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

Detalhes bibliográficos
Autor(a) principal: Gomes, Liliana J.
Data de Publicação: 2023
Outros Autores: Carrilho, João P., Pereira, Pedro M., Moro, Artur J.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10362/154610
Resumo: P.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.
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spelling A Near InfraRed Emissive Chemosensor for Zn2+ and Phosphate Derivatives Based on a Di-(2-picolyl)amine-styrylflavylium Push-Pull Fluorophoreadenosine 5′-triphosphate detectiondi-(2-picolyl)amineNear InfraRed fluorescent sensorstyrylflavyliumzinc bindingAnalytical ChemistryInformation SystemsBiochemistryAtomic and Molecular Physics, and OpticsInstrumentationElectrical and Electronic EngineeringP.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.A 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.DQ - Departamento de QuímicaLAQV@REQUIMTEInstituto de Tecnologia Química e Biológica António Xavier (ITQB)RUNGomes, Liliana J.Carrilho, João P.Pereira, Pedro M.Moro, Artur J.2023-06-29T22:15:51Z2023-01-012023-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article13application/pdfhttp://hdl.handle.net/10362/154610eng1424-8220PURE: 64805189https://doi.org/10.3390/s23010471info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2024-03-11T05:37:04Zoai:run.unl.pt:10362/154610Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T03:55:41.500278Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse
dc.title.none.fl_str_mv A Near InfraRed Emissive Chemosensor for Zn2+ and Phosphate Derivatives Based on a Di-(2-picolyl)amine-styrylflavylium Push-Pull Fluorophore
title A Near InfraRed Emissive Chemosensor for Zn2+ and Phosphate Derivatives Based on a Di-(2-picolyl)amine-styrylflavylium Push-Pull Fluorophore
spellingShingle A Near InfraRed Emissive Chemosensor for Zn2+ and Phosphate Derivatives Based on a Di-(2-picolyl)amine-styrylflavylium Push-Pull Fluorophore
Gomes, Liliana J.
adenosine 5′-triphosphate detection
di-(2-picolyl)amine
Near InfraRed fluorescent sensor
styrylflavylium
zinc binding
Analytical Chemistry
Information Systems
Biochemistry
Atomic and Molecular Physics, and Optics
Instrumentation
Electrical and Electronic Engineering
title_short A Near InfraRed Emissive Chemosensor for Zn2+ and Phosphate Derivatives Based on a Di-(2-picolyl)amine-styrylflavylium Push-Pull Fluorophore
title_full A Near InfraRed Emissive Chemosensor for Zn2+ and Phosphate Derivatives Based on a Di-(2-picolyl)amine-styrylflavylium Push-Pull Fluorophore
title_fullStr A Near InfraRed Emissive Chemosensor for Zn2+ and Phosphate Derivatives Based on a Di-(2-picolyl)amine-styrylflavylium Push-Pull Fluorophore
title_full_unstemmed A Near InfraRed Emissive Chemosensor for Zn2+ and Phosphate Derivatives Based on a Di-(2-picolyl)amine-styrylflavylium Push-Pull Fluorophore
title_sort A Near InfraRed Emissive Chemosensor for Zn2+ and Phosphate Derivatives Based on a Di-(2-picolyl)amine-styrylflavylium Push-Pull Fluorophore
author Gomes, Liliana J.
author_facet Gomes, Liliana J.
Carrilho, João P.
Pereira, Pedro M.
Moro, Artur J.
author_role author
author2 Carrilho, João P.
Pereira, Pedro M.
Moro, Artur J.
author2_role author
author
author
dc.contributor.none.fl_str_mv DQ - Departamento de Química
LAQV@REQUIMTE
Instituto de Tecnologia Química e Biológica António Xavier (ITQB)
RUN
dc.contributor.author.fl_str_mv Gomes, Liliana J.
Carrilho, João P.
Pereira, Pedro M.
Moro, Artur J.
dc.subject.por.fl_str_mv adenosine 5′-triphosphate detection
di-(2-picolyl)amine
Near InfraRed fluorescent sensor
styrylflavylium
zinc binding
Analytical Chemistry
Information Systems
Biochemistry
Atomic and Molecular Physics, and Optics
Instrumentation
Electrical and Electronic Engineering
topic adenosine 5′-triphosphate detection
di-(2-picolyl)amine
Near InfraRed fluorescent sensor
styrylflavylium
zinc binding
Analytical Chemistry
Information Systems
Biochemistry
Atomic and Molecular Physics, and Optics
Instrumentation
Electrical and Electronic Engineering
description P.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.
publishDate 2023
dc.date.none.fl_str_mv 2023-06-29T22:15:51Z
2023-01-01
2023-01-01T00:00:00Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://hdl.handle.net/10362/154610
url http://hdl.handle.net/10362/154610
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 1424-8220
PURE: 64805189
https://doi.org/10.3390/s23010471
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 13
application/pdf
dc.source.none.fl_str_mv reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron:RCAAP
instname_str Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron_str RCAAP
institution RCAAP
reponame_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
collection Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
repository.name.fl_str_mv Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
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