A Comparative Study of New Fluorescent Anthraquinone and Benzanthrone α-Aminophosphonates: Synthesis, Spectroscopy, Toxicology, X-ray Crystallography, and Microscopy of Opisthorchis felineus
Maļeckis A. Cvetinska M. Kirjušina M. Mežaraupe L. Kecko S. Gavarāne I. Kiyan V. Lider L. Pavlova V. Savicka M. Belyakov S. Kirilova E.
March 2024Multidisciplinary Digital Publishing Institute (MDPI)
Molecules
2024#29Issue 5
In this research, we explore the synthesis of and characterize α-aminophosphonates derived from anthraquinone and benzanthrone, focusing on their fluorescence properties and potential applications in confocal laser scanning microscopy (CLSM). The synthesized compounds exhibit notable solvatochromic behavior, emitting fluorescence from green to red across various solvents. Spectroscopic analysis, including 1H-, 13C-, and 31P-NMR, FTIR, and mass spectrometry, confirms the chemical structures. The compounds’ toxicity is evaluated using etiolated wheat sprouts, revealing varying degrees of impact on growth and oxidative damage. Furthermore, the study introduces these α-aminophosphonates for CLSM imaging of the parasitic flatworm Opisthorchis felineus, demonstrating their potential in visualizing biological specimens. Additionally, an X-ray crystallographic study of an anthraquinone α-aminophosphonate provides valuable structural insights.
aminophosphonate , anthraquinone , benzanthrone , confocal laser scanning microscopy , crystal structure , fluorescence , Kabachnik–Fields reaction , one-pot reaction , solvatochromism , toxicology
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Institute of Chemistry and Chemical Technology, Faculty of Natural Sciences and Technology, Riga Technical University, P. Valdena Str. 3, Riga, LV-1048, Latvia
Department of Ecology, Institute of Life Sciences and Technology, Daugavpils University, Daugavpils, LV-5401, Latvia
Laboratory of Biodiversity and Genetic Resources, National Center for Biotechnology, 13/5 Kurgalzhynskoye Road, Astana, 010000, Kazakhstan
Faculty of Veterinary Medicine and Animal Husbandry Technology, S. Seifullin Kazakh Agro Technical Research University, 62 Zhenis Avenue, Astana, 010011, Kazakhstan
Latvian Institute of Organic Synthesis, Aizkraukles Str. 21, Riga, LV-1006, Latvia
Department of Environment and Technologies, Faculty of Natural Sciences and Healthcare, Daugavpils University, Daugavpils, LV-5401, Latvia
Institute of Chemistry and Chemical Technology
Department of Ecology
Laboratory of Biodiversity and Genetic Resources
Faculty of Veterinary Medicine and Animal Husbandry Technology
Latvian Institute of Organic Synthesis
Department of Environment and Technologies
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