Poly-histidine grafting leading to fishbone-like architectures
| Autor: | 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, Filippo Samperi |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2018 |
| Předmět: |
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 |
| Zdroj: | RSC advances 8 (2018): 8638–8656. doi:10.1039/c8ra00315g info:cnr-pdr/source/autori:Razzano V.; Paolino M.; Reale A.; Giuliani G.; Donati A.; Giorgi G.; Artusi R.; Caselli G.; Visintin M.; Makovec F.; Battiato S.; Samperi F.; Villafiorita-Monteleone F.; Botta C.; Cappelli A./titolo:Poly-histidine grafting leading to fishbone-like architectures/doi:10.1039%2Fc8ra00315g/rivista:RSC advances/anno:2018/pagina_da:8638/pagina_a:8656/intervallo_pagine:8638–8656/volume:8 |
| DOI: | 10.1039/c8ra00315g |
| Popis: | 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. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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