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S153

SQ 22536

Name: SQ 22536
Brand: SIGMA

≥97% (HPLC), Adenylate cyclase inhibitor, powder

Synonyme(s) :

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

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A propos de cet article

Formule empirique (notation de Hill) :

C₉H₁₁N₅O

Numéro CAS:

17318-31-9

Poids moléculaire :

205.22

UNSPSC Code:

41106305

PubChem Substance ID:

24278057

NACRES:

NA.77

MDL number:

MFCD00210216

Assay:

≥97% (HPLC)

Form:

powder

Quality level:

100

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Propriétés

Nom du produit

SQ 22,536, ≥97% (HPLC), powder

Quality Level

100

assay

≥97% (HPLC)

form

powder

color

white to off-white

solubility

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)

InChI key

UKHMZCMKHPHFOT-UHFFFAOYSA-N

Gene Information

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

Description

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.

Biochem/physiol Actions

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

Features and Benefits

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.

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Classe de stockage

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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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.

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

Phosphorylation of CREB and mechanical hyperalgesia is reversed by blockade of the cAMP pathway in a time-dependent manner after repeated intramuscular acid injections.

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

Actions of vasopressin and isoprenaline on the ionic transport across the isolated frog skin in the presence and the absence of adenyl cyclase inhibitors MDL12330A and SQ22536.

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

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