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B6396

Sigma-Aldrich

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

≥93%

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Synonym(s):
Benzoylbenzoyl-ATP, Bz-ATP
Empirical Formula (Hill Notation):
C24H24N5O15P3 · xC6H15N × yH2O
CAS Number:
Molecular Weight:
715.39 (anhydrous free acid basis)
MDL number:
PubChem Substance ID:
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

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This Item
A5763D7159809608
assay

≥93%

assay

≥96%

assay

≥90% (HPLC)

assay

≥95% (CP)

form

powder

form

powder

form

powder

form

powder

solubility

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

solubility

water: 25 mg/mL, clear, colorless to very faintly yellow

solubility

water: 1 mg/mL, clear, colorless

solubility

-

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

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

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Osmotic surveillance mediates rapid wound closure through nucleotide release
Gault WJ, et al.
The Journal of Cell Biology, 207(6), 767-782 (2014)
Diabetes-induced Neuropathic Mechanical Hyperalgesia Depends on P2X4 Receptor Activation in Dorsal Root Ganglia
Teixeira JM, et al.
Neuroscience, 398, 158-170 (2019)
Molecular and functional properties of P2X receptors?recent progress and persisting challenges
Kaczmarek-Hajek K, et al.
Purinergic Signaling, 8(3), 375-417 (2012)
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)
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)

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