2024-03-29T11:07:49Zhttps://riubu.ubu.es/oai/requestoai:riubu.ubu.es:10259/61382022-11-29T12:04:26Zcom_10259_4354com_10259_5086com_10259_2604col_10259_4355
Synthesis of Catechol Derived Rosamine Dyes and Their Reactivity toward Biogenic Amines
Monteiro-Silva, Filipe
Queirós, Carla
Leite, Andreia
Rodríguez Rodríguez, Mª Teresa
Rojo Cámara, Mª Josefa
Torroba Pérez, Tomás
Martins, Rui C.
Silva, Ana M. G.
Rangel, Maria
Microwave-assisted synthesis
Catecholated rosamines
9-aminopyronins
Photophysical properties
Biogenic amines detection
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.
2021-11-11T13:52:19Z
2021-11-11T13:52:19Z
2021-11-11T13:52:19Z
2021-08
info:eu-repo/semantics/article
1420-3049
http://hdl.handle.net/10259/6138
10.3390/molecules26165082
eng
Molecules. 2021, V. 26, n. 16, 5082
https://doi.org/10.3390/molecules26165082
info:eu-repo/grantAgreement/FCT//PTDC%2FQUI-QOR%2F29426%2F2017/PT
info:eu-repo/grantAgreement/FCT//UIDB%2F50006%2F2020/PT
info:eu-repo/grantAgreement/FCT//PTDC%2FQUI-QIN%2F28142%2F2017/PT
info:eu-repo/grantAgreement/Junta de Castilla y León//BU263P18//Sondas fluorescentes en materiales nanoestructurados para la detección y modificación de toxinas medioambientales o contaminantes traza y su incorporación a estrategias terapéuticas [fluonano]
info:eu-repo/grantAgreement/FCT//DFA%2FBD%2F9136%2F2020/PT
http://creativecommons.org/licenses/by/4.0/
info:eu-repo/semantics/openAccess
Atribución 4.0 Internacional
MDPI