B6396

2′(3′)-O-(4-Benzoylbenzoyl)adenosine 5′-triphosphate triethylammonium salt

≥93%

• Synonym(s): Benzoylbenzoyl-ATP, Bz-ATP
• Empirical Formula (Hill Notation): C₂₄H₂₄N₅O₁₅P₃ · xC₆H₁₅N × yH₂O
• CAS Number: 112898-15-4
• Molecular Weight: 715.39 (anhydrous free acid basis)
• MDL number: MFCD00058547
• UNSPSC Code: 12352202
• PubChem Substance ID: 329773276
• NACRES: NA.77

Properties

• biological source: synthetic (organic)
• Quality Level: 200
• assay: ≥93%
• form: powder
• solubility: water: 50 mg/mL, clear, colorless to faintly yellow
• storage temp.: −20°C
• SMILES string: CCN(CC)CC.Nc1ncnc2n(cnc12)[C@@H]3O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](OC(=O)c4ccc(cc4)C(=O)c5ccccc5)[C@H]3O
• InChI: 1S/C24H24N5O15P3.C6H15N/c25-21-17-22(27-11-26-21)29(12-28-17)23-19(31)20(16(41-23)10-40-46(36,37)44-47(38,39)43-45(33,34)35)42-24(32)15-8-6-14(7-9-15)18(30)13-4-2-1-3-5-13;1-4-7(5-2)6-3/h1-9,11-12,16,19-20,23,31H,10H2,(H,36,37)(H,38,39)(H2,25,26,27)(H2,33,34,35);4-6H2,1-3H3/t16-,19-,20-,23-;/m1./s1
• InChI key: HVOVBTNCGADRTH-WBLDMZOZSA-N

Description

General description

2′(3′)-O-(4-Benzoylbenzoyl)adenosine 5′-triphosphate is a photoreactive analog of ATP.[1]

Application

2′(3′)-O-(4-Benzoylbenzoyl)adenosine 5′-triphosphate triethylammonium salt has been used as a P2X4 receptor agonist in rat kidney sections,[2] type I diabetes induced rats[3] and astrocyte−neuron coculture.[4] It has also been used as a synthetic ATP analog in isotonic E3 medium.[5]

Useful as a photoaffinity label for proteins and enzymes that bind ATP.

Biochem/physiol Actions

2′(3′)-O-(4-Benzoylbenzoyl)adenosine 5′-triphosphate triethylammonium salt is a selective purinergic receptor (P2X) agonist.[6] It is more potent than ATP at homodimeric P2X7 receptors. It also effectively activates P2X1, P2X2, and P2X3 receptors.[7] Useful as a photoaffinity label for proteins and enzymes that bind ATP.[8]

Selective P2X purinergic agonist. It is more potent than ATP at homodimeric P2X7 receptors.

Other Notes

Mixed isomers

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)