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B6396

Sigma-Aldrich

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

≥93%

Synonym(s):

Benzoylbenzoyl-ATP, Bz-ATP

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About This Item

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

biological source

synthetic (organic)

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

General description

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

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.

Other Notes

Mixed isomers

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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