MedKoo Cat#: 206567 | Name: Terephthalamidine

Description:

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

Terephthalamidine is a derivative of the phthalanilide compounds. Terephthalamidine belongs to a family of compounds which appear to reversibly bind to the minor groove of the DNA double helix but not intercalate DNA. This agent also has been suggested to form ionic complexes with many biological components in vitro, including nucleic acids, proteins and lipids.

Chemical Structure

Terephthalamidine
Terephthalamidine
CAS#15411-54-8

Theoretical Analysis

MedKoo Cat#: 206567

Name: Terephthalamidine

CAS#: 15411-54-8

Chemical Formula: C8H10N4

Exact Mass: 162.0905

Molecular Weight: 162.20

Elemental Analysis: C, 59.24; H, 6.21; N, 34.54

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
terephthalimidamide; Terephthalamidine
IUPAC/Chemical Name
1,4-Benzenedicarboximidamide
InChi Key
UNMMLGAPDZGRJJ-UHFFFAOYSA-N
InChi Code
InChI=1S/C8H10N4/c9-7(10)5-1-2-6(4-3-5)8(11)12/h1-4H,(H3,9,10)(H3,11,12)
SMILES Code
N=C(C1=CC=C(C(N)=N)C=C1)N
Appearance
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

Preparing Stock Solutions

The following data is based on the product molecular weight 162.20 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.

Recalculate based on batch purity %
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
1: Shu Y, Lei H, Tan YN, Meng M, Zhang XC, Liu CY. Tuning the electronic coupling in Mo2-Mo2 systems by variation of the coordinating atoms of the bridging ligands. Dalton Trans. 2014 Oct 21;43(39):14756-65. doi: 10.1039/c4dt00786g. PubMed PMID: 25157859. 2: Abergel RJ, Raymond KN. Multidentate terephthalamidate and hydroxypyridonate ligands: towards new orally active chelators. Hemoglobin. 2011;35(3):276-90. doi: 10.3109/03630269.2011.560771. PubMed PMID: 21599440. 3: Leyden R, Velasco-Torrijos T, André S, Gouin S, Gabius HJ, Murphy PV. Synthesis of bivalent lactosides based on terephthalamide, N,N'-diglucosylterephthalamide, and glycophane scaffolds and assessment of their inhibitory capacity on medically relevant lectins. J Org Chem. 2009 Dec 4;74(23):9010-26. doi: 10.1021/jo901667r. PubMed PMID: 19899775. 4: Procacci P, Ferrari F, Bettini G, Bissolotti G, Trevisiol L, Nocini PF. Soccer-related facial fractures: postoperative management with facial protective shields. J Craniofac Surg. 2009 Jan;20(1):15-20. doi: 10.1097/SCS.0b013e3181909c55. PubMed PMID: 19164981. 5: Abergel RJ, Raymond KN. Synthesis and thermodynamic evaluation of mixed hexadentate linear iron chelators containing hydroxypyridinone and terephthalamide units. Inorg Chem. 2006 May 1;45(9):3622-31. PubMed PMID: 16634594; PubMed Central PMCID: PMC3685440. 6: Yin H, Lee GI, Sedey KA, Rodriguez JM, Wang HG, Sebti SM, Hamilton AD. Terephthalamide derivatives as mimetics of helical peptides: disruption of the Bcl-x(L)/Bak interaction. J Am Chem Soc. 2005 Apr 20;127(15):5463-8. PubMed PMID: 15826183. 7: Yin H, Hamilton AD. Terephthalamide derivatives as mimetics of the helical region of Bak peptide target Bcl-xL protein. Bioorg Med Chem Lett. 2004 Mar 22;14(6):1375-9. PubMed PMID: 15006365. 8: Kraft A, Peters L, Fröhlich R. N,N',N",N"'-Tetraethylterephthalamidinium bis(tetrazolate). Acta Crystallogr C. 2002 May;58(Pt 5):o272-4. Epub 2002 Apr 11. PubMed PMID: 11983988. 9: Rodriguez GI, Kuhn JG, Weiss G, De La Cruz P, New P, Fields SM, Eckardt JR, Campbell L, Clark GM, Hilsenbeck SG, Von Hoff DD. A phase I and pharmacokinetic trial of terephthalamidine (NSC 57155) as a 120-hour continuous infusion. Invest New Drugs. 1998;16(1):57-67. PubMed PMID: 9740545. 10: Fisherman JS, Cline EM, Plowman J, Quinn FR, Hawkins MJ. Terephthalamidine: past and future. Invest New Drugs. 1991 Nov;9(4):295-303. Review. PubMed PMID: 1804802. 11: Waud WR, Hill DL. High-performance liquid chromatographic determination of terephthalamidine in plasma. J Chromatogr. 1988 Mar 4;425(1):220-6. PubMed PMID: 3360873. 12: Voyksner RD, Williams FP, Hines JW. Analysis of candidate anticancer drugs by thermospray high-performance liquid chromatography-mass spectrometry and by high-resolution mass spectrometry. J Chromatogr. 1985 Oct 25;347(1):137-46. PubMed PMID: 4086628. 13: Winkler A, Kreis W, Gregg VC, Purple JR, Burchenal JH. In vitro and in vivo studies of the antileukemic action of n,n'-bos [p-(n'-methylamidino)phenyl]terephthalamidine, tetrahydrochloride (NSC 57155) on P815 leukemic cells. Cancer Res. 1966 Jul;26(7):1502-7. PubMed PMID: 5916484.