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New 1,3-Disubstituted Benzo[h]Isoquinoline Cyclen-Based Ligand Platform: Synthesis, Eu(3+) Multiphoton Sensitization and Imaging Applications
The development of lanthanide-based luminescent probes with a long emission lifetime has the potential to revolutionize imaging-based diagnostic techniques. By a rational design strategy taking advantage of computational predictions, a novel, water-soluble Eu(3+) complex from a cyclen-based ligand b...
Autores principales: | , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7795479/ https://www.ncbi.nlm.nih.gov/pubmed/33374449 http://dx.doi.org/10.3390/molecules26010058 |
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author | Di Pietro, Sebastiano Iacopini, Dalila Storti, Barbara Nifosì, Riccardo Di Bussolo, Valeria Pineschi, Mauro Moscardini, Aldo Signore, Giovanni Bizzarri, Ranieri |
author_facet | Di Pietro, Sebastiano Iacopini, Dalila Storti, Barbara Nifosì, Riccardo Di Bussolo, Valeria Pineschi, Mauro Moscardini, Aldo Signore, Giovanni Bizzarri, Ranieri |
author_sort | Di Pietro, Sebastiano |
collection | PubMed |
description | The development of lanthanide-based luminescent probes with a long emission lifetime has the potential to revolutionize imaging-based diagnostic techniques. By a rational design strategy taking advantage of computational predictions, a novel, water-soluble Eu(3+) complex from a cyclen-based ligand bearing 1,3-disubstituted benzo[h]isoquinoline arms was realized. The ligand has been obtained overcoming the lack of reactivity of position 3 of the isoquinoline moiety. Notably, steric hindrance of the heteroaromatic chromophore allowed selective and stoichiometry-controlled insertion of two or three antennas on the cyclen platform without any protection strategy. The complex bears a fourth heptanoic arm for easy conjugation to biomolecules. This new chromophore allowed the sensitization of the metal center either with one or two photons excitation. The suitability as a luminescent bioprobe was validated by imaging BMI1 oncomarker in lung carcinoma cells following an established immunofluorescence approach. The use of a conventional epifluorescence microscope equipped with a linear structured illumination module disclosed a simple and inexpensive way to image confocally Ln-bioprobes by single photon excitation in the 350–400 nm window, where ordinary confocal systems have no excitation sources. |
format | Online Article Text |
id | pubmed-7795479 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-77954792021-01-10 New 1,3-Disubstituted Benzo[h]Isoquinoline Cyclen-Based Ligand Platform: Synthesis, Eu(3+) Multiphoton Sensitization and Imaging Applications Di Pietro, Sebastiano Iacopini, Dalila Storti, Barbara Nifosì, Riccardo Di Bussolo, Valeria Pineschi, Mauro Moscardini, Aldo Signore, Giovanni Bizzarri, Ranieri Molecules Article The development of lanthanide-based luminescent probes with a long emission lifetime has the potential to revolutionize imaging-based diagnostic techniques. By a rational design strategy taking advantage of computational predictions, a novel, water-soluble Eu(3+) complex from a cyclen-based ligand bearing 1,3-disubstituted benzo[h]isoquinoline arms was realized. The ligand has been obtained overcoming the lack of reactivity of position 3 of the isoquinoline moiety. Notably, steric hindrance of the heteroaromatic chromophore allowed selective and stoichiometry-controlled insertion of two or three antennas on the cyclen platform without any protection strategy. The complex bears a fourth heptanoic arm for easy conjugation to biomolecules. This new chromophore allowed the sensitization of the metal center either with one or two photons excitation. The suitability as a luminescent bioprobe was validated by imaging BMI1 oncomarker in lung carcinoma cells following an established immunofluorescence approach. The use of a conventional epifluorescence microscope equipped with a linear structured illumination module disclosed a simple and inexpensive way to image confocally Ln-bioprobes by single photon excitation in the 350–400 nm window, where ordinary confocal systems have no excitation sources. MDPI 2020-12-24 /pmc/articles/PMC7795479/ /pubmed/33374449 http://dx.doi.org/10.3390/molecules26010058 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Di Pietro, Sebastiano Iacopini, Dalila Storti, Barbara Nifosì, Riccardo Di Bussolo, Valeria Pineschi, Mauro Moscardini, Aldo Signore, Giovanni Bizzarri, Ranieri New 1,3-Disubstituted Benzo[h]Isoquinoline Cyclen-Based Ligand Platform: Synthesis, Eu(3+) Multiphoton Sensitization and Imaging Applications |
title | New 1,3-Disubstituted Benzo[h]Isoquinoline Cyclen-Based Ligand Platform: Synthesis, Eu(3+) Multiphoton Sensitization and Imaging Applications |
title_full | New 1,3-Disubstituted Benzo[h]Isoquinoline Cyclen-Based Ligand Platform: Synthesis, Eu(3+) Multiphoton Sensitization and Imaging Applications |
title_fullStr | New 1,3-Disubstituted Benzo[h]Isoquinoline Cyclen-Based Ligand Platform: Synthesis, Eu(3+) Multiphoton Sensitization and Imaging Applications |
title_full_unstemmed | New 1,3-Disubstituted Benzo[h]Isoquinoline Cyclen-Based Ligand Platform: Synthesis, Eu(3+) Multiphoton Sensitization and Imaging Applications |
title_short | New 1,3-Disubstituted Benzo[h]Isoquinoline Cyclen-Based Ligand Platform: Synthesis, Eu(3+) Multiphoton Sensitization and Imaging Applications |
title_sort | new 1,3-disubstituted benzo[h]isoquinoline cyclen-based ligand platform: synthesis, eu(3+) multiphoton sensitization and imaging applications |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7795479/ https://www.ncbi.nlm.nih.gov/pubmed/33374449 http://dx.doi.org/10.3390/molecules26010058 |
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