Application of pyrrolo[2,3-b]quinoxaline with an N,N-bis(pyridin-2-ylmethyl)ethylenediamine chain for Zn(II) detection in Candida albicans and fibroblast cells
| Autor: | Bogdan Musielak, Miriam González-González, Katarzyna Stadnicka, Katarzyna Ostrowska, Piotr Goszczycki, Łukasz J. Witek, Marcin Zawrotniak, Majka Duda, Maria Rąpała-Kozik |
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| Rok vydání: | 2019 |
| Předmět: |
Fluorophore
Stereochemistry General Chemical Engineering General Physics and Astronomy Ethylenediamine 02 engineering and technology General Chemistry 010402 general chemistry 021001 nanoscience & nanotechnology Ligand (biochemistry) 01 natural sciences Fluorescence 0104 chemical sciences chemistry.chemical_compound Quinoxaline chemistry Proton NMR Chelation 0210 nano-technology Two-dimensional nuclear magnetic resonance spectroscopy |
| Zdroj: | Journal of Photochemistry and Photobiology A: Chemistry. 382:111944 |
| ISSN: | 1010-6030 |
| DOI: | 10.1016/j.jphotochem.2019.111944 |
| Popis: | In the present study, a new 'turn on' fluorescent sensor, (E/Z)-enaminone containing a pyrrolo[2,3-b]quinoxaline group as the fluorophore and a N,N-bis(pyridin-2-ylmethyl)ethylenediamine group as a specific chelator capable of selective detection of Zn2+ is reported. The structure of the ligand was determined by IR, MS, and 1D and 2D NMR, including 1H-15N HMBC correlations. X-ray analysis for (E/Z)-2 confirmed the presence of 90.3% E-diastereoisomer and 9.7% Z-one in the structure of the crystals obtained from acetonitrile. The mechanism of zinc ion recognition is related to the restriction of E/Z-isomerisation of enaminone occurring upon Zn2+ binding that alters the electronic structure of the ligand. Sensing of Zn2+ was confirmed in detail using UV–vis, fluorescent, and 1H NMR titrations, which allowed us to propose the binding mode for complexes formed in the solution during the zinc ion recognition. The ligand functions under physiological conditions and retains its activity in buffer solutions over a wide pH range 2.4–10.6. The developed sensor allowed for intracellular sensing of Zn2+ in human (fibroblast) and fungal (Candida albicans) cells through fluorescence imaging studies. |
| Databáze: | OpenAIRE |
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