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T3455

Sigma-Aldrich

Terameprocol

≥98% (HPLC)

Synonym(s):

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

Empirical Formula (Hill Notation):
C22H30O4
CAS Number:
24150-24-1
Molecular Weight:
358.47
MDL number:
MFCD11113155
UNSPSC Code:
12352200
PubChem Substance ID:
329826768
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to off-white

solubility

DMSO: ≥10 mg/mL

storage temp.

−20°C

SMILES string

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+

InChI key

ORQFDHFZSMXRLM-IYBDPMFKSA-N

Biochem/physiol Actions

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.

Preparation Note

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

Pictograms

Environment
GHS09

Signal Word

Warning

Hazard Statements

H410

Precautionary Statements

P273 - P391 - P501

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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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
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
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
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
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
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