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S153

Sigma-Aldrich

SQ 22,536

≥97% (HPLC), powder

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C9H11N5O
CAS Number:
17318-31-9
Molecular Weight:
205.22
MDL number:
MFCD00210216
UNSPSC Code:
41106305
PubChem Substance ID:
24278057
NACRES:
NA.77

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)

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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.

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

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.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
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
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Cyclic nucleotides, including cyclic AMP (cAMP), cyclic GMP (cGMP) and cyclic ADP-ribose, have been extensively studied as second messengers of intracellular events initiated by activation of GPCRs. cAMP modifies cell function in all eukaryotic cells, principally through the activation of cAMP-dependent protein kinase (PKA), but also through cAMP-gated ion channels and guanine nucleotide exchange factors directly activated by cAMP.

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