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Synthesis of Catechol Derived Rosamine Dyes and Their Reactivity toward Biogenic Amines

Functional organic dyes play a key role in many fields, namely in biotechnology and medical diagnosis. Herein, we report two novel 2,3- and 3,4-dihydroxyphenyl substituted rosamines (3 and 4, respectively) that were successfully synthesized through a microwave-assisted protocol. The best reaction yi...

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Autores principales: Monteiro-Silva, Filipe, Queirós, Carla, Leite, Andreia, Rodríguez, María T., Rojo, María J., Torroba, Tomás, Martins, Rui C., Silva, Ana M. G., Rangel, Maria
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8401866/
https://www.ncbi.nlm.nih.gov/pubmed/34443671
http://dx.doi.org/10.3390/molecules26165082
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author Monteiro-Silva, Filipe
Queirós, Carla
Leite, Andreia
Rodríguez, María T.
Rojo, María J.
Torroba, Tomás
Martins, Rui C.
Silva, Ana M. G.
Rangel, Maria
author_facet Monteiro-Silva, Filipe
Queirós, Carla
Leite, Andreia
Rodríguez, María T.
Rojo, María J.
Torroba, Tomás
Martins, Rui C.
Silva, Ana M. G.
Rangel, Maria
author_sort Monteiro-Silva, Filipe
collection PubMed
description Functional organic dyes play a key role in many fields, namely in biotechnology and medical diagnosis. Herein, we report two novel 2,3- and 3,4-dihydroxyphenyl substituted rosamines (3 and 4, respectively) that were successfully synthesized through a microwave-assisted protocol. The best reaction yields were obtained for rosamine 4, which also showed the most interesting photophysical properties, specially toward biogenic amines (BAs). Several amines including n- and t-butylamine, cadaverine, and putrescine cause spectral changes of 4, in UV–Vis and fluorescence spectra, which are indicative of their potential application as an effective tool to detect amines in acetonitrile solutions. In the gas phase, the probe response is more expressive for spermine and putrescine. Additionally, we found that methanolic solutions of rosamine 4 and n-butylamine undergo a pink to yellow color change over time, which has been attributed to the formation of a new compound. The latter was isolated and identified as 5 (9−aminopyronin), whose solutions exhibit a remarkable increase in fluorescence intensity together with a shift toward more energetic wavelengths. Other 9-aminopyronins 6a, 6b, 7a, and 7b were obtained from methanolic solutions of 4 with putrescine and cadaverine, demonstrating the potential of this new xanthene entity to react with primary amines.
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spelling pubmed-84018662021-08-29 Synthesis of Catechol Derived Rosamine Dyes and Their Reactivity toward Biogenic Amines Monteiro-Silva, Filipe Queirós, Carla Leite, Andreia Rodríguez, María T. Rojo, María J. Torroba, Tomás Martins, Rui C. Silva, Ana M. G. Rangel, Maria Molecules Article Functional organic dyes play a key role in many fields, namely in biotechnology and medical diagnosis. Herein, we report two novel 2,3- and 3,4-dihydroxyphenyl substituted rosamines (3 and 4, respectively) that were successfully synthesized through a microwave-assisted protocol. The best reaction yields were obtained for rosamine 4, which also showed the most interesting photophysical properties, specially toward biogenic amines (BAs). Several amines including n- and t-butylamine, cadaverine, and putrescine cause spectral changes of 4, in UV–Vis and fluorescence spectra, which are indicative of their potential application as an effective tool to detect amines in acetonitrile solutions. In the gas phase, the probe response is more expressive for spermine and putrescine. Additionally, we found that methanolic solutions of rosamine 4 and n-butylamine undergo a pink to yellow color change over time, which has been attributed to the formation of a new compound. The latter was isolated and identified as 5 (9−aminopyronin), whose solutions exhibit a remarkable increase in fluorescence intensity together with a shift toward more energetic wavelengths. Other 9-aminopyronins 6a, 6b, 7a, and 7b were obtained from methanolic solutions of 4 with putrescine and cadaverine, demonstrating the potential of this new xanthene entity to react with primary amines. MDPI 2021-08-22 /pmc/articles/PMC8401866/ /pubmed/34443671 http://dx.doi.org/10.3390/molecules26165082 Text en © 2021 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
Monteiro-Silva, Filipe
Queirós, Carla
Leite, Andreia
Rodríguez, María T.
Rojo, María J.
Torroba, Tomás
Martins, Rui C.
Silva, Ana M. G.
Rangel, Maria
Synthesis of Catechol Derived Rosamine Dyes and Their Reactivity toward Biogenic Amines
title Synthesis of Catechol Derived Rosamine Dyes and Their Reactivity toward Biogenic Amines
title_full Synthesis of Catechol Derived Rosamine Dyes and Their Reactivity toward Biogenic Amines
title_fullStr Synthesis of Catechol Derived Rosamine Dyes and Their Reactivity toward Biogenic Amines
title_full_unstemmed Synthesis of Catechol Derived Rosamine Dyes and Their Reactivity toward Biogenic Amines
title_short Synthesis of Catechol Derived Rosamine Dyes and Their Reactivity toward Biogenic Amines
title_sort synthesis of catechol derived rosamine dyes and their reactivity toward biogenic amines
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8401866/
https://www.ncbi.nlm.nih.gov/pubmed/34443671
http://dx.doi.org/10.3390/molecules26165082
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