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Highly Selective Fluorescent Sensors: Polyethylenimine Derivatives of Triphenylamine and Coumarin for GTP and ATP Interaction via Fluorescence Lifetime Imaging Microscopy

[Image: see text] Chemical derivatives of polyethylenimine (PEI) receptors with either triphenylamine (TPA) or 7-hydroxy-4-methyl-coumarin (Cou) form stable complexes with adenine and guanine nucleotides in water. The host–guest complex modulation is found to be based on noncovalent molecular intera...

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Autores principales: Delgado-Pinar, Estefanía, Medeiros, Matilde, Costa, Telma, Seixas de Melo, J. Sérgio
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10426326/
https://www.ncbi.nlm.nih.gov/pubmed/37588082
http://dx.doi.org/10.1021/acsapm.3c00834
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author Delgado-Pinar, Estefanía
Medeiros, Matilde
Costa, Telma
Seixas de Melo, J. Sérgio
author_facet Delgado-Pinar, Estefanía
Medeiros, Matilde
Costa, Telma
Seixas de Melo, J. Sérgio
author_sort Delgado-Pinar, Estefanía
collection PubMed
description [Image: see text] Chemical derivatives of polyethylenimine (PEI) receptors with either triphenylamine (TPA) or 7-hydroxy-4-methyl-coumarin (Cou) form stable complexes with adenine and guanine nucleotides in water. The host–guest complex modulation is found to be based on noncovalent molecular interactions such as π–π stacking and hydrogen bonding, which are dependent on the aromatic moieties attached to the polyaminic (PEI) backbone. PEI-TPA acts as a chemosensor with a recognition driving force based on aggregation-induced emission (AIE), involving π–π interaction between the nucleic base and TPA. It detects GTP by a chelation enhancement quenching effect of fluorescence (CHEQ) with a measured logarithm stability constant, log β = 7.7. By varying the chemical characteristics of the fluorophore, as in the PEI-Cou system, the driving force for recognition changes from a π–π interaction to an electrostatic interaction. The coumarin derivative detects ATP with a log β value one order of magnitude higher than that for GTP, allowing for the selective recognition of the two nucleotides in a 100% aqueous solution. Furthermore, fluorescence lifetime imaging microscopy (FLIM) allows for a correlation between the selectivity of PEI-TPA toward nucleotides and the morphology of the structures formed upon ATP and GTP recognition. This study offers valuable insights into the design of receptors for the selective recognition of nucleotides in water.
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spelling pubmed-104263262023-08-16 Highly Selective Fluorescent Sensors: Polyethylenimine Derivatives of Triphenylamine and Coumarin for GTP and ATP Interaction via Fluorescence Lifetime Imaging Microscopy Delgado-Pinar, Estefanía Medeiros, Matilde Costa, Telma Seixas de Melo, J. Sérgio ACS Appl Polym Mater [Image: see text] Chemical derivatives of polyethylenimine (PEI) receptors with either triphenylamine (TPA) or 7-hydroxy-4-methyl-coumarin (Cou) form stable complexes with adenine and guanine nucleotides in water. The host–guest complex modulation is found to be based on noncovalent molecular interactions such as π–π stacking and hydrogen bonding, which are dependent on the aromatic moieties attached to the polyaminic (PEI) backbone. PEI-TPA acts as a chemosensor with a recognition driving force based on aggregation-induced emission (AIE), involving π–π interaction between the nucleic base and TPA. It detects GTP by a chelation enhancement quenching effect of fluorescence (CHEQ) with a measured logarithm stability constant, log β = 7.7. By varying the chemical characteristics of the fluorophore, as in the PEI-Cou system, the driving force for recognition changes from a π–π interaction to an electrostatic interaction. The coumarin derivative detects ATP with a log β value one order of magnitude higher than that for GTP, allowing for the selective recognition of the two nucleotides in a 100% aqueous solution. Furthermore, fluorescence lifetime imaging microscopy (FLIM) allows for a correlation between the selectivity of PEI-TPA toward nucleotides and the morphology of the structures formed upon ATP and GTP recognition. This study offers valuable insights into the design of receptors for the selective recognition of nucleotides in water. American Chemical Society 2023-07-11 /pmc/articles/PMC10426326/ /pubmed/37588082 http://dx.doi.org/10.1021/acsapm.3c00834 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Delgado-Pinar, Estefanía
Medeiros, Matilde
Costa, Telma
Seixas de Melo, J. Sérgio
Highly Selective Fluorescent Sensors: Polyethylenimine Derivatives of Triphenylamine and Coumarin for GTP and ATP Interaction via Fluorescence Lifetime Imaging Microscopy
title Highly Selective Fluorescent Sensors: Polyethylenimine Derivatives of Triphenylamine and Coumarin for GTP and ATP Interaction via Fluorescence Lifetime Imaging Microscopy
title_full Highly Selective Fluorescent Sensors: Polyethylenimine Derivatives of Triphenylamine and Coumarin for GTP and ATP Interaction via Fluorescence Lifetime Imaging Microscopy
title_fullStr Highly Selective Fluorescent Sensors: Polyethylenimine Derivatives of Triphenylamine and Coumarin for GTP and ATP Interaction via Fluorescence Lifetime Imaging Microscopy
title_full_unstemmed Highly Selective Fluorescent Sensors: Polyethylenimine Derivatives of Triphenylamine and Coumarin for GTP and ATP Interaction via Fluorescence Lifetime Imaging Microscopy
title_short Highly Selective Fluorescent Sensors: Polyethylenimine Derivatives of Triphenylamine and Coumarin for GTP and ATP Interaction via Fluorescence Lifetime Imaging Microscopy
title_sort highly selective fluorescent sensors: polyethylenimine derivatives of triphenylamine and coumarin for gtp and atp interaction via fluorescence lifetime imaging microscopy
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10426326/
https://www.ncbi.nlm.nih.gov/pubmed/37588082
http://dx.doi.org/10.1021/acsapm.3c00834
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