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S153

Sigma-Aldrich

SQ 22,536

≥97% (HPLC), powder

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C9H11N5O
Número de CAS:
17318-31-9
Peso molecular:
205.22
Número MDL:
MFCD00210216
Código UNSPSC:
41106305
ID de la sustancia en PubChem:
24278057
NACRES:
NA.77

Ensayo

≥97% (HPLC)

Formulario

powder

color

white to off-white

solubilidad

DMSO: >10 mg/mL
H2O: insoluble

cadena 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)

Clave InChI

UKHMZCMKHPHFOT-UHFFFAOYSA-N

Información sobre el 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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Aplicación

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.

Acciones bioquímicas o fisiológicas

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

Características y beneficios

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.

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análisis (COA)

Lot/Batch Number
0000432345
0000432345
0000282379
126M4714V

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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
Soo Hyeon Kim et al.
Blood, 120(24), 4892-4902 (2012-10-18)
In cancer, VEGF-induced increase in vascular permeability results in increased interstitial pressure, reducing perfusion and increasing hypoxia, which reduce delivery of chemotherapeutic agents and increase resistance to ionizing radiation. Here, we show that both TIMP-2 and Ala + TIMP-2, a
William M Connelly et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 33(9), 3780-3785 (2013-03-01)
Tonic inhibitory GABA(A) receptor-mediated currents are observed in numerous cell types in the CNS, including thalamocortical neurons of the ventrobasal thalamus, dentate gyrus granule cells, and cerebellar granule cells. Here we show that in rat brain slices, activation of postsynaptic
Peng Li et al.
Experimental physiology, 98(2), 435-443 (2012-08-09)
Central melanocortin 3/4 receptors (MC3/4Rs) are known to regulate energy balance. Activation of MC3/4Rs causes a greater increase in the firing activity of the PVN neurons in obese Zucker rats than in lean Zucker rats. The present study was undertaken
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