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Defant A.,University of Trento | Mancini I.,University of Trento | Matucci R.,University of Florence | Bellucci C.,University of Florence | And 5 more authors.
Organic and Biomolecular Chemistry | Year: 2015

Cellulose represents a key component of a renewable biomass source, from which chiral compounds with a high added value in the application for the synthesis of potentially bioactive molecules can be obtained. The anhydrosugar (1R,5S)-1-hydroxy-3,6-dioxa-bicyclo[3.2.1]octan-2-one (LAC), produced on the gram-scale by catalytic pyrolysis of cellulose, was used as a building block in the synthesis of five new enantiomerically pure muscarine-like products. The structures of the target compounds 4-8 showed different substituents at the C-2 and C-4 positions, but each of them had the same (2S,4R) configuration as the natural (+)-muscarine. A renewed interest in new muscarinic analogues is due to the design and synthesis of molecules exhibiting a higher selectivity for a specific muscarinic receptor and due to the development of effective agents in the treatment of Alzheimer's disease and other cognitive disorders. In this context, products 4-8 were investigated with respect to their binding affinity to human M1-M5 muscarinic acetylcholine receptors. The data indicated that compound 8, emerging as the most active in the series with values comparable to natural (+)-muscarine and a moderate selectivity in favor of the hM2 subtype receptor, also exhibited the highest stability during the interaction with the hM2 (3UON) subtype muscarinic receptor by using a docking calculation. © The Royal Society of Chemistry 2015.


Malferrari D.,Centro Interdipartimentale Of Ricerca Industriale Energia E Ambiente Ciri | Armenise N.,University of Bologna | Decesari S.,CNR Institute of atmospheric Sciences and Climate | Galletti P.,Centro Interdipartimentale Of Ricerca Industriale Energia E Ambiente Ciri | And 3 more authors.
ACS Sustainable Chemistry and Engineering | Year: 2015

Surfactants are a wide class of compounds used in a broad spectrum of industrial and everyday applications. In this paper, we present the synthesis of a new family of surfactants having C12 and C18 alkyl chains obtained from itaconic acid and fatty amines, molecules industrially obtained from renewable resources. Main physicochemical properties of synthesized surfactants have been measured and their rheological behaviors have been evaluated at the air-water interface using the pendant drop technique. Some of the synthesized surfactants are stimuli responsive compounds, switchable to a polar form in the presence of CO2. The synthetic strategies have been optimized aiming at the sustainability of the process employing a complete set of green metrics and the software EATOS. (Graph Presented). © 2015 American Chemical Society.


Galletti P.,University of Bologna | Galletti P.,Centro Interdipartimentale Of Ricerca Industriale Energia E Ambiente Ciri | Malferrari D.,Centro Interdipartimentale Of Ricerca Industriale Energia E Ambiente Ciri | Samori C.,Centro Interdipartimentale Of Ricerca Industriale Energia E Ambiente Ciri | And 3 more authors.
Colloids and Surfaces B: Biointerfaces | Year: 2015

In this study we have explored the effects of different groups of ionic liquids (ILs) on membrane fusion. The ILs used contain different head groups: N-methylimidazolium, 3-methylpyridinium and N-methylpyrrolidinium; short alkyl or ether functionalized side chains (with one or two ethoxy functionalities), paired with chloride anion. These ILs have been compared with 1-dodecyl-3-methylimidazolium bromide as example of a highly lipophilic IL. The effect of ILs on membrane fusion was investigated through pyrene steady state fluorescence probing, using the IE factor and excimer/monomer ratio (IE/IM) as parameters. The ratio between the vibronic bands of pyrene (I1/I3 ratio) has been used to monitor the effect of ILs on the aggregation properties of egg-PC liposomes. The effect of different ILs' families was evident; the pyridinium ILs induced a greater extent of fusion than pyrrolidinium and imidazolium ILs having the same side chain. Marginal effect could be attributed to different anions. ILs with short alkyl chains were usually more effective than ether functionalized ones. The aggregation behaviors of ILs having dioxygenated chains have been measured in buffer solution. © 2014 Elsevier B.V.

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