Microwave-assisted synthesis of new triangulenium dyes for lifetime imaging microscopy (FLIM)

This paper is dedicated to Dr. Rosario Herranz, whose leadership and mentorship have been a source of inspiration.

Bibliographic Details
Authors: Viedma-Barba, Carmen, Ortega-Naranjo, Esther M, Movilla, Federico, Reinoso, Antonio, Andrades-Amate, Marta, Peñalver, Pablo, Morales, Juan Carlos, González-Vera, Juan A, Gutiérrez-Rodríguez, Marta, Orte, Angel
Format: article
Status:Published version
Publication Date:2025
Country:España
Institution:Consejo Superior de Investigaciones Científicas (CSIC)
Repository:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/413312
Online Access:http://hdl.handle.net/10261/413312
Access Level:Open access
Keyword:Advanced microscopy
Cell imaging
Dyes
Microwave synthesis
Photophysics
Solvatochromism
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spelling Microwave-assisted synthesis of new triangulenium dyes for lifetime imaging microscopy (FLIM)Viedma-Barba, CarmenOrtega-Naranjo, Esther MMovilla, FedericoReinoso, AntonioAndrades-Amate, MartaPeñalver, PabloMorales, Juan CarlosGonzález-Vera, Juan AGutiérrez-Rodríguez, MartaOrte, AngelAdvanced microscopyCell imagingDyesMicrowave synthesisPhotophysicsSolvatochromismThis paper is dedicated to Dr. Rosario Herranz, whose leadership and mentorship have been a source of inspiration.We introduce a novel microwave-assisted method for the rapid and efficient synthesis of triangulenium dyes, enabling the creation of a broader range of these fluorophores, which are characterized by very long fluorescence lifetimes. We prepared different azadioxatriangulenium (ADOTA) and diazaoxatriangulenium (DAOTA) derivatives and thoroughly characterized their photophysical properties. We investigated their solvatochromic properties and the effects of the solvent, aided by computational chemistry results. The new ADOTA and DAOTA dyes were applied in multiple in cellulo microscopy modalities, including confocal, fluorescence lifetime imaging microscopy (FLIM), and super-resolution imaging. ADOTA derivatives predominantly accumulated in mitochondria, while DAOTAs showed pronounced nuclear staining and participation in endocytic pathways. Notably, these dyes enable clear discrimination of subcellular compartments via lifetime contrast in FLIM: mitochondria, where ADOTAs undergo electron transfer-driven quenching and display short lifetimes; nuclei and DNA, where lifetimes remain long; and endocytic vesicles, where partial dye aggregation leads to lifetime reduction.This work has been funded by grants PID2023-148243OB-I00 and PID2022-137214OB-C22 funded by MCIN/AEI/https://doi.org/10.13039/501100011033 and “ERDF A way of making Europe”, EU; grant PID2020-114256RB-I00 funded by AEI/https://doi.org/10.13039/501100011033; CSIC grant 202180E073; C. Viedma-Barba holds a FPI Predoctoral contracts subsidized by Spanish Minister of Science and Innovation (PRE2020-093542) granted by MCIN/AEI/https://doi.org/10.13039/501100011033 and “ESF Investing in your future”.Peer reviewedSpringer NatureMinisterio de Ciencia e Innovación (España)European CommissionPeñalver, Pablo [0000-0002-2884-282X]Morales, Juan Carlos [0000-0003-2400-405X]Gutiérrez-Rodríguez, Marta [0000-0001-9855-834]Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]202620262025info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Publisher's versioninfo:eu-repo/semantics/publishedVersionhttp://hdl.handle.net/10261/413312reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglés#PLACEHOLDER_PARENT_METADATA_VALUE##PLACEHOLDER_PARENT_METADATA_VALUE##PLACEHOLDER_PARENT_METADATA_VALUE##PLACEHOLDER_PARENT_METADATA_VALUE#info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023/PID2023-148243OB-I00info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023/PID2022-137214OB-C22info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2020-114256RB-I00info:eu-repo/grantAgreement/AEI//PRE2020-093542https://doi.org/10.1038/s41598-025-31688-6Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/4133122026-05-22T06:33:51Z
dc.title.none.fl_str_mv Microwave-assisted synthesis of new triangulenium dyes for lifetime imaging microscopy (FLIM)
title Microwave-assisted synthesis of new triangulenium dyes for lifetime imaging microscopy (FLIM)
spellingShingle Microwave-assisted synthesis of new triangulenium dyes for lifetime imaging microscopy (FLIM)
Viedma-Barba, Carmen
Advanced microscopy
Cell imaging
Dyes
Microwave synthesis
Photophysics
Solvatochromism
title_short Microwave-assisted synthesis of new triangulenium dyes for lifetime imaging microscopy (FLIM)
title_full Microwave-assisted synthesis of new triangulenium dyes for lifetime imaging microscopy (FLIM)
title_fullStr Microwave-assisted synthesis of new triangulenium dyes for lifetime imaging microscopy (FLIM)
title_full_unstemmed Microwave-assisted synthesis of new triangulenium dyes for lifetime imaging microscopy (FLIM)
title_sort Microwave-assisted synthesis of new triangulenium dyes for lifetime imaging microscopy (FLIM)
dc.creator.none.fl_str_mv Viedma-Barba, Carmen
Ortega-Naranjo, Esther M
Movilla, Federico
Reinoso, Antonio
Andrades-Amate, Marta
Peñalver, Pablo
Morales, Juan Carlos
González-Vera, Juan A
Gutiérrez-Rodríguez, Marta
Orte, Angel
author Viedma-Barba, Carmen
author_facet Viedma-Barba, Carmen
Ortega-Naranjo, Esther M
Movilla, Federico
Reinoso, Antonio
Andrades-Amate, Marta
Peñalver, Pablo
Morales, Juan Carlos
González-Vera, Juan A
Gutiérrez-Rodríguez, Marta
Orte, Angel
author_role author
author2 Ortega-Naranjo, Esther M
Movilla, Federico
Reinoso, Antonio
Andrades-Amate, Marta
Peñalver, Pablo
Morales, Juan Carlos
González-Vera, Juan A
Gutiérrez-Rodríguez, Marta
Orte, Angel
author2_role author
author
author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Ministerio de Ciencia e Innovación (España)
European Commission
Peñalver, Pablo [0000-0002-2884-282X]
Morales, Juan Carlos [0000-0003-2400-405X]
Gutiérrez-Rodríguez, Marta [0000-0001-9855-834]
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Advanced microscopy
Cell imaging
Dyes
Microwave synthesis
Photophysics
Solvatochromism
topic Advanced microscopy
Cell imaging
Dyes
Microwave synthesis
Photophysics
Solvatochromism
description This paper is dedicated to Dr. Rosario Herranz, whose leadership and mentorship have been a source of inspiration.
publishDate 2025
dc.date.none.fl_str_mv 2025
2026
2026
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
Publisher's version
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/413312
url http://hdl.handle.net/10261/413312
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
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#PLACEHOLDER_PARENT_METADATA_VALUE#
#PLACEHOLDER_PARENT_METADATA_VALUE#
#PLACEHOLDER_PARENT_METADATA_VALUE#
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023/PID2023-148243OB-I00
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023/PID2022-137214OB-C22
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2020-114256RB-I00
info:eu-repo/grantAgreement/AEI//PRE2020-093542
https://doi.org/10.1038/s41598-025-31688-6
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Springer Nature
publisher.none.fl_str_mv Springer Nature
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
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