SQ 22,536 Chemical Properties

Melting point:

160-161℃

Boiling point:

474.8±55.0 °C(Predicted)

Density 

1.70±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

solubility 

H₂O: 21 mg/mL

form 

solid

pka

3.82±0.10(Predicted)

color 

white to off-white

InChI

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)

InChIKey

UKHMZCMKHPHFOT-UHFFFAOYSA-N

SMILES

N1C2C(=NC=NC=2N)N(C2CCCO2)C=1

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

2934.99.9001

MSDS

• Language:English Provider:SigmaAldrich

SQ 22,536 Usage And Synthesis

Description

SQ 22,536 is an inhibitor of adenylyl cyclase with an IC₅₀ value of 13 μM for inhibition of prostaglandin E₁-stimulated increase in cAMP in intact platelets. It has been used to evaluate adenylyl cyclase activity during iloprost-induced vasorelaxation of isolated pulmonary veins or aorta in several research paradigms, inhibiting cAMP elevation at concentrations of 100-300 μM without effecting relaxation.

Uses

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.

Definition

ChEBI: A nucleoside analogue that is adenine in which the nitrogen at position 9 has been substituted by a tetrahydrofuran-2-yl group. It is an adenylate cyclase inhibitor.

Biological Activity

Inhibitor of adenylyl cyclase (IC 50 = 1.4 μ M). Inhibits PGE 1 -stimulated increases in cAMP levels in intact human platelets.

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

storage

Store at +4°C

References

[1] R J HASLAM  J V D  M M Davidson. 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.[J]. Biochemical Journal, 1978, 176 1: 83-95. DOI: 10.1042/bj1760083
[2] SALLY TURCATO  Lucie H C. Effects of the adenylyl cyclase inhibitor SQ22536 on iloprost-induced vasorelaxation and cyclic AMP elevation in isolated guinea-pig aorta[J]. British Journal of Pharmacology, 2009, 126 4: 845-847. DOI: 10.1038/sj.bjp.0702383
[3] YUANSHENG GAO  J U R. Effects of SQ 22536, an adenylyl cyclase inhibitor, on isoproterenol-induced cyclic AMP elevation and relaxation in newborn ovine pulmonary veins[J]. European journal of pharmacology, 2002, 436 3: Pages 227-233. DOI: 10.1016/s0014-2999(02)01261-x

SQ 22,536(17318-31-9)Related Product Information

• Cyclic AMP
• 5'-IODO-5'-DEOXYADENOSINE
• ADENOSINE-2':3'-CYCLIC MONOPHOSPHATE, SODIUM SALT
• 2'-Deoxyadenosine monohydrate
• 8-BROMOADENOSINE
• 3'-ADENYLIC ACID
• N6-ISOPENTENYLADENOSINE-D6
• 2',3'-O-Isopropylideneadenosine
• 5'-Tosyladenosine
• 2-Chloroadenosine
• 2'-Deoxyadenosine 5'-phosphate
• Vidarabine
• Adenosine 5'-monophosphate monohydrate
• Bucladesine sodium
• N6-BENZYLADENOSINE
• N6-Benzoyl-2'-deoxyadenosine
• 6-METHYLAMINOPURINE 9-RIBOFURANOSIDE
• 5'-ACETYL-2',3'-ISOPROPYLIDENEADENOSINE