Synthetic strategies for the fluorescent labeling of epichlorohydrin-branched cyclodextrin polymers
| Autor: | Éva Fenyvesi, Laszlo Jicsinszky, Kata Tuza, Lajos Szente, Milo Malanga, István Puskás, Tamás Sohajda, Mihály Bálint |
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| Rok vydání: | 2014 |
| Předmět: |
fluorescein
rhodamine Branching (polymer chemistry) coumarin Full Research Paper lcsh:QD241-441 chemistry.chemical_compound lcsh:Organic chemistry Organic chemistry Epichlorohydrin lcsh:Science chemistry.chemical_classification Cyclodextrin Chemistry Organic Chemistry Polymer Combinatorial chemistry Fluorescence Monomer coumarin fluorescein functionalized monomers and polymers nitrobenzofurazan rhodamine nitrobenzofurazan functionalized monomers and polymers lcsh:Q Fluorescent tag Macromolecule |
| Zdroj: | Beilstein Journal of Organic Chemistry, Vol 10, Iss 1, Pp 3007-3018 (2014) Beilstein Journal of Organic Chemistry |
| ISSN: | 1860-5397 |
| DOI: | 10.3762/bjoc.10.319 |
| Popis: | The fluorescent tagging of cyclodextrin derivatives enlarges their spectroscopic properties thus generating chemosensors, biological tools for visualization and sophisticated photoresponsive devices. Cyclodextrin polymers, due to the cooperative interactions, exhibit additional properties compared to their monomeric counterpart. These macromolecules can be prepared either in well water-soluble form or as gels of high swelling. Two versatile synthetic strategies for introducing a fluorescent tag (rhodamine, fluorescein, nitrobenzofuran or coumarin) into the water-soluble epichlorohydrin branched cyclodextrin polymers were worked out and compared. The fluorescent labeling was realized in three steps: 1) building in azido moieties, 2) transforming the azido groups into amino groups and 3) coupling the proper fluorescent compound to the amino groups. The other strategy started by functionalization of the monomer prior to the branching. Either the fluorescent-labeled monomer or the intermediate azido derivative of the monomer was branched. Further tuning of the properties of the polymer was achieved via branching of the methylated cyclodextrin derivative. The key intermediates and the fluorescent final products were characterized by various spectroscopic techniques and capillary electrophoresis. The applied synthetic routes were evaluated based on the molecular weight, cyclodextrin content of the products and the efficiency of labeling. |
| Databáze: | OpenAIRE |
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