Cargando…

Lighting-Up the Far-Red Fluorescence of RNA-Selective Dyes by Switching from Ortho to Para Position

Fluorescence imaging is constantly searching for new far-red emitting probes whose turn-on response is selective upon the interaction with specific biological targets. Cationic push-pull dyes could indeed respond to these requirements due to their intramolecular charge transfer (ICT) character, by w...

Descripción completa

Detalles Bibliográficos
Autores principales: Cesaretti, Alessio, Calzoni, Eleonora, Montegiove, Nicolò, Bianconi, Tommaso, Alebardi, Martina, La Serra, Maria Antonietta, Consiglio, Giuseppe, Fortuna, Cosimo Gianluca, Elisei, Fausto, Spalletti, Anna
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10003335/
https://www.ncbi.nlm.nih.gov/pubmed/36902248
http://dx.doi.org/10.3390/ijms24054812
_version_ 1784904582262947840
author Cesaretti, Alessio
Calzoni, Eleonora
Montegiove, Nicolò
Bianconi, Tommaso
Alebardi, Martina
La Serra, Maria Antonietta
Consiglio, Giuseppe
Fortuna, Cosimo Gianluca
Elisei, Fausto
Spalletti, Anna
author_facet Cesaretti, Alessio
Calzoni, Eleonora
Montegiove, Nicolò
Bianconi, Tommaso
Alebardi, Martina
La Serra, Maria Antonietta
Consiglio, Giuseppe
Fortuna, Cosimo Gianluca
Elisei, Fausto
Spalletti, Anna
author_sort Cesaretti, Alessio
collection PubMed
description Fluorescence imaging is constantly searching for new far-red emitting probes whose turn-on response is selective upon the interaction with specific biological targets. Cationic push-pull dyes could indeed respond to these requirements due to their intramolecular charge transfer (ICT) character, by which their optical properties can be tuned, and their ability to interact strongly with nucleic acids. Starting from the intriguing results recently achieved with some push-pull dimethylamino-phenyl dyes, two isomers obtained by switching the cationic electron acceptor head (either a methylpyridinium or a methylquinolinium) from the ortho to the para position have been scrutinized for their ICT dynamics, their affinity towards DNA and RNA, and in vitro behavior. By exploiting the marked fluorescence enhancement observed upon complexation with polynucleotides, fluorimetric titrations were employed to evaluate the dyes’ ability as efficient DNA/RNA binders. The studied compounds exhibited in vitro RNA-selectivity by localizing in the RNA-rich nucleoli and within the mitochondria, as demonstrated by fluorescence microscopy. The para-quinolinium derivative showed some modest antiproliferative effect on two tumor cell lines as well as improved properties as an RNA-selective far-red probe in terms of both turn-on response (100-fold fluorescence enhancement) and localized staining ability, attracting interest as a potential theranostic agent.
format Online
Article
Text
id pubmed-10003335
institution National Center for Biotechnology Information
language English
publishDate 2023
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-100033352023-03-11 Lighting-Up the Far-Red Fluorescence of RNA-Selective Dyes by Switching from Ortho to Para Position Cesaretti, Alessio Calzoni, Eleonora Montegiove, Nicolò Bianconi, Tommaso Alebardi, Martina La Serra, Maria Antonietta Consiglio, Giuseppe Fortuna, Cosimo Gianluca Elisei, Fausto Spalletti, Anna Int J Mol Sci Article Fluorescence imaging is constantly searching for new far-red emitting probes whose turn-on response is selective upon the interaction with specific biological targets. Cationic push-pull dyes could indeed respond to these requirements due to their intramolecular charge transfer (ICT) character, by which their optical properties can be tuned, and their ability to interact strongly with nucleic acids. Starting from the intriguing results recently achieved with some push-pull dimethylamino-phenyl dyes, two isomers obtained by switching the cationic electron acceptor head (either a methylpyridinium or a methylquinolinium) from the ortho to the para position have been scrutinized for their ICT dynamics, their affinity towards DNA and RNA, and in vitro behavior. By exploiting the marked fluorescence enhancement observed upon complexation with polynucleotides, fluorimetric titrations were employed to evaluate the dyes’ ability as efficient DNA/RNA binders. The studied compounds exhibited in vitro RNA-selectivity by localizing in the RNA-rich nucleoli and within the mitochondria, as demonstrated by fluorescence microscopy. The para-quinolinium derivative showed some modest antiproliferative effect on two tumor cell lines as well as improved properties as an RNA-selective far-red probe in terms of both turn-on response (100-fold fluorescence enhancement) and localized staining ability, attracting interest as a potential theranostic agent. MDPI 2023-03-02 /pmc/articles/PMC10003335/ /pubmed/36902248 http://dx.doi.org/10.3390/ijms24054812 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/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 (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Cesaretti, Alessio
Calzoni, Eleonora
Montegiove, Nicolò
Bianconi, Tommaso
Alebardi, Martina
La Serra, Maria Antonietta
Consiglio, Giuseppe
Fortuna, Cosimo Gianluca
Elisei, Fausto
Spalletti, Anna
Lighting-Up the Far-Red Fluorescence of RNA-Selective Dyes by Switching from Ortho to Para Position
title Lighting-Up the Far-Red Fluorescence of RNA-Selective Dyes by Switching from Ortho to Para Position
title_full Lighting-Up the Far-Red Fluorescence of RNA-Selective Dyes by Switching from Ortho to Para Position
title_fullStr Lighting-Up the Far-Red Fluorescence of RNA-Selective Dyes by Switching from Ortho to Para Position
title_full_unstemmed Lighting-Up the Far-Red Fluorescence of RNA-Selective Dyes by Switching from Ortho to Para Position
title_short Lighting-Up the Far-Red Fluorescence of RNA-Selective Dyes by Switching from Ortho to Para Position
title_sort lighting-up the far-red fluorescence of rna-selective dyes by switching from ortho to para position
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10003335/
https://www.ncbi.nlm.nih.gov/pubmed/36902248
http://dx.doi.org/10.3390/ijms24054812
work_keys_str_mv AT cesarettialessio lightingupthefarredfluorescenceofrnaselectivedyesbyswitchingfromorthotoparaposition
AT calzonieleonora lightingupthefarredfluorescenceofrnaselectivedyesbyswitchingfromorthotoparaposition
AT montegiovenicolo lightingupthefarredfluorescenceofrnaselectivedyesbyswitchingfromorthotoparaposition
AT bianconitommaso lightingupthefarredfluorescenceofrnaselectivedyesbyswitchingfromorthotoparaposition
AT alebardimartina lightingupthefarredfluorescenceofrnaselectivedyesbyswitchingfromorthotoparaposition
AT laserramariaantonietta lightingupthefarredfluorescenceofrnaselectivedyesbyswitchingfromorthotoparaposition
AT consigliogiuseppe lightingupthefarredfluorescenceofrnaselectivedyesbyswitchingfromorthotoparaposition
AT fortunacosimogianluca lightingupthefarredfluorescenceofrnaselectivedyesbyswitchingfromorthotoparaposition
AT eliseifausto lightingupthefarredfluorescenceofrnaselectivedyesbyswitchingfromorthotoparaposition
AT spallettianna lightingupthefarredfluorescenceofrnaselectivedyesbyswitchingfromorthotoparaposition