution of cytochrome P-450 1B1[J]. American Journal of Physiology-Heart and Circulatory Physiology, 2010, 299(6): H1891-H1901.
[7]Jennings B L, Montanez D E, May M E, et al. Cytochrome P450 1B1 contributes to increased blood pressure and cardiovascular and renal dysfunction in spontaneously hypertensive rats[J]. Cardiovascular drugs and therapy, 2014, 28: 145-161.
TMS（2,3',4,5'-tetramethoxystilbene）是一种特异性强效的CYP1B1抑制剂，IC50值为6±2nmol/L[1]。TMS已被用于CYP1B1酶活性研究以及TMS类似物的筛选与比对研究[2]。
在体外，在MCF-7、MCF-10A和HL-60细胞中，0-20μmol/L浓度的TMS孵育24小时后，能以浓度依赖方式显著抑制2,3,7,8-四氯二苯并二噁英（TCDD）刺激的CYP1B1蛋白及mRNA表达[3]。10μmol/L的TMS处理72小时可显著抑制MDA-MB-231细胞活力并诱导细胞凋亡[4]。当以20μmol/L浓度处理48小时后，TMS能提高细胞周期抑制蛋白p27kip1水平，并促进PC-3前列腺癌细胞的凋亡[5]。
在体内，高血压模型大鼠每3天腹腔注射300μg/kg剂量的TMS后，血压恢复正常水平，同时CYP1B1活性降低，心血管及肾脏肥大状态得到抑制，并预防了血管反应性增强和内皮功能障碍[6]。自发性高血压大鼠（SHR）连续6周每日腹腔注射600μg/kg的TMS后，不仅减少了活性氧（ROS）生成和NADPH氧化酶活性升高，还抑制了促炎细胞因子和儿茶酚胺的增加，同时血浆中炎症性细胞因子水平相应降低[7]。
| Cell experiment [1]: | |
Cell lines | MCF-7 cells |
Preparation Method | Seed MCF-7 cells into 12-well plates at a density of 7.5×104 cells per well and performed this procedure in triplicate. The attached cells underwent treatment with 1μmol/L benzo[a]pyrene(BP) and received 0, 1, or 4μmol/L TMS. Cells underwent lysis by adding RIPA Lysis Buffer at time points of 4 hours, 12 hours, 24 hours, or 72 hours. Two identical samples of homogeneous cell lysate were placed into a 96-well plate and mixed with the same volume of Luminescence solution. Luminescence was measured using the microplate Luminometer. The viability assessment of cells exposed to BP alone involved performing the 72-hour treatment two times with triplicate assays for each experiment. The results are presented as percentages relative to the control with only DMSO solvent. |
Reaction Conditions | 0, 1, and 4μmol/L; 4, 12, 24, or 72h |
Applications | TMS exposure combined with BP increased overall CYP1A1 and CYP1B1 gene expression in a dose-dependent manner without influence on cell activity. |
| Animal experiment [2]: | |
Animal models | Spontaneously hypertensive rats (SHR) and Wistar-Kyoto rats |
Preparation Method | The study used 36 male SHR rats aged three weeks and 36 age-matched Wistar-Kyoto rats. From 8 weeks of age every strain of rats was divided into two groups where one received daily intraperitoneal injections of TMS at 600μg/kg and the other group received DMSO vehicle solution (100μl). Samples were gathered for analysis when the rats reached 14 weeks old. Measure both systolic blood pressure and mean arterial pressure (MAP) two times each week starting at 4 weeks of age using a noninvasive method that involves a tail cuff. Rats underwent a week of acclimation to the blood pressure measuring device before commencing each experiment. |
Dosage form | 600μg/kg/day for 6 weeks; i.p. |
Applications | TMS reversed the increase in blood pressure and inhibited the increase in CYP1B1 activity of SHR. TMS maximally attenuated enhanced vascular reactivity, cardiovascular hypertrophy, endothelial and renal dysfunction, and cardiac and renal fibrosis in SHR. |
References: | |
| Cas No. | 24144-92-1 | SDF | |
| 别名 | 2,3',4,5'-四甲氧基二苯乙烯,(E)-2,3',4,5'-tetramethoxystilbene | ||
| 化学名 | (E)-1-(3,5-dimethoxystyryl)-2,4-dimethoxybenzene | ||
| Canonical SMILES | COC1=CC(OC)=CC=C1/C=C/C2=CC(OC)=CC(OC)=C2 | ||
| 分子式 | C18H20O4 | 分子量 | 300.35 |
| 溶解度 | DMF: 30 mg/ml,DMF:PBS (pH 7.2)(1:1): 500 µ g/ml,DMSO: 20 mg/ml,Ethanol: 400 µ g/ml | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.3294 mL | 16.6472 mL | 33.2945 mL |
| 5 mM | 0.6659 mL | 3.3294 mL | 6.6589 mL |
| 10 mM | 0.3329 mL | 1.6647 mL | 3.3294 mL |
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| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
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| % DMSO % % Tween 80 % saline | ||||||||||
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计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
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2.
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Quality Control & SDS
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- Purity: >98.00%
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