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Sigma-Aldrich

ARL 67156 trisodium salt hydrate

≥98% (HPLC), solid, ecto-ATPase inhibitor

Synonym(s):

6-N,N-Diethyl-β-γ-dibromomethylene-D-adenosine-5′-triphosphate trisodium salt hydrate, FPL 67156

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About This Item

Empirical Formula (Hill Notation):
C15H21Br2N5Na3O12P3 · xH2O
CAS Number:
160928-38-1
Molecular Weight:
785.05 (anhydrous basis)
MDL number:
MFCD12910436
UNSPSC Code:
12352200
PubChem Substance ID:
24278252
NACRES:
NA.77

product name

ARL 67156 trisodium salt hydrate, ≥98% (HPLC), solid

Quality Level

100

assay

≥98% (HPLC)

form

solid

color

white to off-white

solubility

H2O: >20 mg/mL
DMSO: insoluble

storage temp.

−20°C

SMILES string

O.[Na+].[Na+].[Na+].CCN(CC)c1ncnc2n(cnc12)[C@@H]3O[C@H](COP(O)(=O)OP([O-])(=O)C(Br)(Br)P([O-])([O-])=O)[C@@H](O)[C@H]3O

InChI

1S/C15H24Br2N5O12P3.3Na.H2O/c1-3-21(4-2)12-9-13(19-6-18-12)22(7-20-9)14-11(24)10(23)8(33-14)5-32-37(30,31)34-36(28,29)15(16,17)35(25,26)27;;;;/h6-8,10-11,14,23-24H,3-5H2,1-2H3,(H,28,29)(H,30,31)(H2,25,26,27);;;;1H2/q;3*+1;/p-3/t8-,10-,11-,14-;;;;/m1..../s1

InChI key

UWMONIJVKGTUGE-OPKBHZIBSA-K

Gene Information

human ... ENTPD2(954)

General description

ARL 67156, a nucleotide/ATP analog is a competitive inhibitor of CD39. This ecto-ATPase inhibitor is presumed to be metabolically stable in biological studies due to its β, γ-dibromomethylene bridge.
ARL-67156 preferentially inhibits the degradation of ADP compared to the degradation of ATP in the murine colon. It is commonly employed to inhibit ATP hydrolysis in tissue preparations.

Application

ARL 67156 trisodium salt hydrate has been used:
  • to prevent ATP degradation during cerebrospinal fluid extraction
  • as an ATPase inhibitor in ATP quantification assay for preventing ATP degradation in cytoplasm and mitochondrion
  • as an ecto-ATPase inhibitor to treat cancer cells for ATP release assay

Biochem/physiol Actions

ecto-ATPase inhibitor; prevents metabolism of P2 purinoceptor agonists.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

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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Charlie H T Kwok et al.
Frontiers in immunology, 12, 626884-626884 (2021-04-27)
Increased afferent input resulting from painful injury augments the activity of central nociceptive circuits via both neuron-neuron and neuron-glia interactions. Microglia, resident immune cells of the central nervous system (CNS), play a crucial role in the pathogenesis of chronic pain.
T D Westfall et al.
European journal of pharmacology, 329(2-3), 169-173 (1997-06-25)
The influence of enzymatic degradation on the neurotransmitter actions of ATP was studied using the ecto-ATPase inhibitor 6-N,N-diethyl-D-beta,gamma-dibromomethyleneATP (ARL 67156). Field stimulation of the parasympathetic nerves innervating guinea-pig urinary bladder muscle strips (1-8 Hz for 20 s) produced characteristic biphasic
B E Crack et al.
British journal of pharmacology, 114(2), 475-481 (1995-01-01)
1. FPL 67156 (6-N,N-diethyl-beta, gamma-dibromomethylene-D-ATP), is a newly synthesized analogue of ATP. 2. In a rabbit isolated tracheal epithelium preparation, measuring P2U-purinoceptor-dependent chloride secretion, FPL 67156 was discovered to potentiate the responses to UTP but not those to ATP-gamma-S. UTP
S A Lévesque et al.
British journal of pharmacology, 152(1), 141-150 (2007-07-03)
ARL 67156, 6-N,N-Diethyl-D-beta-gamma-dibromomethylene adenosine triphosphate, originally named FPL 67156, is the only commercially available inhibitor of ecto-ATPases. Since the first report on this molecule, various ectonucleotidases responsible for the hydrolysis of ATP at the cell surface have been cloned and
A commonly used ecto-ATPase inhibitor, ARL-67156, blocks degradation of ADP more than the degradation of ATP in murine colon
Durnin L, et al.
Neurogastroenterology and Motility (2016)
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