Terameprocol

Terameprocol (CAS 24150-24-1)

Terameprocol | CAS 24150-24-1 is rated 5.0 out of 5 by 1.
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Synonym: tetramethyl NDGA; TMNDGA; Tetramethyl nordihydroguaiaretic acid
Application: A synthetic derivative of NDGA and non-selective lipoxygenase inhibitor
CAS Number: 24150-24-1
Molecular Weight: 358.47
Molecular Formula: C22H30O4
Supplemental Information: This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
* Refer to Certificate of Analysis for lot specific data (including water content).
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Tetramethyl Nordihydroguaiaretic Acid is a synthetic derivative of NDGA and a non-selective LO (lipoxygenase) inhibitor. Tetramethyl Nordihydroguaiaretic Acid inhibits Sp1 transcription factor binding at the HIV long terminal repeat promoter and at the α-ICP4 promoter (a gene essential for HSV replication).


References

1 Hwu, J.R., Tseng, W.N., Gnabre, J., et al. Antiviral activities of methylated nordihydroguaiaretic acids. 1. Synthesis, structure identification, and inhibition of tat-regulated HIV transactivation. J Med Chem 41 2994-3000 (1998). 2 Chen, H., Teng, L., Li, J., et al. Antiviral activities of methylated nordihydroguaiaretic acids. 2. Targeting herpes simplex virus replication by the mutation insensitive transcription inhibitor tetra-O-methyl-NDGA. J Med Chem 41 3001-3007 (1998). 3 Chang, C., Heller, J.D., Kuo, J., et al. Tetra-O-methyl nordihydroguaiaretic acid induces growth arrest and cellular apoptosis by inhibiting Cdc2 and survivin expression. Proc Natl Acad Sci USA 101(36) 13239-13244 (2004). 4 Park, R., Chang, C., Liang, Y., et al. Systemic treatment with tetra-O-methyl nordihydroguaiaretic acid suppresses the growth of human xenograft tumors. Clin Cancer Res 11(12) 4601-4609 (2005). 5 Lambert, J.D., Meyers, R.O., Timmermann, B.N., et al. Tetra-O-methylnordihydroguaiaretic acid inhibits melanoma in vivo. Cancer Lett 171 47-56 (2001).

Physical State :
Solid
Solubility :
Soluble in 1:3 DMF: PBS(pH 7.2) (~0.25 mg/ml), ethanol (~0.2 mg/ml), DMSO (~2 mg/ml), and DMF (~2 mg/ml).
Storage :
Store at -20° C
Melting Point :
155.67° C (Predicted)
Boiling Point :
~458.5° C at 760 mmHg (Predicted)
Density :
~1.0 g/cm3 (Predicted)
Refractive Index :
n20D 1.52 (Predicted)
IC50 :
A375: IC50 = 2.5 µM (human); Vero: IC50 = 4.18 µM (human); Vero: IC50 = 5.97 µM (monkey); HIV long terminal repeat promoter: IC50 = 11 µM; α-ICP4 promoter: IC50 = 43.5 µM
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
Transport :
UN 3077, Class 9, Packing group III
PubChem CID :
476861
MDL Number :
MFCD11113155
SMILES :
C[C@H](CC1=CC(=C(C=C1)OC)OC)[C@@H](C)CC2=CC(=C(C=C2)OC)OC

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Certificate of Analysis

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Rated 5 out of 5 by from Eads et al Eads et al. (PubMed ID 19133137) found that terameprocol blocked the production of prostaglandins from RAW 264.7 cells and normal peritoneal macrophages by reducing COX-2 mRNA levels and COX-2 activity. -SCBT Publication Review
Date published: 2015-06-21
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