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S153

Sigma-Aldrich

SQ 22,536

≥97% (HPLC), powder

Synonyme(s) :

9-(Tetrahydro-2-furanyl)-9H-purin-6-amine, 9-THF-Ade

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About This Item

Formule empirique (notation de Hill):
C9H11N5O
Numéro CAS:
17318-31-9
Poids moléculaire :
205.22
Numéro MDL:
MFCD00210216
Code UNSPSC :
41106305
ID de substance PubChem :
24278057
Nomenclature NACRES :
NA.77

Pureté

≥97% (HPLC)

Forme

powder

Couleur

white to off-white

Solubilité

DMSO: >10 mg/mL
H2O: insoluble

Chaîne SMILES 

Nc1ncnc2n(cnc12)C3CCCO3

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)

Clé InChI

UKHMZCMKHPHFOT-UHFFFAOYSA-N

Informations sur le gène

human ... ADCY1(107) , ADCY2(108) , ADCY3(109) , ADCY4(196883) , ADCY5(111) , ADCY6(112) , ADCY7(113) , ADCY8(114) , ADCY9(115)
rat ... Adora1(29290) , Adora2a(25369)

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Application

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.

Actions biochimiques/physiologiques

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
SQ 22,536 is a cell-permeable adenylyl cyclase inhibitor. IC50 = 20 μM in detergent-dispersed rat brain preparation.

Caractéristiques et avantages

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Adenylyl cyclases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

R J Haslam et al.
The Biochemical journal, 176(1), 83-95 (1978-10-15)
Whereas adenosine itself exerted independent stimulatory and inhibitory effects on the adenylate cyclase activity of a platelet particulate fraction at low and high concentrations respectively, 2-substituted and N6-monosubstituted adenosines had stimulatory but greatly decreased inhibitory effects. Deoxyadenosines, on the other
Kausar M Ansari et al.
Molecular cancer research : MCR, 6(6), 1003-1016 (2008-06-24)
Although prostaglandin E2 (PGE2) has been shown by pharmacologic and genetic studies to be important in skin cancer, the molecular mechanism(s) by which it contributes to tumor growth is not well understood. In this study, we investigated the mechanisms by
C Lippe et al.
Comparative biochemistry and physiology. C, Comparative pharmacology and toxicology, 99(1-2), 209-211 (1991-01-01)
1. The effects of both adenyl cyclase inhibitors (MDL12330A and SQ22536) have been studied on the ionic transport induced by vasopressin and isoprenaline across the frog skin. 2. MDL12330A inhibits the vasopressin action on the short-circuit current (SCC), confirming that
Hari Hendarto et al.
Metabolism: clinical and experimental, 61(10), 1422-1434 (2012-05-05)
Accumulating evidence has implicated that GLP-1 may have a beneficial effect on cardiovascular and renal diseases but the mechanism is not fully understood. Here we show that GLP-1 analog, liraglutide, inhibits oxidative stress and albuminuria in streptozotocin (STZ)-induced type 1
Marie K Hoeger-Bement et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 23(13), 5437-5445 (2003-07-05)
Spinal activation of the cAMP pathway produces mechanical hyperalgesia, sensitizes nociceptive spinal neurons, and phosphorylates the transcription factor cAMP-responsive element binding protein (CREB), which initiates gene transcription. This study examined the role of the cAMP pathway in a model of
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