A Comparative Study of New Fluorescent Anthraquinone and Benzanthrone α-Aminophosphonates: Synthesis, Spectroscopy, Toxicology, X-ray Crystallography, and Microscopy of <i>Opisthorchis felineus</i>
Armands Maļeckis,
Marija Cvetinska,
Muza Kirjušina,
Ligita Mežaraupe,
Sanita Kecko,
Inese Gavarāne,
Vladimir Kiyan,
Lyudmila Lider,
Veronika Pavlova,
Marina Savicka,
Sergey Belyakov,
Elena Kirilova
Affiliations
Armands Maļeckis
Institute of Chemistry and Chemical Technology, Faculty of Natural Sciences and Technology, Riga Technical University, P. Valdena Str. 3, LV-1048 Riga, Latvia
Marija Cvetinska
Institute of Chemistry and Chemical Technology, Faculty of Natural Sciences and Technology, Riga Technical University, P. Valdena Str. 3, LV-1048 Riga, Latvia
Muza Kirjušina
Department of Ecology, Institute of Life Sciences and Technology, Daugavpils University, LV-5401 Daugavpils, Latvia
Ligita Mežaraupe
Department of Ecology, Institute of Life Sciences and Technology, Daugavpils University, LV-5401 Daugavpils, Latvia
Sanita Kecko
Department of Ecology, Institute of Life Sciences and Technology, Daugavpils University, LV-5401 Daugavpils, Latvia
Inese Gavarāne
Department of Ecology, Institute of Life Sciences and Technology, Daugavpils University, LV-5401 Daugavpils, Latvia
Vladimir Kiyan
Laboratory of Biodiversity and Genetic Resources, National Center for Biotechnology, 13/5 Kurgalzhynskoye Road, Astana 010000, Kazakhstan
Lyudmila Lider
Faculty of Veterinary Medicine and Animal Husbandry Technology, S. Seifullin Kazakh Agro Technical Research University, 62 Zhenis Avenue, Astana 010011, Kazakhstan
Veronika Pavlova
Department of Ecology, Institute of Life Sciences and Technology, Daugavpils University, LV-5401 Daugavpils, Latvia
Marina Savicka
Department of Ecology, Institute of Life Sciences and Technology, Daugavpils University, LV-5401 Daugavpils, Latvia
Sergey Belyakov
Latvian Institute of Organic Synthesis, Aizkraukles Str. 21, LV-1006 Riga, Latvia
Elena Kirilova
Department of Environment and Technologies, Faculty of Natural Sciences and Healthcare, Daugavpils University, LV-5401 Daugavpils, Latvia
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.
