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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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MXP 3,040.00
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MXP 8,454.00

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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

MXP 3,040.00

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biological source

synthetic (organic)

Quality Level

200

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
A5763ATPDS-RO809608
2′(3′)-O-(4-Benzoylbenzoyl)adenosine 5′-triphosphate triethylammonium salt ≥93%

B6396

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

Adenosine 3′,5′-diphosphate disodium salt ≥96%

A5763

Adenosine 3′,5′-diphosphate disodium salt

Adenosine 5′-triphosphate disodium salt trihydrate =99%, pkg of 1 g (10519979001), pkg of 5 g (10519987001)

ATPDS-RO

Adenosine 5′-triphosphate disodium salt trihydrate

Biotin-2′,2′,3′,3′-d4 ≥98 atom % D, ≥95% (CP)

809608

Biotin-2′,2′,3′,3′-d4

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

solubility

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

solubility

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

solubility

-

solubility

-

storage temp.

−20°C

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

−20°C

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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Certificates of Analysis (COA)

Lot/Batch Number
0000461342
0000461342
0000454221
0000454221
0000422252

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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)
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
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