Selective Coordination of Cu<sup>2+</sup> and Subsequent Anion Detection Based on a Naphthalimide-Triazine-(DPA)<sub>2</sub> Chemosensor
A new fluorescent chemosensor for copper (II) and subsequent anion sensing was designed and fully characterized. The sensor consisted of a 1,8-naphthalimide core, bearing two terminal dipicolylamine (DPA) receptor units for binding metal cations, and an ethoxyethanol moiety for enhanced water solubi...
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| Format: | Article |
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MDPI AG
2020-09-01
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| Series: | Biosensors |
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| Online Access: | https://www.mdpi.com/2079-6374/10/9/129 |
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| author | Artur J. Moro Miguel Santos Mani Outis Pedro Mateus Pedro M. Pereira |
| author_facet | Artur J. Moro Miguel Santos Mani Outis Pedro Mateus Pedro M. Pereira |
| author_sort | Artur J. Moro |
| collection | DOAJ |
| description | A new fluorescent chemosensor for copper (II) and subsequent anion sensing was designed and fully characterized. The sensor consisted of a 1,8-naphthalimide core, bearing two terminal dipicolylamine (DPA) receptor units for binding metal cations, and an ethoxyethanol moiety for enhanced water solubility. The DPA units are connected to position 4 of the fluorophore via a triazine-ethylenediamine spacer. Fluorescence titration studies of the chemosensor revealed a high selectivity for Cu<sup>2+</sup> over other divalent ions, the emissions were strongly quenched upon binding, and a stability constant of 5.52 log units was obtained. Given the distance from DPA chelating units and the fluorophore, quenching from the Cu<sup>2+</sup> complexation suggests an electron transfer or an electronic energy transfer mechanism. Furthermore, the Cu<sup>2+</sup>-sensor complex proved to be capable of sensing anionic phosphate derivatives through the displacement of the Cu<sup>2+</sup> cation, which translated into a full recovery of the luminescence from the naphthalimide. Super-resolution fluorescence microscopy studies performed in HeLa cells showed there was a high intracellular uptake of the chemosensor. Incubation in Cu<sup>2+</sup> spiked media revealed a strong fluorescent signal from mitochondria and cell membranes, which is consistent with a high concentration of ATP at these intracellular sites. |
| first_indexed | 2024-03-10T16:09:17Z |
| format | Article |
| id | doaj.art-01ae94855c094366ab0e93b8e8ca35a8 |
| institution | Directory Open Access Journal |
| issn | 2079-6374 |
| language | English |
| last_indexed | 2024-03-10T16:09:17Z |
| publishDate | 2020-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Biosensors |
| spelling | doaj.art-01ae94855c094366ab0e93b8e8ca35a82023-11-20T14:36:25ZengMDPI AGBiosensors2079-63742020-09-0110912910.3390/bios10090129Selective Coordination of Cu<sup>2+</sup> and Subsequent Anion Detection Based on a Naphthalimide-Triazine-(DPA)<sub>2</sub> ChemosensorArtur J. Moro0Miguel Santos1Mani Outis2Pedro Mateus3Pedro M. Pereira4LAQV-REQUIMTE, Departamento de Química, CQFB, Universidade Nova de Lisboa, 2829-516 Caparica, PortugalLAQV-REQUIMTE, Departamento de Química, CQFB, Universidade Nova de Lisboa, 2829-516 Caparica, PortugalLAQV-REQUIMTE, Departamento de Química, CQFB, Universidade Nova de Lisboa, 2829-516 Caparica, PortugalLAQV-REQUIMTE, Departamento de Química, CQFB, Universidade Nova de Lisboa, 2829-516 Caparica, PortugalBacterial Cell Biology, MOSTMICRO, Instituto de Tecnologia Química e Biológica António Xavier, Universidade Nova de Lisboa, 2780-157 Oeiras, PortugalA new fluorescent chemosensor for copper (II) and subsequent anion sensing was designed and fully characterized. The sensor consisted of a 1,8-naphthalimide core, bearing two terminal dipicolylamine (DPA) receptor units for binding metal cations, and an ethoxyethanol moiety for enhanced water solubility. The DPA units are connected to position 4 of the fluorophore via a triazine-ethylenediamine spacer. Fluorescence titration studies of the chemosensor revealed a high selectivity for Cu<sup>2+</sup> over other divalent ions, the emissions were strongly quenched upon binding, and a stability constant of 5.52 log units was obtained. Given the distance from DPA chelating units and the fluorophore, quenching from the Cu<sup>2+</sup> complexation suggests an electron transfer or an electronic energy transfer mechanism. Furthermore, the Cu<sup>2+</sup>-sensor complex proved to be capable of sensing anionic phosphate derivatives through the displacement of the Cu<sup>2+</sup> cation, which translated into a full recovery of the luminescence from the naphthalimide. Super-resolution fluorescence microscopy studies performed in HeLa cells showed there was a high intracellular uptake of the chemosensor. Incubation in Cu<sup>2+</sup> spiked media revealed a strong fluorescent signal from mitochondria and cell membranes, which is consistent with a high concentration of ATP at these intracellular sites.https://www.mdpi.com/2079-6374/10/9/129fluorescent chemosensornaphthalimidecopper (II)phosphate derivativessuper-resolution fluorescence microscopy |
| spellingShingle | Artur J. Moro Miguel Santos Mani Outis Pedro Mateus Pedro M. Pereira Selective Coordination of Cu<sup>2+</sup> and Subsequent Anion Detection Based on a Naphthalimide-Triazine-(DPA)<sub>2</sub> Chemosensor Biosensors fluorescent chemosensor naphthalimide copper (II) phosphate derivatives super-resolution fluorescence microscopy |
| title | Selective Coordination of Cu<sup>2+</sup> and Subsequent Anion Detection Based on a Naphthalimide-Triazine-(DPA)<sub>2</sub> Chemosensor |
| title_full | Selective Coordination of Cu<sup>2+</sup> and Subsequent Anion Detection Based on a Naphthalimide-Triazine-(DPA)<sub>2</sub> Chemosensor |
| title_fullStr | Selective Coordination of Cu<sup>2+</sup> and Subsequent Anion Detection Based on a Naphthalimide-Triazine-(DPA)<sub>2</sub> Chemosensor |
| title_full_unstemmed | Selective Coordination of Cu<sup>2+</sup> and Subsequent Anion Detection Based on a Naphthalimide-Triazine-(DPA)<sub>2</sub> Chemosensor |
| title_short | Selective Coordination of Cu<sup>2+</sup> and Subsequent Anion Detection Based on a Naphthalimide-Triazine-(DPA)<sub>2</sub> Chemosensor |
| title_sort | selective coordination of cu sup 2 sup and subsequent anion detection based on a naphthalimide triazine dpa sub 2 sub chemosensor |
| topic | fluorescent chemosensor naphthalimide copper (II) phosphate derivatives super-resolution fluorescence microscopy |
| url | https://www.mdpi.com/2079-6374/10/9/129 |
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