Picci Giacomo, Aragoni M Carla, Arca Massimiliano, Caltagirone Claudia, Formica Mauro, Fusi Vieri, Giorgi Luca, Ingargiola Filippo, Lippolis Vito, Macedi Eleonora, Mancini Luca, Mummolo Liviana, Prodi Luca
Dipartimento di Scienze Chimiche e Geologiche, Università degli Studi di Cagliari, S.S. 554 Bivio per Sestu, 09042 Monserrato, CA, Italy.
Department of Pure and Applied Science, University of Urbino, Via della Stazione 4, I-61029 Urbino, Italy.
Org Biomol Chem. 2023 Apr 5;21(14):2968-2975. doi: 10.1039/d3ob00324h.
Bis-squaramide receptors L1-L4 bearing a dansyl moiety were synthesised and their potential applications as fluorescent probes towards non steroidal anti-inflammatory drugs naproxen and ketoprofen was investigated. A detailed photophysical characterization in CHCN/DMSO solution (9 : 1 v/v) was conducted and demonstrated that the two macrocyclic receptors L1 and L2 show good sensitivity towards ketoprofen with an ON-OFF fluorescent response, while the two open chain receptors L3 and L4 behave similarly with the three guests considered. DFT theoretical calculations carried out on L2 and L4 as model receptors allowed to propose a possible coordination mode towards the guests. Finally, H-NMR spectroscopy in DMSO-/0.5% water solution demonstrated that the four receptors interact with the considered guests H-bonds.
合成了带有丹磺酰基部分的双方酰胺受体L1-L4，并研究了它们作为非甾体抗炎药萘普生和酮洛芬荧光探针的潜在应用。在CHCN/DMSO溶液（9:1 v/v）中进行了详细的光物理表征，结果表明，两个大环受体L1和L2对酮洛芬表现出良好的敏感性，具有开-关荧光响应，而两个开链受体L3和L4对所考虑的三种客体表现出相似的行为。对作为模型受体的L2和L4进行的DFT理论计算，有助于提出与客体可能的配位模式。最后，在DMSO-/0.5%水溶液中的1H-NMR光谱表明，这四种受体与所考虑的客体通过氢键相互作用。
