The molecular weight listed for this material is the anhydrous-free acid. The triethylammonium and water content are variable from lot to lot. The maximum allowable water content is 6%, while the expected triethylammonium specification range is 0.5-4.4 mol/mol BzATP. The triethylammonium and water content are reported on the lot-specific Certificate of Analysis.
B6396
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:
Molecular Weight:
715.39 (anhydrous free acid basis)
MDL number:
UNSPSC Code:
12352202
PubChem Substance ID:
NACRES:
NA.77
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biological source
synthetic (organic)
Quality Level
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
Related Categories
1 of 4
This Item | A5763 | ATPDS-RO | 809608 |
|---|---|---|---|
| biological source synthetic (organic) | biological source synthetic (inorganic) | biological source - | biological source - |
| assay ≥93% | assay ≥96% | assay 99% | assay ≥95% (CP) |
| Quality Level 200 | Quality Level 200 | Quality Level 100 | Quality Level 200 |
| form powder | form powder | form crystals | form powder |
| storage temp. −20°C | storage temp. −20°C | storage temp. 2-8°C | storage temp. −20°C |
| solubility water: 50 mg/mL, clear, colorless to faintly yellow | solubility water: 25 mg/mL, clear, colorless to very faintly yellow | solubility - | solubility - |
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
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
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Molecular and functional properties of P2X receptors?recent progress and persisting challenges
Kaczmarek-Hajek K, et al.
Purinergic Signaling, 8(3), 375-417 (2012)
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
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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The molecular weight of this reagent is displayed as 715.39 on the specification sheet, but it actually contains triphosphate triethylammonium and water, so how should I think about the molecular weight?
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