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Synthesis of inverse push-pull coumarin dyes and their application as solvatochromic probes and labelling agents for bacterial cell membranes

2024-09Artigo científico Acesso aberto
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dc.contributor.authorSarrato, João
dc.contributor.authorRaimundo, Bernardo
dc.contributor.authorDomingues, Luís
dc.contributor.authorFilipe, Sérgio R.
dc.contributor.authorLima, J. Carlos
dc.contributor.authorBranco, Paula S.
dc.contributor.institutionLAQV@REQUIMTE
dc.contributor.institutionDQ - Departamento de Química
dc.contributor.institutionDCV - Departamento de Ciências da Vida
dc.contributor.institutionUCIBIO - Applied Molecular Biosciences Unit
dc.contributor.pblElsevier
dc.date.accessioned2024-09-17T22:20:07Z
dc.date.available2024-09-17T22:20:07Z
dc.date.issued2024-09
dc.descriptionFunding Information: The authors acknowledge their respective, current institutions of affiliation: Universidade NOVA de Lisboa, the financial support under the projects PTDC/QUI-QOR/7450/2020 ″Organic Redox Mediators For Energy Conversion" through FCT – Fundação para a Ciência e a Tecnologia I. P. as well as the assistance of MSc Tânia Moreira in the MIC assays performed for the coumarin dyes. This work was also financed by national funds from FCT - Fundação para a Ciência e a Tecnologia, I.P., in the scope of the project, Associate Laboratory for Green Chemistry – LAQV: LA/P/0008/2020 (10.54499/LA/P/0008/2020), UIDB/50006/2020 (10.54499/UIDP/50006/2020) and UIDP/50006/2020 (10.54499/UIDB/50006/2020), as well as UIDP/04378/2020 (10.54499/UIDP/04378/2020) and UIDB/04378/2020 (10.54499/UIDB/04378/2020) of the Research Unit on Applied Molecular Biosciences - UCIBIO and the project LA/P/0140/2020 of the Associate Laboratory Institute for Health and Bioeconomy - i4HB. FCT/MCTES is also acknowledged for the PhD grant 2020.09047.BD (João Sarrato; 10.54499/2020.09047.BD). Publisher Copyright: © 2024
dc.description.abstractCoumarin derivatives have been widely employed across a great number of applications, such as laser dyes, bioimaging or chemossensors, owing to their strong fluorescence and high-quantum yields. These properties are highly tunable through structural modification, namely by the inclusion of electron-withdrawing groups (EWG) and electron-donating groups (EDG) at positions 3 and 7 of the coumarin scaffold, respectively. Comparatively, there aren't many reports of EDGs being employed at position 3, prompting us to investigate this new class of potential fluorophores. We undertook the synthesis of three novel ethynyl-linked aminophenyl-coumarin dyes, employing a key Sonogashira-coupling reaction to introduce the electron-rich tertiary aniline moiety. Two different amine donors were used, diphenylamino (coumarins A and B) and dimethylamino (coumarin C), as well as two alkoxy substituents, dibenzyloxy (A and C) and methylenedioxy (B), in the phenyl ring of the coumarin. All dyes show strong emission and significant positive solvatochromism. Additionally, they were employed as staining agents for the cellular membrane of S. pneumoniae, a Gram-positive bacterial pathogen. None of the three derivatives presented cytotoxic effects. Only A and B successfully labelled the bacterial membrane. In the case of B a very similar staining pattern and performance to that of standard dye Nile Red was observed, while A seemed to possess a more selective distribution.en
dc.description.versionpublishersversion
dc.description.versionpublished
dc.format.extent10
dc.format.extent3077553
dc.identifier.doi10.1016/j.dyepig.2024.112204
dc.identifier.issn0143-7208
dc.identifier.otherPURE: 94067066
dc.identifier.otherPURE UUID: c00562d2-9645-44a8-a04f-414edccfbf88
dc.identifier.otherScopus: 85192555317
dc.identifier.otherWOS: 001240816700001
dc.identifier.otherORCID: /0000-0003-0528-1967/work/167715019
dc.identifier.otherORCID: /0000-0002-7312-8596/work/167715252
dc.identifier.urihttp://hdl.handle.net/10362/171949
dc.identifier.urlhttps://www.scopus.com/pages/publications/85192555317
dc.language.isoeng
dc.peerreviewedyes
dc.subjectCell-imaging
dc.subjectCoumarin
dc.subjectFluorescence
dc.subjectMicroscopy
dc.subjectSolvatochromism
dc.subjectGeneral Chemical Engineering
dc.subjectProcess Chemistry and Technology
dc.subjectSDG 3 - Good Health and Well-being
dc.titleSynthesis of inverse push-pull coumarin dyes and their application as solvatochromic probes and labelling agents for bacterial cell membranesen
dc.typejournal article
degois.publication.titleDyes and Pigments
degois.publication.volume228
dspace.entity.typePublication
rcaap.rightsopenAccess

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