A carregar...
Publicação
Host-Guest Chemosensor Ensembles based on Water-Soluble Sulfonated Calix[n]arenes and a Pyranoflavylium Dye for the Optical Detection of Biogenic Amines
| Nome: | Descrição: | Tamanho: | Formato: | |
|---|---|---|---|---|
| 3.77 MB | Adobe PDF |
Orientador(es)
Resumo(s)
Biogenic amines (BAs) are biologically active nitrogen-containing compounds formed during the food spoilage process and are often related as key markers of food quality, safety, and freshness. Because their presence in foods at high levels can cause significant health problems, researchers have been focused on developing novel strategies and methods for early detection and capture of these analytes. Herein, water-soluble sulfonated calix[n]arene macrocycles (SC4, SC6, and SC8) and a pH-sensitive dye (4′-hydroxy-10-methylpyranoflavylium) were investigated as host-guest systems for BA sensing. The hosts were able to bind the flavylium cation of the dye with association constants of 103 to 104 M-1. The dye complexation also allowed tuning its pKa from 6.72 (free) toward high values: 7.68 (SC4), 7.79 (SC6), and 8.45 (SC8). These data were crucial to optimize the host-guest complexes as optical sensing systems for putrescine/tyramine (pH 7.2-7.6), yielding a colorimetric redshift from yellow to red. The BA sensing was also demonstrated by fluorescence quenching for the calix[n]arene/dye complexes and fluorescence recovery after the addition of BAs. 1H NMR spectroscopy was used to demonstrate the interaction mode, confirming an encapsulation-driven mechanism. Overall, these host-guest systems demonstrated great potential for the detection of BAs, one of the main key markers of food spoilage.
Descrição
Funding Information:
The authors acknowledge Dr. Mariana Andrade for the NMR analysis. This work was supported by the Associate Laboratory for Sustainable Chemistry, Clean Processes and Technologies LAQV. K.D.M. acknowledges the ANID Doctoral Fellowship Folio N°21210424.
Publisher Copyright:
© 2024 The Authors. Published by American Chemical Society.
Palavras-chave
biogenic amines fluorescence food spoilage host−guest complexes macrocyclic receptors NMR pyranoflavylium dyes UV-vis General Chemistry General Agricultural and Biological Sciences