WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 571493
CAS#: 1349848-90-3
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.
MedKoo Cat#: 571493
Name: GEBR-7b
CAS#: 1349848-90-3
Chemical Formula: C21H30N2O5
Exact Mass: 390.2155
Molecular Weight: 390.48
Elemental Analysis: C, 64.60; H, 7.74; N, 7.17; O, 20.49
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Synonym: GEBR-7b; GEBR 7b; GEBR7b;
IUPAC/Chemical Name: (E)-3-(cyclopentyloxy)-4-methoxybenzaldehyde, O-2-(2,6-dimethylmorpholino)-2-oxoethyl oxime
InChi Key: JEXHQZPMUKFOIV-SSDVNMTOSA-N
InChi Code: InChI=1S/C21H30N2O5/c1-15-12-23(13-16(2)27-15)21(24)14-26-22-11-17-8-9-19(25-3)20(10-17)28-18-6-4-5-7-18/h8-11,15-16,18H,4-7,12-14H2,1-3H3/b22-11+
SMILES Code: COC1=CC=C(C=C1OC2CCCC2)/C=N/OCC(N3CC(C)OC(C)C3)=O
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).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 390.48 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 |
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.
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.
