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A265

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)
UNSPSC Code:
12352200
PubChem Substance ID:
24278252
NACRES:
NA.77
MDL number:
MFCD12910436
Assay:
≥98% (HPLC)
Form:
solid
Quality level:
100
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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)

Related Categories

General description

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.
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.

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

WGK 3

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Certificates of Analysis (COA)

Lot/Batch Number
0000212156
0000212151
0000212156
0000212151
0000210941

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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
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
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.
Wanfeng Xu et al.
Cell metabolism, 33(2), 424-436 (2020-12-15)
Caspase-4 is an intracellular sensor for cytosolic bacterial lipopolysaccharide (LPS) and underlies infection-elicited pyroptosis. It is unclear whether and how caspase-4 detects host-derived factors to trigger pyroptosis. Here we show that mitochondrial permeability transition (MPT) activates caspase-4 by promoting the
T D Westfall et al.
British journal of pharmacology, 117(5), 867-872 (1996-03-01)
1. Field stimulation of the sympathetic nerves of the guinea-pig isolated vas deferens with trains of pulses of 20 s at 1-8 Hz produced characteristic biphasic contractions. The effect of the novel ecto-ATPase inhibitor, 6-N,N-diethyl-D-beta, gamma-dibromomethyleneATP (ARL 67156, formerly known
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Global Trade Item Number

SKUGTIN
A265-25MG04061832945231
A265-5MG04061833359600
SAB4100313-200UL04061836269586

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