SQ-22536
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 530604

CAS#: 17318-31-9

Description: 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.


Price and Availability

Size
Price

100mg
USD 750
1g
USD 2950
Size
Price

200mg
USD 1250
2g
USD 3950
Size
Price

500mg
USD 1950
5g
USD 5950

SQ-22536, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 530604
Name: SQ-22536
CAS#: 17318-31-9
Chemical Formula: C9H11N5O
Exact Mass: 205.0964
Molecular Weight: 205.221
Elemental Analysis: C, 52.67; H, 5.40; N, 34.13; O, 7.80


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

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


Technical Data

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

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).

Harmonized System Code:
293490


References

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. Life Sci. 2016 Jan 1;144:19-25. doi: 10.1016/j.lfs.2015.11.015. Epub 2015 Nov 18. PubMed PMID: 26596264.

8: Wei R, Ma S, Wang C, Ke J, Yang J, Li W, Liu Y, Hou W, Feng X, Wang G, Hong T. Exenatide exerts direct protective effects on endothelial cells through the AMPK/Akt/eNOS pathway in a GLP-1 receptor-dependent manner. Am J Physiol Endocrinol Metab. 2016 Jun 1;310(11):E947-57. doi: 10.1152/ajpendo.00400.2015. Epub 2016 Apr 12. PubMed PMID: 27072494.

9: Shahi PK, Choi S, Zuo DC, Kim MY, Park CG, Kim YD, Lee J, Park KJ, So I, Jun JY. The possible roles of hyperpolarization-activated cyclic nucleotide channels in regulating pacemaker activity in colonic interstitial cells of Cajal. J Gastroenterol. 2014 Jun;49(6):1001-10. doi: 10.1007/s00535-013-0849-3. Epub 2013 Jun 19. PubMed PMID: 23780559; PubMed Central PMCID: PMC4048466.

10: Jeong HY, Yun HJ, Kim BW, Lee EW, Kwon HJ. Widdrol-induced lipolysis is mediated by PKC and MEK/ERK in 3T3-L1 adipocytes. 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. PLoS One. 2013 Jun 24;8(6):e67117. doi: 10.1371/journal.pone.0067117. Print 2013. PubMed PMID: 23826207; PubMed Central PMCID: PMC3691129.

14: Simões LO, Conceição-Filho G, Ribeiro TS, Jesus AM, Fregoneze JB, Silva AQ, Petreanu M, Cechinel-Filho V, Niero R, Niero H, Tamanaha MS, Silva DF. Evidences of antihypertensive potential of extract from Solanum capsicoides All. in spontaneously hypertensive rats. Phytomedicine. 2016 May 15;23(5):498-508. doi: 10.1016/j.phymed.2016.02.020. Epub 2016 Mar 5. PubMed PMID: 27064009.

15: Hajra S, Das D, Ghosh P, Pal S, Nath P, Maitra S. Regulation of recombinant human insulin-induced maturational events in Clarias batrachus (L.) oocytes in vitro. Zygote. 2016 Apr;24(2):181-94. doi: 10.1017/S0967199415000015. Epub 2015 Feb 24. PubMed PMID: 25707854.

16: Kim HW, Li H, Kim HS, Shin SE, Jung WK, Ha KS, Han ET, Hong SH, Choi IW, Firth AL, Bang H, Park WS. 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.