GLPBio

TMS

Catalog No.: GC15445Purity:>98.00%Synonyms: 2,3',4,5'Tetramethoxystilbene
TMS (2,3′,4,5′-tetramethoxystilbene) is a specific and powerful CYP1B1 inhibitor, with an IC50 value of 6±2nmol/L.

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TMS
Cas No.: 24144-92-1
10mM (in 1mL DMSO)In Stock
$55.00
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5mgIn Stock
$50.00
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10mgIn Stock
$80.00
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50mgIn Stock
$297.00
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100mgIn Stock
$477.00
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Description

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.

Protocol

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:
[1] Einem Lindeman T, Poirier M C, Divi R L. The resveratrol analogue, 2, 3′, 4, 5′-tetramethoxystilbene, does not inhibit CYP gene expression, enzyme activity and benzo [a] pyrene–DNA adduct formation in MCF-7 cells exposed to benzo [a] pyrene[J]. Mutagenesis, 2011, 26(5): 629-635.
[2] 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.

Product Documents

Purity:>98.00%Appearance:A solid

Chemical Properties

CAS No.
24144-92-1
Synonyms
2,3',4,5'Tetramethoxystilbene
Chemical Name
(E)-1-(3,5-dimethoxystyryl)-2,4-dimethoxybenzene
SMILES
COC1=CC(OC)=CC=C1/C=C/C2=CC(OC)=CC(OC)=C2
Molecular Formula
C18H20O4
Molecular Weight
300.35
Solubility
DMF: 30 mg/ml,DMF:PBS (pH 7.2)(1:1): 500 µ g/ml,DMSO: 20 mg/ml,Ethanol: 400 µ g/ml
Storage
Store at -20°C
General tips
Select a suitable solvent according to the product solubility data. Once prepared, aliquot the stock solution to avoid repeated freeze-thaw cycles.
Use stock solutions within 6 months when stored at -80°C or within 1 month when stored at -20°C.
To improve solubility, warm the tube to 37°C and sonicate it for an appropriate period.
Shipping Condition
Evaluation samples are shipped with blue ice. Other available sizes are shipped at room temperature or with blue ice upon request.

CalculatorsMolarity / Dilution / Molecular Weight / Unit Conversion / In Vivo Formulation / Solubility

g/mol

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