Referencia número: HY-10447

Terameprocol

(Synonyms: EM-1421)

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Terameprocol is an inhibitor targeting the Sp1 transcription factor, which can selectively inhibit the transcription of Sp1-dependent genes. Terameprocol exerts its effects by inhibiting Sp1-mediated gene transcription, such as reducing the expression of genes like CDC2, survivin and HMGB1, thereby arresting the cell cycle, inducing apoptosis, and suppressing the inflammatory response. Terameprocol exhibits anti-proliferative, pro-apoptotic, and anti-inflammatory activities and is currently mainly used in the research of diseases such as cancer and pulmonary arterial hypertension[1][2][3].

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Pureza: 99.50%
No. CAS: 24150-24-1
Fòrmula: C₂₂H₃₀O₄
Peso molecular:358.47

Almacenamiento:

Powder -20°C, 3 years ; In solvent -80°C, 6 months , -20°C, 1 month

Terameprocol Chemical Structure

No. CAS: 24150-24-1

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Fluorescent Dye

Strong Fluorescence Signal / Multi-Disciplinary Applications / High Fluorescence Specificity

Actividad biológica
- Descripciòn
- IC₅₀ & Target
- Cellular Effect
- In Vitro
- In Vivo
- Ensayo clínico
Chemical Information
Solvente y solubilidad
- In Vitro
Pureza y Documentación
Referencias
Help & FAQs
Classifications
Bioz

Actividad biológica

Descripciòn

IC₅₀ & Target

COX-2

Ver todos los productos específicos de isoformas COX :

Ver todos los productos específicos de isoformas TNF Receptor :

Cellular Effect

Cell Line	Type	Value	Description	References
786-0	GI₅₀	4.54 μM Compound: Terameprocol, M4N, EM-1421	Cytotoxicity against human 786-0 cells after 72 hrs by MTT assay Cytotoxicity against human 786-0 cells after 72 hrs by MTT assay	[PMID: 24080463]
A-375	IC₅₀	16.6 μM Compound: 1a, M4N	Cytotoxicity against human A375 cells after 5 days by MTT assay Cytotoxicity against human A375 cells after 5 days by MTT assay	[PMID: 19615898]
A-375	IC₅₀	2.5 μM Compound: 1a, M4N	Cytotoxicity against human A375 cells Cytotoxicity against human A375 cells	[PMID: 19615898]
A-375	IC₅₀	16.6 μM Compound: 2; EM-1424, M4N	Antiproliferative activity against human A-375 cells assessed as reduction in cell growth Antiproliferative activity against human A-375 cells assessed as reduction in cell growth	[PMID: 38092421]
BXPC-3	GI₅₀	17.1 μM Compound: Terameprocol, M4N, EM-1421	Cytotoxicity against human BxPC3 cells after 72 hrs by MTT assay Cytotoxicity against human BxPC3 cells after 72 hrs by MTT assay	[PMID: 24080463]
C8166	CC₅₀	28.8 μM Compound: 21	Cytotoxicity against human C8166 cells by MTT assay Cytotoxicity against human C8166 cells by MTT assay	[PMID: 19413342]
C8166	EC₅₀	14.8 μM Compound: 21	Antiviral activity against HIV1 3B in human C8166 cells assessed as inhibition of virus-induced cytopathogenicity Antiviral activity against HIV1 3B in human C8166 cells assessed as inhibition of virus-induced cytopathogenicity	[PMID: 19413342]
COS-1	IC₅₀	11.09 μM Compound: 10	Inhibitory activity against HIV Tat-regulated Transactivation in COS cells. Inhibitory activity against HIV Tat-regulated Transactivation in COS cells.	[PMID: 9685238]
HaCaT	IC₅₀	85 μM Compound: 2; EM-1424, M4N	Cytotoxicity against human HaCaT cells assessed as reduction in cell viability Cytotoxicity against human HaCaT cells assessed as reduction in cell viability	[PMID: 38092421]
HeLa	GI₅₀	>50 μM Compound: Terameprocol, M4N, EM-1421	Cytotoxicity against human HeLa cells after 72 hrs by MTT assay Cytotoxicity against human HeLa cells after 72 hrs by MTT assay	[PMID: 24080463]
Hep 3B2	IC₅₀	≤10 μM Compound: 3, M4N	Cytotoxicity against human Hep3B cells after 3 days by MTT assay Cytotoxicity against human Hep3B cells after 3 days by MTT assay	[PMID: 21123067]
HepG2	IC₅₀	44.5 μM Compound: 1a, M4N	Cytotoxicity against human HepG2 cells after 5 days by MTT assay Cytotoxicity against human HepG2 cells after 5 days by MTT assay	[PMID: 19615898]
HepG2	IC₅₀	44.5 μM Compound: 2; EM-1424, M4N	Antiproliferative activity against human HepG2 cells assessed as reduction in cell viability incubated for 24 hrs by MTT assay Antiproliferative activity against human HepG2 cells assessed as reduction in cell viability incubated for 24 hrs by MTT assay	[PMID: 38092421]
HT-29	IC₅₀	61.5 μM Compound: 1a, M4N	Cytotoxicity against human HT-29 cells after 5 days by MTT assay Cytotoxicity against human HT-29 cells after 5 days by MTT assay	[PMID: 19615898]
HT-29	IC₅₀	≤10 μM Compound: 3, M4N	Cytotoxicity against human HT-29 cells after 3 days by MTT assay Cytotoxicity against human HT-29 cells after 3 days by MTT assay	[PMID: 21123067]
HT-29	IC₅₀	61.5 μM Compound: 2; EM-1424, M4N	Antiproliferative activity against human HT-29 cells assessed as cell growth inhibition Antiproliferative activity against human HT-29 cells assessed as cell growth inhibition	[PMID: 38092421]
K562	IC₅₀	5.87 mg/L Compound: 2, EM-1421, M4N, Terameprocol	Inhibition of growth metabolism of human K562 cells at 37 degC by TAM air microcalorimetry Inhibition of growth metabolism of human K562 cells at 37 degC by TAM air microcalorimetry	[PMID: 23434529]
LNCaP	IC₅₀	≤10 μM Compound: 3, M4N	Cytotoxicity against human LNCAP cells after 3 days by MTT assay Cytotoxicity against human LNCAP cells after 3 days by MTT assay	[PMID: 21123067]
MCF7	IC₅₀	42.4 μM Compound: 1a, M4N	Cytotoxicity against human MCF7 cells after 5 days by MTT assay Cytotoxicity against human MCF7 cells after 5 days by MTT assay	[PMID: 19615898]
MCF7	IC₅₀	≤10 μM Compound: 3, M4N	Cytotoxicity against human MCF7 cells after 3 days by MTT assay Cytotoxicity against human MCF7 cells after 3 days by MTT assay	[PMID: 21123067]
MCF7	IC₅₀	42.4 μM Compound: 2; EM-1424, M4N	Antiproliferative activity against human MCF7 cells assessed as cell growth inhibition Antiproliferative activity against human MCF7 cells assessed as cell growth inhibition	[PMID: 38092421]
NCI/ADR-RES	IC₅₀	≤10 μM Compound: 3, M4N	Cytotoxicity against human NCI/ADR-RES cells after 3 days by MTT assay Cytotoxicity against human NCI/ADR-RES cells after 3 days by MTT assay	[PMID: 21123067]
T47D	GI₅₀	5.36 μM Compound: Terameprocol, M4N, EM-1421	Cytotoxicity against human T47D cells after 72 hrs by MTT assay Cytotoxicity against human T47D cells after 72 hrs by MTT assay	[PMID: 24080463]
T98G	GI₅₀	>50 μM Compound: Terameprocol, M4N, EM-1421	Cytotoxicity against human T98G cells after 72 hrs by MTT assay Cytotoxicity against human T98G cells after 72 hrs by MTT assay	[PMID: 24080463]
U-87MG ATCC	GI₅₀	>50 μM Compound: Terameprocol, M4N, EM-1421	Cytotoxicity against human U87 cells after 72 hrs by MTT assay Cytotoxicity against human U87 cells after 72 hrs by MTT assay	[PMID: 24080463]
Vero	IC₅₀	11.08 μM Compound: M4N	Comparative Potency (IC50s) at HSV-2 passage 2 in vero cells Comparative Potency (IC50s) at HSV-2 passage 2 in vero cells	[PMID: 9685239]
Vero	IC₅₀	11.08 μM Compound: M4N	Comparative Potency (IC50s) at HSV-2 passage 3 in vero cells Comparative Potency (IC50s) at HSV-2 passage 3 in vero cells	[PMID: 9685239]
Vero	IC₅₀	11.08 μM Compound: M4N	Comparative Potency (IC50s) at HSV-2 passage 4 in vero cells Comparative Potency (IC50s) at HSV-2 passage 4 in vero cells	[PMID: 9685239]
Vero	IC₅₀	4.18 μM Compound: M4N	Comparative Potency (IC50s) at HSV-2 passage 1 in vero cells Comparative Potency (IC50s) at HSV-2 passage 1 in vero cells	[PMID: 9685239]
Vero	IC₅₀	4.4 μM Compound: M4N	Comparative Potency (IC50s) at HSV-1 passage 2 in vero cells Comparative Potency (IC50s) at HSV-1 passage 2 in vero cells	[PMID: 9685239]
Vero	IC₅₀	5.97 μM Compound: M4N	Comparative Potency (IC50s) at HSV-1 passage 4 in vero cells Comparative Potency (IC50s) at HSV-1 passage 4 in vero cells	[PMID: 9685239]
Vero	IC₅₀	6.48 μM Compound: M4N	Comparative Potency (IC50s) at HSV-1 passage 5 in vero cells Comparative Potency (IC50s) at HSV-1 passage 5 in vero cells	[PMID: 9685239]
Vero	IC₅₀	6.98 μM Compound: M4N	Comparative Potency (IC50s) at HSV-1 passage 6 in vero cells Comparative Potency (IC50s) at HSV-1 passage 6 in vero cells	[PMID: 9685239]
Vero	IC₅₀	6.98 μM Compound: M4N	Comparative Potency (IC50s) at HSV-1 passage 7 in vero cells Comparative Potency (IC50s) at HSV-1 passage 7 in vero cells	[PMID: 9685239]
Vero	IC₅₀	8.24 μM Compound: M4N	Comparative Potency (IC50s) at HSV-1 passage 3 in vero cells Comparative Potency (IC50s) at HSV-1 passage 3 in vero cells	[PMID: 9685239]
Vero	IC₅₀	8.82 μM Compound: M4N	Comparative Potency (IC50s) at HSV-1 passage 9 in vero cells Comparative Potency (IC50s) at HSV-1 passage 9 in vero cells	[PMID: 9685239]
Vero	IC₅₀	9.91 μM Compound: M4N	Comparative Potency (IC50s) at HSV-1 passage 8 in vero cells Comparative Potency (IC50s) at HSV-1 passage 8 in vero cells	[PMID: 9685239]

In Vitro

Terameprocol (25 μM; 16 h) inhibited the production of prostaglandins (PGE2), some cytokines and chemokines induced by lipopolysaccharide (LPS) in RAW 264.7 cells, and also inhibited the expression and activity of COX-2, and inhibited the growth of RAW264.7 cells, but did not induce cell apoptosis^[1]. Terameprocol (10 μM; 24 h, 48 h) downregulated survivin transcription and protein expression in HCC2429 and H460 non-small cell lung cancer cell experiments, while enhancing the sensitivity of cells to radiotherapy, but did not induce cell apoptosis and did not affect the cell cycle^[2]. Terameprocol (0.1-20 μM; 24 h) inhibited cell proliferation in a dose-dependent manner in rat pulmonary artery smooth muscle cells (PASMCs) experiments, and induced cell apoptosis at 20 μM^[3].

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

Cell Viability Assay^[1]

Cell Line:

RAW 264.7 cells
Concentration:

25 μM
Incubation Time:

16 h
Result:

Inhibited the LPS-induced production of prostaglandins, including PGE2, PGF2α, and 6-keto - PGF1α.
Suppressed the production of several cytokines and chemokines, such as TNF-α and MCP-1.
Reduced the expression of COX-2 mRNA and protein, inhibited the enzymatic activity of COX-2, and inhibited the growth of RAW 264.7 cells, but did not induce apoptosis.

Cell Cycle Analysis^[2]

Cell Line:

HCC2429 and H460 cells
Concentration:

10 μM
Incubation Time:

24 h or 48 h
Result:

Down-regulated the transcription and protein expression of survivin.
Enhanced the radiosensitivity of both HCC2429 and H460 cells.
Did not induce apoptosis in either cell line and had no significant effect on the cell cycle.

Apoptosis Analysis^[3]

Cell Line:

Rat pulmonary artery smooth muscle cells (PASMCs)
Concentration:

0.1 μM, 1 μM, 10 μM, 20 μM
Incubation Time:

24 h
Result:

Inhibited the proliferation of PASMCs in a dose-dependent manner. At 20μM, induced apoptosis of PASMCs.

In Vivo

Terameprocol (1 mg; intraperitoneal injection; 1 time; administered 1 hour before lipopolysaccharide (LPS) injection) reduces the levels of TNF-α and MCP-1 in the serum of C57BL6/J mice in the endotoxemia model^[1].
Terameprocol (166mg/kg; intraperitoneal injection; on days 7, 12, and 17; for 21 days) improves cardiac function, alleviates cardiac and pulmonary remodeling, inhibits the proliferation and induces the apoptosis of pulmonary artery smooth muscle cells in the monocrotaline (MCT)-induced pulmonary hypertension model of male Wistar rats (weighing 180-200g, age not mentioned)^[3].

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

Animal Model:

C57BL6/J mice (15-16g, 6-8 weeks old)^[1]
Dosage:

1 mg (in CPE vehicle)
Administration:

Intraperitoneal injection, 1 time, 1 hour before LPS injection
Result:

Offset the increase in serum TNF-α induced by LPS by 41% and significantly suppressed the LPS-induced accumulation of MCP-1 in serum.

Ensayo clínico

NCT Number	Sponsor	Condition	Start Date	Phase A549
NCT01329991	Plexxikon\|		2011-05	PHASE1

Chemical Information

No. CAS 24150-24-1
Appearance Solid
Peso molecular 358.47
Fòrmula C₂₂H₃₀O₄
Color White to off-white
SMILES

COC1=CC(C[C@H](C)[C@H](C)CC2=CC=C(OC)C(OC)=C2)=CC=C1OC
Synonyms

EM-1421
Envío

Room temperature in continental US; may vary elsewhere.

Almacenamiento

Powder	-20°C	3 years
In solvent	-80°C	6 months
	-20°C	1 month

Solvente y solubilidad

In Vitro:

DMSO : 100 mg/mL (278.96 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

View the Complete Stock Solution Preparation Table

Preparing Stock Solutions

View the Complete Stock Solution Preparation Table

Concentration Solvent Mass

1 mg

5 mg

10 mg

Concentration

Solvent

Mass

1 mM

2.7896 mL

13.9482 mL

27.8963 mL

5 mM

0.5579 mL

2.7896 mL

5.5793 mL

10 mM

0.2790 mL

1.3948 mL

2.7896 mL

Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.

Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Calculadora de molaridad

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass Mass

Concentration Concentration

Volume Volume

Molecular Weight Molecular Weight

Calculadora de dilución

Concentration _(start) × Volume _(start) = Concentration _(final) × Volume _(final)

Concentration _(start) Concentration _(start)

Volume _(start) Volume _(start)

Concentration _(final) Concentration _(final)

Volume _(final) Volume _(final)

Pureza y Documentación

Select Batch:

Pureza: 99.98%

Assay: 99.98%

ee.: 99.98%

Ficha de datos (277 KB)
SDS (459 KB)
- English - EN (459 KB)
- Français - FR (459 KB)
- Deutsch - DE (459 KB)
- Norwegian - NO (459 KB)
- Español - ES (459 KB)
- Swedish - SV (459 KB)
- Italian - IT (459 KB)
- Korean - KR (459 KB)
- Portuguese - PT (459 KB)
COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Instrucciones de manejo (2659 KB)

Referencias

[1]. Eads D, et al. Terameprocol, a methylated derivative of nordihydroguaiaretic acid, inhibits production of prostaglandins and several key inflammatory cytokines and chemokines. J Inflamm (Lond). 2009 Jan 8;6:2. [Content Brief]

[2]. Sun Y, et al. Terameprocol (tetra-O-methyl nordihydroguaiaretic acid), an inhibitor of Sp1-mediated survivin transcription, induces radiosensitization in non-small cell lung carcinoma. J Thorac Oncol. 2011 Jan;6(1):8-14. [Content Brief]

[3]. Nogueira-Ferreira R, et al. HMGB1 down-regulation mediates terameprocol vascular anti-proliferative effect in experimental pulmonary hypertension. J Cell Physiol. 2017 Nov;232(11):3128-3138. [Content Brief]

Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

Complete Stock Solution Preparation Table

Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg
DMSO	1 mM	2.7896 mL	13.9482 mL	27.8963 mL	69.7408 mL
	5 mM	0.5579 mL	2.7896 mL	5.5793 mL	13.9482 mL
	10 mM	0.2790 mL	1.3948 mL	2.7896 mL	6.9741 mL
	15 mM	0.1860 mL	0.9299 mL	1.8598 mL	4.6494 mL
	20 mM	0.1395 mL	0.6974 mL	1.3948 mL	3.4870 mL
	25 mM	0.1116 mL	0.5579 mL	1.1159 mL	2.7896 mL
	30 mM	0.0930 mL	0.4649 mL	0.9299 mL	2.3247 mL
	40 mM	0.0697 mL	0.3487 mL	0.6974 mL	1.7435 mL
	50 mM	0.0558 mL	0.2790 mL	0.5579 mL	1.3948 mL
	60 mM	0.0465 mL	0.2325 mL	0.4649 mL	1.1623 mL
	80 mM	0.0349 mL	0.1744 mL	0.3487 mL	0.8718 mL
	100 mM	0.0279 mL	0.1395 mL	0.2790 mL	0.6974 mL

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Terameprocol

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Ver todos los productos específicos de isoformas COX

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Actividad biológica

Chemical Information

Solvente y solubilidad

Pureza y Documentación

Referencias

Help & FAQs

Complete Stock Solution Preparation Table

Terameprocol Related Classifications

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