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S153

Sigma-Aldrich

SQ 22,536

≥97% (HPLC), powder

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C9H11N5O
CAS-Nummer:
17318-31-9
Molekulargewicht:
205.22
MDL-Nummer:
MFCD00210216
UNSPSC-Code:
41106305
PubChem Substanz-ID:
24278057
NACRES:
NA.77

Assay

≥97% (HPLC)

Form

powder

Farbe

white to off-white

Löslichkeit

DMSO: >10 mg/mL
H2O: insoluble

SMILES String

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)

InChIKey

UKHMZCMKHPHFOT-UHFFFAOYSA-N

Angaben zum Gen

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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Anwendung

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. Wirkung

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.

Leistungsmerkmale und Vorteile

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.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves

Analysenzertifikate (COA)

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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
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
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
Sören Brandenburg et al.
Journal of molecular and cellular cardiology, 165, 141-157 (2022-01-17)
Axial tubule junctions with the sarcoplasmic reticulum control the rapid intracellular Ca2+-induced Ca2+ release that initiates atrial contraction. In atrial myocytes we previously identified a constitutively increased ryanodine receptor (RyR2) phosphorylation at junctional Ca2+ release sites, whereas non-junctional RyR2 clusters
Sangwoo Shim et al.
Proceedings of the National Academy of Sciences of the United States of America, 120(23), e2220037120-e2220037120 (2023-05-30)
The balance between neural stem cell proliferation and neuronal differentiation is paramount for the appropriate development of the nervous system. Sonic hedgehog (Shh) is known to sequentially promote cell proliferation and specification of neuronal phenotypes, but the signaling mechanisms responsible
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