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Merck
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Key Documents

Altri documenti

T3455

Sigma-Aldrich

Terameprocol

≥98% (HPLC)

Sinonimo/i:

2,3-Dimethyl-1,4-bis-(3,4-dimethoxyphenyl)butane, EM-1421, M4N, TMNDGA, Tetra-O-methyl nordihydroguaiaretic acid, rel-4-[(2R,3S)-4-(3,4-Dimethoxyphenyl)-2,3-dimethylbutyl]-1,2-dimethoxybenzene, tetra-O-methyl-NDGA, tetramethyl NDGA, tetramethyl Nordihydroguaiaretic Acid

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About This Item

Formula empirica (notazione di Hill):
C22H30O4
Numero CAS:
24150-24-1
Peso molecolare:
358.47
Numero MDL:
MFCD11113155
Codice UNSPSC:
12352200
ID PubChem:
329826768
NACRES:
NA.77

Livello qualitativo

100

Saggio

≥98% (HPLC)

Forma fisica

powder

Colore

white to off-white

Solubilità

DMSO: ≥10 mg/mL

Temperatura di conservazione

−20°C

Stringa SMILE

COc1ccc(C[C@H](C)[C@H](C)Cc2ccc(OC)c(OC)c2)cc1OC

InChI

1S/C22H30O4/c1-15(11-17-7-9-19(23-3)21(13-17)25-5)16(2)12-18-8-10-20(24-4)22(14-18)26-6/h7-10,13-16H,11-12H2,1-6H3/t15-,16+
ORQFDHFZSMXRLM-IYBDPMFKSA-N

Azioni biochim/fisiol

Terameprocol is a synthetic derivative of NDGA, a non-selective lipoxygenase inhibitor. It inhibits Sp1 transcription factor binding at the HIV long terminal repeat promoter and at the α-ICP4 promoter, a gene essential for HSV replication, with IC50 values of 11 and 43.5 μM respectively. TMNDGA induces growth arrest and apoptosis by suppressing Sp1-dependent Cdc2 and survivin gene expression giving rise to its antitumorigenic activity. The in vivo growth of xenografts in numerous human tumor types was suppressed upon treatment with TMNDGA It also inhibits the growth of murine and human melanomas and human colon cancer in vivo without causing other tissue toxicity.
Terameprocol is known to reduce angiogenesis1.

Nota sulla preparazione

Terameprocol is soluble in DMSO at a concentration that is greater than or equal to 10 mg/ml.

Pittogrammi

Environment
GHS09

Avvertenze

Warning

Indicazioni di pericolo

H410

Consigli di prudenza

P273 - P391 - P501

Classi di pericolo

Aquatic Acute 1 - Aquatic Chronic 1

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Certificati d'analisi (COA)

Cerca il Certificati d'analisi (COA) digitando il numero di lotto/batch corrispondente. I numeri di lotto o di batch sono stampati sull'etichetta dei prodotti dopo la parola ‘Lotto’ o ‘Batch’.

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Hsueh-Liang Chu et al.
ACS applied materials & interfaces, 5(15), 7509-7516 (2013-07-10)
To develop a drug delivery system (DDS), it is critical to address challenging tasks such as the delivery of hydrophobic and amphiphilic compounds, cell uptake, and the metabolic fate of the drug delivery carrier. Low-density lipoprotein (LDL) has been acknowledged
Piotr Smolewski
IDrugs : the investigational drugs journal, 11(3), 204-214 (2008-03-04)
Terameprocol, a novel, semisynthetic derivative of a naturally occurring plant lignan, is under development by Erimos Pharmaceuticals LLC for the potential treatment of cancer. The antitumor activity of terameprocol is based on the selective inhibition of specificity protein 1 (Sp1)-regulated
Kotohiko Kimura et al.
PloS one, 11(2), e0148685-e0148685 (2016-02-18)
The ability of Tetra-O-methyl nordihydroguaiaretic acid (M4N) to induce rapid cell death in combination with Etoposide, Rapamycin, or UCN-01 was examined in LNCaP cells, both in cell culture and animal experiments. Mice treated with M4N drug combinations with either Etoposide
Angel Chao et al.
Journal of molecular medicine (Berlin, Germany), 96(11), 1251-1266 (2018-10-10)
Oncogenic PIK3CA mutations are common in endometrial cancers, and the PI3K/AKT/mTOR pathway is targetable by drugs. We sought to investigate whether the combination of an mTOR inhibitor, everolimus (RAD001), and an AKT inhibitor, terameprocol (M4N), exerts better antiproliferative effects in
Thidarath Rattanaburee et al.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 129, 110361-110361 (2020-06-15)
Kusunokinin, a lignan compound, inhibits cancer cell proliferation and induces apoptosis; however, the role of kusunokinin is not fully understood. Here, we aimed to identify a target protein of (-)-kusunokinin and determine the protein levels of its downstream molecules. We
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