ARL 67156

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 531470

CAS#: 1021868-83-6

Description: ARL 67156 is a research compound used experimantally as the trisodium salt. It is an inhibitor of ecto-ATPase activity. Structurally, ARL 67156 is an analogue of ATP and therefore competes with substrate at the enzyme.

Chemical Structure

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ARL 67156
CAS# 1021868-83-6
Instruction

Theoretical Analysis

MedKoo Cat#: 531470
Name: ARL 67156
CAS#: 1021868-83-6
Chemical Formula: C15H24Br2N5O12P3
Exact Mass: 716.90
Molecular Weight: 719.109
Elemental Analysis: C, 25.05; H, 3.36; Br, 22.22; N, 9.74; O, 26.70; P, 12.92

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: ARL 67156; ARL-67156; ARL67156

IUPAC/Chemical Name: [dibromo-[[[(2R,3S,4R,5R)-5-(6-diethylaminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]methyl]phosphonic acid

InChi Key: FGVPLSHBVJFZKC-WHIQPUKWSA-N

InChi Code: InChI=1S/C15H24Br2N5O12P3/c1-4-21(5-2)11-8-12(19-6-18-11)22(7-20-8)13-9(23)10(24)14(32-13)33-37(30,31-3)34-36(28,29)15(16,17)35(25,26)27/h6-7,9-10,13-14,23-24H,4-5H2,1-3H3,(H,28,29)(H2,25,26,27)/t9-,10+,13-,14-,37?/m1/s1

SMILES Code: O=P(C(Br)(P(O)(O)=O)Br)(OP(O[C@H]1O[C@@H](N2C=NC3=C(N(CC)CC)N=CN=C23)[C@H](O)[C@@H]1O)(OC)=O)O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 719.11 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Rocha JN. Extracellular adenosine 5'-triphosphate concentrations changes in rat spinal cord associated with the activation of urinary bladder afferents. A microdialysis study. Einstein (Sao Paulo). 2016 Oct-Dec;14(4):541-546. doi: 10.1590/S1679-45082016AO3794. English, Portuguese. PubMed PMID: 28076603.

2: Durnin L, Moreland N, Lees A, Mutafova-Yambolieva VN. A commonly used ecto-ATPase inhibitor, ARL-67156, blocks degradation of ADP more than the degradation of ATP in murine colon. Neurogastroenterol Motil. 2016 Sep;28(9):1370-81. doi: 10.1111/nmo.12836. PubMed PMID: 27060478; PubMed Central PMCID: PMC5002237.

3: Lam M, Mitsui R, Hashitani H. Electrical properties of purinergic transmission in smooth muscle of the guinea-pig prostate. Auton Neurosci. 2016 Jan;194:8-16. doi: 10.1016/j.autneu.2015.11.003. PubMed PMID: 26657181.

4: Bogacheva PO, Balezina OP. Postsynaptic Potentiation in Mouse Motor Synapses Induced by ATP Accumulation in Synaptic Cleft. Bull Exp Biol Med. 2015 Sep;159(5):583-7. doi: 10.1007/s10517-015-3018-2. PubMed PMID: 26463054.

5: George J, Gonçalves FQ, Cristóvão G, Rodrigues L, Meyer Fernandes JR, Gonçalves T, Cunha RA, Gomes CA. Different danger signals differently impact on microglial proliferation through alterations of ATP release and extracellular metabolism. Glia. 2015 Sep;63(9):1636-45. doi: 10.1002/glia.22833. PubMed PMID: 25847308.

6: Wang L, Hu L, Grygorczyk R, Shen X, Schwarz W. Modulation of extracellular ATP content of mast cells and DRG neurons by irradiation: studies on underlying mechanism of low-level-laser therapy. Mediators Inflamm. 2015;2015:630361. doi: 10.1155/2015/630361. PubMed PMID: 25691809; PubMed Central PMCID: PMC4322657.

7: Lopatář J, Dale N, Frenguelli BG. Pannexin-1-mediated ATP release from area CA3 drives mGlu5-dependent neuronal oscillations. Neuropharmacology. 2015 Jun;93:219-28. doi: 10.1016/j.neuropharm.2015.01.014. PubMed PMID: 25645390.

8: Schachter J, Delgado KV, Barreto-de-Souza V, Bou-Habib DC, Persechini PM, Meyer-Fernandes JR. Inhibition of ecto-ATPase activities impairs HIV-1 infection of macrophages. Immunobiology. 2015 May;220(5):589-96. doi: 10.1016/j.imbio.2014.12.004. PubMed PMID: 25577295.

9: Aldi S, Marino A, Tomita K, Corti F, Anand R, Olson KE, Marcus AJ, Levi R. E-NTPDase1/CD39 modulates renin release from heart mast cells during ischemia/reperfusion: a novel cardioprotective role. FASEB J. 2015 Jan;29(1):61-9. doi: 10.1096/fj.14-261867. PubMed PMID: 25318477; PubMed Central PMCID: PMC4285537.

10: Gao YD, Cao J, Li P, Huang G, Yang J. Th2 cytokine-primed airway smooth muscle cells induce mast cell chemotaxis via secretion of ATP. J Asthma. 2014 Dec;51(10):997-1003. doi: 10.3109/02770903.2014.939283. PubMed PMID: 25272186.

11: Syed SK, Kauffman AL, Beavers LS, Alston JT, Farb TB, Ficorilli J, Marcelo MC, Brenner MB, Bokvist K, Barrett DG, Efanov AM. Ectonucleotidase NTPDase3 is abundant in pancreatic β-cells and regulates glucose-induced insulin secretion. Am J Physiol Endocrinol Metab. 2013 Nov 15;305(10):E1319-26. doi: 10.1152/ajpendo.00328.2013. PubMed PMID: 24085034.

12: Ho CL, Yang CY, Lin WJ, Lin CH. Ecto-nucleoside triphosphate diphosphohydrolase 2 modulates local ATP-induced calcium signaling in human HaCaT keratinocytes. PLoS One. 2013;8(3):e57666. doi: 10.1371/journal.pone.0057666. PubMed PMID: 23536768; PubMed Central PMCID: PMC3594229.

13: Sakowicz-Burkiewicz M, Grden M, Maciejewska I, Szutowicz A, Pawelczyk T. High glucose impairs ATP formation on the surface of human peripheral blood B lymphocytes. Int J Biochem Cell Biol. 2013 Jul;45(7):1246-54. doi: 10.1016/j.biocel.2013.03.008. PubMed PMID: 23523697.

14: Chávez J, Vargas MH, Rebollar-Ayala DC, Díaz-Hernández V, Cruz-Valderrama JE, Flores-Soto E, Flores-García M, Jiménez-Vargas NN, Barajas-López C, Montaño LM. Inhibition of extracellular nucleotides hydrolysis intensifies the allergic bronchospasm. A novel protective role of ectonucleotidases. Allergy. 2013 Apr;68(4):462-71. doi: 10.1111/all.12113. PubMed PMID: 23414231.

15: Côté N, El Husseini D, Pépin A, Bouvet C, Gilbert LA, Audet A, Fournier D, Pibarot P, Moreau P, Mathieu P. Inhibition of ectonucleotidase with ARL67156 prevents the development of calcific aortic valve disease in warfarin-treated rats. Eur J Pharmacol. 2012 Aug 15;689(1-3):139-46. doi: 10.1016/j.ejphar.2012.05.016. PubMed PMID: 22659116.

16: Yegutkin GG, Wieringa B, Robson SC, Jalkanen S. Metabolism of circulating ADP in the bloodstream is mediated via integrated actions of soluble adenylate kinase-1 and NTPDase1/CD39 activities. FASEB J. 2012 Sep;26(9):3875-83. doi: 10.1096/fj.12-205658. PubMed PMID: 22637533; PubMed Central PMCID: PMC3425827.

17: Iglesias RM, Spray DC. Pannexin1-mediated ATP release provides signal transmission between Neuro2A cells. Neurochem Res. 2012 Jun;37(6):1355-63. doi: 10.1007/s11064-012-0720-6. PubMed PMID: 22359052; PubMed Central PMCID: PMC3626166.

18: Amobi NI, Guillebaud J, Smith IC. Perspective on the role of P2X-purinoceptor activation in human vas deferens contractility. Exp Physiol. 2012 May;97(5):583-602. doi: 10.1113/expphysiol.2011.063206. PubMed PMID: 22227201.

19: Witts EC, Panetta KM, Miles GB. Glial-derived adenosine modulates spinal motor networks in mice. J Neurophysiol. 2012 Apr;107(7):1925-34. doi: 10.1152/jn.00513.2011. PubMed PMID: 22205649; PubMed Central PMCID: PMC3331664.

20: Vetri F, Xu H, Mao L, Paisansathan C, Pelligrino DA. ATP hydrolysis pathways and their contributions to pial arteriolar dilation in rats. Am J Physiol Heart Circ Physiol. 2011 Oct;301(4):H1369-77. doi: 10.1152/ajpheart.00556.2011. PubMed PMID: 21803949; PubMed Central PMCID: PMC3197358.