4 results on '"Roberto Artusi"'
Search Results
2. Poly-histidine grafting leading to fishbone-like architectures
- Author
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Gianluca Giorgi, Alessandro Donati, Andrea Cappelli, Francesca Villafiorita-Monteleone, Vincenzo Razzano, Gianfranco Caselli, Francesco Makovec, Germano Giuliani, Salvatore Battiato, Michela Visintin, Annalisa Reale, Chiara Botta, Marco Paolino, Roberto Artusi, and Filippo Samperi
- Subjects
General Chemical Engineering ,02 engineering and technology ,010402 general chemistry ,polymer brushes ,01 natural sciences ,Adduct ,poly-histidine ,chemistry.chemical_compound ,Imidazole ,Chemical Engineering (all) ,Reactivity (chemistry) ,Histidine ,chemistry.chemical_classification ,Chemistry (all) ,fluorogens ,General Chemistry ,Nuclear magnetic resonance spectroscopy ,Polymer ,021001 nanoscience & nanotechnology ,Combinatorial chemistry ,0104 chemical sciences ,chemistry ,PEGylation ,0210 nano-technology ,Ethylene glycol - Abstract
A small series of Morita–Baylis–Hillman adduct (MBHA) derivatives was synthesized and made to react with imidazole, N-acetylhistidine, and N-acetylhexahistidine as models of poly-histidine derivatives. Intriguingly, the reaction of MBHA derivatives 1a and b with imidazole in acetonitrile–phosphate buffered saline (PBS) gave the imidazolium salt biadducts 3a and b as the main reaction products. These results were confirmed by experiments performed with N-acetylhistidine and 1b and suggested the possible occurrence of these structures in the products of poly-histidine labeling with MBHA derivatives 1a and b. These compounds were then transformed into the corresponding water-soluble derivatives 1c–e by introducing oligo(ethylene glycol) chains and their reactivity was evaluated in preliminary experiments with imidazole and then with N-acetylhexahistidine in PBS. The structure of polymeric materials Ac-His-6-MBHA-1d and Ac-His-6-MBHA-1e obtained using ten-fold excesses of compounds 1d and e was investigated using mass spectrometry, NMR spectroscopy, and photophysical studies, which suggested the presence of biadduct residues in both polymeric materials. These results provide the basis for the preparation of fishbone-like polymer brushes, the characterization of their properties, and the exploration of their potential applications in different fields of science such as in vivo fluorogenic labeling, fluorescence microscopy, protein PEGylation, up to the production of smart materials and biosensors.
- Published
- 2018
- Full Text
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3. Development of Imidazole-Reactive Molecules Leading to a New Aggregation-Induced Emission Fluorophore Based on the Cinnamic Scaffold
- Author
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Francesca Villafiorita-Monteleone, Alessandro Donati, Gianfranco Caselli, Chiara Botta, Francesco Makovec, Michela Visintin, Annalisa Reale, Vincenzo Razzano, Andrea Cappelli, Germano Giuliani, Marco Paolino, and Roberto Artusi
- Subjects
Scaffold ,fluorophore ,Fluorophore ,010405 organic chemistry ,General Chemical Engineering ,Solid-state ,General Chemistry ,010402 general chemistry ,Photochemistry ,01 natural sciences ,Blue emission ,Article ,imidazole labeling ,0104 chemical sciences ,aggregation induced emission ,lcsh:Chemistry ,chemistry.chemical_compound ,chemistry ,lcsh:QD1-999 ,Cinnamic Scaffold ,Intramolecular force ,Imidazole ,Molecule ,Aggregation-induced emission - Abstract
In order to obtain new fluorophores potentially useful in imidazole labeling and subsequent conjugation, a small series of Morita- Baylis-Hillman acetates (3a-c) was designed, synthesized, and reacted with imidazole. The optical properties of the corresponding imidazole derivatives 4a-c were analyzed both in solution and in the solid state. Although the solutions display a very weak emission, the powders show a blue emission, particularly enhanced in the case of compound 4c possessing two methoxy groups in the cinnamic scaffold. The photophysical study confirmed the hypothesis that the molecular rigidity of the solid state enhances the emission properties of these compounds by triggering the restriction of intramolecular motions, paving the way for their applications in fluorogenic labeling.
- Published
- 2017
4. Hyaluronan derivatives bearing variable densities of ferulic acid residues
- Author
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Salvatore Vomero, Raniero Mendichi, Andrea Zanardi, Giorgio Grisci, Germano Giuliani, Marco Paolino, M. Demiranda, Andrea Cappelli, Roberto Artusi, Alessandro Donati, and Gianluca Giorgi
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Reactive intermediate ,Biomedical Engineering ,General Chemistry ,General Medicine ,Grafting ,Ferulic acid ,chemistry.chemical_compound ,chemistry ,Reagent ,Organic chemistry ,General Materials Science ,Reactivity (chemistry) ,Solubility ,Conjugate ,Macromolecule - Abstract
A synthetic procedure has been developed to conjugate ferulic acid (FA) to an important natural polysaccharide derivative such as hyaluronic acid (HA). The activation of FA with 1,1'-carbonyldiimidazole (CDI) has been investigated. Two reactive intermediates, namely monoimidazolide 2 [i.e. (E)-3-(4-hydroxy-3-methoxyphenyl)-1-(1H-imidazol-1-yl)prop-2-en-1-one] and bisimidazolide 3 [i.e. (E)-4-(3-(1H-imidazol-1-yl)-3-oxoprop-1-enyl)-2-methoxyphenyl 1H-imidazole-1-carboxylate] were characterized from the point of view of their structure and reactivity. The ready isolation of bisimidazolide 3 and its reactivity support its potential usefulness in the feruloylation of molecular or macromolecular materials bearing hydroxyl moieties. Bisimidazolide derivative 3 has been found to be an effective reagent in the feruloylation of HA to give HAFA graft copolymers showing different grafting degrees (GD), which could be modulated by varying the reaction conditions. A series of HAFA derivatives showing different GD values has been prepared and submitted to an extensive macromolecular and rheological characterization in order to ascertain that the grafting of HA with FA does not degrade the polysaccharide backbone and to evaluate the role of GD in affecting solubility and rheological properties. The results suggested that relatively low GD values were sufficient to confer physical cross-linking capabilities resulting in the features of a strong gel of HAFA dispersions.
- Published
- 2014
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