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Title: | Highly Selective Fluorescent Sensors: Polyethylenimine Derivatives of Triphenylamine and Coumarin for GTP and ATP Interaction via Fluorescence Lifetime Imaging Microscopy | Authors: | Delgado Pinar, Estefanía Medeiros, Matilde Costa, Telma Melo, J. Sérgio Seixas de |
Keywords: | PEI; fluorescence; AIE; adenosine-5′-triphosphate (ATP); guanosine-5′-triphosphate (GTP); FLIM imaging | Issue Date: | 11-Aug-2023 | Publisher: | American Chemical Society | Project: | The authors thank CQC-IMS, which is financially supported by the Portuguese Agency for Scientific Research, FCT through projects UIDB/00313/2020 and UIDP/00313/2020, cofounded by COMPETE2020-UC. E.D.-P. thanks the “Concurso de Estímulo ao Emprego Científico” for the junior contract CEECIND/04136/2018 from the Fundação para a Ciência e a Tecnologia and for the M. Zambrano contract UP2021-044 from the Spanish Ministry of Science, Innovation and Universities financed by the European Union, Next Generation EU. This work has received support from Laserlab- Europe (EU-H2020 871124). NMR data collected at the UCNMR facility are supported in part by the EDRF through the COMPETE Program and by national funds from the FCT through Grants RECI/QEQ-QFI/0168/2012 and CENTRO- 07-CT62-FEDER-002012 and also through support to Rede Nacional de Ressonância Magnética Nuclear (RNRMN) and to Coimbra Chemistry Centre through Grant UID/QUI/ 00313/2019 | Serial title, monograph or event: | ACS Applied Polymer Materials | Volume: | 5 | Issue: | 8 | Abstract: | 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. | URI: | https://hdl.handle.net/10316/111990 | ISSN: | 2637-6105 2637-6105 |
DOI: | 10.1021/acsapm.3c00834 | Rights: | openAccess |
Appears in Collections: | FCTUC Química - Artigos em Revistas Internacionais I&D CQC - Artigos em Revistas Internacionais |
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