cis-Trismethoxy resveratrol (Synonyms: (Z)-3,5,4'-Trimethoxystilbene)

Name: cis-Trismethoxy resveratrol
Brand: MedChemExpress
SKU: HY-121989
Rating: 4.5 (1 reviews)

Cat. No.: HY-121989 Purity: 99.87%: Data Sheet
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cis-Trismethoxy resveratrol ((Z)-3,5,4'-Trimethoxystilbene) is an anti-HCV agent and Tubulin inhibitor, with an IC₅₀ of 4 μM against Tubulin. cis-Trismethoxy resveratrol induces G2/M phase cell cycle arrest, reduces DCLK1, decreases CDK1 levels, blocks phosphorylation of Akt Ser⁴⁷³, and induces the expression of p21^Cip1/Waf1. cis-Trismethoxy resveratrol exhibits anti-tumor and hepatoprotective activities. cis-Trismethoxy resveratrol can be used in studies related to colon adenocarcinoma, hepatocellular carcinoma, hepatitis C, and liver injury.

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cis-Trismethoxy resveratrol Chemical Structure

CAS No. : 94608-23-8

Size	Stock	Quantity
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5 mg (184.97 mM * 100 μL in Ethanol)	In-stock	Estimated Time of Arrival: December 31
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10 mg (184.97 mM * 200 μL in Ethanol)	In-stock	Estimated Time of Arrival: December 31

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Based on 1 publication(s) in Google Scholar

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CDK1 CDK2 CDK3 CDK4 CDK5 CDK6 CDK7 CDK8 CDK9 CDK11 CDK12 CDK13 CDK14 CDK16 CDK19 CDC CLK Pho85 CDK10 CDK15 CDK17 CDK18 CDK20 PITSLRE

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Akt Akt1 Akt2 Akt3

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PAK1 PAK2 PAK3 PAK4 PAK5 PAK6

Biological Activity
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Description

IC₅₀ & Target^[1]

CDK1

Cellular Effect

Cell Line	Type	Value	Description	References
A549	ED₅₀	1.3 μM Compound: 6i	Compound was evaluated for cytotoxicity against human A-549 non-small cell lung cancer cell line. Compound was evaluated for cytotoxicity against human A-549 non-small cell lung cancer cell line.	[PMID: 1613753]
B16-F10	IC₅₀	1 μM Compound: 72	Anti cancer activity against mouse B16-F10 cells assessed as cell growth inhibition incubated for 40 hrs by Almar Blue stained fluorescence-based assay Anti cancer activity against mouse B16-F10 cells assessed as cell growth inhibition incubated for 40 hrs by Almar Blue stained fluorescence-based assay	[PMID: 32485531]
BXPC-3	GI₅₀	0.0034 μg/mL Compound: 1d	Growth inhibition of human BxPC3 cells after 48 hrs by sulforhodamine B assay Growth inhibition of human BxPC3 cells after 48 hrs by sulforhodamine B assay	[PMID: 19719153]
BXPC-3	GI₅₀	0.0034 μg/mL Compound: 4a	Cell growth inhibition against pancreatic BXPC-3 cells, 50% reduction in the net protein increase Cell growth inhibition against pancreatic BXPC-3 cells, 50% reduction in the net protein increase	[PMID: 12036362]
Caco-2	IC₅₀	0.08 μM Compound: 10	Cytotoxicity against human Caco-2 cells after 3 days by [3H]thymidine incorporation assay Cytotoxicity against human Caco-2 cells after 3 days by [3H]thymidine incorporation assay	[PMID: 20627379]
Caco-2	IC₅₀	0.145 μM Compound: 72	Anti cancer activity against human Caco-2 cell assessed as cell growth inhibition incubated for 48 hrs by Brdu assay Anti cancer activity against human Caco-2 cell assessed as cell growth inhibition incubated for 48 hrs by Brdu assay	[PMID: 32485531]
DU-145	GI₅₀	0.0054 μg/mL Compound: 1d	Growth inhibition of human DU145 cells after 48 hrs by sulforhodamine B assay Growth inhibition of human DU145 cells after 48 hrs by sulforhodamine B assay	[PMID: 19719153]
DU-145	GI₅₀	0.0054 μg/mL Compound: 4a	Cell growth inhibition of prostate DU-145 cells, expressed as 50% reduction in the net protein increase Cell growth inhibition of prostate DU-145 cells, expressed as 50% reduction in the net protein increase	[PMID: 12036362]
HCT-116	IC₅₀	0.22 μM Compound: 8Z	Cytotoxicity against human HCT116 cells after 24 hrs by MTT assay Cytotoxicity against human HCT116 cells after 24 hrs by MTT assay	[PMID: 21215623]
HL-60	IC₅₀	0.15 μM Compound: 6b	Antiproliferative activity against human HL60 cells Antiproliferative activity against human HL60 cells	[PMID: 16580204]
HT-29	ED₅₀	3.4 μM Compound: 6i	Cytotoxicity against human HT-29 colon cell line. Cytotoxicity against human HT-29 colon cell line.	[PMID: 1613753]
HT-29	IC₅₀	0.04 μM Compound: 10	Cytotoxicity against human HT-29 cells after 3 days by [3H]thymidine incorporation assay Cytotoxicity against human HT-29 cells after 3 days by [3H]thymidine incorporation assay	[PMID: 20627379]
HT-29	IC₅₀	0.115 μM Compound: 72	Anti cancer activity against human HT-29 cell assessed as cell growth inhibition incubated for 48 hrs by Brdu assay Anti cancer activity against human HT-29 cell assessed as cell growth inhibition incubated for 48 hrs by Brdu assay	[PMID: 32485531]
HT-29	IC₅₀	54 nM Compound: 17	Antiproliferative activity against human HT29 cell line by methylene blue dye assay Antiproliferative activity against human HT29 cell line by methylene blue dye assay	[PMID: 17034147]
HepG2	IC₅₀	0.473 μM Compound: 72	Anti cancer activity against human HepG2 cell assessed as cell growth inhibition incubated for 48 hrs by Brdu assay Anti cancer activity against human HepG2 cell assessed as cell growth inhibition incubated for 48 hrs by Brdu assay	[PMID: 32485531]
IMR-90	IC₅₀	0.23 μM Compound: 8Z	Cytotoxicity against human IMR90 cells after 24 hrs by MTT assay Cytotoxicity against human IMR90 cells after 24 hrs by MTT assay	[PMID: 21215623]
KB	IC₅₀	280 nM Compound: 17	Antiproliferative activity against human KB cell line by methylene blue dye assay Antiproliferative activity against human KB cell line by methylene blue dye assay	[PMID: 17034147]
MCF7	ED₅₀	1.6 μM Compound: 6i	Cytotoxicity against human MCF-7 breast cancer cell line. Cytotoxicity against human MCF-7 breast cancer cell line.	[PMID: 1613753]
MCF7	IC₅₀	0.12 μM Compound: 8Z	Cytotoxicity against human MCF7 cells after 24 hrs by MTT assay Cytotoxicity against human MCF7 cells after 24 hrs by MTT assay	[PMID: 21215623]
MKN-45	IC₅₀	218 nM Compound: 17	Antiproliferative activity against human MKN45 cell line by methylene blue dye assay Antiproliferative activity against human MKN45 cell line by methylene blue dye assay	[PMID: 17034147]
MLM	ED₅₀	9.8 μM Compound: 6i	Cytotoxicity against human MLM melanoma cell line. Cytotoxicity against human MLM melanoma cell line.	[PMID: 1613753]
NCI-H460	GI₅₀	0.0028 μg/mL Compound: 1d	Growth inhibition of human NCI-H460 cells after 48 hrs by sulforhodamine B assay Growth inhibition of human NCI-H460 cells after 48 hrs by sulforhodamine B assay	[PMID: 19719153]
NCI-H460	GI₅₀	0.0028 μg/mL Compound: 4a	Cell growth inhibition of lung-NSC NCI-H460 cells, expressed as 50% reduction in the net protein increase Cell growth inhibition of lung-NSC NCI-H460 cells, expressed as 50% reduction in the net protein increase	[PMID: 12036362]
NCI-H460	IC₅₀	253 nM Compound: 17	Antiproliferative activity against human H460 cell line by methylene blue dye assay Antiproliferative activity against human H460 cell line by methylene blue dye assay	[PMID: 17034147]
P388	ED₅₀	0.0262 μg/mL Compound: 4a	Evaluated for cell growth inhibition of the mouse leukemia P388 cells in 10% horse serum/Fisher media Evaluated for cell growth inhibition of the mouse leukemia P388 cells in 10% horse serum/Fisher media	[PMID: 12036362]
SF-268	GI₅₀	0.0044 μg/mL Compound: 1d	Growth inhibition of human SF268 cells after 48 hrs by sulforhodamine B assay Growth inhibition of human SF268 cells after 48 hrs by sulforhodamine B assay	[PMID: 19719153]
SF-268	GI₅₀	0.0044 μg/mL Compound: 4a	Cell growth inhibition of central nervous system (CNS) SF-268 cells, expressed as 50% reduction in the net protein increase Cell growth inhibition of central nervous system (CNS) SF-268 cells, expressed as 50% reduction in the net protein increase	[PMID: 12036362]
SK-MEL-5	ED₅₀	4.2 μM Compound: 6i	Compound was evaluated for cytotoxicity against human SKMEL-5 melanoma cell line. Compound was evaluated for cytotoxicity against human SKMEL-5 melanoma cell line.	[PMID: 1613753]
SW480	IC₅₀	0.3 μM Compound: 4	Antiproliferative activity against human SW480 cells assessed as cell viability using propidium iodide staining after 48 hrs Antiproliferative activity against human SW480 cells assessed as cell viability using propidium iodide staining after 48 hrs	[PMID: 20395019]
SW480	IC₅₀	0.3 μM Compound: 4	Antiproliferative activity against human SW480 cells assessed as cell viability using propidium iodide staining after 72 hrs Antiproliferative activity against human SW480 cells assessed as cell viability using propidium iodide staining after 72 hrs	[PMID: 20395019]
TSGH 9201	IC₅₀	324 nM Compound: 17	Antiproliferative activity against human TSGH stomach carcinoma cell line by methylene blue dye assay Antiproliferative activity against human TSGH stomach carcinoma cell line by methylene blue dye assay	[PMID: 17034147]

In Vitro

cis-Trismethoxy resveratrol potently inhibits the growth of various cancer cell lines, with IC₅₀ values ranging from 0.08 μM (KB cells) to 0.25 μM (Caco-2 cells), and the activity of its cis conformation is 100-fold higher than that of the trans isomer^[1].
cis-Trismethoxy resveratrol (0.3 μM; 16-48 hr, second treatment after 48 h) induces G2/M phase arrest in Caco-2 cells, and a second treatment administered after 48 h potentiates this effect^[1].
cis-Trismethoxy resveratrol (0.1-30 μM; up to 30 min) inhibits tubulin polymerization in vitro, with an IC₅₀ of 4 μM, and completely blocks the polymerization process at a concentration of 30 μM^[1].
cis-Trismethoxy resveratrol (0.3 μM; 1-3 days) reduces ODC activity by 52% after 1 day, AdoMetDC activity by 40% after 2 days, and AdoMetDC activity by 50% after 3 days in Caco-2 cells^[1].
cis-Trismethoxy resveratrol (0.05-2.5 μM; 48 h) dose-dependently inhibits the expression of HCV NS5B polymerase in FCA4 hepatocellular carcinoma cells; when applied at concentrations ranging from 0.1 to 1.0 μM for 48 h, it shows no cytotoxicity to either FCA4 cells or normal hepatocytes^[2].
cis-Trismethoxy resveratrol (1 μM; 48 h) inhibits HCV replication by approximately 10-fold in JFH1 HCVcc-infected Huh7.5 hepatocellular carcinoma cells and reduces NS3 protein levels after 48 h of treatment^[2].
Treatment with cis-Trismethoxy resveratrol (1 μM; 48 h) induces G₂/M phase arrest in over 90% of GS5, Huh7.5, Huh7 and FCA4 hepatocellular carcinoma cells^[2].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Cell Cycle Analysis^[1]

Cell Line:	human colon adenocarcinoma Caco-2 cells
Concentration:	0.3 μM
Incubation Time:	16 hr, 48 hr; second treatment initiated after 48 hr
Result:	Caused accumulation of Caco-2 cells at the G2/M phase, reaching 54% of cells at 16 hours and 46% at 48 hours. Increased the proportion of cells blocked at G2/M to 77% after a second 0.3 μM treatment at 48 hours. Decreased the proportion of cells in the G1 phase, while the S phase proportion remained unchanged.

Cell Cycle Analysis^[2]

Cell Line:	GS5, Huh7.5, Huh7, and FCA4 hepatoma cells
Concentration:	1 μM
Incubation Time:	48 h
Result:	Caused >90% of cells to arrest in the G2/M phase, with concomitant reduction in G1 and S phase populations.

In Vivo

Cis-trismethoxy resveratrol (20-40 mg/kg body weight; injection; twice weekly; for 7 weeks) protects C57BL/6 mice from DEN/CCl₄(HY-Y0298)-induced liver injury by reducing the number of DCLK1⁺ cells and improving histological morphology^[2].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model:	C57BL/6 (8 weeks old, in-house bred, 5 per group, DEN/CCl4-induced liver injury)^[2]
Dosage:	20 mg/kg BW; 40 mg/kg BW
Administration:	injection; twice weekly; 7 weeks
Result:	Reduced serum total bilirubin to 0.6 and alanine aminotransferase to 60.0 at 20 mg/kg BW compared to DEN/CCl4-only controls (ALT 78.6). Reduced serum total bilirubin to 0.7 at 40 mg/kg BW compared to DEN/CCl4-only controls, but resulted in an alanine aminotransferase level of 109.0, which is higher than the DEN/CCl4-only control's 78.6. Significantly reduced the number of DCLK1+ cells in liver injury sites and improved liver histologic appearance at both doses. Showed serum liver biomarker levels (ALB 2.6, ALT 50.7, AST 128.7, ALKP 52.3, TBIL 0.9) within or near normal ranges in mice treated with 40 mg/kg BW alone, indicating no hepatotoxicity. Caused gastrointestinal emptying complications in 20% of treated mice.

Molecular Weight

270.32

Formula

C₁₇H₁₈O₃

CAS No.

94608-23-8

Appearance

Liquid

Color

Colorless to light yellow

SMILES

COC1=CC(/C=C\C2=CC=C(C=C2)OC)=CC(OC)=C1

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

Solution, -20°C, protect from light, 2 years

Purity & Documentation

Purity: 99.87%

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Data Sheet (278 KB) SDS (393 KB)

COA (253 KB) RP-HPLC (226 KB) LCMS (105 KB)

Handling Instructions (2659 KB)

References

[1]. Schneider Y, et al. Resveratrol analog (Z)-3,5,4'-trimethoxystilbene is a potent anti-mitotic drug inhibiting tubulin polymerization. Int J Cancer. 2003;107(2):189-196. [Content Brief]

[2]. Nguyen CB, et al. (Z)-3,5,4'-Trimethoxystilbene Limits Hepatitis C and Cancer Pathophysiology by Blocking Microtubule Dynamics and Cell-Cycle Progression. Cancer Res. 2016;76(16):4887-4896.

cis-Trismethoxy resveratrol Related Classifications

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cis-Trismethoxy resveratrol (Synonyms: (Z)-3,5,4'-Trimethoxystilbene)

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