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Merck
CN

T3455

Terameprocol

≥98% (HPLC)

别名:

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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关于此项目

经验公式(希尔记法):
C22H30O4
化学文摘社编号:
分子量:
358.47
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
MDL number:
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
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Quality Level

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.
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

signalword

Warning

hcodes

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1

存储类别

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

法规信息

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历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

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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



全球贸易项目编号

货号GTIN
T3455-10MG04061832639451
T3455-50MG04061832639468