Lorenzo Guazzelli

Lorenzo Guazzelli
Università di Pisa | UNIPI · Department of Pharmacy

Professor

About

96
Publications
6,974
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Introduction
Preparation, characterization and application on novel ionic liquids (ILs), especially bio-based ionic liquids, and deep eutectic solvents (DESs). Use of ILs and DESs in the transformation of biomass into either valuable building blocks or new materials, and in new area of research. Synthesis of carbohydrate structures starting from largely available sugars. Development of carbohydrate-based vaccines and their analogous (zwitterionic polysaccharides). Synthesis of amino- and carbasugars.

Publications

Publications (96)
Article
Ionic liquids (ILs), either chiral in themselves (CILs) or modified with small quantities of CILs or related chiral molecular salts as chiral additives, have been proposed as an effective tool to achieve enantiodiscrimination in terms of potential differences in voltammetric electroanalysis, on account of their high local order at the electrode | s...
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Ionic gating has emerged as an effective and versatile tool to tune the charge-carrier density of a material and control its electronic ground state, as well as to develop low-temperature devices such as electrochemical transistors. Ionic liquids are a promising gating agent due to their high thermal- and electrochemical stability for both fundamen...
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Broadband dielectric spectroscopy in a broad temperature range was employed to study ionic conductivity and dynamics in tetraalkylammonium- and tetraalkylphosphonium-based ionic liquids (ILs) having levulinate as a common anion. Combining data for ionic conductivity with data obtained for viscosity in a Walden plot, we show that ionic conductivity...
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Cellulose, a natural, renewable, and environment friendly biopolymer, has been considered as a sustainable feedstock in the near future. However, only 0.3% of cellulose is today processed since it is not soluble in conventional solvents due to the strong hydrogen bonding network and highly ordered structure. Hence, the search of effective and eco-f...
Article
In the context of bio-based ionic liquids (ILs), in recent years levulinate ILs have been explored in various applications with appreciable performances. To expand their scope of use, seven selected levulinate ILs featuring different cationic moieties have been prepared and their physico-chemical properties compared. While all the ILs generated dis...
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The objective of this study was to examine the bioactivity of extracts from apple pomace obtained by non-conventional green extraction methods (DES systems). Bioactivity was antioxidant capacity and ability to stimulate insulin secretion from pancreatic beta-cells. The antioxidant capacity of extracts was examined using the DPPH and the FRAP assay....
Article
Herein, we report the first application of deep eutectic solvents (DESs) in radical-mediated hydrothiolation reactions.
Article
Key features of the deep eutectic solvent-microwave assisted simultaneous extraction of polyphenols and delignification pretreatment of chestnut shell waste are presented.
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Cannabis sativa L. is a multi-purpose crop, whose resilience, adaptability and soil-enriching properties make it a low-impact production. In the last years, the cultivation of the “industrial” hemp varieties (THC < 0.2%) has been promoted by many Countries, opening a whole new market of hemp-derived products, such as its essential oil (EO). Its dis...
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Semiconductor nanostructures have raised much hope for the implementation of high‐performance thermoelectric generators. Indeed, they are expected to make available reduced thermal conductivity without a heavy trade‐off on electrical conductivity, a key requirement to optimize the thermoelectric figure of merit. Here, a novel nanodevice architectur...
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Electrolyte Gating In article number 2104175, Domenic Prete, Francesco Rossella, and co-workers present a boost in thermoelectric energy conversion technology via a novel device platform featuring high aspect ratio semiconductor nanostructures and soft-matter systems, allowing the simultaneous and all-electrical benchmark and modulation of the ther...
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Four divalent ionic liquids based on imidazolium cations with alkyl or ether functionalized side-chains were synthesised and characterized: 3,3'-(tetraethyleneglycol-1,11-diyl)bis(1-methyl-1H-imidazolium)bromide, [tetraEG(mim)2][Br]2, 3,3'-(tetraethyleneglycol-1,11-diyl)bis(1-methyl-1H-imidazolium)acetate, [tetraEG(mim)2][OAc]2, 1-butyl-3-methylimi...
Article
Two series of ionic liquids (ILs) consisting in metal-EDTA complex anions ([MEDTA], with V, Cr, Mn, Fe and Co as metal center) and 1-butyl-3-methylimidazolium ([BMIM]) or trioctylmethylphosphonium ([TOMP]) cations have been prepared via a new synthetic approach based on the related acidic EDTA complexes (HMEDTA). A strong influence of both the coor...
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Benzimidazole dicationic ionic liquids (BDILs) have not yet been widely explored in spite 12 of their potential. Therefore, two structurally related families of BDILs, paired with either bromide 13 or bistriflimide anions and bearing alkyl spacers ranging from C3 to C6, have been prepared. Their 14 thermal properties have been studied by thermograv...
Article
Developing new materials for the separation of gas mixtures is a key subject in setting up a circular economy. In this work, we report the synthesis and application of novel polymeric membranes, based on polymerized ionic liquids (PILs), to be used for CO2 separation from different gas pairs. Phosphonium-based PILs have been copolymerized within an...
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Carbohydrates represent a promising option in transitioning from oil-based chemical resources to renewable ones, with the goal of developing chemistries for a sustainable future. Cellulose, hemicellulose, and largely available monosaccharides already provide useful chemical building blocks, so-called platform chemicals, such as levulinic acid and h...
Article
Six esters of both betaine and l-carnitine bromides, featuring alkyl groups ranging from C8 to C18 in length, have been synthesized. The thermal behaviour of these twelve bio-based salts has been analyzed and compared by thermal gravimetric analysis and differential scanning calorimetry. The l-carnitine alkyl ester bromides melted below 100 °C and...
Article
Six N-morpholinium dicationic ionic liquids (DILs) with the following general formula [C4H8NO]2(CH2)n[X]2, being n = 4, 6 and 8 and X = Br, NTf2 (where NTf2 = bis(trifluoromethane)sulfonimide) have been synthesized. Their thermal behavior was studied by thermogravimetry (TG) using five different heating rates (2, 4, 8, 10 and 12 K min⁻¹) aiming at...
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Chiral ionic liquids CILs, or ionic liquids ILs with chiral additives, look very attractive chiral media for enantioselective electroanalysis, on account of their high chiral structural order at the electrochemical interphase. A family is now introduced of molecular salts with CIL properties, based on the chiral steroid building block of deoxycholi...
Article
The evaporation/thermaldecompositionbehaviour of twoionicliquids with phosphoniumcation (PhosphoniumIonicLiquids, PhosphoniumILs,), namelytetraoctylphosphonium bis(trifluoromethylsulfonyl)imide ([P8888]NTf2) and tetraoctylphosphonium perfluorobutylphosphonate ([P8888]NFBS) wasstudied by thermogravimetryand by the effusion-basedtechniques Knudsen Ef...
Article
Deep Eutectic Solvents (DESs) offer advantages similar to ionic liquid (IL) ones, with easier and more sustainable synthesis; moreover, bio-based DESs often include chiral components, surprisingly underexploited. A proof of concept is now offered of the impressive potential of enantiopure chiral DESs as chiral media for enantioselective electroanal...
Article
Ionic liquids (ILs) have progressively acquired a central position in chemical and material sciences landscapes due to their peculiar physical and solvation properties. Thanks to their metal-complexing ability as well as wide thermal stability and the capability to be easily reused, ILs constitute ideal candidates for applications in metal-catalyze...
Article
A panel of ionic liquids has been synthesized and their effect on the vanadyl acetylacetonate solubility in acetonitrile has been firstly assessed. 1-Butyl-3-methylimidazolium acetate showed an unprecedented result, increasing the VO(acac)2 solubility in acetonitrile of more than one magnitude order (from 0.06 M to 1.1 M) opening new interesting ho...
Article
We fabricate dual-gated electric double layer field effect transistors based on InAs nanowires gated with an ionic liquid, and we perform electrical transport measurements in the temperature range from room temperature to 4.2 K. By adjusting the spatial distribution of ions inside the ionic liquid employed as gate dielectric, we electrostatically i...
Article
Three novel deep eutectic solvents (DESs) were prepared with choline acetate (ChOAc) as the hydrogen bond acceptor (HBA) and three hydrogen bond donors (HBD): glycolic acid (GlyA), levulinic acid (LevA) and imidazole (Im). They showed different, albeit remarkable capabilities of dissolving lignin (from 35% to 100%) and hemicellulose (from 40% to 50...
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The full utilization of agricultural waste and its recycle into a new chain of value are of primary importance for the development of a sustainable and profitable agricultural industry. Chestnut shell waste (CSW) is an interesting case of study, whose valorization has been though partially investigated to date. This work aims at exploring the compl...
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Aldose reductase is a key enzyme in the development of long term diabetic complications and its inhibition represents a viable therapeutic solution for people affected by these pathologies. Therefore, the search for effective aldose reductase inhibitors is a timely and pressing challenge. Herein we describe the access to a novel class of oxyimino d...
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An amendment to this paper has been published and can be accessed via a link at the top of the paper.
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For topical treatment of skin cancer, the design of pH-responsive nanocarriers able to selectively release the drug in the tumor acidic microenvironment represents a reliable option for targeted delivery. In this context, a series of newly synthesized surface-active fatty acid-protic ionic liquids (FA-PILs), based on tetramethylguanidinium cation a...
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This study reports an ionic liquid (IL) promoted green method to obtain diaryl thioethers useful as key intermediates for the synthesis of matrix metalloproteinase (MMP) inhibitors. The synthetic pathway includes a sequential Ullmann reaction and Suzuki cross-coupling. The Ullmann conditions were optimized as regards the catalyst, the ionic liquid,...
Article
New bis-quinolinium chiral ionic liquids (CILs) were synthesized in good yields starting from isomannide and isosorbide by a straightforward procedure that maintains the absolute stereostructure of the isohexide scaffolds. Thermal gravimetric analysis and differential scanning calorimetry, aimed at investigating the short thermal stability and the...
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The syntheses of six thiol-exhibiting monosaccharides towards suicide inhibition of Helicobacter pylori are reported. Blood group Antigen Binding Adhesin (BabA), a bacterial membrane-bound lectin, binds to human ABO and Lewis b blood group structures displayed on the surface of host epithelial cells. Crystal structures of the carbohydrate-recogniti...
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A convergent synthetic strategy to Cryptococcus neoformans glucuronoxylomannan (GXM) capsular polysaccharide part structures was developed based on di-, tri-, tetra-, penta- and hexasaccharide thioglycoside building blocks. The approach permitted the synthesis of a library of spacer-containing serotype A and D related GXM oligosaccharide structures...
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The preparation of Fe-decorated sporopollenins was achieved using pollen grains and an ionic liquid as solvent and functionalizing agent. The integrity of the organic capsules was ascertained through scanning electron microscopy studies. The presence of Fe in the capsule was investigated using FT-IR, X-ray photoemission spectroscopy and energy-disp...
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Objectives Ionic liquids have shown potential for applications as antimicrobials. Their antimicrobial activity has been shown to be higher against Gram-positive than Gram-negative bacteria, suggesting a protective role for the outer membrane of Gram-negative microorganisms. Colistin is a last-resort antibiotic often used for treating infections sus...
Preprint
A block synthetic strategy to Cryptococcus neoformans glucuronoxylomannan (GXM) capsular polysaccharide part structures has been developed based on di-, tri-, tetra-, penta- and hexasaccharide thioglycoside building blocks. The approach permitted the synthesis of a library of spacer-containing serotype A and D related GXM oligosaccharide structures...
Preprint
A block synthetic strategy to Cryptococcus neoformans glucuronoxylomannan (GXM) capsular polysaccharide part structures has been developed based on di-, tri-, tetra-, penta- and hexasaccharide thioglycoside building blocks. The approach permitted the synthesis of a library of spacer-containing serotype A and D related GXM oligosaccharide structures...
Article
Full-text available
Chemical biology is an emerging field that enables the study and manipulation of biological systems with probes whose reactivities provide structural insights. The opportunistic fungal pathogen Cryptococcus neoformans possesses a polysaccharide capsule that is a major virulence factor, but is challenging to study. We report here the synthesis of a...
Preprint
Full-text available
Chemical biology is an emerging field that allows the study and manipulation of biological systems using probes that inform on structure based on their reactivity. We report the synthesis of a hydroxylamine-armed fluorescent probe that reacts with reducing glycans and its application to study the architecture of the Cryptococcus neoformans capsule...
Article
Pollen grains are microstructures produced in very large quantity in nature. Their main structural component, spopropollenin, is a very resisitant organic polymer presenting numerous hydroxyl functional groups. This abundant and...
Article
The cycloaddition of CO2 to epoxides has attracted a great deal of interest in recent years as an atom efficient way to employ this greenhouse gas as a useful C1 building block. While several ionic liquids have been tested as catalysts for the reaction, little attention has been devoted to dicationic ionic liquids (DILs). Herein, the catalytic acti...
Article
The development of microwave (MW) assisted processes involving the use of deep eutectic solvents (DESs) is a fast-expanding research topic. However, there is a lack of information about the heating behavior of DESs under MW irradiation. In this work, a family of DESs composed by choline chloride and two types of hydrogen bond donors (carboxylic aci...
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In a previous paper a thermosensitive hydrogel formulation based on chitosan or its derivatives (TSOH), containing medicated chitosan nanoparticles (Ch NP) for transcorneal administration of 5-fluorouracil (5-FU) was described. The Ch NP-containing TSOH allowed a time-constant 5-FU concentration in the aqueous for 7 h from instillation. The aim of...
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The title compound 1-octyl-3-(3-(1-methylpyrrolidiniumyl)propyl)imidazolium bis(trifluoromethane)sulfonimide was prepared in three steps. This asymmetrical dicationic ionic liquid (ADIL) is composed of two different positively charged head groups (1-octylimidazolium and methylpyrrolidinium cations), which are linked through a propyl alkyl chain and...
Article
Ionic liquids (ILs) are neoteric solvents characterized by unique physicochemical properties and considerable structural variability. The thermal behavior of 24 ILs, belonging to two structurally related families with either bromide or Tf2N as counteranion, was analyzed. For bromide mono- and dicationic ionic liquids (DILs), thermal gravimetric ana...
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New thiol-functionalized carboxylate ionic liquids (ILs), varying both for the cation and for the anion structures, have been prepared as new potential redox switching systems by reacting either 3-mercapto propionic acid (3-MPA) or N-acetyl-cysteine (NAC) with commercially available methyl carbonate ILs. Different ratios of thiol/disulfide ILs were...
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Conjugation of known biologically active molecules to carbohydrate frameworks represents a valuable option for the preparation of hybrid, structurally-related families of compounds with the aim of modulating their biological response. Therefore, we present here a study on the preparation of d-galacto, d-manno, d-gluco, and d-lactose glycoconjugates...
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Dicationic ionic liquids (DILs) are a subclass of the ionic liquid (IL) family and are characterized by two cationic head groups linked by means of a spacer. While DILs are increasingly attracting interest due to their peculiar physico-chemical properties, there is still a lack of understanding of their intermolecular interactions. Herein, we repor...
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Zwitterionic polysaccharides (ZPs) have been shown in recent years to display peculiar immunological properties, thus attracting the interest of the carbohydrate research community. To fully elucidate the mechanisms underlying these properties and exploit the potential of this kind of structures, in depth studies are still required. In this context...
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Carba analogues of biologically relevant natural carbohydrates are promising structures for the development of future drugs endowed with enhanced hydrolytic stability. An open synthetic challenge in this field is the optimization of new methodologies for the stereo-and regioselective opening of α-gluco carbasugar 1,2-epoxides that allow for the pre...
Article
Novel ammonium, phosphonium and imidazolium ionic liquids (ILs) based on levulinic acid as the anion were prepared and characterized (NMR, FT-IR, TGA, viscosity). Commercial methyl carbonate precursors were employed to access the target levulinate ILs through a quick, one-step synthetic procedure that does not require the use of halogenated solvent...
Article
Iminosugars are known glycosidase inhibitors which are the subject of drug development efforts against several diseases. The access to structurally-related families of iminosugars is of primary importance for running structure-activity relationship studies. In this work, the double reductive amination (aminocyclization) reaction of a dicarbonyl der...
Article
Nine structurally-related fatty acid ionic liquids have been prepared and their thermal behavior as well as their ability to self-assemble in water has been investigated. The thermal properties were studied by thermal gravimetric analysis (TGA) and differential scanning calorimetry (DSC), while the aggregation behavior was analyzed by tensiometry,...
Article
In order to identify most suitable ionic liquids (ILs) for potential applications in infection prevention and control, in the present study we comparatively evaluated the antimicrobial potency and hemolytic activity of 15 ILs, including 11 previously described and four newly synthesized ILs, using standard microbiological procedures against Gram-po...
Article
Two new levulinate-based protic ionic liquids (Lev PILs) have been synthetized through an easy, scalable neutralization reaction between levulinic acid (LA), which is one of the most promising renewable building blocks obtainable from cellulose, and amidine superbases (either DBU or DBN). The prepared PILs have been characterized (by means of NMR,...
Article
The direct catalytic α‐amidoalkylation of dihydroquinolines with aldehydes bearing oxygen functionalities at different positions in a Mannich‐type reaction has been studied. β‐Alkoxy‐aldehyde 1d gave high enantioselectivity, albeit with an inherently poor diastereoselectivity, while the use of α‐alkoxy aldehydes 1c was detrimental also to enantiose...
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Dicationic ionic liquids (DILs), a subset of the ionic liquid (IL) family, have attracted growing interest in recent years, and the range of applications within which they are investigated is constantly expanding. However, data which allows structure to property correlation of a DIL is still limited, and thus selecting an appropriate salt to addres...
Article
In spite of the increasing fundamental and practical interest of electrochemistry in ionic liquids (ILs), exploration of chiral ionic liquids (CILs) in view of enantioselective electrochemistry and electroanalysis is surprisingly overdue. In this study a family of chiral ionic liquids (CILs) based on natural chiral building blocks, of easy synthesi...
Article
A family of structurally-related guanidinium bistriflimide ionic liquids has been prepared and characterized. TGA analyses showed a high thermal stability for all the proposed ionic liquids while DSC and XPS analyses divided them into distinct subsets depending on whether one or more constraining cycles were present. The results obtained highlighte...
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Thallium is an emerging contaminant, which can be retained in scale encrustation within the pipeline and then released to drinking water. It is included in the Priority Pollutant List of the U.S. EPA. In this study, a sample from the water pipeline of Pietrasanta (Italy), affected by the contamination of thallium, is characterized by SEM-EDS, TGA,...