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Key Documents

B6396

Sigma-Aldrich

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

≥93%

Sinônimo(s):

Benzoylbenzoyl-ATP, Bz-ATP

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About This Item

Fórmula empírica (Notação de Hill):
C24H24N5O15P3 · xC6H15N × yH2O
Número CAS:
Peso molecular:
715.39 (anhydrous free acid basis)
Número MDL:
Código UNSPSC:
12352202
ID de substância PubChem:
NACRES:
NA.77

fonte biológica

synthetic (organic)

Ensaio

≥93%

forma

powder

solubilidade

water: 50 mg/mL, clear, colorless to faintly yellow

temperatura de armazenamento

−20°C

cadeia de caracteres SMILES

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

chave InChI

HVOVBTNCGADRTH-WBLDMZOZSA-N

Descrição geral

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

Aplicação

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

Ações bioquímicas/fisiológicas

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

Outras notas

Mixed isomers

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

Eyeshields, Gloves, type N95 (US)


Certificados de análise (COA)

Busque Certificados de análise (COA) digitando o Número do Lote do produto. Os números de lote e remessa podem ser encontrados no rótulo de um produto após a palavra “Lot” ou “Batch”.

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Visite a Biblioteca de Documentos

P2X7 receptor inhibition increases CNTF in the subventricular zone, but not neurogenesis or neuroprotection after stroke in adult mice
Kang SS, et al.
Translational Stroke Research, 4(5), 533-545 (2013)
Receptor-independent effects of 2?(3?)-O-(4-benzoylbenzoyl) ATP triethylammonium salt on cytosolic pH
Reyes JP, et al.
Purinergic Signaling, 9(4), 687-693 (2013)
Benzophenone-ATP: A photoaffinity label for the active site of ATPases
Test, 126, 667-682 (1986)
Juan Francisco Codocedo et al.
PloS one, 8(3), e57626-e57626 (2013-03-09)
To assess the putative role of adenosine triphosphate (ATP) upon nitric oxide (NO) production in the hippocampus, we used as a model both rat hippocampal slices and isolated hippocampal neurons in culture, lacking glial cells. In hippocampal slices, additions of
Covalent binding of 3'-O-(4-benzoyl) benzoyl adenosine 5'-triphosphate (BzATP) to the isolated alpha and beta subunits and the alpha 3 beta 3 core complex of TF1. Covalent binding of BzATP prevents association of alpha and beta subunits and induces dissociation of the alpha 3 beta 3 core complex.
BarZvi D, et al.
The Journal of Biological Chemistry, 267(16), 11029-11033 (1992)

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