New amino acid-based thiosemicarbazones and hydrazones: synthesis and evaluation as fluorimetric chemosensors in aqueous mixtures
Autor(a) principal: | |
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Data de Publicação: | 2023 |
Outros Autores: | , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | https://hdl.handle.net/1822/87327 |
Resumo: | A series of new phenylalanine derivatives bearing thiosemicarbazone and hydrazone units at the side chain were synthesised and evaluated as fluorimetric chemosensors for ions. They were tested for the recognition of organic and inorganic anions, (such as AcO-, F-, Cl-, Br-, I-, ClO4-, CN-, NO3-, BzO-, OH-, H2PO4- and HSO4-) and of alkaline, alkaline-earth, and transition metal cations, (such as Na+, K+, Cs+, Ag+, Cu+, Cu2+, Ca2+, Cd2+, Co2+, Pb2+, Pd2+, Ni2+, Hg2+, Zn2+, Fe2+, Fe3+ and Cr3+) in acetonitrile and its aqueous mixtures in varying ratio through spectrofluorimetric titrations. The results indicate that there is a strong interaction through the donor N, O and S atoms at the side chain of the various phenylalanines, with higher sensitivity for Cu2+, Fe3+ and F- in a 1:2 ligand-ion stoichiometry. The photophysical and metal ion sensing properties of these phenylalanines suggest that they can be suitable for incorporation into peptidic chemosensory frameworks. |
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New amino acid-based thiosemicarbazones and hydrazones: synthesis and evaluation as fluorimetric chemosensors in aqueous mixturesHydrazoneThiosemicarbazonePhenylalanineUnnatural amino acidsFluorescenceChemosensorsSynthesisHeterocyclesCiências Naturais::Ciências QuímicasSaúde de qualidadeA series of new phenylalanine derivatives bearing thiosemicarbazone and hydrazone units at the side chain were synthesised and evaluated as fluorimetric chemosensors for ions. They were tested for the recognition of organic and inorganic anions, (such as AcO-, F-, Cl-, Br-, I-, ClO4-, CN-, NO3-, BzO-, OH-, H2PO4- and HSO4-) and of alkaline, alkaline-earth, and transition metal cations, (such as Na+, K+, Cs+, Ag+, Cu+, Cu2+, Ca2+, Cd2+, Co2+, Pb2+, Pd2+, Ni2+, Hg2+, Zn2+, Fe2+, Fe3+ and Cr3+) in acetonitrile and its aqueous mixtures in varying ratio through spectrofluorimetric titrations. The results indicate that there is a strong interaction through the donor N, O and S atoms at the side chain of the various phenylalanines, with higher sensitivity for Cu2+, Fe3+ and F- in a 1:2 ligand-ion stoichiometry. The photophysical and metal ion sensing properties of these phenylalanines suggest that they can be suitable for incorporation into peptidic chemosensory frameworks.This research was funded by the Foundation for Science and Technology (FCT) for financial support to CQ-UM [PEst-C/QUI/UI0686/2013 (FCOMP-01-0124-FEDER-037302)], CQUM (UIDB/00686/2020) and a PhD grant to C.I.C. Esteves (SFRH/BD/68360/2010). The NMR spectrometer Bruker Avance III 400 is part of the National NMR Network and was purchased within the framework of the National Program for Scientific Re-equipment with funds from POCI 2010 (FEDER) and FCTMDPIUniversidade do MinhoEsteves, Cátia I. C.Raposo, M. Manuela M.Costa, Susana P. G.20232023-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfapplication/pdfhttps://hdl.handle.net/1822/87327engEsteves, C. I. C.; Raposo, M. M. M.; Costa, S. P. G. New amino acid-based thiosemicarbazones and hydrazones: synthesis and evaluation as fluorimetric chemosensors in aqueous mixtures. Molecules 2023, 28(21), 7256.1420-304910.3390/molecules2821725637959675https://doi.org/10.3390/molecules28217256info: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:RCAAP2023-12-02T01:21:33Zoai:repositorium.sdum.uminho.pt:1822/87327Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T00:40:31.168764Repositório 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 |
New amino acid-based thiosemicarbazones and hydrazones: synthesis and evaluation as fluorimetric chemosensors in aqueous mixtures |
title |
New amino acid-based thiosemicarbazones and hydrazones: synthesis and evaluation as fluorimetric chemosensors in aqueous mixtures |
spellingShingle |
New amino acid-based thiosemicarbazones and hydrazones: synthesis and evaluation as fluorimetric chemosensors in aqueous mixtures Esteves, Cátia I. C. Hydrazone Thiosemicarbazone Phenylalanine Unnatural amino acids Fluorescence Chemosensors Synthesis Heterocycles Ciências Naturais::Ciências Químicas Saúde de qualidade |
title_short |
New amino acid-based thiosemicarbazones and hydrazones: synthesis and evaluation as fluorimetric chemosensors in aqueous mixtures |
title_full |
New amino acid-based thiosemicarbazones and hydrazones: synthesis and evaluation as fluorimetric chemosensors in aqueous mixtures |
title_fullStr |
New amino acid-based thiosemicarbazones and hydrazones: synthesis and evaluation as fluorimetric chemosensors in aqueous mixtures |
title_full_unstemmed |
New amino acid-based thiosemicarbazones and hydrazones: synthesis and evaluation as fluorimetric chemosensors in aqueous mixtures |
title_sort |
New amino acid-based thiosemicarbazones and hydrazones: synthesis and evaluation as fluorimetric chemosensors in aqueous mixtures |
author |
Esteves, Cátia I. C. |
author_facet |
Esteves, Cátia I. C. Raposo, M. Manuela M. Costa, Susana P. G. |
author_role |
author |
author2 |
Raposo, M. Manuela M. Costa, Susana P. G. |
author2_role |
author author |
dc.contributor.none.fl_str_mv |
Universidade do Minho |
dc.contributor.author.fl_str_mv |
Esteves, Cátia I. C. Raposo, M. Manuela M. Costa, Susana P. G. |
dc.subject.por.fl_str_mv |
Hydrazone Thiosemicarbazone Phenylalanine Unnatural amino acids Fluorescence Chemosensors Synthesis Heterocycles Ciências Naturais::Ciências Químicas Saúde de qualidade |
topic |
Hydrazone Thiosemicarbazone Phenylalanine Unnatural amino acids Fluorescence Chemosensors Synthesis Heterocycles Ciências Naturais::Ciências Químicas Saúde de qualidade |
description |
A series of new phenylalanine derivatives bearing thiosemicarbazone and hydrazone units at the side chain were synthesised and evaluated as fluorimetric chemosensors for ions. They were tested for the recognition of organic and inorganic anions, (such as AcO-, F-, Cl-, Br-, I-, ClO4-, CN-, NO3-, BzO-, OH-, H2PO4- and HSO4-) and of alkaline, alkaline-earth, and transition metal cations, (such as Na+, K+, Cs+, Ag+, Cu+, Cu2+, Ca2+, Cd2+, Co2+, Pb2+, Pd2+, Ni2+, Hg2+, Zn2+, Fe2+, Fe3+ and Cr3+) in acetonitrile and its aqueous mixtures in varying ratio through spectrofluorimetric titrations. The results indicate that there is a strong interaction through the donor N, O and S atoms at the side chain of the various phenylalanines, with higher sensitivity for Cu2+, Fe3+ and F- in a 1:2 ligand-ion stoichiometry. The photophysical and metal ion sensing properties of these phenylalanines suggest that they can be suitable for incorporation into peptidic chemosensory frameworks. |
publishDate |
2023 |
dc.date.none.fl_str_mv |
2023 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 |
https://hdl.handle.net/1822/87327 |
url |
https://hdl.handle.net/1822/87327 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Esteves, C. I. C.; Raposo, M. M. M.; Costa, S. P. G. New amino acid-based thiosemicarbazones and hydrazones: synthesis and evaluation as fluorimetric chemosensors in aqueous mixtures. Molecules 2023, 28(21), 7256. 1420-3049 10.3390/molecules28217256 37959675 https://doi.org/10.3390/molecules28217256 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
application/pdf application/pdf |
dc.publisher.none.fl_str_mv |
MDPI |
publisher.none.fl_str_mv |
MDPI |
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 |
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Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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RCAAP |
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RCAAP |
reponame_str |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
collection |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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1799136309878456320 |