In silico and biological activity evaluation of quercetin-boron hybrid compounds,anti-quorum sensing effect as alternative potential against microbial resistance |
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| Institution: | 1. Department of Chemistry, Institute of Science, Dicle University, 21280 Diyarbakir, Turkey;2. Department of Medical Pharmacology, Faculty of Medicine, Yozgat Bozok University, 66000 Yozgat, Turkey;3. Department of Analytical Chemistry, Faculty of Pharmacy, Erzincan Binali Y?ld?r?m University, 24002, Erzincan, Turkey;4. Department of Analytical Chemistry, Faculty of Pharmacy, Dicle University, 21280 Diyarbakir, Turkey;5. Department of Pharmaceutical Microbiology, Faculty of Pharmacy, Düzce University, 81620 Düzce, Turkey;6. Department of Pharmacognosy, Faculty of Pharmacy, Gazi University, 06570 Ankara, Turkey;1. Department of Neurosurgery, 5th Military Clinical Hospital with the SP ZOZ Polyclinic in Krakow, 30-901 Krakow, Poland;2. Department of Histology, Cytophysiology and Embryology, Faculty of Medicine in Zabrze, Academy of Silesia in Katowice, 41-800 Zabrze, Poland;3. Department of Neurosurgery, St. Raphael Hospital, 30-693 Krakow, Poland;4. Department of Neurosurgery, Faculty of Medicine and Health Sciences, Andrzej Frycz Modrzewski University, 30-705 Kraków, Poland;5. Department of Agricultural and Environmental Chemistry, University of Agriculture in Krakow, 31-120 Krakow, Poland;6. Department of Trauma and Orthopedic Surgery, 5th Military Clinical Hospital, Kraków, Poland;7. Department of Rehabilitation in Orthopedics, Faculty of Motor Rehabilitation Bronis?aw Czech University of Physical Education in Kraków, Poland;8. Department of Physiology, School of Medicine in Katowice, Medical University of Silesia, 40-752 Katowice, Poland;9. Department of Neurosurgery, Provincial Specialist Hospital No. 2 in Jastrz?bie-Zdrój, 44-300 Jastrz?bie-Zdrój, Poland;1. NUS Graduate School’s Integrative Sciences & Engineering Programme (ISEP), National University of Singapore, University Hall, Tan Chin Tuan Wing, 119077, Singapore;2. Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore;3. Central Instrument Facility, Office of the Vice Chancellor for Research and Innovation, De La Salle University, 2401 Taft Avenue, Malate, Manila 1004, Philippines;4. Cardiovascular Research Institute, Yong Loo Lin School of Medicine, National University of Singapore, Singapore 117599, Singapore;1. Weldon School of Biomedical Engineering, Purdue University, West Lafayette, IN, USA;2. Department of Radiology, Medical Physics, Medical Center–University of Freiburg, Faculty of Medicine, University of Freiburg, Freiburg, Germany;3. School of Health Sciences, Purdue University, West Lafayette, IN, USA;4. Department of Neurology, School of Medicine, Indiana University, Bloomington, IN, USA;5. Wellcome Centre for Integrative Neuroimaging, University of Oxford, Oxford, UK;1. Graduate Group of Nutritional Biology, Department of Nutrition, University of California at Davis, One Shields Ave., Davis, CA 95616, USA;2. USDA/ARS/Western Human Nutrition Research Center, 430 West Health Sciences Drive, Davis, CA 95616, USA;3. Department of Pathology and Laboratory Medicine, University of California at Davis, 2805 50th Street, Sacramento, CA 95817, USA;1. Department of Clinical Biochemistry, School of Medicine, Tehran University of Medical Sciences, Tehran, Iran;2. Department of Bacterial Vaccines Quality Control, Razi Vaccine and Serum Research Institute, Agricultural Research, Education and Extension Organization (AREEO), Karaj, Iran |
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| Abstract: | Boronic acid compounds and the natural flavonoid compound quercetin were handled to synthesize two novel ligands encoded as B1(2,2′-(1,4-phenylenebis (benzo 1,3,2] dioxaborole-2,5-diyl)) bis (3,5,7-trihydroxy-4H- chromen-4-one) and B2(3.3.6. 3,5,7-trihydroxy-2-(2-(6-methoxypyridin-3-yl)benzod]1,3,2]dioxaborol-5-yl)? 4 H-chromene-4). Antioxidant activities of ligands were investigated by DPPH, ABTS and CUPRAC methods. Cholinesterase inhibition effects of ligands were determined by acetylcholinesterase and butyrylcholinesterase enzyme inhibition methods, cytotoxic effects of ligands were applied to healthy breast and colon cancer cell lines by MTT method, and urease and tyrosinase enzyme activities were determined. Antimicrobial properties of the compounds were analyzed by detecting their anti-QS potentials on Chromobacterium violaceum biosensor strain. Both compounds were found to have significant antioxidant effects compared to controls. It was determined that the compound B1 at 1–10 µg/mL was more active than the reference compounds (α-TOC and BHT). Moreover, the enzyme activity studies on ligands demonstrated that acetylchoinesterase and butyrylcholinesterase enzyme inhibitions were higher than the reference compounds. As expected, boron derivatives exhibited respectable activity against the biofilms of Escherichia coli (E. coli) and P. aeruginosa (P. aeruginosa). These results demonstrate the potential applicability of boron derivatives in the treatment of biofilm-associated infections and provide a practical strategy for the design of new boron-based antimicrobial materials. In silico molecular docking studies were performed on ligands to identify newly synthesized compounds. The binding parameter values and binding sites of the compounds were also determined. In conclusion, our studies showed that newly synthesized hybrid compounds could be solutions for antimicrobial resistance and enzyme-related disorders. |
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| Keywords: | Boron Quercetin Antioxidant Antibacterial Anti-quorum sensing QS MTT method Molecular Docking Studies |
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