TNP-ATP triethylammonium salt| CAS#61368-63-6 | P2X receptor antagonist

MedKoo Cat#: 532820 | Name: TNP-ATP triethylammonium salt

Description:

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

TNP-ATP triethylammonium salt is a high affinity, selective P2X receptor antagonist. TNP-ATP triethylammonium salt inhibits ATP-induced currents in cells expressing P2X1, P2X3 and heteromeric P2X2/3 receptors with IC50 values of 6, 0.9 and 7 nM respectively. It displays 1000-fold selectivity over P2X2, P2X4 and P2X7.

Chemical Structure

TNP-ATP triethylammonium salt

CAS#61368-63-6

Theoretical Analysis

MedKoo Cat#: 532820

Name: TNP-ATP triethylammonium salt

CAS#: 61368-63-6

Chemical Formula: C40H77N12O19P3

Exact Mass:

Molecular Weight: 1123.04

Elemental Analysis: C, 42.78; H, 6.91; N, 14.97; O, 27.07; P, 8.27

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

TNP-ATP; TNPATP; TNP ATP; TNP-ATP triethylammonium salt.

IUPAC/Chemical Name

2',3'-O-(2,4,6-Trinitrophenyl)adenosine-5'-triphosphate tetra(triethylammonium) salt

InChi Key

XTSNRUFLZVGKOU-NRBYJGOSSA-O

InChi Code

InChI=1S/C16H16N8O19P3.4C6H15N/c17-13-10-14(19-4-18-13)21(5-20-10)15-12-11(7(39-15)3-38-45(34,35)43-46(36,37)42-44(31,32)33)40-16(41-12)8(23(27)28)1-6(22(25)26)2-9(16)24(29)30;4*1-4-7(5-2)6-3/h1-2,4-5,7,11-12,15H,3H2,(H6-,17,18,19,25,26,31,32,33,34,35,36,37);4*4-6H2,1-3H3/q-1;;;;/p+1/t7-,11-,12-,15-;;;;/m1..../s1

SMILES Code

CC[NH+](CC)CC.CC[NH+](CC)CC.CC[NH+](CC)CC.CC[NH+](CC)CC.Nc(ncn1)c2c1n([C@@H]3O[C@@H]([C@H]4OC5(C([N+]([O-])=O)=C/C(C=C5[N+]([O-])=O)=[N+]([O-])/[O-])O[C@@H]34)COP([O-])(OP([O-])(OP([O-])(O)=O)=O)=O)cn2

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

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 1,123.04 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

1: Xiao J, Huang Y, Li X, Li L, Yang T, Huang L, Yang L, Jiang H, Li H, Li F. TNP-ATP is Beneficial for Treatment of Neonatal Hypoxia-Induced Hypomyelination and Cognitive Decline. Neurosci Bull. 2016 Feb;32(1):99-107. doi: 10.1007/s12264-015-0003-8. Epub 2016 Jan 15. PubMed PMID: 26769489. 2: Preobrazhenskaya YV, Stenko AI, Shvarts MV, Lugovtsev VY. Binding Stoichiometry of a Recombinant Selenophosphate Synthetase with One Synonymic Substitution E197D to a Fluorescent Nucleotide Analog of ATP, TNP-ATP. J Amino Acids. 2013;2013:983565. doi: 10.1155/2013/983565. Epub 2013 Jan 30. PubMed PMID: 24719756; PubMed Central PMCID: PMC3956282. 3: Guarnieri MT, Blagg BS, Zhao R. A high-throughput TNP-ATP displacement assay for screening inhibitors of ATP-binding in bacterial histidine kinases. Assay Drug Dev Technol. 2011 Apr;9(2):174-83. doi: 10.1089/adt.2010.0289. Epub 2010 Nov 4. PubMed PMID: 21050069; PubMed Central PMCID: PMC3065726. 4: Eaton AK, Stewart RC. Kinetics of ATP and TNP-ATP binding to the active site of CheA from Thermotoga maritima. Biochemistry. 2010 Jul 13;49(27):5799-809. doi: 10.1021/bi100721b. PubMed PMID: 20565117. 5: Yao H, Hersh LB. Characterization of the binding of the fluorescent ATP analog TNP-ATP to insulysin. Arch Biochem Biophys. 2006 Jul 15;451(2):175-81. Epub 2006 May 6. PubMed PMID: 16723115. 6: Trujillo CA, Nery AA, Martins AH, Majumder P, Gonzalez FA, Ulrich H. Inhibition mechanism of the recombinant rat P2X(2) receptor in glial cells by suramin and TNP-ATP. Biochemistry. 2006 Jan 10;45(1):224-33. PubMed PMID: 16388598. 7: Lánský Z, Kubala M, Ettrich R, Kutý M, Plásek J, Teisinger J, Schoner W, Amler E. The hydrogen bonds between Arg423 and Glu472 and other key residues, Asp443, Ser477, and Pro489, are responsible for the formation and a different positioning of TNP-ATP and ATP within the nucleotide-binding site of Na(+)/K(+)-ATPase. Biochemistry. 2004 Jul 6;43(26):8303-11. PubMed PMID: 15222743. 8: Kubala M, Plásek J, Amler E. Limitations in linearized analyses of binding equilibria: binding of TNP-ATP to the H4-H5 loop of Na/K-ATPase. Eur Biophys J. 2003 Jul;32(4):363-9. Epub 2003 Mar 6. PubMed PMID: 12851794. 9: Tsuzuki K, Ase A, Séguéla P, Nakatsuka T, Wang CY, She JX, Gu JG. TNP-ATP-resistant P2X ionic current on the central terminals and somata of rat primary sensory neurons. J Neurophysiol. 2003 Jun;89(6):3235-42. PubMed PMID: 12783957. 10: Honore P, Mikusa J, Bianchi B, McDonald H, Cartmell J, Faltynek C, Jarvis MF. TNP-ATP, a potent P2X3 receptor antagonist, blocks acetic acid-induced abdominal constriction in mice: comparison with reference analgesics. Pain. 2002 Mar;96(1-2):99-105. PubMed PMID: 11932066. 11: Jarvis MF, Wismer CT, Schweitzer E, Yu H, van Biesen T, Lynch KJ, Burgard EC, Kowaluk EA. Modulation of BzATP and formalin induced nociception: attenuation by the P2X receptor antagonist, TNP-ATP and enhancement by the P2X(3) allosteric modulator, cibacron blue. Br J Pharmacol. 2001 Jan;132(1):259-69. PubMed PMID: 11156585; PubMed Central PMCID: PMC1572551. 12: Burgard EC, Niforatos W, van Biesen T, Lynch KJ, Kage KL, Touma E, Kowaluk EA, Jarvis MF. Competitive antagonism of recombinant P2X(2/3) receptors by 2', 3'-O-(2,4,6-trinitrophenyl) adenosine 5'-triphosphate (TNP-ATP). Mol Pharmacol. 2000 Dec;58(6):1502-10. PubMed PMID: 11093790. 13: Stewart RC, VanBruggen R, Ellefson DD, Wolfe AJ. TNP-ATP and TNP-ADP as probes of the nucleotide binding site of CheA, the histidine protein kinase in the chemotaxis signal transduction pathway of Escherichia coli. Biochemistry. 1998 Sep 1;37(35):12269-79. PubMed PMID: 9724541. 14: Lewis CJ, Surprenant A, Evans RJ. 2',3'-O-(2,4,6- trinitrophenyl) adenosine 5'-triphosphate (TNP-ATP)--a nanomolar affinity antagonist at rat mesenteric artery P2X receptor ion channels. Br J Pharmacol. 1998 Aug;124(7):1463-6. PubMed PMID: 9723959; PubMed Central PMCID: PMC1565549. 15: Pratap PR, Hellen EH, Palit A. Binding of TNP-ATP to IAF-labeled Na+/K(+)-ATPase as examined by fluorescence quenching. Ann N Y Acad Sci. 1997 Nov 3;834:445-8. PubMed PMID: 9405840. 16: Weber J, Senior AE. Binding of TNP-ATP and TNP-ADP to the non-catalytic sites of Escherichia coli F1-ATPase. FEBS Lett. 1997 Jul 21;412(1):169-72. PubMed PMID: 9257714. 17: Muneyuki E, Hisabori T, Sasayama T, Mochizuki K, Yoshida M. The heterogeneous interaction of substoichiometric TNP-ATP and F1-ATPase from Escherichia coli. J Biochem. 1996 Nov;120(5):940-5. PubMed PMID: 8982860. 18: Weber J, Senior AE. Binding and hydrolysis of TNP-ATP by Escherichia coli F1-ATPase. J Biol Chem. 1996 Feb 16;271(7):3474-7. PubMed PMID: 8631950.