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Terameprocol

Catalog No. T21746   CAS 24150-24-1
Synonyms: tetramethyl Nordihydroguaiaretic Acid, EM-1421

Terameprocol (EM-1421) is a synthetic tetra-methylated derivative of nordihydroguaiaretic acid (NDGA) and transcriptional inhibitor with potential antiviral, antiangiogenic, and antineoplastic activities. Terameprocol showed the strongest anti-HIV activity.

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Terameprocol Chemical Structure
Terameprocol, CAS 24150-24-1
Pack Size Availability Price/USD Quantity
10 mg In stock $ 45.00
25 mg In stock $ 82.00
50 mg In stock $ 132.00
100 mg In stock $ 216.00
1 mL * 10 mM (in DMSO) In stock $ 50.00
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Purity: 99.79%
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Biological Description
Chemical Properties
Storage & Solubility Information
Description Terameprocol (EM-1421) is a synthetic tetra-methylated derivative of nordihydroguaiaretic acid (NDGA) and transcriptional inhibitor with potential antiviral, antiangiogenic, and antineoplastic activities. Terameprocol showed the strongest anti-HIV activity.
In vitro In Vero cells, Terameprocol inhibited Sp1 transcription factor binding at the HIV long terminal repeat promoter and at the α-ICP4 promoter with IC50 values of 11 and 43.5 μM, respectively. The IC50 of Terameprocol varied between 11.7 and 4 μM in 10 passages of HSV-1 and 4 passages of HSV-2 [2]. Terameprocol inhibited Sp1-dependent Cdc2 gene expression. In M4N-treated transformed C3 cells, Terameprocol induced growth arrest and apoptosis by suppressing Sp1-dependent Cdc2 and survivin gene expression giving rise to its antitumorigenic activity [3]. Terameprocol treatment suppressed expression of the Sp1-dependent survivin gene. In transiently and stably survivin-transfected C3 cells, Terameprocol reduced caspase-3 activation by 50% and 75%, respectively [3]. Terameprocol inhibited the growth of a number of tumor cell lines by inducing apoptosis in a non-schedule-dependent manner [4]. Terameprocol inhibited the synthesis of DNA by melanoma cells and causes cell cycle arrest in G0/G1 and G2/M phases of the cell cycle [4].
In vivo Terameprocol effectively inhibited the growth of human tumors in nude mice [5]. Terameprocol inhibited the growth of both murine and human melanomas and human colon cancer without apparent hepatic or renal toxicity [4]. In nude (nu/nu) mice bearing xenografts of human tumor types (Hep 3B, LNCaP, HT-29, MCF7, and K-562), treatment with Terameprocol (i.v. or i.p.) down-regulated Cdc2 and survivin genes expression [5].
Synonyms tetramethyl Nordihydroguaiaretic Acid, EM-1421
Molecular Weight 358.47
Formula C22H30O4
CAS No. 24150-24-1

Storage

Powder: -20°C for 3 years | In solvent: -80°C for 1 year

Solubility Information

DMSO: 27.5 mg/ml (76.71 mM)

TargetMolReferences and Literature

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]. Journal of medicinal chemistry, 1998, 41(16): 2994-3000. 2. Chen H, Teng L, Li J N, 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]. Journal of medicinal chemistry, 1998, 41(16): 3001-3007. 3. Chang C 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[J]. Proceedings of the National Academy of Sciences of the United States of America, 2004, 101(36): 13239-13244. 4. Lambert J D, Meyers R O, Timmermann B N, et al. Tetra-O-methylnordihydroguaiaretic acid inhibits melanoma in vivo[J]. Cancer letters, 2001, 171(1): 47-56. 5. Park R, Chang C C, Liang Y C, et al. Systemic treatment with tetra-O-methyl nordihydroguaiaretic acid suppresses the growth of human xenograft tumors[J]. Clinical Cancer Research, 2005, 11(12): 4601-4609.

Related compound libraries

This product is contained In the following compound libraries:
Inhibitor Library Anti-Cancer Active Compound Library Bioactive Compounds Library Max ReFRAME Related Library Bioactive Compound Library Anti-Infection Compound Library Anti-Cancer Compound Library Anti-Viral Compound Library NO PAINS Compound Library

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Keywords

Terameprocol 24150-24-1 Microbiology/Virology Proteases/Proteasome HIV Protease EM1421 inhibit LOX tetramethyl Nordihydroguaiaretic Acid Inhibitor Lipoxygenase EM 1421 EM-1421 inhibitor

 

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