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Poly-histidine grafting leading to fishbone-like architectures
- Source :
- 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
- Publication Year :
- 2018
- Publisher :
- RSC Publishing, Cambridge , Regno Unito, 2018.
-
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.
- 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
Subjects
Details
- Language :
- English
- Database :
- OpenAIRE
- Journal :
- 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
- Accession number :
- edsair.doi.dedup.....4489f3317aa60326a7637e5b32613492
- Full Text :
- https://doi.org/10.1039/c8ra00315g