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5.05734

Sigma-Aldrich

BzATP Triethylammonium Salt

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Synonym(s):
BzATP Triethylammonium Salt, 2ʹ(3ʹ)-O-(4-Benzoylbenzoyl)adenosine-­5ʹ-triphosphate tri(triethylammonium) salt, P2X7 Purinergic Receptor Agonist, BZATP, 2 ,3 -O-(4-benzoylbenzoyl)ATP, P2X Purinergic Receptor Agonist, BZATP
Empirical Formula (Hill Notation):
C24H24N5O15P3 · 3C6H15N
CAS Number:
112898-15-4
Molecular Weight:
1018.96
MDL number:
MFCD00058547

Assay

≥98% (HPLC)

Quality Level

100

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

white

solubility

water: 100 mM

storage temp.

−20°C

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

A prototypic P2X7 purinergic receptor agonist that exhibits about 3-fold higher agonistic potency for induction of nucleotide channels than ATP (EC50 = 15 µM vs 50 µM). Serves as a photo-affinity analog of ATP. Its agonistic activity is significantly reduced in the presence of serum albumin. Can serve as a substrate analog for submitochondrial particle ATPase activity (Km = 940 µM). Induces a dose-dependent decrease in wild-type murine neural progenitor cell viability and an increase in caspase-3 activity. These effects are not observed in P2X7-/- mice.

Warning

Toxicity: Standard Handling (A)

Other Notes

Messemer, N., et al. 2013. Neuropharmacology. 73, 122.
Michel, A.D., et al. 2001. Br. J. Pharmacol.132, 1501.
Erb, L., et al. 1990. J. Biol. Chem.265, 7424.

William, N., and Coleman, P.S. 1982. J. Biol. Chem.257, 2834.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Exploring the adenine nucleotide binding sites on mitochondrial F1-ATPase with a new photoaffinity probe, 3'-O-(4-benzoyl)benzoyl adenosine 5'-triphosphate.
N Williams et al.
The Journal of biological chemistry, 257(6), 2834-2841 (1982-03-25)
Nanette Messemer et al.
Neuropharmacology, 73, 122-137 (2013-06-04)
Neurogenesis requires the balance between the proliferation of newly formed progenitor cells and subsequent death of surplus cells. RT-PCR and immunocytochemistry demonstrated the presence of P2X7 receptor mRNA and immunoreactivity in cultured neural progenitor cells (NPCs) prepared from the adult
L Erb et al.
The Journal of biological chemistry, 265(13), 7424-7431 (1990-05-05)
ATP, 3'-O-(4-benzoyl)benzoyl-ATP (BzATP), a photoaffinity analog of ATP, and several other ATP analogs induced an increase in plasma membrane permeability to monovalent ions and normally impermeant metabolites, including nucleotides, in transformed 3T6 mouse fibroblasts. The rank order of agonist potency
A D Michel et al.
British journal of pharmacology, 132(7), 1501-1508 (2001-03-27)
1. 2'-& 3'-O-(4-benzoylbenzoyl)-ATP (BzATP) is the prototypic agonist for P2X(7) receptors. In this study we demonstrate that bovine serum albumin (BSA) can affect the potency of BzATP at P2X receptors. 2. BzATP potency (pEC(50)) to stimulate ethidium accumulation in cells

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