2',3'-O-Trinitrophenyl-adenosine-5'-triphosphate, Triethylammonium salt
For research use only!
Shipping: shipped on blue ice
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: C16H16N8O19P3
Molecular Weight: 718.27 g/mol
Purity: ≥ 95 % (HPLC)
Form: orange solution in water
Concentration: 10 mM - 11 mM
pH: 7.5 ±0.5
Spectroscopic Properties: λmax 259/408/470 nm, ε 25.0/26.4/18.5 L mmol-1 cm-1 (Tris-HCl pH 7.5), λexc 408/470 nm, λem 552 nm
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.
Ligand for purinergic receptors:
Antagonist for purinergic receptors:
P2X1[2,3], P2X3[3,6], P2X4, P2X[5,7]
 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.
 Kur et al. (2014) Purinergic control of vascular tone in retina. J. Physiol. 592 (3):491.
 Alkayed et al. (2012) P2Y11 purinoceptor mediates the ATP-enhanced chemotactic response of neutrophils. J. Pharmacol. Sci. 120 (4):288.
 Manohar et al. (2012) ATP release and autocrine signaling Through P2X4 receptors regulate ?? T cell activation. J. Leukoc. Biol. 92 (4):787.
 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.
 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.
 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.