Terameprocol

• CAT Number: I009764
• CAS Number: 24150-24-1
• Molecular Formula: C22H30O4
• Molecular Weight: 358.478
• Purity: ≥95%
• Solubility: Soluble in DMSO, not in water
• Storage: -20°C
• IUPAC Name: 4-[(2S,3R)-4-(3,4-dimethoxyphenyl)-2,3-dimethylbutyl]-1,2-dimethoxybenzene
• InChI: 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+
• InChIKey: ORQFDHFZSMXRLM-IYBDPMFKSA-N
• SMILES: CC(CC1=CC(=C(C=C1)OC)OC)C(C)CC2=CC(=C(C=C2)OC)OC

Terameprocol, also known as EM-1421, is a semi-synthetic tetra-methylated derivative of nordihydroguaiaretic acid (NDGA) and transcriptional inhibitor with potential antiviral, antiangiogenic, and antineoplastic activities. Terameprocol competes with the transcription factor Sp1 for specific Sp1 DNA binding domains within gene promoter regions during DNA synthesis. In virally-infected cells, blocking of the Sp1 binding site suppresses Sp1-regulated viral promoter activity and gene expression, thereby inhibiting viral transcription and replication.

Reference

1:HMGB1 down-regulation mediates terameprocol vascular anti-proliferative effect in experimental pulmonary hypertension. Nogueira-Ferreira R, Ferreira-Pinto MJ, Silva AF, Vitorino R, Justino J, Costa R, Moreira-Gonçalves D, Quignard JF, Ducret T, Savineau JP, Leite-Moreira AF, Ferreira R, Henriques-Coelho T.J Cell Physiol. 2016 Dec 30. doi: 10.1002/jcp.25763. [Epub ahead of print] PMID: 28036116 2:Phase I study of the novel Cdc2/CDK1 and AKT inhibitor terameprocol in patients with advanced leukemias. Tibes R, McDonagh KT, Lekakis L, Bogenberger JM, Kim S, Frazer N, Mohrland S, Bassett D, Garcia R, Schroeder K, Shanmugam V, Carpten J, Hagelstrom RT, Beaudry C, Von Hoff D, Shea TC.Invest New Drugs. 2015 Apr;33(2):389-96. doi: 10.1007/s10637-014-0198-y. Epub 2014 Dec 19. PMID: 25523151 3:Restraining the flexibility of the central linker in terameprocol results in constrained analogs with improved growth inhibitory activity. Ho SS, Go ML.Bioorg Med Chem Lett. 2013 Nov 15;23(22):6127-33. doi: 10.1016/j.bmcl.2013.09.014. Epub 2013 Sep 13. PMID: 24080463 4:Phase I study of terameprocol in patients with recurrent high-grade glioma. Grossman SA, Ye X, Peereboom D, Rosenfeld MR, Mikkelsen T, Supko JG, Desideri S; Adult Brain Tumor Consortium..Neuro Oncol. 2012 Apr;14(4):511-7. doi: 10.1093/neuonc/nor230. Epub 2012 Feb 8. PMID: 22323663 Free PMC Article5:Tetra-O-methyl nordihydroguaiaretic acid (Terameprocol) inhibits the NF-κB-dependent transcription of TNF-α and MCP-1/CCL2 genes by preventing RelA from binding its cognate sites on DNA. Oyegunwa AO, Sikes ML, Wilson JR, Scholle F, Laster SM.J Inflamm (Lond). 2010 Dec 7;7:59. doi: 10.1186/1476-9255-7-59. PMID: 21138578 Free PMC Article6:Terameprocol (tetra-O-methyl nordihydroguaiaretic acid), an inhibitor of Sp1-mediated survivin transcription, induces radiosensitization in non-small cell lung carcinoma. Sun Y, Giacalone NJ, Lu B.J Thorac Oncol. 2011 Jan;6(1):8-14. doi: 10.1097/JTO.0b013e3181fa646a. PMID: 21107289 Free PMC Article7:Inhibition of poxvirus growth by Terameprocol, a methylated derivative of nordihydroguaiaretic acid. Pollara JJ, Laster SM, Petty IT.Antiviral Res. 2010 Dec;88(3):287-95. doi: 10.1016/j.antiviral.2010.09.017. Epub 2010 Oct 1. PMID: 20888364 8:Terameprocol, a methylated derivative of nordihydroguaiaretic acid, inhibits production of prostaglandins and several key inflammatory cytokines and chemokines. Eads D, Hansen R, Oyegunwa A, Cecil C, Culver C, Scholle F, Petty I, Laster S.J Inflamm (Lond). 2009 Jan 8;6:2. doi: 10.1186/1476-9255-6-2. PMID: 19133137 Free PMC Article9:Phase I clinical trial of repeat dose terameprocol vaginal ointment in healthy female volunteers. Khanna N, Dalby R, Connor A, Church A, Stern J, Frazer N.Sex Transm Dis. 2008 Jun;35(6):577-82. doi: 10.1097/OLQ.0b013e31816766af. PMID: 18418294 10:Terameprocol, a novel site-specific transcription inhibitor with anticancer activity. Smolewski P.IDrugs. 2008 Mar;11(3):204-14. Review. PMID: 18311658