Zur Kurzanzeige

dc.contributor.authorMonteiro-Silva, Filipe
dc.contributor.authorQueirós, Carla
dc.contributor.authorLeite, Andreia
dc.contributor.authorRodríguez Rodríguez, Mª Teresa 
dc.contributor.authorRojo Cámara, Mª Josefa 
dc.contributor.authorTorroba Pérez, Tomás 
dc.contributor.authorMartins, Rui C.
dc.contributor.authorSilva, Ana M. G.
dc.contributor.authorRangel, Maria
dc.date.accessioned2021-11-11T13:52:19Z
dc.date.available2021-11-11T13:52:19Z
dc.date.issued2021-08
dc.identifier.issn1420-3049
dc.identifier.urihttp://hdl.handle.net/10259/6138
dc.description.abstractFunctional organic dyes play a key role in many fields, namely in biotechnology and medical diagnosis. Herein, we report two novel 2,3- and 3,4-dihydroxyphenyl substituted rosamines (3 and 4, respectively) that were successfully synthesized through a microwave-assisted protocol. The best reaction yields were obtained for rosamine 4, which also showed the most interesting photophysical properties, specially toward biogenic amines (BAs). Several amines including n- and t-butylamine, cadaverine, and putrescine cause spectral changes of 4, in UV–Vis and fluorescence spectra, which are indicative of their potential application as an effective tool to detect amines in acetonitrile solutions. In the gas phase, the probe response is more expressive for spermine and putrescine. Additionally, we found that methanolic solutions of rosamine 4 and n-butylamine undergo a pink to yellow color change over time, which has been attributed to the formation of a new compound. The latter was isolated and identified as 5 (9−aminopyronin), whose solutions exhibit a remarkable increase in fluorescence intensity together with a shift toward more energetic wavelengths. Other 9-aminopyronins 6a, 6b, 7a, and 7b were obtained from methanolic solutions of 4 with putrescine and cadaverine, demonstrating the potential of this new xanthene entity to react with primary amines.en
dc.description.sponsorshipFinancial support from PT national funds (FCT/MCTES, Fundação para a Ciência e a Tecnologia and Ministério da Ciência, Tecnologia e Ensino Superior) through the project PTDC/QUI-QOR/29426/2017. The research team would like to thank the projects UIDB/50006/2020, PTDC/QUI-QIN/28142/2017 and Grant BU263P18 (from the Junta de Castilla y León, Consejería de Educación y Cultura y Fondo Social Europeo). F. M. -S. gratefully acknowledges FCT (Portugal’s Foundation for Science and Technology) within grant DFA/BD/9136/2020. A.M.G.S. and A.L. thank FCT for the program DL 57/2016 – Norma transitória.en
dc.format.mimetypeapplication/pdf
dc.language.isoengen
dc.publisherMDPIen
dc.relation.ispartofMolecules. 2021, V. 26, n. 16, 5082en
dc.rightsAtribución 4.0 Internacional*
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/*
dc.subjectMicrowave-assisted synthesisen
dc.subjectCatecholated rosaminesen
dc.subject9-aminopyroninsen
dc.subjectPhotophysical propertiesen
dc.subjectBiogenic amines detectionen
dc.subject.otherQuímica orgánicaes
dc.subject.otherChemistry, Organicen
dc.titleSynthesis of Catechol Derived Rosamine Dyes and Their Reactivity toward Biogenic Aminesen
dc.typeinfo:eu-repo/semantics/articlees
dc.rights.accessRightsinfo:eu-repo/semantics/openAccesses
dc.relation.publisherversionhttps://doi.org/10.3390/molecules26165082es
dc.identifier.doi10.3390/molecules26165082
dc.relation.projectIDinfo:eu-repo/grantAgreement/FCT//PTDC%2FQUI-QOR%2F29426%2F2017/PTes
dc.relation.projectIDinfo:eu-repo/grantAgreement/FCT//UIDB%2F50006%2F2020/PTes
dc.relation.projectIDinfo:eu-repo/grantAgreement/FCT//PTDC%2FQUI-QIN%2F28142%2F2017/PTes
dc.relation.projectIDinfo:eu-repo/grantAgreement/Junta de Castilla y León//BU263P18//Sondas fluorescentes en materiales nanoestructurados para la detección y modificación de toxinas medioambientales o contaminantes traza y su incorporación a estrategias terapéuticas [fluonano]es
dc.relation.projectIDinfo:eu-repo/grantAgreement/FCT//DFA%2FBD%2F9136%2F2020/PTes
dc.type.hasVersioninfo:eu-repo/semantics/publishedVersiones


Dateien zu dieser Ressource

Thumbnail

Das Dokument erscheint in:

Zur Kurzanzeige