SQ-22536 | CAS#17318-31-9 | adenylate-cyclase inhibitor

MedKoo Cat#: 530604 | Name: SQ-22536

Description:

WARNING: This product is for research use only, not for human or veterinary use.

SQ-22536, also known as NSC 53339, is an inhibitor of adenylyl cyclase with an IC50 value of 13 μM. SQ 22536 prevents the antiplatelet effect of dazoxiben, a thromboxane-synthetase inhibitor. SQ 22536 inhibited adenylate cyclase [ATP pyrophosphate-lyase (cyclizing), EC 4.6.1.1] activity of crude membrane preparations from catfish (Ictalurus melas) and rat isolated hepatocytes in a non-competitive manner.

Chemical Structure

SQ-22536

CAS#17318-31-9

Theoretical Analysis

MedKoo Cat#: 530604

Name: SQ-22536

CAS#: 17318-31-9

Chemical Formula: C9H11N5O

Exact Mass: 205.0964

Molecular Weight: 205.22

Elemental Analysis: C, 52.67; H, 5.40; N, 34.13; O, 7.80

Price and Availability

Size	Price	Availability
50mg	USD 450.00	2 Weeks
100mg	USD 750.00	2 Weeks
200mg	USD 1,250.00	2 Weeks
500mg	USD 2,650.00	2 Weeks
1g	USD 3,750.00	2 Weeks
2g	USD 6,250.00	2 Weeks

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Synonym

SQ-22536; SQ22536; SQ 22536; SQ-22,536; SQ22,536; SQ 22,536. NSC 53339; NSC 53339; NSC-53339; NSC53339;

IUPAC/Chemical Name

9-(tetrahydro-2-furanyl)-9H-purin-6-amine

InChi Key

UKHMZCMKHPHFOT-UHFFFAOYSA-N

InChi Code

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)

SMILES Code

NC1=C2N=CN(C3OCCC3)C2=NC=N1

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO and water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

SQ-22536 is an inhibitor of AC with an IC50 value of 13 μM.

In vitro activity:

SQ-22536 effectively inhibited AC in HEK293 cells with a cAMP response element (CRE) reporter gene. SQ-22536 did not inhibit PKA-mediated CREB activation or Epac-mediated Rap1 activation. However, it did inhibit ERK phosphorylation and neuritogenesis, suggesting it also targets a newly described neuritogenic cAMP sensor (NCS). These off-target effects were specific to cAMP signaling and did not affect unrelated pathways. Reference: Mol Pharmacol. 2013 Jan;83(1):95-105. https://pubmed.ncbi.nlm.nih.gov/23053667/

In vivo activity:

The study examined the effect of SQ-22536 on iloprost-induced relaxation and cyclic AMP increase in endothelium-denuded aortic strips. Iloprost caused a concentration-dependent inhibition of phenylephrine contractions, unaffected by SQ-22536 pre-incubation. However, SQ-22536 abolished iloprost-induced cyclic AMP elevation while not significantly affecting relaxation. This indicates that iloprost's vasorelaxant effects in guinea-pig aorta may involve cyclic AMP-independent pathways. Reference: Br J Pharmacol. 1999 Feb;126(4):845-7. https://pubmed.ncbi.nlm.nih.gov/10193763/

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	487.28
	Water	55.0	268.01

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 205.22 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Emery AC, Eiden MV, Eiden LE. A new site and mechanism of action for the widely used adenylate cyclase inhibitor SQ22,536. Mol Pharmacol. 2013 Jan;83(1):95-105. doi: 10.1124/mol.112.081760. Epub 2012 Oct 10. PMID: 23053667; PMCID: PMC3533470. 2. Gao Y, Usha Raj J. Effects of SQ 22536, an adenylyl cyclase inhibitor, on isoproterenol-induced cyclic AMP elevation and relaxation in newborn ovine pulmonary veins. Eur J Pharmacol. 2002 Feb 2;436(3):227-33. doi: 10.1016/s0014-2999(02)01261-x. PMID: 11858802. 3. Turcato S, Clapp LH. Effects of the adenylyl cyclase inhibitor SQ22536 on iloprost-induced vasorelaxation and cyclic AMP elevation in isolated guinea-pig aorta. Br J Pharmacol. 1999 Feb;126(4):845-7. doi: 10.1038/sj.bjp.0702383. PMID: 10193763; PMCID: PMC1571226.

In vitro protocol:

In vivo protocol:

1. Turcato S, Clapp LH. Effects of the adenylyl cyclase inhibitor SQ22536 on iloprost-induced vasorelaxation and cyclic AMP elevation in isolated guinea-pig aorta. Br J Pharmacol. 1999 Feb;126(4):845-7. doi: 10.1038/sj.bjp.0702383. PMID: 10193763; PMCID: PMC1571226.

1: Fabbri E, Brighenti L, Ottolenghi C. Inhibition of adenylate cyclase of catfish and rat hepatocyte membranes by 9-(tetrahydro-2-furyl)adenine (SQ 22536). J Enzyme Inhib. 1991;5(2):87-98. PubMed PMID: 1669444. 2: Gao Y, Usha Raj J. Effects of SQ 22536, an adenylyl cyclase inhibitor, on isoproterenol-induced cyclic AMP elevation and relaxation in newborn ovine pulmonary veins. Eur J Pharmacol. 2002 Feb 2;436(3):227-33. PubMed PMID: 11858802. 3: Bertelé V, Falanga A, Tomasiak M, Cerletti C, de Gaetano G. SQ 22536, an adenylate-cyclase inhibitor, prevents the antiplatelet effect of dazoxiben, a thromboxane-synthetase inhibitor. Thromb Haemost. 1984 Feb 28;51(1):125-8. PubMed PMID: 6326343. 4: Li X, Guo Q, Gao J, Yang J, Zhang W, Liang Y, Wu D, Liu Y, Weng J, Li Q, Zhang Y. The adenylyl cyclase inhibitor MDL-12,330A potentiates insulin secretion via blockade of voltage-dependent K(+) channels in pancreatic beta cells. PLoS One. 2013 Oct 29;8(10):e77934. doi: 10.1371/journal.pone.0077934. eCollection 2013. PubMed PMID: 24205033; PubMed Central PMCID: PMC3812155. 5: Wu MJ, Kee KH, Na J, Kim SW, Bae Y, Shin DH, Choi S, Jun JY, Jeong HS, Park JS. Pituitary Adenylate Cyclase-activating Polypeptide Inhibits Pacemaker Activity of Colonic Interstitial Cells of Cajal. Korean J Physiol Pharmacol. 2015 Sep;19(5):435-40. doi: 10.4196/kjpp.2015.19.5.435. Epub 2015 Aug 20. PubMed PMID: 26330756; PubMed Central PMCID: PMC4553403. 6: Kurowski P, Gawlak M, Szulczyk P. Muscarinic receptor control of pyramidal neuron membrane potential in the medial prefrontal cortex (mPFC) in rats. Neuroscience. 2015 Sep 10;303:474-88. doi: 10.1016/j.neuroscience.2015.07.023. Epub 2015 Jul 14. PubMed PMID: 26186898. 7: Permpoonputtana K, Porter JE, Govitrapong P. Calcitonin gene-related peptide mediates an inflammatory response in Schwann cells via cAMP-dependent ERK signaling cascade. 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Mol Cell Biochem. 2015 Dec;410(1-2):247-54. doi: 10.1007/s11010-015-2558-0. Epub 2015 Sep 10. PubMed PMID: 26359088. 11: Ho YC, Cheng JK, Chiou LC. Impairment of adenylyl cyclase-mediated glutamatergic synaptic plasticity in the periaqueductal grey in a rat model of neuropathic pain. J Physiol. 2015 Jul 1;593(13):2955-73. doi: 10.1113/JP270384. Epub 2015 May 14. PubMed PMID: 25868084; PubMed Central PMCID: PMC4506191. 12: Kortus S, Srinivasan C, Forostyak O, Zapotocky M, Ueta Y, Sykova E, Chvatal A, Verkhratsky A, Dayanithi G. Sodium-calcium exchanger and R-type Ca(2+) channels mediate spontaneous [Ca(2+)]i oscillations in magnocellular neurones of the rat supraoptic nucleus. Cell Calcium. 2016 Jun;59(6):289-98. doi: 10.1016/j.ceca.2016.03.010. Epub 2016 Mar 31. PubMed PMID: 27052156. 13: Burzaco J, Conde M, Parada LA, Zugaza JL, Dehaye JP, Marino A. ATP antagonizes thrombin-induced signal transduction through 12(S)-HETE and cAMP. 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The anti-diabetic drug repaglinide induces vasorelaxation via activation of PKA and PKG in aortic smooth muscle. Vascul Pharmacol. 2016 Sep;84:38-46. doi: 10.1016/j.vph.2016.07.005. Epub 2016 Jul 18. PubMed PMID: 27435474. 17: Lee S, Gim H, Shim JH, Jung Kim H, Lee JR, Kim SC, Kwon YK, Ha KT, So I, Kim BJ. The traditional herbal medicine, Ge-Gen-Tang, inhibits pacemaker potentials by nitric oxide/cGMP dependent ATP-sensitive K(+) channels in cultured interstitial cells of Cajal from mouse small intestine. J Ethnopharmacol. 2015 Jul 21;170:201-9. doi: 10.1016/j.jep.2015.05.025. Epub 2015 May 21. PubMed PMID: 26003723. 18: López-Canales OA, Castillo-Hernandez MC, Vargas-Robles H, Rios A, López-Canales JS, Escalante B. Role of adenylyl cyclase in reduced β-adrenoceptor-mediated vasorelaxation during maturation. Braz J Med Biol Res. 2016 Jul 4;49(7). pii: S0100-879X2016000700605. doi: 10.1590/1414-431X20165285. PubMed PMID: 27383122; PubMed Central PMCID: PMC4942227. 19: Momohara Y, Minami H, Kanai A, Nagayama T. Role of cAMP signalling in winner and loser effects in crayfish agonistic encounters. Eur J Neurosci. 2016 Jul;44(2):1886-95. doi: 10.1111/ejn.13259. Epub 2016 Jun 7. PubMed PMID: 27086724. 20: Pathirana IN, Kawate N, Büllesbach EE, Takahashi M, Hatoya S, Inaba T, Tamada H. Insulin-like peptide 3 stimulates testosterone secretion in mouse Leydig cells via cAMP pathway. Regul Pept. 2012 Oct 10;178(1-3):102-6. doi: 10.1016/j.regpep.2012.07.003. Epub 2012 Jul 16. PubMed PMID: 22800961.