GEBR-7b

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

MedKoo CAT#: 571493

CAS#: 67387-76-2

Description: GEBR-7b is a phosphodiesterase-4 (PDE4) inhibitor that stops or slows the hydrolysis of cAMP. It improves spatial and object recognition memory in late-phase consolidation processes, and increases the level of cAMP in the hippocampus without affecting the level of Aβ.


Price and Availability

Size
Price

5mg
USD 275
Size
Price

Size
Price

GEBR-7b, 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#: 571493
Name: GEBR-7b
CAS#: 67387-76-2
Chemical Formula: C13H16O3
Exact Mass: 220.1099
Molecular Weight: 220.27
Elemental Analysis: C, 70.89; H, 7.32; O, 21.79


Synonym: GEBR-7b, (E)-3-(cyclopentyloxy)-4-methoxybenzaldehyde, O-2-(2,6-dimethylmorpholino)-2-oxoethyl oxime

IUPAC/Chemical Name: 3-cyclopentyloxy-4-methoxybenzylaldehyde

InChi Key: FZFWPURYSWKIRT-UHFFFAOYSA-N

InChi Code: InChI=1S/C13H16O3/c1-15-12-7-6-10(9-14)8-13(12)16-11-4-2-3-5-11/h6-9,11H,2-5H2,1H3

SMILES Code: O=CC1=CC=C(OC)C(OC2CCCC2)=C1


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


Additional Information

Novel phosphodiesterase inhibitors are being studied to treat Alzheimer’s disease. Phosphodiesterases (PDEs) hydrolyze cyclic adenosine monophosphate (cAMP) and cyclic guanosine monophosphate (cGMP). They are prominently expressed in the brain, and thus are targeted in Alzheimer’s disease treatments to regulate cAMP and cGMP concentrations (which can lead to a downstream control of various proteins involved in cognitive maintenance). PDE inhibitors have been shown to effect cognitive improvement in dealing with common dementia symptoms, including progressive memory loss, a decline in language skills, and some other neurodegenerative disorders, in comparison with the available treatments of acetylcholine inhibitors, which do not reverse the progression of Alzheimer’s.


References

1: Brullo C, Massa M, Rocca M, Rotolo C, Guariento S, Rivera D, Ricciarelli R, Fedele E, Fossa P, Bruno O. Synthesis, biological evaluation, and molecular modeling of new 3-(cyclopentyloxy)-4-methoxybenzaldehyde O-(2-(2,6-dimethylmorpholino)-2-oxoethyl) Oxime (GEBR-7b) related phosphodiesterase 4D (PDE4D) inhibitors. J Med Chem. 2014 Aug 28;57(16):7061-72. doi: 10.1021/jm500855w. Epub 2014 Aug 15. PubMed PMID: 25126889.

2: Sierksma AS, van den Hove DL, Pfau F, Philippens M, Bruno O, Fedele E, Ricciarelli R, Steinbusch HW, Vanmierlo T, Prickaerts J. Improvement of spatial memory function in APPswe/PS1dE9 mice after chronic inhibition of phosphodiesterase type 4D. Neuropharmacology. 2014 Feb;77:120-30. doi: 10.1016/j.neuropharm.2013.09.015. Epub 2013 Sep 22. PubMed PMID: 24067928.

3: Liu X, Guo H, Sayed MD, Lu Y, Yang T, Zhou D, Chen Z, Wang H, Wang C, Xu J. cAMP/PKA/CREB/GLT1 signaling involved in the antidepressant-like effects of phosphodiesterase 4D inhibitor (GEBR-7b) in rats. Neuropsychiatr Dis Treat. 2016 Jan 21;12:219-27. doi: 10.2147/NDT.S90960. eCollection 2016. PubMed PMID: 26855578; PubMed Central PMCID: PMC4725689.

4: Bruno O, Fedele E, Prickaerts J, Parker LA, Canepa E, Brullo C, Cavallero A, Gardella E, Balbi A, Domenicotti C, Bollen E, Gijselaers HJ, Vanmierlo T, Erb K, Limebeer CL, Argellati F, Marinari UM, Pronzato MA, Ricciarelli R. GEBR-7b, a novel PDE4D selective inhibitor that improves memory in rodents at non-emetic doses. Br J Pharmacol. 2011 Dec;164(8):2054-63. doi: 10.1111/j.1476-5381.2011.01524.x. PubMed PMID: 21649644; PubMed Central PMCID: PMC3246667.

5: Bruno O, Ricciarelli R, Prickaerts J, Parker L, Fedele E. PDE4D inhibitors: a potential strategy for the treatment of memory impairment? Neuropharmacology. 2014 Oct;85:290-2. doi: 10.1016/j.neuropharm.2014.05.038. Epub 2014 Jun 2. PubMed PMID: 24942130.

6: Brullo C, Ricciarelli R, Prickaerts J, Arancio O, Massa M, Rotolo C, Romussi A, Rebosio C, Marengo B, Pronzato MA, van Hagen BTJ, van Goethem NP, D'Ursi P, Orro A, Milanesi L, Guariento S, Cichero E, Fossa P, Fedele E, Bruno O. New insights into selective PDE4D inhibitors: 3-(Cyclopentyloxy)-4-methoxybenzaldehyde O-(2-(2,6-dimethylmorpholino)-2-oxoethyl) oxime (GEBR-7b) structural development and promising activities to restore memory impairment. Eur J Med Chem. 2016 Nov 29;124:82-102. doi: 10.1016/j.ejmech.2016.08.018. Epub 2016 Aug 13. PubMed PMID: 27560284.

7: Mishra RR, Belder N, Ansari SA, Kayhan M, Bal H, Raza U, Ersan PG, Tokat ÜM, Eyüpoğlu E, Saatci Ö, Jandaghi P, Wiemann S, Üner A, Cekic C, Riazalhosseini Y, Şahin Ö. Re-activation of cAMP pathway by PDE4D inhibition represents a novel druggable axis for overcoming tamoxifen resistance in ER-positive breast cancer. Clin Cancer Res. 2018 Jan 31. pii: clincanres.2776.2017. doi: 10.1158/1078-0432.CCR-17-2776. [Epub ahead of print] PubMed PMID: 29386221.