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Chemistry in Industry : Journal of Chemists and Chemical Engineers of Croatia, Vol. 71 No. 3-4, 2022.

Original scientific paper

https://doi.org/10.15255/KUI.2021.030

Antimicrobial and Antiproliferative Activities and Enzyme Binding Affinity of Xanthen-3-one Derivatives

Elma Veljović orcid id orcid.org/0000-0003-1129-1491 ; University of Sarajevo, Faculty of Pharmacy, Zmaja od Bosne 8, 71 000 Sarajevo, Bosnia and Herzegovina
Anja Harej ; University of Rijeka, Department of Biotechnology, Centre for High-Throughput Technologies, Radmile Matejčić 2, 51 000 Rijeka, Croatia
Marko Klobučar ; University of Rijeka, Department of Biotechnology, Centre for High-Throughput Technologies, Radmile Matejčić 2, 51 000 Rijeka, Croatia
Sandra Kraljević Pavelić ; University of Rijeka, Department of Biotechnology, Centre for High-Throughput Technologies, Radmile Matejčić 2, 51 000 Rijeka, Croatia
Selma Špirtović-Halilović orcid id orcid.org/0000-0001-8845-969X ; University of Sarajevo, Faculty of Pharmacy, Zmaja od Bosne 8, 71 000 Sarajevo, Bosnia and Herzegovina
Amar Osmanović orcid id orcid.org/0000-0002-4206-6177 ; University of Sarajevo, Faculty of Pharmacy, Zmaja od Bosne 8, 71 000 Sarajevo, Bosnia and Herzegovina
Samija Muratović ; University of Sarajevo, Faculty of Pharmacy, Zmaja od Bosne 8, 71 000 Sarajevo, Bosnia and Herzegovina
Mirsada Salihović orcid id orcid.org/0000-0001-7497-4084 ; University of Sarajevo, Faculty of Pharmacy, Zmaja od Bosne 8, 71 000 Sarajevo, Bosnia and Herzegovina
Davorka Završnik orcid id orcid.org/0000-0001-6486-6813 ; University of Sarajevo, Faculty of Pharmacy, Zmaja od Bosne 8, 71 000 Sarajevo, Bosnia and Herzegovina

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Abstract

Ten biologically active derivatives of 2,6,7-trihydroxyxanthen-3-one, previously synthesized and characterised, were investigated for their in vitro antimicrobial and antiproliferative activity. Compounds were tested on three bacteria, Staphylococcus aureus, Bacillus subtilis and Escherichia coli, and two fungi strains, Candida albicans, and Saccharomyces cerevisiae. The best activity against E. coli showed non-substituted compound 1. The most potent against fungi strains was compound 7 with ortho methoxy substituent. Compound 4 exerted the most potent antiproliferative activity in the micromolar range (0.1–10 µM) on tested tumour cell lines except on SW620. Additional Western blot analyses showed increased cyclin B1 levels in HeLa cells treated with compound 4, which is a major mitotic catastrophe’s marker and decreased levels of Wee1 and Erk ½ kinases involved in regulation of the mitotic process. The most potent compounds after in vitro tests were subjected to molecular docking simulations to evaluate enzyme binding affinity, and provide further evidence for experimentally observed biological effects in vitro.




This work is licensed under a Creative Commons Attribution 4.0 International License.

Keywords

xanthenes; antibacterial and antifungal activity; induction of cell death; enzyme binding modes; docking study; bioavailability prediction

Hrčak ID:

274106

URI

https://hrcak.srce.hr/274106

Publication date:

16.3.2022.

Article data in other languages: croatian

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