SQ22536

Names

[ Name ]:
SQ22536

[Synonym ]:
9-(Tetrahydro-2-furanyl)-9H-purin-6-amine,9-THF-Ade
9H-Purin-6-amine, 9-(tetrahydro-2-furanyl)-
9-(oxolan-2-yl)purin-6-amine
9-(tetrahydrofuran-2-yl)-9h-purin-6-amine
9-(Tetrahydrofuryl)adenine
MFCD00210216
9-(Tetrahydro-2-furanyl)-9H-purin-6-amine
SQ 22536
SQ22536

Biological Activity

[Description]:

SQ22536 is an effective adenylate cyclase (AC) inhibitor.

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Adenylate Cyclase

Research Areas >> Metabolic Disease

[Target]

adenylate cyclase (AC)[1]

[In Vitro]

SQ22536 (SQ22,536) effectively inhibits the effect of forskolin with respective IC50 values of 5 μM.Preincubation with graded concentrations of SQ22536 reveals that both SQ22536 effectively inhibits PACAP-induced reporter gene activation with approximate IC50 value of 5 μM. SQ22536 more potently inhibits forskolin-induced Elk activation (IC50=10 μM) than 8-Br-cAMP-induced Elk activation (IC50=170 μM). Most notably, there are substantial differences in the reported potencies of SQ22536 to inhibit the activities of recombinant AC5 and AC6, with respective IC50 values of 2 μM and 360 μM. At a greater concentration (500 μM), SQ22536 significantly inhibits neurite elongation due to either forskolin or 8-Br-cAMP[1].

[Cell Assay]

HEK293 CRE-luc2P GloResponse luciferase reporter cells are transduced with retroviral vectors expressing rat PAC1hop receptors. Individual cell lines are obtained by limiting dilution cloning, and a clonal PAC1-expressing line is propagated and used for CRE luciferase assays. In brief, HEK293 CRE-luc2P cells are plated in 96-well plates (10,000 cells in 80 μL media per well) in assay media (DMEM supplemented with 1% fetal bovine serum). One day after plating, cells are treated with AC inhibitors (10 μL in assay media/well) for 30 minutes, followed by agonists (10 μL in assay media/well), and are incubated for 4 hours. Luciferase activity is determined after the addition of 100 μL/well Bright-Glo Luciferase Assay Reagent. Luminescence (RLU) is measured in a Victor3 microtiter plate reader after 2 minutes of agitation at room temperature. Cyclic AMP is measured in NS-1 cells. In brief, NS-1 cells are seeded and grown overnight in 96-well plates. The next day, cells are pretreated for 20 minutes in media containing the phosphodiesterase inhibitor 3-isobutyl-1-methylxanthine (0.5 mM) with or without SQ22536. After pretreatment with inhibitors, cells are stimulated with agonists, added as 10× solutions, for an additional 20 minutes. Intracellular cAMP is then assayed using the cAMP Biotrak enzyme immunoassay kit for measurement of nonacetylated cAMP[1].

[References]

[1]. Emery AC, et al. A new site and mechanism of action for the widely used adenylate cyclase inhibitor SQ22,536. Mol Pharmacol. 2013 Jan;83(1):95-105.

[Related Small Molecules]

Forskolin | α-MSH trifluoroacetate salt | ST 034307 | CB-7921220 | Small Cardioactive Peptide B (SCPB)

Chemical & Physical Properties

[ Density]:
1.7±0.1 g/cm3

[ Boiling Point ]:
474.8±55.0 °C at 760 mmHg

[ Melting Point ]:
160-161ºC

[ Molecular Formula ]:
C₉H₁₁N₅O

[ Molecular Weight ]:
205.217

[ Flash Point ]:
241.0±31.5 °C

[ Exact Mass ]:
205.096359

[ PSA ]:
78.85000

[ LogP ]:
-0.17

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.831

Safety Information

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
26-36

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
2934999090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2934999090

[ Summary ]:
2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Compartmentalization of distinct cAMP signaling pathways in mammalian sperm.

J. Biol. Chem. 288(49) , 35307-20, (2013)

Fertilization competence is acquired in the female tract in a process known as capacitation. Capacitation is needed for the activation of motility (e.g. hyperactivation) and to prepare the sperm for a...

Ibudilast, a mixed PDE3/4 inhibitor, causes a selective and nitric oxide/cGMP-independent relaxation of the intracranial vertebrobasilar artery.

Eur. J. Pharmacol. 650(2-3) , 605-11, (2011)

Ibudilast, a mixed phosphodiesterase (PDE) 3/4 inhibitor, is a cerebral vasodilator widely used in Japan for treating post-stroke dizziness. However, little studies have been conducted on the vasorela...

IL-6, A1 and A2aR: a crosstalk that modulates BDNF and induces neuroprotection.

Biochem. Biophys. Res. Commun. 449(4) , 477-82, (2014)

Several diseases are related to retinal ganglion cell death, such as glaucoma, diabetes and other retinopathies. Many studies have attempted to identify factors that could increase neuroprotection aft...

Related Compounds

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