| Identification | Back Directory | [Name]
SQ 22,536 | [CAS]
17318-31-9 | [Synonyms]
Ax 100
CS-2551
SQ 22,536
Nsc 53339
9-THF-Ade
SQ 22536;SQ-22536
SQ22,536/Inhibitor
SQ22536 (NSC-53339)
9-(Tetrahydrofuran-2-yl)
Tetrahydrofuryl-9-adenine
9-(Tetrahydrofuryl)adenine
9-(2-tetrahydrofuryl)adenine
9-(oxolan-2-yl)purin-6-amine
9-(TETRAHYDRO-2'-FURYL)ADENINE
SQ 22,536 ADENYLATE CYCLASE INH
Adenine, 9-(tetrahydro-2-furyl)-
9-(oxolan-2-yl)-9H-purin-6-amine
SQ 22536 - CAS 17318-31-9 - Calbiochem
6-Amino-9-(tetrahydro-2-furyl)-9H-purine
Adenine, 9-(tetrahydro-2-furanyl)- (8ci)
9-(Tetrahydrofuran-2-yl)-9H-purin-6-aMine
9-(Tetrahydro-2-furynal)-9H-purin-6-amine
9-(TETRAHYDRO-2-FURANYL)-9H-PURIN-6-AMINE
9-(TETRAHYDRO-2-FURANYL)-9H-PURINE-6-AMINE
9-(Tetrahydrofuran-2-yl)-9H-purine-6-amine
9H-Purin-6-aMine, 9-(tetrahydro-2-furanyl)-
6-Amino-9-[(tetrahydrofuran)-2-yl]-9H-purine
9H-Purin-6-amine, 9-(tetrahydro-2-furanyl)- (9ci)
9-THF-ADE;9-(TETRAHYDROFURAN-2-YL)-9H-PURIN-6-AMINE
9-(Tetrahydro-2-furanyl)-9H-purin-6-amine, 9-THF-Ade | [EINECS(EC#)]
633-987-7 | [Molecular Formula]
C9H11N5O | [MDL Number]
MFCD00210216 | [MOL File]
17318-31-9.mol | [Molecular Weight]
205.22 |
| Chemical Properties | Back Directory | [Melting point ]
160-161℃ | [Boiling point ]
474.8±55.0 °C(Predicted) | [density ]
1.70±0.1 g/cm3(Predicted) | [storage temp. ]
0-6°C | [solubility ]
H2O: 21 mg/mL
| [form ]
solid
| [pka]
3.82±0.10(Predicted) | [color ]
white to off-white
| [InChI]
InChI=1S/C9H11N5O/c10-8-7-9(12-4-11-8)14(5-13-7)6-2-1-3-15-6/h4-6H,1-3H2,(H2,10,11,12) | [InChIKey]
UKHMZCMKHPHFOT-UHFFFAOYSA-N | [SMILES]
N1C2C(=NC=NC=2N)N(C2CCCO2)C=1 |
| Hazard Information | Back Directory | [Definition]
ChEBI: A nucleoside analogue that is adenine in which the nitrogen at position 9 has been substituted by a tetrahydrofuran-2-yl group. It is an adenylate cyclase inhibitor. | [Biological Activity]
Inhibitor of adenylyl cyclase (IC 50 = 1.4 μ M). Inhibits PGE 1 -stimulated increases in cAMP levels in intact human platelets. | [Description]
SQ 22,536 is an inhibitor of adenylyl cyclase with an IC50 value of 13 μM for inhibition of prostaglandin E1-stimulated increase in cAMP in intact platelets. It has been used to evaluate adenylyl cyclase activity during iloprost-induced vasorelaxation of isolated pulmonary veins or aorta in several research paradigms, inhibiting cAMP elevation at concentrations of 100-300 μM without effecting relaxation. | [Uses]
SQ 22,536 was used to study the role of adenylate cyclase in differentiation of PC12 cells and in gap junctional intercellular communication in breast cancer cells. | [Biochem/physiol Actions]
SQ 22,536 is an effective inhibitor of not only basal but also prosptaglandin E1-activated adenylate cyclase activities in platelets.1 It reverses hyperalgesia contralaterally and ipsilaterally when injected intramuscularly in rats.2 | [storage]
Store at +4°C | [References]
[1] R J HASLAM J V D M M Davidson. Inhibition of adenylate cyclase by adenosine analogues in preparations of broken and intact human platelets. Evidence for the unidirectional control of platelet function by cyclic AMP.[J]. Biochemical Journal, 1978, 176 1: 83-95. DOI: 10.1042/bj1760083
[2] SALLY TURCATO Lucie H C. Effects of the adenylyl cyclase inhibitor SQ22536 on iloprost-induced vasorelaxation and cyclic AMP elevation in isolated guinea-pig aorta[J]. British Journal of Pharmacology, 2009, 126 4: 845-847. DOI: 10.1038/sj.bjp.0702383
[3] YUANSHENG GAO J U R. Effects of SQ 22536, an adenylyl cyclase inhibitor, on isoproterenol-induced cyclic AMP elevation and relaxation in newborn ovine pulmonary veins[J]. European journal of pharmacology, 2002, 436 3: Pages 227-233. DOI: 10.1016/s0014-2999(02)01261-x |
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