TNP-ATP

For general laboratory use.

Please centrifuge briefly before opening (volume ≤2 ml).

Shipping: shipped on gel packs

Storage Conditions: store at -20 °C
Short term exposure (up to 1 week cumulative) to ambient temperature possible.

Shelf Life: 12 months after date of delivery

Molecular Formula: C₁₆H₁₇N₈O₁₉P₃

Molecular Weight: 718.27 g/mol

Exact Mass: 717.98 g/mol

CAS#: 120360-48-7

Purity: ≥ 95 % (HPLC)

Form: solution in water

Color: orange

Concentration: 10 mM - 11 mM

pH: 7.5 ±0.5

Spectroscopic Properties: λ_max 259/408/470 nm, ε 25.0/26.4/18.5 L mmol^-1 cm^-1 (Tris-HCl pH 7.5), λ_exc 408/470 nm, λ_em 552 nm

Applications:
Agonistic ligand, mainly for nucleoside receptor A₁
Nucleoside-triphosphates can be converted by different membrane-bound phosphatases into nucleosides acting as nucleoside receptor ligands. The ester form is protected during uptake and transport and can be well-directed released through activation.

Specific Ligands:

Ligand for purinergic receptors:
P2X₁, P2X₂^[1]

Antagonist for purinergic receptors:
P2X₁^[2,3], P2X₃^[3,6], P2X₄^[4], P2X^[5,7]

Selected References:
[1] Linan-Rico et al. (2015) Neuropharmacology of purinergic receptors in human sub- mucous plexus: Involvement of P2X1, P2X2, P2X3 channels, P2Y and A3 metabotropic receptors in neurotransmission. Neuropharmacology 95:83.
[2] Kur et al. (2014) Purinergic control of vascular tone in retina. J. Physiol. 592 (3):491.
[3] Alkayed et al. (2012) P2Y11 purinoceptor mediates the ATP-enhanced chemotactic response of neutrophils. J. Pharmacol. Sci. 120 (4):288.
[4] Manohar et al. (2012) ATP release and autocrine signaling Through P2X4 receptors regulate ?? T cell activation. J. Leukoc. Biol. 92 (4):787.
[5] Kamai et al. (2006) Involvement of ionotropic purinergic receptors in the histamine-induced enhancement of the cough reflex sensitivity in guinea pigs. Eur. J. Pharmacol. 547 (1-3):160.
[6] Jarvis et al. (2001) Modulation of BzATP and formalin induced nociception: attenuation by the P2X receptor antagonist, TNP-ATP and enhancement by the P2X3 allosteric modulator, cibacron blue. Br. J. Pharmacol. 132:259.
[7] Ruan et al. (2004) Identification of P2X receptors in cultured mouse and rat parasympathetic otic ganglion neurones including P2X knockout studies. Neuropharmacology 46:1039.
Seifert et al. (2012) Inhibitors of membranous adenylyl cyclases. Trends Pharmacol. Sci. 33 (2):64.
Adina-Zada et al. (2011) Probing the allosteric activation of pyruvate carboxylase using 2',3'-O- (2,4,6-trinitrophenyl) adenosine 5'-triphosphate as a fluorescent mimic of the allosteric activator acetyl CoA. Arch. Biochem. Biophys. 509 (2):117.
Volonte et al. (2009) Membrane components and purinergic signalling: the purinome, a complex interplay among ligands, degrading enzymes, receptors and transporters. FEBS J. 276:318.
Yegutkin (2008) Nucleotide and nucleoside converting enzymes: Important modulators of purinergic signalling cascade. Biochim. Biophys. Acta 1783:673.
Goettle et al. (2007) Molecular analysis of the interaction of Bordetella pertussis adenylyl cyclase with fluorescent nucleotides. Molecular Pharmacology 72 (3):526.
Sprang et al. (2006) Broad Specifity of Mammalian Adenylyl Cyclase for Interaction with 2',3'-Substituted Purine- and Pyrimidine Nucleotide Inhibitors. Mol. Pharmacol. 70:878.
Berman et al. (2003) Interaction of an aromatic dibromoisothiouronium derivative with the Ca (2+)-ATPase of skeletal muscle sarcoplasmic reticulum. Biochemistry 42:3556.
Milgrom et al. (1998) Bi-site activation occurs with the native and nucleotide-depleted mitochondrial F1-ATPase. Biochem J. 330:1037.
Faller et al. (1990) Binding of the fluorescent substrate analogue 2',3'-O- (2,4,6-trinitrophenylcyclohexadienylidene)-adenosine 5'-triphosphate to the gastric H+,K (+)-ATPase: evidence for cofactor-induced conformational changes in the enzyme. Biochemistry 29:3179.
Hiratsuka et al. (1982) Biological activities and spectroscopic properties of chromophoric and fluorescent analogs of adenine nucleoside and nucleotides, 2',3'-O- (2,4,6-trinitrocyclohexadienylidene) adenosine derivatives. Biochim Biophys Acta. 719:509.