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5.05758

Oxidized ATP (oATP)

≥97% (HPLC), Schiff-base-forming reagent, powder

Synonym(s):

Oxidized ATP (oATP), Purinergic Receptor Antagonist, Oxidized ATP, Purinergic Receptor P2X7 Antagonist, Oxidized ATP, Purinergic Receptor Inhibitor, Oxidized ATP, O-ATP

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About This Item

Empirical Formula (Hill Notation):
C10H14N5O13P3
CAS Number:
71997-40-5
Molecular Weight:
505.17
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD00056956
Assay:
≥97% (HPLC)
Form:
powder
Quality level:
100
Storage condition:
OK to freeze, protect from light
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Product Name

Oxidized ATP (oATP),

assay

≥97% (HPLC)

Quality Level

100

form

powder

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze, protect from light

color

white

solubility

water: 50 mg/mL

storage temp.

−20°C

SMILES string

[Na].[P](=O)(O[P](=O)(OCC(OC([n]1c2ncnc(c2nc1)N)C=O)C=O)O)(O[P](=O)(O)O)O

InChI

1S/C10H14N5O13P3.Na/c11-9-8-10(13-4-12-9)15(5-14-8)7(2-17)26-6(1-16)3-25-30(21,22)28-31(23,24)27-29(18,19)20;/h1-2,4-7H,3H2,(H,21,22)(H,23,24)(H2,11,12,13)(H2,18,19,20);

InChI key

KOCWSVPHHGJWHA-UHFFFAOYSA-N

General description

Oxidized ATP (oATP) is a Schiff-base-forming reagent is utilized as an antagonist at the P2X7 receptor for several years. It was initially identified as an affinity reagent for nucleotide-binding proteins. oATP reduces nuclear factor kappa B (NF-κB) activation and IL-8 release in cells lacking P2X7R, suggesting that some anti-inflammatory effects of oATP may not be solely attributed to the blockade of the P2X7R. This effect of oATP is reminiscent of the action of other natural or synthetic Schiff-base-forming reagents with immunomodulatory activity.

Application

Oxidized ATP (oATP) may be used to study its effects on the proinflammatory responses in human umbilical vein endothelial cells (HUVEC), HEK293 cells, and 1321N1 astrocytes that lack expression of P2X7R.

Biochem/physiol Actions

Reversible: no

Other Notes

Vergani, A., et al. 2013. Diabetes62, 1665.
DellʹAntonio, G., et al. 2002. Arthritis Rheum.46, 3378.
Wiley, J.S., et al. 1994. Br. J. Pharmacol.112, 946.

Murgia, M., et al. 1992. J. Biol. Chem.268, 8199.

Legal Information

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

Disclaimer

Toxicity: Standard Handling (A)

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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Oxidized ATP (oATP) attenuates proinflammatory signaling via P2 receptor-independent mechanisms
Beigi RD, et al.
British Journal of Pharmacology, 140(3), 507-519 (2003)
Novel data point to a broader mechanism of action of oxidized ATP: the P2X7 receptor is not the only target
Di Virgilio F, et al.
British Journal of Pharmacology, 140(3), 441-443 (2003)

Global Trade Item Number

SKUGTIN
505758000104055977243482