ANTIMICROBIAL AND ANTIFUNGAL ACTIVITIES OF SOME ANTHRACENEDIONE DERIVATIVES
DOI:
https://doi.org/10.11603/2312-0967.2026.1.15939Keywords:
заміщені антрахінони, синтез, протимікробна активність, SwissADME, ProTox IIIAbstract
The aim of the work. To carry out the synthesis of a series of functionally substituted anthraquinone derivatives, to investigate their antimicrobial activity, and to predict the drug-likeness of the obtained compounds using modern web-based tools.
Materials and methods. Standard methods of organic synthesis were employed, and physicochemical characterization of the synthesized compounds was performed. The antimicrobial activity was evaluated using the agar diffusion method and the serial dilution method in accordance with generally accepted microbiological protocols. In silico drug-likeness screening of the synthesized compounds was carried out using the SwissADME online service.
Results and discussion. A series of new functionally substituted anthraquinone derivatives was synthesized. Based on the results of antimicrobial activity screening, compound 5 was identified as the hit compound, exhibiting the highest level of activity among the tested compounds. It was found that other anthracenedione derivatives do not exhibit pronounced antimicrobial and fungistatic activity, which may be due to the peculiarities of their chemical structure. The results obtained indicate the prospects for further research into anthracenedione derivatives as potential antimicrobial agents.
Conclusions. A series of four functionally substituted anthraquinone derivatives was synthesized and their antimicrobial activity was evaluated. Compound 5 was found to exhibit antimicrobial activity against Gram-positive microorganisms, whereas the other tested compounds showed no detectable activity under the same conditions. In silico prediction of drug-likeness and potential toxicity for compound 5 using modern web-based tools indicated favorable pharmacokinetic properties and no obvious signs of toxicity. These results highlight the potential of functionally substituted anthraquinone derivatives for further investigation as prospective antimicrobial agents.
References
World Health Organization. Antimicrobial resistance [Internet]. Geneva: WHO; 2023 [cited 2025 Feb 3]. Available from: https://www.who.int/news-room/fact-sheets/detail/antimicrobial-resistance
Thermo Fisher Scientific. Addressing the rising global threat of antimicrobial resistance (AMR) [Internet]. 2024 [cited 2025 Feb 3]. Available from: https://www.thermofisher.com/blog/clinical-conversations/addressing-the-rising-global-threat-of-antimicrobial-resistance-amr/
World Health Organization. WHO releases report on state of development of antibacterials [Internet]. Geneva: WHO; 2024 [cited 2025 Feb 3]. Available from: https://www.who.int/news/item/14-06-2024-who-releases-report-on-state-of-development-of-antibacterials
Malik E, Müller C. Anthraquinones as pharmacological tools and drugs. Med Res Rev. 2016;36(4):705-48. DOI:10.1002/med.21391 DOI: https://doi.org/10.1002/med.21391
Malmir M, Serrano R, Silva O. Anthraquinones as potential antimicrobial agents: a review. Antimicrob Res. 2017;20:55-61.
Adhikari A, Mahar AS. DNA targeted anthraquinone derivatives: important anticancer agents. Int J Pharm Pharm Sci. 2016;17-25.
Zhao L, Zheng L. Bioactive anthraquinone and derivatives as regulators for ROS. Molecules. 2023;28(24):8139. DOI:10.3390/molecules28248139 DOI: https://doi.org/10.3390/molecules28248139
Mullaivendhan J, Akbar I, Ahamed A, Gatasheh MK, Hatamleh AA, Raman G, et al. Synthesis of anthraquinone-linked cyclopentanone derivatives and biological activity evaluation. Drug Des Devel Ther. 2024;18:597-612. DOI:10.2147/DDDT.S439633 DOI: https://doi.org/10.2147/DDDT.S439633
Celik S, Vagifli F, Akyuz S, Ozkok F, Ozel AE, Dosler S, et al. Synthesis and antimicrobial studies of a new anthraquinone derivative. Spectrosc Lett. 2022;55(4):259-77. DOI:10.1080/00387010.2022.2056615 DOI: https://doi.org/10.1080/00387010.2022.2056615
Kirilova E, Maļeckis A, Kirjušina M, Mežaraupe L, Rubeniņa I, Brakovska A, et al. Structural and spectroscopic study of benzoperimidines derived from 1-aminoanthraquinone. Molecules. 2025;30(22):4472. DOI:10.3390/molecules30224472 DOI: https://doi.org/10.3390/molecules30224472
Lozynskyi AV, Konechnyi YT, Roman OM, Horishny VY, Sabadakh OP, Pasichnyk SM, et al. New polyfunctionalized 2-hydrazinoanthraquinone derivatives as antimicrobial agents. Biopolym Cell. 2023;39(1):42-53. DOI:10.7124/bc.000A84 DOI: https://doi.org/10.7124/bc.000A84
Lozynskyi A, Holota S, Yushyn I, Sabadakh O, Karpenko O, Novikov V, et al. Synthesis and biological activity of polyfunctionalized anthraquinonehydrazones. Lett Drug Des Discov. 2021;18(2):199-209. DOI:10.2174/1570180817999200802032844 DOI: https://doi.org/10.2174/1570180817999200802032844
Raghuveer D, Pai VV, Murali TS, Nayak R. Exploring anthraquinones as antibacterial and antifungal agents. ChemistrySelect. 2023;8(6):e202204537. DOI:10.1002/slct.202204537 DOI: https://doi.org/10.1002/slct.202204537
Qun T, Zhou T, Hao J, Wang C, Zhang K, Xu J, et al. Antibacterial activities of anthraquinones: structure–activity relationships and mechanisms. RSC Med Chem. 2023;14(8):1446-71. DOI:10.1039/D3MD00116D DOI: https://doi.org/10.1039/D3MD00116D
Balouiri M, Sadiki M, Ibnsouda SK. Methods for in vitro evaluating antimicrobial activity. J Pharm Anal. 2016;6(2):71-9. DOI:10.1016/j.jpha.2015.11.005 DOI: https://doi.org/10.1016/j.jpha.2015.11.005
European Committee on Antimicrobial Susceptibility Testing. EUCAST disk diffusion method, version 8.0 [Internet]. 2020 [cited 2025 Feb 3]. Available from: http://www.eucast.org/fileadmin/src/media/PDFs/EUCAST_files/Disk_test_documents/2020_manuals/Manual_v_8.0_EUCAST_Disk_Test_2020.pdf
Sweidan K, Zalloum H, Sabbah DA, Idris G, Abudosh K, Mubarak MS. Synthesis and anticancer evaluation of N¹-(anthraquinon-2-yl) amidrazone derivatives. Can J Chem. 2018;96(12):1123-28. DOI:10.1139/cjc-2018-0145 DOI: https://doi.org/10.1139/cjc-2018-0145
Stasevich M, Zvarych V, Novikov V, Vovk M. Synthetic potential of 9,10-anthraquinonyldiazonium salts. Ukr Chem J. 2020;86(9):55-72. DOI:10.33609/2708-129X.86.9.2020.55-72 DOI: https://doi.org/10.33609/2708-129X.86.9.2020.55-72
Shupeniuk VI, Zavhorodnii MP, Derevianko NP, Taras TN, Shkopynska TY, Brazhko OA, et al. Search of regulators among anthracenedione derivatives for microclonal plant propagation. J Chem Technol. 2023;31(1):20-7. DOI:10.15421/jchemtech.v31i1.271400 DOI: https://doi.org/10.15421/jchemtech.v31i1.271400
Shupeniuk VI, Nepolraj A, Taras TN, Sabadakh OP, Matkivskyi MP, Luchkevych YR. In silico study of anthraquinone derivatives as potential COVID-19 inhibitors. J Chem Technol. 2022;30(2):151-8. DOI:10.15421/jchemtech.v30i2.244728 DOI: https://doi.org/10.15421/jchemtech.v30i2.244728
SwissADME [Internet]. Lausanne: Swiss Institute of Bioinformatics; 2025 [cited 2025 Jul 10]. Available from: http://www.swissadme.ch/
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Accepted 2026-02-11
Published 2026-03-31
