Description
Key facts
CAS number:85416-73-5,
Purity:>99%,
Form:SolidSee storage information,
Molecular weight:275.34 Da,
Molecular formula:C16H21NO3,
PubChem:158758,
Nature:Synthetic,
Solubility:Soluble in DMSO to 100 mM,
Biochemical name:(S)-(+)-rolipram,
Biological description:PDE4 inhibitor (IC50 = 0.58 μM). Less active enantiomer.,
Canonical smiles:COC1=C(C=C(C=C1)C2CC(=O)NC2)OC3CCCC3,
Isomeric smiles:COC1=C(C=C(C=C1)[C@@H]2CC(=O)NC2)OC3CCCC3,
InChi:InChI=1S/C16H21NO3/c1-19-14-7-6-11(12-9-16(18)17-10-12)8-15(14)20-13-4-2-3-5-13/h6-8,12-13H,2-5,9-10H2,1H3,(H,17,18)/t12-/m1/s1,
InChiKey:HJORMJIFDVBMOB-GFCCVEGCSA-N,
IUPAC Name:(4S)-4-(3-cyclopentyloxy-4-methoxyphenyl)pyrrolidin-2-one
Properties and Storage Information:
Shipped at conditions-Ambient - Can Ship with Ice, Appropriate short-term storage conditions-+4°C, Appropriate long-term storage conditions-+4°C, Storage information-Store under desiccating conditions, The product can be stored for up to 12 months
Supplementary Information:
This supplementary information is collated from multiple sources and compiled automatically.
The PDE4 family including PDE4A PDE4B PDE4C and PDE4D constitutes a group of phosphodiesterases involved in cyclic AMP (cAMP) hydrolysis. PDE4 enzymes commonly referred to as cAMP-specific phosphodiesterases play a mechanical role by breaking down cAMP into AMP therefore regulating intracellular levels of cAMP. These enzymes vary in molecular mass with PDE4A ranging from approximately 66 to 85 kDa depending on isoform variants. Expression of PDE4 subtypes differs across tissues but they are widely expressed in the brain immune cells and smooth muscle tissues. Understanding their mechanical action allows targeting with PDE4 inhibitors which are relevant in various therapeutic areas.
Biological function summary
These PDE4 enzymes serve critical functions in modulating cellular responses to extracellular signals. By regulating cAMP levels they influence processes such as inflammation and smooth muscle contraction. PDE4 enzymes do not typically form part of large protein complexes but may interact with other proteins such as signaling scaffolds. Their ability to regulate cAMP a second messenger makes them important players in cellular signaling pathways. Each PDE4 subtype plays specialized roles depending on their expression patterns and local cellular environments.
Pathways
PDE4 enzymes critically impact the regulation of the cAMP signaling pathway and the MAPK/ERK pathway. cAMP is a pivotal signaling molecule in transferring hormonal signals into cellular responses. PDE4 enzymes modulate intracellular cAMP levels affecting processes like activation of protein kinase A (PKA) and cAMP-response element-binding protein (CREB). Relation exists between PDE4 and other proteins like EPAC which also bind cAMP to elicit distinct cellular responses. The modulation of MAPK/ERK pathway by PDE4 enzymes further integrates them into the wider network of cellular signal transduction.
PDE4 enzymes have links to inflammatory conditions and neuropsychiatric disorders like depression. By controlling cAMP levels PDE4 affects inflammatory responses relevant in conditions such as chronic obstructive pulmonary disease (COPD). PDE4 inhibitors show promise in managing inflammation by preventing excess cAMP breakdown. In the brain altered PDE4 activity influences mood regulation connecting it to proteins like CREB which play a role in neuroplasticity pivotal to depression management. Targeting specific PDE4 subtypes offers potential in developing treatments for these conditions.
