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Merck

B6396

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

≥93%

Sinónimos:

Benzoylbenzoyl-ATP, Bz-ATP

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About This Item

Fórmula empírica (notación de Hill):
C24H24N5O15P3 · xC6H15N × yH2O
Número CAS:
112898-15-4
Peso molecular:
715.39 (anhydrous free acid basis)
NACRES:
NA.77
PubChem Substance ID:
329773276
UNSPSC Code:
12352202
MDL number:
MFCD00058547

Nombre del producto

2′(3′)-O-(4-Benzoylbenzoyl)adenosine 5′-triphosphate triethylammonium salt, ≥93%

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

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 key

HVOVBTNCGADRTH-WBLDMZOZSA-N

biological source

synthetic (organic)

assay

≥93%

form

powder

solubility

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

storage temp.

−20°C

Quality Level

200

Categorías relacionadas

Other Notes

Mixed isomers

Application

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.

Biochem/physiol Actions

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.

General description

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

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number
0000515108
0000515108
0000473415
0000473415
0000461342

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Visite la Librería de documentos

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)
Diabetes-induced Neuropathic Mechanical Hyperalgesia Depends on P2X4 Receptor Activation in Dorsal Root Ganglia
Teixeira JM, et al.
Neuroscience, 398, 158-170 (2019)
Ji Zhao et al.
Molecular neurodegeneration, 4, 4-4 (2009-01-16)
Insulin-degrading enzyme (IDE) is a ubiquitously expressed zinc-metalloprotease that degrades several pathophysiologically significant extracellular substrates, including insulin and the amyloid beta-protein (Abeta), and accumulating evidence suggests that IDE dysfunction may be operative in both type 2 diabetes mellitus and Alzheimer
Molecular and functional properties of P2X receptors?recent progress and persisting challenges
Kaczmarek-Hajek K, et al.
Purinergic Signaling, 8(3), 375-417 (2012)
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