Terameprocol Chemical Properties

Melting point:

101-102 °C

Boiling point:

458.5±40.0 °C(Predicted)

Density 

1.036±0.06 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

DMSO: ≥10mg/mL

form 

powder

color 

white to off-white

Safety Information

Hazard Codes 

N

Risk Statements 

50/53

Safety Statements 

60-61

RIDADR 

UN 3077 9 / PGIII

WGK Germany 

3

Terameprocol Usage And Synthesis

Uses

Terameprocol is a synthetic derivative of NDGA and non-selective lipoxygenase inhibitor.

Definition

ChEBI: Terameprocol is a lignan.

Biological Activity

tetramethyl nordihydroguaiaretic acid (tmndga) is a synthetic derivative of ndga (nordihydroguaiaretic acid), a non-selective lipoxygenase inhibitor. tmndga showed the strongest anti-hiv activity.

in vitro

in vero cells, tmndga 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 tmndga varied between 11.7 and 4 μm in 10 passages of hsv-1 and 4 passages of hsv-2 [2]. tmndga inhibited sp1-dependent cdc2 gene expression. in m4n-treated transformed c3 cells, tmndga induced growth arrest and apoptosis by suppressing sp1-dependent cdc2 and survivin gene expression giving rise to its antitumorigenic activity [3]. tmndga treatment suppressed expression of the sp1-dependent survivin gene. in transiently and stably survivin-transfected c3 cells, tmndga reduced caspase-3 activation by 50% and 75%, respectively [3]. tmndga inhibited the growth of a number of tumor cell lines by inducing apoptosis in a non-schedule-dependent manner [4]. tmndga 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

tmndga effectively inhibited the growth of human tumors in nude mice [5]. tmndga 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 tmndga (i.v. or i.p.) down-regulated cdc2 and survivin genes expression [5].

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]. 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.

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