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A Near InfraRed Emissive Chemosensor for Zn2+ and Phosphate Derivatives Based on a Di-(2-picolyl)amine-styrylflavylium Push-Pull Fluorophore

2023-01-01Artigo científico Acesso aberto
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dc.contributor.authorGomes, Liliana J.
dc.contributor.authorCarrilho, João P.
dc.contributor.authorPereira, Pedro M.
dc.contributor.authorMoro, Artur J.
dc.contributor.institutionDQ - Departamento de Química
dc.contributor.institutionLAQV@REQUIMTE
dc.contributor.institutionInstituto de Tecnologia Química e Biológica António Xavier (ITQB)
dc.contributor.pblMDPI - Multidisciplinary Digital Publishing Institute
dc.date.accessioned2023-06-29T22:15:51Z
dc.date.available2023-06-29T22:15:51Z
dc.date.issued2023-01-01
dc.descriptionP.M.P acknowledges funding by: (1) a La Caixa Junior Leader Fellowship (LCF/BQ/PI20/11760012) financed by “la Caixa” Foundation (ID 100010434); Project LISBOA-01-0145-FEDER-007660 Microbiologia Molecular, Estrutural e Celular (ITQB-NOVA); LS4FUTURE—Associated Laboratory (LA/P/0087/2020). Publisher Copyright: © 2023 by the authors.
dc.description.abstractA new Near InfraRed (NIR) fluorescent chemosensor for metal ions and anions is herein presented. The fluorophore is based on a styrylflavylium dye, a synthetic analogue of the natural anthocyanin family, with a di-(2-picolyl)amine (DPA) moiety as the metal chelating unit. The substitution pattern of the styrylflavylium core (with tertiary amines on positions 7 and 4′) shifts the optical properties of the dye towards the NIR region of the electronic spectra, due to a strong push-pull character over the π-conjugated system. The NIR chemosensor is highly sensitive to the presence of Zn2+, which induces a strong CHelation Enhanced Fluorescence (CHEF) effect upon binding to the DPA unit (2.7 fold increase). The strongest competing ion is Cu2+, with a complete fluorescence quenching, while other metals induce lower responses on the optical properties of the chemosensor. Subsequent anion screening of the Zn2+-chemosensor coordination compound has demonstrated a distinct selectivity towards adenosine 5′-triphosphate (ATP) and adenosine 5′-diphosphate (ADP), with high association constants (K ~ 106 M−1) and a strong CHEF effect (2.4 and 2.9 fold fluorescence increase for ATP and ADP, respectively). Intracellular studies with the Zn2+-complexed sensor showed strong luminescence in the cellular membrane of Gram– bacteria (E. coli) and mitochondrial membrane of mammalian cells (A659), which highlights its possible application for intracellular labelling.en
dc.description.versionpublishersversion
dc.description.versionpublished
dc.format.extent13
dc.format.extent4308333
dc.identifier.doi10.3390/s23010471
dc.identifier.issn1424-8220
dc.identifier.otherPURE: 64805189
dc.identifier.otherPURE UUID: 45228e2f-79cd-4fbb-9e32-5d6535cb86f9
dc.identifier.otherScopus: 85145972805
dc.identifier.otherWOS: 000911137700001
dc.identifier.otherPubMed: 36617069
dc.identifier.otherPubMedCentral: PMC9823994
dc.identifier.urihttp://hdl.handle.net/10362/154610
dc.identifier.urlhttps://www.scopus.com/pages/publications/85145972805
dc.language.isoeng
dc.peerreviewedyes
dc.relationFunding Information: info:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB%2F50006%2F2020/PT
dc.relationinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDP%2F50006%2F2020/PT
dc.relationAssociated Laboratory for Green Chemistry - Clean Technologies and Processes
dc.relationPortuguese Nuclear Magnetic Resonance Network
dc.relationJunior Leader la Caixa Postdoctoral Fellowship Programme: Shaping the new generation of leaders in research
dc.relationInvestigating the mechanisms underpinning the interaction between autonomous immunity and intracellular S. aureus cell division and persistence.
dc.relationMolecular, Structural and Cellular Microbiology – Instituto de Tecnologia Química e Biológica António Xavier
dc.relationMolecular, Structural and Cellular Microbiology – Instituto de Tecnologia Química e Biológica António Xavier
dc.relationSelective Fluorescent Chemosensors and Functionalized Materials for Lithium Detection
dc.relationinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDP%2F04612%2F2020/PT
dc.relationinfo:eu-repo/grantAgreement/FCT/OE/UI%2FBD%2F153617%2F2022/PT
dc.subjectadenosine 5′-triphosphate detection
dc.subjectdi-(2-picolyl)amine
dc.subjectNear InfraRed fluorescent sensor
dc.subjectstyrylflavylium
dc.subjectzinc binding
dc.subjectAnalytical Chemistry
dc.subjectInformation Systems
dc.subjectBiochemistry
dc.subjectAtomic and Molecular Physics, and Optics
dc.subjectInstrumentation
dc.subjectElectrical and Electronic Engineering
dc.titleA Near InfraRed Emissive Chemosensor for Zn2+ and Phosphate Derivatives Based on a Di-(2-picolyl)amine-styrylflavylium Push-Pull Fluorophoreen
dc.typejournal article
degois.publication.issue1
degois.publication.titleSensors
degois.publication.volume23
dspace.entity.typePublication
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oaire.awardTitleAssociated Laboratory for Green Chemistry - Clean Technologies and Processes
oaire.awardTitlePortuguese Nuclear Magnetic Resonance Network
oaire.awardTitleJunior Leader la Caixa Postdoctoral Fellowship Programme: Shaping the new generation of leaders in research
oaire.awardTitleInvestigating the mechanisms underpinning the interaction between autonomous immunity and intracellular S. aureus cell division and persistence.
oaire.awardTitleMolecular, Structural and Cellular Microbiology – Instituto de Tecnologia Química e Biológica António Xavier
oaire.awardTitleMolecular, Structural and Cellular Microbiology – Instituto de Tecnologia Química e Biológica António Xavier
oaire.awardTitleSelective Fluorescent Chemosensors and Functionalized Materials for Lithium Detection
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDP%2F50006%2F2020/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/9444 - RNIIIE/PINFRA%2F22161%2F2016/PT
oaire.awardURIinfo:eu-repo/grantAgreement/EC/H2020/847648/EU
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/3599-PPCDT/PTDC%2FBIA-MIC%2F2422%2F2020/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB%2F04612%2F2020/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDP%2F04612%2F2020/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/OE/UI%2FBD%2F153617%2F2022/PT
oaire.fundingStream6817 - DCRRNI ID
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oaire.fundingStreamH2020
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