Selective Determination of Glutathione Using a Highly Emissive Fluorescent Probe Based on a Pyrrolidine-Fused Chlorin
We report the use of a carboxylated pyrrolidine-fused chlorin (TCPC) as a fluorescent probe for the determination of glutathione (GSH) in 7.4 pH phosphate buffer. TCPC is a very stable, highly emissive molecule that has been easily obtained from meso-tetrakis(4-methoxycarbonylphenyl) porphyrin (TCPP...
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| Format: | Article |
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MDPI AG
2023-01-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/2/568 |
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| author | Francisco G. Moscoso Carla Queirós Paula González Tânia Lopes-Costa Ana M. G. Silva Jose M. Pedrosa |
| author_facet | Francisco G. Moscoso Carla Queirós Paula González Tânia Lopes-Costa Ana M. G. Silva Jose M. Pedrosa |
| author_sort | Francisco G. Moscoso |
| collection | DOAJ |
| description | We report the use of a carboxylated pyrrolidine-fused chlorin (TCPC) as a fluorescent probe for the determination of glutathione (GSH) in 7.4 pH phosphate buffer. TCPC is a very stable, highly emissive molecule that has been easily obtained from meso-tetrakis(4-methoxycarbonylphenyl) porphyrin (TCPP) through a 1,3-dipolar cycloaddition approach. First, we describe the coordination of TCPC with Hg(II) ions and the corresponding spectral changes, mainly characterized by a strong quenching of the chlorin emission band. Then, the TCPC-Hg<sup>2+</sup> complex exhibits a significant fluorescence turn-on in the presence of low concentrations of the target analyte GSH. The efficacy of the sensing molecule was tested by using different TCPC:Hg<sup>2+</sup> concentration ratios (1:2, 1:5 and 1:10) that gave rise to sigmoidal response curves in all cases with modulating detection limits, being the lowest 40 nM. The experiments were carried out under physiological conditions and the selectivity of the system was demonstrated against a number of potential interferents, including cysteine. Furthermore, the TCPC macrocycle did not showed a significant fluorescent quenching in the presence of other metal ions. |
| first_indexed | 2024-03-09T11:35:58Z |
| format | Article |
| id | doaj.art-768cd9dd04404371b4fb6fe3f502aca9 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T11:35:58Z |
| publishDate | 2023-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-768cd9dd04404371b4fb6fe3f502aca92023-11-30T23:41:40ZengMDPI AGMolecules1420-30492023-01-0128256810.3390/molecules28020568Selective Determination of Glutathione Using a Highly Emissive Fluorescent Probe Based on a Pyrrolidine-Fused ChlorinFrancisco G. Moscoso0Carla Queirós1Paula González2Tânia Lopes-Costa3Ana M. G. Silva4Jose M. Pedrosa5Departamento de Sistemas Físicos, Químicos y Naturales, Universidad Pablo de Olavide, Ctra. Utrera km. 1, 41013 Seville, SpainLAQV-REQUIMTE, Departamento de Química e Bioquímica, Faculdade de Ciências da Universidade do Porto, 4169-007 Porto, PortugalDepartamento de Sistemas Físicos, Químicos y Naturales, Universidad Pablo de Olavide, Ctra. Utrera km. 1, 41013 Seville, SpainDepartamento de Sistemas Físicos, Químicos y Naturales, Universidad Pablo de Olavide, Ctra. Utrera km. 1, 41013 Seville, SpainLAQV-REQUIMTE, Departamento de Química e Bioquímica, Faculdade de Ciências da Universidade do Porto, 4169-007 Porto, PortugalDepartamento de Sistemas Físicos, Químicos y Naturales, Universidad Pablo de Olavide, Ctra. Utrera km. 1, 41013 Seville, SpainWe report the use of a carboxylated pyrrolidine-fused chlorin (TCPC) as a fluorescent probe for the determination of glutathione (GSH) in 7.4 pH phosphate buffer. TCPC is a very stable, highly emissive molecule that has been easily obtained from meso-tetrakis(4-methoxycarbonylphenyl) porphyrin (TCPP) through a 1,3-dipolar cycloaddition approach. First, we describe the coordination of TCPC with Hg(II) ions and the corresponding spectral changes, mainly characterized by a strong quenching of the chlorin emission band. Then, the TCPC-Hg<sup>2+</sup> complex exhibits a significant fluorescence turn-on in the presence of low concentrations of the target analyte GSH. The efficacy of the sensing molecule was tested by using different TCPC:Hg<sup>2+</sup> concentration ratios (1:2, 1:5 and 1:10) that gave rise to sigmoidal response curves in all cases with modulating detection limits, being the lowest 40 nM. The experiments were carried out under physiological conditions and the selectivity of the system was demonstrated against a number of potential interferents, including cysteine. Furthermore, the TCPC macrocycle did not showed a significant fluorescent quenching in the presence of other metal ions.https://www.mdpi.com/1420-3049/28/2/568carboxylated pyrrolidine-fused chlorinfluorescenceglutathione detection |
| spellingShingle | Francisco G. Moscoso Carla Queirós Paula González Tânia Lopes-Costa Ana M. G. Silva Jose M. Pedrosa Selective Determination of Glutathione Using a Highly Emissive Fluorescent Probe Based on a Pyrrolidine-Fused Chlorin Molecules carboxylated pyrrolidine-fused chlorin fluorescence glutathione detection |
| title | Selective Determination of Glutathione Using a Highly Emissive Fluorescent Probe Based on a Pyrrolidine-Fused Chlorin |
| title_full | Selective Determination of Glutathione Using a Highly Emissive Fluorescent Probe Based on a Pyrrolidine-Fused Chlorin |
| title_fullStr | Selective Determination of Glutathione Using a Highly Emissive Fluorescent Probe Based on a Pyrrolidine-Fused Chlorin |
| title_full_unstemmed | Selective Determination of Glutathione Using a Highly Emissive Fluorescent Probe Based on a Pyrrolidine-Fused Chlorin |
| title_short | Selective Determination of Glutathione Using a Highly Emissive Fluorescent Probe Based on a Pyrrolidine-Fused Chlorin |
| title_sort | selective determination of glutathione using a highly emissive fluorescent probe based on a pyrrolidine fused chlorin |
| topic | carboxylated pyrrolidine-fused chlorin fluorescence glutathione detection |
| url | https://www.mdpi.com/1420-3049/28/2/568 |
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