Francesco Sansone
Università degli Studi di Parma (Italy), Dipartimento di Chimica, Department Member
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Research Interests: Calixarene and Lubricant
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full... more
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
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Thanks to their specific structural features and a wide variety of functionalization options, in the last twenty years calixarenes have demonstrated their relevance as scaffolds to design very interesting ligands for biomacromolecules.... more
Thanks to their specific structural features and a wide variety of functionalization options, in the last twenty years calixarenes have demonstrated their relevance as scaffolds to design very interesting ligands for biomacromolecules. With the introduction of properly and wisely selected ligating units and epitopes, charged head groups, lipophilic tails, at the upper and at the lower rim of these macrocycles, an impressive number of potent multivalent ligands have been obtained for relevant functions such as the disruption of protein-protein interactions, enzyme and lectin inhibition, nucleic acid recognition and transport into cells, among others. The important results achieved in term of biological activity suggest, for a near future, the possibility to explore the application of some of these derivatives and of others that will come, in nanomedicine and in biomedical fields as new potential drugs and as tools for diagnosis.
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We report the first macrocycle-based ratiometric molecular thermometer exploiting the conformational thermosensitivity of a calixarene functionalized with two different fluorophores.
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ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full... more
ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
Research Interests: Chemistry and Calixarene
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Growing insights into the functionality of lectin-carbohydrate interactions are identifying attractive new targets for drug design. As glycan recognition is regulated by the structure of the sugar epitope and also by topological aspects... more
Growing insights into the functionality of lectin-carbohydrate interactions are identifying attractive new targets for drug design. As glycan recognition is regulated by the structure of the sugar epitope and also by topological aspects of its presentation, a suitable arrangement of ligands in synthetic glycoclusters has the potential to enhance their avidity and selectivity. If adequately realized, such compounds might find medical applications. This is why we focused on lectins of clinical interest, acting either as a potent biohazard (a toxin from Viscum album L. akin to ricin) or as a factor in tumor progression (human galectins-1, -3, and -4). Using a set of 14 calix[n]arenes (n=4, 6, and 8) with thiourea-linked galactose or lactose moieties, we first ascertained the lectin-binding properties of the derivatized sugar head groups conjugated to the synthetic macrocycles. Despite their high degree of flexibility, the calix[6,8]arenes proved especially effective for the plant AB-toxin, in the solid-phase model system with a single glycoprotein (asialofetuin) and with human tumor cells in vitro. The bioactivity of the calix[n]arenes was also proven for human galectins. Notably, selectivity for the tested tandem-repeat-type galectin-4 among the three subgroups was determined at the level of solid-phase and cell assays, the large flexible macrocycles again figuring prominently as inhibitors. Alternate and cone versions of calix[4]arene with lactose units distinguished between galectins-1 and -4 versus galectin-3 in cell assays. The results thus revealed bioactivity of galactose-/lactose-presenting calix[n]arenes for medically relevant lectins and selectivity within the family of adhesion/growth-regulatory human galectins.
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Carbonic anhydrases (CAs) continue to represent a relevant pharmaceutical target. The need of selective inhibitors and the involvement of these metalloenzymes in many multifaceted diseases boost the search for new ligands able to... more
Carbonic anhydrases (CAs) continue to represent a relevant pharmaceutical target. The need of selective inhibitors and the involvement of these metalloenzymes in many multifaceted diseases boost the search for new ligands able to distinguish among the different CA isoforms, and for multifunctional systems simultaneously able to inhibit CAs and to interfere with other pathological events by interacting with additional targets. In this work, we successfully explored the possibility of preparing new CAs ligands by combining calixarenes with benzensulfonamide units. Inhibition tests towards three human CA isoforms evidenced, for some of the ligands, Ki values in the nanomolar range and promising selectivity. X‐ray and molecular modeling studies provided information on the mode of binding of these calixarene derivatives. Thanks to the encouraging results and the structural features typical of the calixarene scaffold, it is then possible to plan for the future the design of multifunctiona...
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After having been extensively studied as a receptor for small guests (both neutral and charged), the last 20 years have witnessed the progressive use of the calixarene macrocycle as a ligand for the recognition of large biomacromolecules.... more
After having been extensively studied as a receptor for small guests (both neutral and charged), the last 20 years have witnessed the progressive use of the calixarene macrocycle as a ligand for the recognition of large biomacromolecules. Thanks to the easy functionalization of both rims, to the multivalent nature of the scaffold, and to the possibility of controlling its three-dimensional shape and conformation, a number of calixarene derivatives able to selectively interact with proteins (including specific areas of a protein surface or an active site) or with nucleic acids have been reported. This review critically covers the results obtained in the field of biomacromolecule recognition by calixarene derivatives, giving a special emphasis to those examples where the interaction with the target leads to a specific and potentially medically relevant activity, such as protein inhibition, disruption of protein–protein interactions, and gene delivery.
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ABSTRACT New 1,2-proximalN,N,C,C-linked and 1,3-distalN,C,N,C-linked tetra-peptidocalix[4]arenes have been synthesised by functionalisation of the corresponding calixarene bis-amino acids. Their conformational properties in solution,... more
ABSTRACT New 1,2-proximalN,N,C,C-linked and 1,3-distalN,C,N,C-linked tetra-peptidocalix[4]arenes have been synthesised by functionalisation of the corresponding calixarene bis-amino acids. Their conformational properties in solution, which have been studied by H NMR, are determined by the presence of an extensive network of intramolecular hydrogen bonds. Electrospray ionisation mass spectrometry studies show that the 1,2-proximal peptidocalix[4]arene 19 is a more efficient receptor than the 1,3-distal isomer 8 in the gas phase and that it is able to recognise aromatic amino acids both as methyl esters and N-acetyl derivatives. Interestingly, these observations indicate that 19 is a bifunctional receptor since it displays both the selectivity of N-linked peptidocalixarenes for ammonium groups and that of C-linked peptidocalixarenes for carboxylates.
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Bisurea calix[4]arenes 1 and 2 possessing L-amino acid moieties at the lower rim were synthesized by reaction of the methyl esters of glycine, L-alanine, or L-isoleucine with the appropriate isocyanate (12 or 13), obtained with a safe and... more
Bisurea calix[4]arenes 1 and 2 possessing L-amino acid moieties at the lower rim were synthesized by reaction of the methyl esters of glycine, L-alanine, or L-isoleucine with the appropriate isocyanate (12 or 13), obtained with a safe and efficient Curtius rearrangement from the corresponding carboxylic acid derivatives. The conformational properties of the ligands 1 and 2 were investigated by means of a combined NMR and molecular modeling study which evidences that they are deeply influenced by strong intramolecular H-bonds between the urea NH groups and the vicinal phenolic oxygen atoms or the opposite urea C=O group. Complexation studies performed by ESI-MS and NMR spectroscopy in acetone solution show that the binding ability of these bisurea hosts decreases by increasing the side chain size of the amino acid. Host 2b has a remarkable binding ability for the N-acetyl-D-phenylalaninate anion with an interesting enantioselectivity (KDass/KLass=4.14), which is explained on the basis of a three-point interaction mode of binding.
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Research Interests: Chemistry, Carbon, Magnetic Resonance Spectroscopy, Medicine, Multidisciplinary, and 12 moreMacromolecular X-Ray Crystallography, Stereochemistry, Peptides, Phenol, Anions, Hydrogen Bonding, Protein Conformation, Pyridine, Hydrogen-Ion Concentration, Ligands, Calixarenes, and Electrospray Ionization
The present survey summarizes some of the most relevant properties of calixarenes as cation ligands that strongly contributed to the success of this class of synthetic receptors in supramolecular chemistry. After a first general... more
The present survey summarizes some of the most relevant properties of calixarenes as cation ligands that strongly contributed to the success of this class of synthetic receptors in supramolecular chemistry. After a first general introduction on the synthesis and conformational properties of calixarenes we will try to point out the main features that influence selectivity in metal and ammonium ion binding, analyzing in sequence the ligands for (1) alkali and alkaline-earth ions, (2) lanthanide and actinide ions, (3) transition and posttransition metal ions, and (4) ammonium, alkylammonium, and quaternary ammonium cations. More than to be comprehensive, this article strives to transmit the reader the calixarene distinctive features which govern selectivity and efficiency in metal ion binding.
Research Interests: Chemistry and Calixarene
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... Full Paper. Synthesis and Properties of Upper Rim C-Linked Peptidocalix[4]arenes. Marcio Lazzarotto 1 ,; Francesco Sansone 1 ,; Laura Baldini 1 ,; Alessandro Casnati 1 ,; Pietro Cozzini 2 ,; Rocco Ungaro 1. ... M. Fabbi , A. Pochini ,... more
... Full Paper. Synthesis and Properties of Upper Rim C-Linked Peptidocalix[4]arenes. Marcio Lazzarotto 1 ,; Francesco Sansone 1 ,; Laura Baldini 1 ,; Alessandro Casnati 1 ,; Pietro Cozzini 2 ,; Rocco Ungaro 1. ... M. Fabbi , A. Pochini , F. Ugozzoli , R. Ungaro , Eur. J. Org. Chem. ...
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The photogeneration of electricity and solar fuels by solar irradiation in photoelectrochemical cells is one of the sectors with the highest growth potential in the decarbonised society. However, the use of different components, in... more
The photogeneration of electricity and solar fuels by solar irradiation in photoelectrochemical cells is one of the sectors with the highest growth potential in the decarbonised society. However, the use of different components, in particular photosensitizers and catalysts, can present problems of charge transfer efficiency at the interface, leading to lower final efficiencies. In this work we present novel integrated photosensitizer‐catalyst dyads based on robust and, at the same time, flexible host‐guest non‐covalent interactions through the use of calix[4]arene cavities. Current photogeneration in photoelectrochemical cells showed twice greater efficiency in the integrated calixarene‐based host‐guest dyads compared to the traditional architecture based on the separate photosensitizer‐catalyst pair. Molecular dynamics studies have shown that the enhanced performance originates from an optimization of the distances between the centres of the photosensitizer, catalyst and semiconductor involved in the charge transfer processes, thus allowing a higher final efficiency of the charge photogeneration process.
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The calix[4]arene scaffold, blocked in the cone conformation through alkylation with long alkyl chains, and decorated at the upper rim with four guanidine or arginine units, effectively catalyzes the cleavage of the phosphodiester bond of... more
The calix[4]arene scaffold, blocked in the cone conformation through alkylation with long alkyl chains, and decorated at the upper rim with four guanidine or arginine units, effectively catalyzes the cleavage of the phosphodiester bond of DNA and RNA model compounds in water. An exhaustive kinetic investigation unequivocally points to the existence of spontaneous aggregation phenomena, driven by hydrophobic effect, occurring at different critical concentrations that depend on the identity of the compound. A pronounced superiority of the assembled structures compared with the monomers in solution was observed. Moreover, the catalytically active units, clustered on the macrocyclic tetrafunctional scaffold, were proved to efficiently cooperate in the catalytic mechanism and result in improved reaction rates compared to those of the monofunctional model compounds. The kinetic analysis is also integrated and corroborated with further experiments based on fluorescence spectroscopy and lig...
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\uabMasterLab - Challenge the Science\ubb is a serious video-game designed to help high school students to self-evaluate the adequacy of their educational background in view of a University degree program in Chemistry. The project is... more
\uabMasterLab - Challenge the Science\ubb is a serious video-game designed to help high school students to self-evaluate the adequacy of their educational background in view of a University degree program in Chemistry. The project is developed by a joint working group at the Universities of Bologna and Parma together with a professional videogame producer, in the framework and with the funding of the Italian Scientific Degrees Plan (PLS) \u2013 Chemistry. \uabMasterLab - Challenge the Science\ubb is conceived as a Role Playing Game where the student/player moves throughout different rooms, each containing a different puzzle to solve. The puzzles consist in basic chemistry, mathematics and physics problems at a high school difficulty level and require virtual laboratory operations, measurements and calculations. The puzzles are built up and "gamified" in a modular manner, so they can be quickly written by the experts involved in the project. The game map develops randomly in order to offer to players different kind of problems in each game session. The project is easily expandable, by adding new puzzles, rooms, graphic elements, etc. and could be also extended to other scientific areas. When the player decides to end the game session, she/he will get a score (i.e. a piece of the \u201cseal of science\u201d) depending on the type of skill she/he has demonstrated. Game data will be recorded (according to privacy), in order to obtain accurate and detailed statistics regarding the knowledge of the individual topics useful also for high school teachers. \uabMasterLab - Challenge the Science\ubb will be free, playable both on mobile devices (smartphone or tablet) and PC/MAC and easily accessible without the need of installation. A collaboration with a Science of Education Department was activated to provide the video-game with validity in term of pedagogical content and approach, to evaluate the effectiveness of the project in term of self-evaluation and to prevent discouraging effects on low score students. A preliminary beta-1 version of the video-game will be presented on the next November to the network of National Scientific Degrees Plan (PLS) \u2013 Chemistry. The official release will be delivered and tested in schools starting from spring 2020
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In the field of direct production of hydrogen from solar energy and water, photocatalytic methods hold great potential especially when metal‐free molecular components are preferred. In this work, we have developed a new class of... more
In the field of direct production of hydrogen from solar energy and water, photocatalytic methods hold great potential especially when metal‐free molecular components are preferred. In this work, we have developed a new class of calix[4]arene‐based molecular photosensitizers to be used as antenna systems in the photocatalytic production of hydrogen. The structure of the dyes has a typical donor‐π‐acceptor molecular architecture where a calix[4]arene scaffold is used as an embedded donor. The new materials have been fully characterized in their optical, electrochemical, and photocatalytic properties. The properties conferred by the calix[4]arene donor afforded twice larger performances compared to the corresponding linear system though showing similar quantitative optical properties. The new molecular design paves the way to a new strategy for photocatalytic hydrogen production where the calix[4]arene scaffold can afford more efficient systems and can offer the potential for host‐gue...
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The key features of calixarene derivatives as multivalent ligands for biomacromolecules and as multifunctional catalysts are reviewed herein. The ease of functionalization and the possibility to control the regio‐ and stereochemical... more
The key features of calixarene derivatives as multivalent ligands for biomacromolecules and as multifunctional catalysts are reviewed herein. The ease of functionalization and the possibility to control the regio‐ and stereochemical disposition of multiple ligating units around a central core allow to obtain ligands with high affinity and selectivity especially for proteins and nucleic acids. The hydrophilic/lipophilic character can also be finely tuned, allowing to obtain monomeric hybrid derivatives or amphiphiles able to self‐assemble alone or in co‐formulation with lipids to give nanoparticles and liposomes that incorporate calixarenes. The knowledge acquired up to now sheds light on the future applications of calixarenes in bionanotechnology and nanomedicine.
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The main rules that can be used to mould multivalent calixarene macrocycles for obtaining efficient and successful ligands for biomacromolecule recognition are outlined and described with the help of selected literature examples.
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The catalytic activity of an artificial phosphodiesterase that combines a ligated metal ion (Cu(II), Zn(II)) with a guanidinium unit connected by a 1,2-vicinal calix[4]arene spacer was investigated in the transesterification of RNA models... more
The catalytic activity of an artificial phosphodiesterase that combines a ligated metal ion (Cu(II), Zn(II)) with a guanidinium unit connected by a 1,2-vicinal calix[4]arene spacer was investigated in the transesterification of RNA models HPNP and four diribonucleoside 3',5'-monophosphates. Comparison with previous data related to the 1,3-distal regioisomeric metal complexes confirms the superiority of the Cu(II) complexes over the Zn(II) analogs and shows that in the reactions of HPNP, GpU, and UpU, the catalytic efficiency depends very little on whether the substitution pattern is 1,2-vicinal or 1,3-distal. On the other hand, CpA turned out to be a good substrate for the Cu(II) complex of the 1,2-vicinal catalyst and a bad substrate for the corresponding 1,3-distal regioisomer, whereas the opposite holds for GpA. Extension of the investigation to the cleavage of the DNA model BNPP showed that both Zn(II) and Cu(II) complexes exhibit good catalytic efficiency, with a superiority of the 1,2-vicinal catalyst in both cases. The data reported in this work show that rate accelerations over background for the best catalyst-substrate combinations at 0.5 mM catalyst concentration are 3.6 × 10(5)-fold for HPNP, 1.1 × 10(6)-fold for BNPP, and range from 1.3 × 10(6)- to 1.3 × 10(7)-fold for diribonucleoside monophosphates.
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The main goal of this project is to demonstrate the advantages of sensor integration on a remotely controlled robotic platform for increasing operator safety and improving the classification of explosive targets. This is accomplished by... more
The main goal of this project is to demonstrate the advantages of sensor integration on a remotely controlled robotic platform for increasing operator safety and improving the classification of explosive targets. This is accomplished by combining the imaging provided by radars and an optoelectronic sensor, a time-of-flight (ToF) depth camera. An additional aim is to demonstrate the operability and practicality of the system in a field with landmine simulants having plastic cases.
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As of 2017, there are an estimated 100 million abandoned land mines littered across 61 countries. Following the wars in Afghanistan, Libya, Syria, Yemen, and Ukraine, there has been a rise in casualties due to the triggering of... more
As of 2017, there are an estimated 100 million abandoned land mines littered across 61 countries. Following the wars in Afghanistan, Libya, Syria, Yemen, and Ukraine, there has been a rise in casualties due to the triggering of previously-abandoned explosive devices. The above institutions combined specialties to develop a remotely-operable, multisensor, robotic device for the detection of land mines, UXO (1), and IEDs (2). The robotic detection device uses novel subsurface radar with imaging and target classification to differentiate between threatening landmines and innocuous clutter. The expected outcome of this research is the creation of a multi-sensor system on a semi-autonomous vehicle for detection and discrimination of explosive devices. This robotic platform will change the approach to detecting landmines in post-war zones, all the meanwhile lessening direct human-to-mine or animal-to-mine contact in detecting landmines. Architecture has a high potential to move the procedures of explosive detection toward completely remote and autonomous system.
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One of the most appealing approaches for regulating gene expression, named the “microRNA therapeutic” method, is based on the regulation of the activity of microRNAs (miRNAs), the intracellular levels of which are dysregulated in many... more
One of the most appealing approaches for regulating gene expression, named the “microRNA therapeutic” method, is based on the regulation of the activity of microRNAs (miRNAs), the intracellular levels of which are dysregulated in many diseases, including cancer. This can be achieved by miRNA inhibition with antimiRNA molecules in the case of overexpressed microRNAs, or by using miRNA-mimics to restore downregulated microRNAs that are associated with the target disease. The development of new efficient, low-toxic, and targeted vectors of such molecules represents a key topic in the field of the pharmacological modulation of microRNAs. We compared the delivery efficiency of a small library of cationic calix[4]arene vectors complexed with fluorescent antimiRNA molecules (Peptide Nucleic Acids, PNAs), pre-miRNA (microRNA precursors), and mature microRNAs, in glioma- and colon-cancer cellular models. The transfection was assayed by cytofluorimetry, cell imaging assays, and RT-qPCR. The c...
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Fast and efficient triplet formation via charge separation followed by radical pair intersystem crossing is reported in a calixarene-based donor/acceptor dyad.