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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:
Molecular Weight:
785.05 (anhydrous basis)
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

product name

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

Quality Level

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 Code

11 - Combustible Solids

WGK

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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Laura Schäkel et al.
Frontiers in pharmacology, 11, 1294-1294 (2020-10-06)
Nucleoside triphosphate diphosphohydrolase1 (NTPDase1, CD39) inhibitors have potential as novel drugs for the (immuno)therapy of cancer. They increase the extracellular concentration of immunostimulatory ATP and reduce the formation of AMP, which can be further hydrolyzed by ecto-5'-nucleotidase (CD73) to immunosuppressive
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)
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
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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