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S153

SQ 22536

Name: SQ 22536
Brand: SIGMA

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

Sinónimos:

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

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Fórmula empírica (notación de Hill):

C₉H₁₁N₅O

Número CAS:

17318-31-9

Peso molecular:

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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Nombre del producto

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)

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Categorías relacionadas

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

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Este artículo	568500	P5234	SML0060
Sigma-Aldrich S153 SQ 22,536	Sigma-Aldrich 568500 SQ 22536	Sigma-Aldrich P5234 Purvalanol B	Sigma-Aldrich SML0060 NB001
assay ≥97% (HPLC)	assay ≥98% (HPLC)	assay ≥97% (HPLC)	assay ≥98% (HPLC)
form powder	form solid	form solid	form powder
Quality Level 100	Quality Level 100	Quality Level -	Quality Level 100
solubility DMSO: >10 mg/mL, H₂O: insoluble	solubility DMSO: 25 mg/mL, water: 5 mg/mL	solubility DMSO: soluble 37 mg/mL, H₂O: insoluble	solubility H₂O: ≥24 mg/mL
color white to off-white	color off-white	color -	color white to tan
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)	Gene Information -	Gene Information -	Gene Information -

Application

SQ 22,536 was used to study the role of adenylate cyclase in differentiation of PC12 cells[1] and in gap junctional intercellular communication in breast cancer cells.[2]

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.

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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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

Antagonism of VEGF-A-induced increase in vascular permeability by an integrin α3β1-Shp-1-cAMP/PKA pathway.

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

A junctional cAMP compartment regulates rapid Ca2+ signaling in atrial myocytes.

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

Calcium dynamics at the neural cell primary cilium regulate Hedgehog signaling-dependent neurogenesis in the embryonic neural tube.

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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Número de artículo de comercio global

SKU	GTIN
S153-25MG	04061832899442
S153-5MG	04061836911614
SAB5201396-100UG	04061832157122
SAB5201403-100UG	04061832157191
SAB5201408-100UG	04061832157245
SAB5201394-100UG	04061832157108
SAB5201404-100UG	04061832157207
SAB5201392-100UG	04061832157085
SAB5201393-100UG	04061832157092
SAB5201402-100UG	04061832157184
SAB5201407-100UG	04061832157238
SAB5201405-100UG	04061832157214

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