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tetramethyl Nordihydroguaiaretic Acid Exclusive

Cayman Chemical Item Number 70302

tetramethyl NDGA; TMNDGA; Tetrameprocol; M4N; EM-1421 (CAS 24150-24-1)

tetramethyl Nordihydroguaiaretic Acid (CAS 24150-24-1)

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Description

tetramethyl Nordihydroguaiaretic acid (TMNDGA) 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 respectively1,2 TMNDGA induces growth arrest and apoptosis by suppressing Sp1-dependent Cdc2 and survivin gene expression giving rise to its antitumorigenic activity.3 The in vivo growth of xenografts in numerous human tumor types was suppressed upon treatment with TMNDGA.4 It also inhibits the growth of mouse and human melanomas and human colon cancer in vivo without causing other tissue toxicity.5 TMNDGA is currently in Phase I & II clinical trials for treatment of high grade glioma brain tumors.

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).

Synonyms
  • tetramethyl NDGA
  • TMNDGA
  • Tetrameprocol
  • M4N
  • EM-1421
Formal Name 4-​[(2R,​3S)-​4-​(3,​4-​dimethoxyphenyl)-​2,​3-​dimethylbutyl]-​1,​2-​dimethoxy-​benzene
CAS Number 24150-24-1
Molecular Formula C22H30O4
Formula Weight 358.5
Formulation A crystalline solid
Purity ≥98%
λmax 230, 280 nm
Stability 2 years
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES
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COc1cc(ccc1OC)​CC(C)​C(C)​Cc1ccc(OC)​c(OC)​c1

Background Reading

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).

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).

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).

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).

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).

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Size Price Quantity Subtotal
50 mg $11.00 $0.00
100 mg $21.00 $0.00
500 mg $88.00 $0.00
1 g $154.00 $0.00
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Cart Total $0.00

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Pricing updated 2012-05-26. Prices are subject to change without notice.

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Warning This product is not for human or veterinary use.

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