Terameprocol | EM-1421 | CAS#24150-24-1

MedKoo Cat#: 202880 | Name: Terameprocol

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

Terameprocol

CAS#24150-24-1

Theoretical Analysis

MedKoo Cat#: 202880

Name: Terameprocol

CAS#: 24150-24-1

Chemical Formula: C22H30O4

Exact Mass: 358.2144

Molecular Weight: 358.47

Elemental Analysis: C, 73.71; H, 8.44; O, 17.85

Price and Availability

Size	Price	Availability
500mg	USD 150.00	Ready to ship
1g	USD 250.00	Ready to ship
2g	USD 450.00	Ready to ship
5g	USD 950.00	Ready to ship

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Synonym

tetramethyl-nordihydroguaiaretic acid; tetra-O-methyl nordihydroguaiaretic acid. Abbreviations: M4N; tetramethyl-NDGA; TMNDGA; Code name: EM1421; EM-1421; EM 1421.

IUPAC/Chemical Name

(2R,3S)-2,3-dimethyl-1,4-bis(3,4-bimethoxylphenyl)-butane

InChi Key

ORQFDHFZSMXRLM-IYBDPMFKSA-N

InChi Code

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+

SMILES Code

COC1=CC=C(C[C@H](C)[C@H](C)CC2=CC=C(OC)C(OC)=C2)C=C1OC

Appearance

white solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: previous batch, Lot#SCX-A4488

QC Data

View QC data, current batch, Lot#SCX40926

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Terameprocol 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 respectively.

In vitro activity:

To clarify the role of Sp1 in MM cell growth and survival, this study next examined the effects of the Sp1 inhibitor terameprocol (TMP), which competitively inhibits Sp1 binding to DNA. Treatment with TMP dose-dependently suppressed MM cell viability (Figure 1B). These results suggest therapeutic potential of targeting Sp1 up-regulated in MM cells. Reference: Oncotarget. 2016 Nov 29; 7(48): 79064–79075. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5346698/

In vivo activity:

Treatment with TMP (terameprocol), compared to vehicle alone, significantly inhibited MM tumor growth in all 3 murine models of MM (Fig. 5A). As seen in Fig. 5B, treatment with TMP also significantly prolonged survival in treated animals compared to control (p=0.017); the median overall survival was 18 days in the control group and 28 days in the TMP-treated group. TMP-related toxicity was not observed in mice, as determined by daily evaluation of activity and overall body weight change during the course of treatment. Histological examinations of tumor retrieved from MM1S-bearing mice confirmed decreased proliferation (as highlighted by Ki-67 staining), significant tumor cell apoptosis (caspase-3 and TUNEL staining) (Fig. 5C) as well as decreased expression of Survivin (Fig. 5D) following TMP treatment in vivo. Reference: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4318245/

	Solvent	mg/mL	mM
Solubility
	DMSO	2.0	5.58
	DMF	2.5	6.97
	DMF:PBS (pH 7.2) (1:3)	0.3	0.70
	Ethanol	0.2	0.56

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 358.47 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Bat-Erdene A, Miki H, Oda A, Nakamura S, Teramachi J, Amachi R, Tenshin H, Hiasa M, Iwasa M, Harada T, Fujii S, Sogabe K, Kagawa K, Yoshida S, Endo I, Aihara K, Abe M. Synergistic targeting of Sp1, a critical transcription factor for myeloma cell growth and survival, by panobinostat and proteasome inhibitors. Oncotarget. 2016 Nov 29;7(48):79064-79075. doi: 10.18632/oncotarget.12594. PMID: 27738323; PMCID: PMC5346698. 2. Davies C, Hogarth LA, Mackenzie KL, Hall AG, Lock RB. p21(WAF1) modulates drug-induced apoptosis and cell cycle arrest in B-cell precursor acute lymphoblastic leukemia. Cell Cycle. 2015;14(22):3602-12. doi: 10.1080/15384101.2015.1100774. PMID: 26506264; PMCID: PMC4825786. 3. Fulciniti M, Amin S, Nanjappa P, Rodig S, Prabhala R, Li C, Minvielle S, Tai YT, Tassone P, Avet-Loiseau H, Hideshima T, Anderson KC, Munshi NC. Significant biological role of sp1 transactivation in multiple myeloma. Clin Cancer Res. 2011 Oct 15;17(20):6500-9. doi: 10.1158/1078-0432.CCR-11-1036. Epub 2011 Aug 19. PMID: 21856768; PMCID: PMC4318245. 4. Eads D, Hansen R, Oyegunwa A, Cecil C, Culver C, Scholle F, Petty I, Laster S. Terameprocol, a methylated derivative of nordihydroguaiaretic acid, inhibits production of prostaglandins and several key inflammatory cytokines and chemokines. J Inflamm (Lond). 2009 Jan 8;6:2. doi: 10.1186/1476-9255-6-2. PMID: 19133137; PMCID: PMC2631502.

In vitro protocol:

In vivo protocol:

1. Fulciniti M, Amin S, Nanjappa P, Rodig S, Prabhala R, Li C, Minvielle S, Tai YT, Tassone P, Avet-Loiseau H, Hideshima T, Anderson KC, Munshi NC. Significant biological role of sp1 transactivation in multiple myeloma. Clin Cancer Res. 2011 Oct 15;17(20):6500-9. doi: 10.1158/1078-0432.CCR-11-1036. Epub 2011 Aug 19. PMID: 21856768; PMCID: PMC4318245. 2. Eads D, Hansen R, Oyegunwa A, Cecil C, Culver C, Scholle F, Petty I, Laster S. Terameprocol, a methylated derivative of nordihydroguaiaretic acid, inhibits production of prostaglandins and several key inflammatory cytokines and chemokines. J Inflamm (Lond). 2009 Jan 8;6:2. doi: 10.1186/1476-9255-6-2. PMID: 19133137; PMCID: PMC2631502.

1: Ho SS, Go ML. Restraining the flexibility of the central linker in terameprocol results in constrained analogs with improved growth inhibitory activity. Bioorg Med Chem Lett. 2013 Nov 15;23(22):6127-33. doi: 10.1016/j.bmcl.2013.09.014. Epub 2013 Sep 13. PubMed PMID: 24080463. 2: Grossman SA, Ye X, Peereboom D, Rosenfeld MR, Mikkelsen T, Supko JG, Desideri S; Adult Brain Tumor Consortium. Phase I study of terameprocol in patients with recurrent high-grade glioma. Neuro Oncol. 2012 Apr;14(4):511-7. doi: 10.1093/neuonc/nor230. Epub 2012 Feb 8. PubMed PMID: 22323663; PubMed Central PMCID: PMC3309850. 3: Oyegunwa AO, Sikes ML, Wilson JR, Scholle F, Laster SM. 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. J Inflamm (Lond). 2010 Dec 7;7:59. doi: 10.1186/1476-9255-7-59. PubMed PMID: 21138578; PubMed Central PMCID: PMC3002343. 4: Sun Y, Giacalone NJ, Lu B. Terameprocol (tetra-O-methyl nordihydroguaiaretic acid), an inhibitor of Sp1-mediated survivin transcription, induces radiosensitization in non-small cell lung carcinoma. J Thorac Oncol. 2011 Jan;6(1):8-14. doi: 10.1097/JTO.0b013e3181fa646a. PubMed PMID: 21107289; PubMed Central PMCID: PMC3010256. 5: Pollara JJ, Laster SM, Petty IT. Inhibition of poxvirus growth by Terameprocol, a methylated derivative of nordihydroguaiaretic acid. Antiviral Res. 2010 Dec;88(3):287-95. doi: 10.1016/j.antiviral.2010.09.017. Epub 2010 Oct 1. PubMed PMID: 20888364. 6: Eads D, Hansen R, Oyegunwa A, Cecil C, Culver C, Scholle F, Petty I, Laster S. Terameprocol, a methylated derivative of nordihydroguaiaretic acid, inhibits production of prostaglandins and several key inflammatory cytokines and chemokines. J Inflamm (Lond). 2009 Jan 8;6:2. doi: 10.1186/1476-9255-6-2. PubMed PMID: 19133137; PubMed Central PMCID: PMC2631502. 7: Khanna N, Dalby R, Connor A, Church A, Stern J, Frazer N. Phase I clinical trial of repeat dose terameprocol vaginal ointment in healthy female volunteers. Sex Transm Dis. 2008 Jun;35(6):577-82. doi: 10.1097/OLQ.0b013e31816766af. PubMed PMID: 18418294. 8: Smolewski P. Terameprocol, a novel site-specific transcription inhibitor with anticancer activity. IDrugs. 2008 Mar;11(3):204-14. Review. PubMed PMID: 18311658. 9: Khanna N, Dalby R, Tan M, Arnold S, Stern J, Frazer N. Phase I/II clinical safety studies of terameprocol vaginal ointment. Gynecol Oncol. 2007 Dec;107(3):554-62. Epub 2007 Oct 1. PubMed PMID: 17905420. 10: Lopez RA, Goodman AB, Rhodes M, Blomberg JA, Heller J. The anticancer activity of the transcription inhibitor terameprocol (meso-tetra-O-methyl nordihydroguaiaretic acid) formulated for systemic administration. Anticancer Drugs. 2007 Sep;18(8):933-9. PubMed PMID: 17667599.