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Host-Guest Chemosensor Ensembles based on Water-Soluble Sulfonated Calix[n]arenes and a Pyranoflavylium Dye for the Optical Detection of Biogenic Amines

2024-02-21Artigo científico Acesso aberto
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dc.contributor.authorPires, Ana Sofia
dc.contributor.authorDroguett Muñoz, Kevin
dc.contributor.authorde Freitas, Victor
dc.contributor.authorBasílio, Nuno
dc.contributor.authorCruz, Luís
dc.contributor.institutionDQ - Departamento de Química
dc.contributor.institutionLAQV@REQUIMTE
dc.contributor.pblACS - American Chemical Society
dc.date.accessioned2024-04-27T00:08:53Z
dc.date.available2024-04-27T00:08:53Z
dc.date.issued2024-02-21
dc.descriptionFunding 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.
dc.description.abstractBiogenic 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.en
dc.description.versionpublishersversion
dc.description.versionpublished
dc.format.extent11
dc.format.extent3950479
dc.identifier.doi10.1021/acs.jafc.3c08695
dc.identifier.issn0021-8561
dc.identifier.otherPURE: 84507179
dc.identifier.otherPURE UUID: 24251136-5c6c-41cb-b1f7-2e5bc4fa52b6
dc.identifier.otherScopus: 85185594026
dc.identifier.otherWOS: 001167201900001
dc.identifier.otherPubMed: 38345747
dc.identifier.otherPubMedCentral: PMC10885154
dc.identifier.urihttp://hdl.handle.net/10362/166670
dc.identifier.urlhttps://www.scopus.com/pages/publications/85185594026
dc.language.isoeng
dc.peerreviewedyes
dc.relationinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB%2F50006%2F2020/PT
dc.relationAssociated Laboratory for Green Chemistry - Clean Technologies and Processes
dc.relationNot Available
dc.relationNot Available
dc.relationDesenvolvimento de novos sistemas colorimétricos e fluorescentes baseados em piranoflavílios para reconhecimento seletivo de metabolitos resultantes da degradação alimentar
dc.relationinfo:eu-repo/grantAgreement/FCT/POR_NORTE/2021.08670.BD/PT
dc.subjectbiogenic amines
dc.subjectfluorescence
dc.subjectfood spoilage
dc.subjecthost−guest complexes
dc.subjectmacrocyclic receptors
dc.subjectNMR
dc.subjectpyranoflavylium dyes
dc.subjectUV-vis
dc.subjectGeneral Chemistry
dc.subjectGeneral Agricultural and Biological Sciences
dc.titleHost-Guest Chemosensor Ensembles based on Water-Soluble Sulfonated Calix[n]arenes and a Pyranoflavylium Dye for the Optical Detection of Biogenic Aminesen
dc.typejournal article
degois.publication.firstPage
degois.publication.issue7
degois.publication.lastPage
degois.publication.titleJournal of Agricultural and Food Chemistry
degois.publication.volume72
dspace.entity.typePublication
oaire.awardNumberUIDB/50006/2020
oaire.awardNumberDL 57/2016/CP1334/CT0008
oaire.awardNumberCEECIND/00466/2017/CP1462/CT0013
oaire.awardNumber2021.08670.BD
oaire.awardTitleAssociated Laboratory for Green Chemistry - Clean Technologies and Processes
oaire.awardTitleNot Available
oaire.awardTitleNot Available
oaire.awardTitleDesenvolvimento de novos sistemas colorimétricos e fluorescentes baseados em piranoflavílios para reconhecimento seletivo de metabolitos resultantes da degradação alimentar
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB%2F50006%2F2020/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/DL 57%2F2016/DL 57%2F2016%2FCP1334%2FCT0008/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/CEEC IND 2017/CEECIND%2F00466%2F2017%2FCP1462%2FCT0013/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/POR_NORTE/2021.08670.BD/PT
oaire.fundingStream6817 - DCRRNI ID
oaire.fundingStreamDL 57/2016
oaire.fundingStreamCEEC IND 2017
oaire.fundingStreamPOR_NORTE
project.funder.identifierhttp://doi.org/10.13039/501100001871
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project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
rcaap.rightsopenAccess
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