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Synthesis of inverse push-pull coumarin dyes and their application as solvatochromic probes and labelling agents for bacterial cell membranes
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Resumo(s)
Coumarin derivatives have been widely employed across a great number of applications, such as laser dyes, bioimaging or chemossensors, owing to their strong fluorescence and high-quantum yields. These properties are highly tunable through structural modification, namely by the inclusion of electron-withdrawing groups (EWG) and electron-donating groups (EDG) at positions 3 and 7 of the coumarin scaffold, respectively. Comparatively, there aren't many reports of EDGs being employed at position 3, prompting us to investigate this new class of potential fluorophores. We undertook the synthesis of three novel ethynyl-linked aminophenyl-coumarin dyes, employing a key Sonogashira-coupling reaction to introduce the electron-rich tertiary aniline moiety. Two different amine donors were used, diphenylamino (coumarins A and B) and dimethylamino (coumarin C), as well as two alkoxy substituents, dibenzyloxy (A and C) and methylenedioxy (B), in the phenyl ring of the coumarin. All dyes show strong emission and significant positive solvatochromism. Additionally, they were employed as staining agents for the cellular membrane of S. pneumoniae, a Gram-positive bacterial pathogen. None of the three derivatives presented cytotoxic effects. Only A and B successfully labelled the bacterial membrane. In the case of B a very similar staining pattern and performance to that of standard dye Nile Red was observed, while A seemed to possess a more selective distribution.
Descrição
Funding Information: The authors acknowledge their respective, current institutions of affiliation: Universidade NOVA de Lisboa, the financial support under the projects PTDC/QUI-QOR/7450/2020 ″Organic Redox Mediators For Energy Conversion" through FCT – Fundação para a Ciência e a Tecnologia I. P. as well as the assistance of MSc Tânia Moreira in the MIC assays performed for the coumarin dyes. This work was also financed by national funds from FCT - Fundação para a Ciência e a Tecnologia, I.P., in the scope of the project, Associate Laboratory for Green Chemistry – LAQV: LA/P/0008/2020 (10.54499/LA/P/0008/2020), UIDB/50006/2020 (10.54499/UIDP/50006/2020) and UIDP/50006/2020 (10.54499/UIDB/50006/2020), as well as UIDP/04378/2020 (10.54499/UIDP/04378/2020) and UIDB/04378/2020 (10.54499/UIDB/04378/2020) of the Research Unit on Applied Molecular Biosciences - UCIBIO and the project LA/P/0140/2020 of the Associate Laboratory Institute for Health and Bioeconomy - i4HB. FCT/MCTES is also acknowledged for the PhD grant 2020.09047.BD (João Sarrato; 10.54499/2020.09047.BD). Publisher Copyright: © 2024
Palavras-chave
Cell-imaging Coumarin Fluorescence Microscopy Solvatochromism General Chemical Engineering Process Chemistry and Technology SDG 3 - Good Health and Well-being