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S153

SQ 22536

Name: SQ 22536
Brand: SIGMA

≥97% (HPLC), Adenylate cyclase inhibitor, 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

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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Properties

Product Name

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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Storage Class

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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Articles

Discover Bioactive Molecules for Nucleotides

Cyclic nucleotides like cAMP modulate cell function via PKA activation and ion channels.

Multiple signaling pathways are responsible for prostaglandin E2-induced murine keratinocyte proliferation.

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

Effects of polybrominated diphenyl ethers on steroidogenesis in rat Leydig cells.

Kai-Lee Wang et al.

Human reproduction (Oxford, England), 26(8), 2209-2217 (2011-06-07)

Polybrominated diphenyl ethers (PBDEs) are brominated flame retardants that have been defined as major environmental pollutants. While previous studies have found that PBDEs may enhance the levels of sex-steroid hormones, their effects on testosterone secretion from rat Leydig cells are

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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Global Trade Item Number

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