BAY60-7550

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

MedKoo CAT#: 522495

CAS#: 439083-90-6

Description: BAY-60-7550 is a potent PDE2 inhibitor with IC50 values of 2.0 nM (bovine) and 4.7 nM (human). BAY-60-7550 antagonizes oxidative stress-induced anxiety-like behavioral effects in mice by increasing cGMP signaling. Phosphodiesterases (PDEs) are key regulatory enzymes of intracellular cAMP/cGMP levels. These second messengers play important regulatory roles in controlling steroidogenesis in the adrenal. Disruption of PDEs has been associated with a number of adrenal diseases


Price and Availability

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1g
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2g
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Size
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5g
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BAY60-7550, purity > 98%, is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 522495
Name: BAY60-7550
CAS#: 439083-90-6
Chemical Formula: C27H32N4O4
Exact Mass: 476.24236
Molecular Weight: 476.577
Elemental Analysis: C, 68.05; H, 6.77; N, 11.76; O, 13.43


Synonym: BAY60-7550; BAY 60-7550; BAY-60-7550; BAY-607550; BAY 607550; BAY607550.

IUPAC/Chemical Name: 2-(3,4-dimethoxybenzyl)-7-((2R,3R)-2-hydroxy-6-phenylhexan-3-yl)-5-methylimidazo[5,1-f][1,2,4]triazin-4(3H)-one

InChi Key: MYTWFJKBZGMYCS-NQIIRXRSSA-N

InChi Code: InChI=1S/C27H32N4O4/c1-17-25-27(33)29-24(16-20-13-14-22(34-3)23(15-20)35-4)30-31(25)26(28-17)21(18(2)32)12-8-11-19-9-6-5-7-10-19/h5-7,9-10,13-15,18,21,32H,8,11-12,16H2,1-4H3,(H,29,30,33)/t18-,21+/m1/s1

SMILES Code: O=C1NC(CC2=CC=C(OC)C(OC)=C2)=NN3C1=C(C)N=C3[C@H]([C@H](O)C)CCCC4=CC=CC=C4


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, not in 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).

Harmonized System Code:
293490


References

1: Galindo-Tovar A, Vargas ML, Kaumann AJ. Inhibitors of phosphodiesterases PDE2, PDE3, and PDE4 do not increase the sinoatrial tachycardia of noradrenaline and prostaglandin PGE(1) in mice. Naunyn Schmiedebergs Arch Pharmacol. 2015 Nov 3. [Epub ahead of print] PubMed PMID: 26531832.

2: Lueptow LM, Zhan CG, O'Donnell JM. Cyclic GMP-mediated memory enhancement in the object recognition test by inhibitors of phosphodiesterase-2 in mice. Psychopharmacology (Berl). 2015 Nov 2. [Epub ahead of print] PubMed PMID: 26525565.

3: Rahnama'i MS, Hohnen R, Van Kerrebroeck PE, van Koeveringe GA. Phosphodiesterase type 2 distribution in the guinea pig urinary bladder. World J Urol. 2015 Oct;33(10):1623-33. doi: 10.1007/s00345-014-1455-6. Epub 2014 Dec 6. PubMed PMID: 25480469.

4: Xu Y, Pan J, Sun J, Ding L, Ruan L, Reed M, Yu X, Klabnik J, Lin D, Li J, Chen L, Zhang C, Zhang H, O'Donnell JM. Inhibition of phosphodiesterase 2 reverses impaired cognition and neuronal remodeling caused by chronic stress. Neurobiol Aging. 2015 Feb;36(2):955-70. doi: 10.1016/j.neurobiolaging.2014.08.028. Epub 2014 Aug 30. PubMed PMID: 25442113; PubMed Central PMCID: PMC4315741.

5: Serpa A, Sebastião AM, Cascalheira JF. Modulation of cGMP accumulation by adenosine A1 receptors at the hippocampus: influence of cGMP levels and gender. Eur J Pharmacol. 2014 Dec 5;744:83-90. doi: 10.1016/j.ejphar.2014.09.045. Epub 2014 Oct 7. PubMed PMID: 25300679.

6: Rentsendorj O, D'Alessio FR, Pearse DB. Phosphodiesterase 2A is a major negative regulator of iNOS expression in lipopolysaccharide-treated mouse alveolar macrophages. J Leukoc Biol. 2014 Nov;96(5):907-15. doi: 10.1189/jlb.3A0314-152R. Epub 2014 Jul 25. PubMed PMID: 25063878; PubMed Central PMCID: PMC4197568.

7: Inserte J, Hernando V, Ruiz-Meana M, Poncelas-Nozal M, Fernández C, Agulló L, Sartorio C, Vilardosa U, Garcia-Dorado D. Delayed phospholamban phosphorylation in post-conditioned heart favours Ca2+ normalization and contributes to protection. Cardiovasc Res. 2014 Sep 1;103(4):542-53. doi: 10.1093/cvr/cvu163. Epub 2014 Jun 27. PubMed PMID: 25020913.

8: Bubb KJ, Trinder SL, Baliga RS, Patel J, Clapp LH, MacAllister RJ, Hobbs AJ. Inhibition of phosphodiesterase 2 augments cGMP and cAMP signaling to ameliorate pulmonary hypertension. Circulation. 2014 Aug 5;130(6):496-507. doi: 10.1161/CIRCULATIONAHA.114.009751. Epub 2014 Jun 4. PubMed PMID: 24899690; PubMed Central PMCID: PMC4124037.

9: Kallenborn-Gerhardt W, Lu R, Bothe A, Thomas D, Schlaudraff J, Lorenz JE, Lippold N, Real CI, Ferreirós N, Geisslinger G, Del Turco D, Schmidtko A. Phosphodiesterase 2A localized in the spinal cord contributes to inflammatory pain processing. Anesthesiology. 2014 Aug;121(2):372-82. doi: 10.1097/ALN.0000000000000270. PubMed PMID: 24758774.

10: Ding L, Zhang C, Masood A, Li J, Sun J, Nadeem A, Zhang HT, O'Donnell JM, Xu Y. Protective effects of phosphodiesterase 2 inhibitor on depression- and anxiety-like behaviors: involvement of antioxidant and anti-apoptotic mechanisms. Behav Brain Res. 2014 Jul 15;268:150-8. doi: 10.1016/j.bbr.2014.03.042. Epub 2014 Mar 30. PubMed PMID: 24694839; PubMed Central PMCID: PMC4075066.

11: Zhai K, Chang Y, Wei B, Liu Q, Leblais V, Fischmeister R, Ji G. Phosphodiesterase types 3 and 4 regulate the phasic contraction of neonatal rat bladder smooth myocytes via distinct mechanisms. Cell Signal. 2014 May;26(5):1001-10. doi: 10.1016/j.cellsig.2014.01.020. Epub 2014 Jan 23. PubMed PMID: 24463006.

12: Zhu J, Yang Q, Dai D, Huang Q. X-ray crystal structure of phosphodiesterase 2 in complex with a highly selective, nanomolar inhibitor reveals a binding-induced pocket important for selectivity. J Am Chem Soc. 2013 Aug 14;135(32):11708-11. doi: 10.1021/ja404449g. Epub 2013 Aug 2. PubMed PMID: 23899287.

13: Mehel H, Emons J, Vettel C, Wittköpper K, Seppelt D, Dewenter M, Lutz S, Sossalla S, Maier LS, Lechêne P, Leroy J, Lefebvre F, Varin A, Eschenhagen T, Nattel S, Dobrev D, Zimmermann WH, Nikolaev VO, Vandecasteele G, Fischmeister R, El-Armouche A. Phosphodiesterase-2 is up-regulated in human failing hearts and blunts β-adrenergic responses in cardiomyocytes. J Am Coll Cardiol. 2013 Oct 22;62(17):1596-606. doi: 10.1016/j.jacc.2013.05.057. Epub 2013 Jun 26. PubMed PMID: 23810893.

14: van Donkelaar EL, Prickaerts J, Akkerman S, Rutten K, Steinbusch HW, Blokland A. No effect of acute tryptophan depletion on phosphodiesterase inhibition--related improvements of short-term object memory in male Wistar rats. Acta Psychiatr Scand. 2013 Aug;128(2):107-13. doi: 10.1111/acps.12166. Epub 2013 Jun 17. PubMed PMID: 23772681.

15: Reneerkens OA, Sambeth A, Blokland A, Prickaerts J. PDE2 and PDE10, but not PDE5, inhibition affect basic auditory information processing in rats. Behav Brain Res. 2013 Aug 1;250:251-6. doi: 10.1016/j.bbr.2013.05.014. Epub 2013 May 17. PubMed PMID: 23688598.

16: Tanaka S, Tanaka R, Harada S, Kohda Y, Matsumura H, Shimamoto C, Sawabe Y, Marunaka Y, Kuwabara H, Takahashi Y, Ito S, Nakahari T. A PKG inhibitor increases Ca(2+)-regulated exocytosis in guinea pig antral mucous cells: cAMP accumulation via PDE2A inhibition. Am J Physiol Gastrointest Liver Physiol. 2013 May 1;304(9):G773-80. doi: 10.1152/ajpgi.00281.2012. Epub 2013 Feb 28. PubMed PMID: 23449671.

17: Reneerkens OA, Rutten K, Bollen E, Hage T, Blokland A, Steinbusch HW, Prickaerts J. Inhibition of phoshodiesterase type 2 or type 10 reverses object memory deficits induced by scopolamine or MK-801. Behav Brain Res. 2013 Jan 1;236(1):16-22. doi: 10.1016/j.bbr.2012.08.019. Epub 2012 Aug 19. PubMed PMID: 22951181.

18: Xu Y, Pan J, Chen L, Zhang C, Sun J, Li J, Nguyen L, Nair N, Zhang H, O'Donnell JM. Phosphodiesterase-2 inhibitor reverses corticosterone-induced neurotoxicity and related behavioural changes via cGMP/PKG dependent pathway. Int J Neuropsychopharmacol. 2013 May;16(4):835-47. doi: 10.1017/S146114571200065X. Epub 2012 Jul 31. PubMed PMID: 22850435.

19: Thumova M, Pech V, Froehlich O, Agazatian D, Wang X, Verlander JW, Kim YH, Wall SM. Pendrin protein abundance in the kidney is regulated by nitric oxide and cAMP. Am J Physiol Renal Physiol. 2012 Sep 15;303(6):F812-20. doi: 10.1152/ajprenal.00577.2011. Epub 2012 Jul 18. PubMed PMID: 22811483; PubMed Central PMCID: PMC3468526.

20: Sierksma AS, Rutten K, Sydlik S, Rostamian S, Steinbusch HW, van den Hove DL, Prickaerts J. Chronic phosphodiesterase type 2 inhibition improves memory in the APPswe/PS1dE9 mouse model of Alzheimer's disease. Neuropharmacology. 2013 Jan;64:124-36. doi: 10.1016/j.neuropharm.2012.06.048. Epub 2012 Jul 4. PubMed PMID: 22771768.