A Comparative Study of New Fluorescent Anthraquinone and Benzanthrone α-Aminophosphonates: Synthesis, Spectroscopy, Toxicology, X-ray Crystallography, and Microscopy of <i>Opisthorchis felineus</i>
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...
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MDPI AG
2024-03-01
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| Online Access: | https://www.mdpi.com/1420-3049/29/5/1143 |
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| author | Armands Maļeckis Marija Cvetinska Muza Kirjušina Ligita Mežaraupe Sanita Kecko Inese Gavarāne Vladimir Kiyan Lyudmila Lider Veronika Pavlova Marina Savicka Sergey Belyakov Elena Kirilova |
| author_facet | Armands Maļeckis Marija Cvetinska Muza Kirjušina Ligita Mežaraupe Sanita Kecko Inese Gavarāne Vladimir Kiyan Lyudmila Lider Veronika Pavlova Marina Savicka Sergey Belyakov Elena Kirilova |
| author_sort | Armands Maļeckis |
| collection | DOAJ |
| description | 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 <sup>1</sup>H-, <sup>13</sup>C-, and <sup>31</sup>P-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 <i>Opisthorchis felineus</i>, demonstrating their potential in visualizing biological specimens. Additionally, an X-ray crystallographic study of an anthraquinone α-aminophosphonate provides valuable structural insights. |
| first_indexed | 2024-04-25T00:22:59Z |
| format | Article |
| id | doaj.art-1c1c0d17d3154bea9231259fe4954540 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-25T00:22:59Z |
| publishDate | 2024-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-1c1c0d17d3154bea9231259fe49545402024-03-12T16:51:15ZengMDPI AGMolecules1420-30492024-03-01295114310.3390/molecules29051143A Comparative Study of New Fluorescent Anthraquinone and Benzanthrone α-Aminophosphonates: Synthesis, Spectroscopy, Toxicology, X-ray Crystallography, and Microscopy of <i>Opisthorchis felineus</i>Armands Maļeckis0Marija Cvetinska1Muza Kirjušina2Ligita Mežaraupe3Sanita Kecko4Inese Gavarāne5Vladimir Kiyan6Lyudmila Lider7Veronika Pavlova8Marina Savicka9Sergey Belyakov10Elena Kirilova11Institute of Chemistry and Chemical Technology, Faculty of Natural Sciences and Technology, Riga Technical University, P. Valdena Str. 3, LV-1048 Riga, LatviaInstitute of Chemistry and Chemical Technology, Faculty of Natural Sciences and Technology, Riga Technical University, P. Valdena Str. 3, LV-1048 Riga, LatviaDepartment of Ecology, Institute of Life Sciences and Technology, Daugavpils University, LV-5401 Daugavpils, LatviaDepartment of Ecology, Institute of Life Sciences and Technology, Daugavpils University, LV-5401 Daugavpils, LatviaDepartment of Ecology, Institute of Life Sciences and Technology, Daugavpils University, LV-5401 Daugavpils, LatviaDepartment of Ecology, Institute of Life Sciences and Technology, Daugavpils University, LV-5401 Daugavpils, LatviaLaboratory of Biodiversity and Genetic Resources, National Center for Biotechnology, 13/5 Kurgalzhynskoye Road, Astana 010000, KazakhstanFaculty of Veterinary Medicine and Animal Husbandry Technology, S. Seifullin Kazakh Agro Technical Research University, 62 Zhenis Avenue, Astana 010011, KazakhstanDepartment of Ecology, Institute of Life Sciences and Technology, Daugavpils University, LV-5401 Daugavpils, LatviaDepartment of Ecology, Institute of Life Sciences and Technology, Daugavpils University, LV-5401 Daugavpils, LatviaLatvian Institute of Organic Synthesis, Aizkraukles Str. 21, LV-1006 Riga, LatviaDepartment of Environment and Technologies, Faculty of Natural Sciences and Healthcare, Daugavpils University, LV-5401 Daugavpils, LatviaIn 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 <sup>1</sup>H-, <sup>13</sup>C-, and <sup>31</sup>P-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 <i>Opisthorchis felineus</i>, demonstrating their potential in visualizing biological specimens. Additionally, an X-ray crystallographic study of an anthraquinone α-aminophosphonate provides valuable structural insights.https://www.mdpi.com/1420-3049/29/5/1143fluorescencesolvatochromismaminophosphonatebenzanthroneanthraquinoneKabachnik–Fields reaction |
| spellingShingle | Armands Maļeckis Marija Cvetinska Muza Kirjušina Ligita Mežaraupe Sanita Kecko Inese Gavarāne Vladimir Kiyan Lyudmila Lider Veronika Pavlova Marina Savicka Sergey Belyakov Elena Kirilova A Comparative Study of New Fluorescent Anthraquinone and Benzanthrone α-Aminophosphonates: Synthesis, Spectroscopy, Toxicology, X-ray Crystallography, and Microscopy of <i>Opisthorchis felineus</i> Molecules fluorescence solvatochromism aminophosphonate benzanthrone anthraquinone Kabachnik–Fields reaction |
| title | A Comparative Study of New Fluorescent Anthraquinone and Benzanthrone α-Aminophosphonates: Synthesis, Spectroscopy, Toxicology, X-ray Crystallography, and Microscopy of <i>Opisthorchis felineus</i> |
| title_full | A Comparative Study of New Fluorescent Anthraquinone and Benzanthrone α-Aminophosphonates: Synthesis, Spectroscopy, Toxicology, X-ray Crystallography, and Microscopy of <i>Opisthorchis felineus</i> |
| title_fullStr | A Comparative Study of New Fluorescent Anthraquinone and Benzanthrone α-Aminophosphonates: Synthesis, Spectroscopy, Toxicology, X-ray Crystallography, and Microscopy of <i>Opisthorchis felineus</i> |
| title_full_unstemmed | A Comparative Study of New Fluorescent Anthraquinone and Benzanthrone α-Aminophosphonates: Synthesis, Spectroscopy, Toxicology, X-ray Crystallography, and Microscopy of <i>Opisthorchis felineus</i> |
| title_short | A Comparative Study of New Fluorescent Anthraquinone and Benzanthrone α-Aminophosphonates: Synthesis, Spectroscopy, Toxicology, X-ray Crystallography, and Microscopy of <i>Opisthorchis felineus</i> |
| title_sort | comparative study of new fluorescent anthraquinone and benzanthrone α aminophosphonates synthesis spectroscopy toxicology x ray crystallography and microscopy of i opisthorchis felineus i |
| topic | fluorescence solvatochromism aminophosphonate benzanthrone anthraquinone Kabachnik–Fields reaction |
| url | https://www.mdpi.com/1420-3049/29/5/1143 |
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