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Molecular Docking and In Vitro Antibacterial Properties of Several Chalcone Derivatives
Abstract
Chalcones are flavonoid-derived secondary metabolites known for diverse biological activities, including antibacterial effects. This study investigates the antibacterial properties of two chalcone derivatived i.e. 4-dimethylamino-4-hydroxychalcone (DMAHC) and 6-fluoro-2-chloro-4-hydroxychalcone (FCHC) against Staphylococcus aureus and Escherichia coli through integrated in vitro and in silico analyses. Antibacterial activity assessed using the agar diffusion method at concentrations of 1; 5; and 10% (w/v) revealed that DMAHC exhibited dose-dependent inhibition of both bacterial species, whereas FCHC demonstrated activity only against S. aureus. Molecular docking was performed using target proteins from S. aureus (1MWT) and E. coli (7ONW). Both chalcones were capable of binding to the active-site residues of the respective proteins; however, DMAHC showed a more favorable binding affinity toward E. coli (deltaG = -7.04 kcal/mol) compared to FCHC (deltaG = -6.75 kcal/mol). Despite its negative binding energy, FCHC failed to inhibit E. coli in vitro, likely due to reduced membrane permeability associated with its halogen substituents. Overall, the combined results highlight DMAHC as a more promising antibacterial candidate than FCHC, particularly against Gram-negative bacteria, and underscore the importance of electron-donating substituents in enhancing chalcone bioactivity.
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Ahmed, R.M., Sastry, G.V., Bano, N., Ravichandra, S., and Raghavendra, M. (2011), Synthesis and Cytotoxic, Antioxidant Activities of new Chalcone Derivates. Rasayan Journal Chemistry, 4(2): 289-294.
Bathelemy, N., Charles, F., Pantaleon, A., Azeh, N., Estella, T., Hortense, G., Ngadjui, B. (2016), Synthesis and Evaluation of Antimicrobial Properties of Some Chalcones. British Journal of Pharmaceutical Research, 14(2): 1-11. DOI: https://doi.org/10.9734/BJPR/2016/28243
Bhuiyan, M.M.M., Hossain, M.I., Mahmud, M.M., & Amin, M.A. (2011), Microwave-assisted efficient synthesis of chalcones as probes for antimicrobial activities. Chemistry journal, Vol. 01, Issue 01, pp. 21-28.
Capuccino and Suherman. (2011), Microbiology a Laboratory Manual 9 Edition. Canada: SUNY Rocckland Community College.
Dan, W., Dai, J. (2020), Recent developments of chalcones as potential antibacterial agents in medicinal chemistry. European Journal of Medicinal Chemistry, Vol. 187, 111980. DOI: https://doi.org/10.1016/j.ejmech.2019.111980
Davis, W.W., and Stout, T.R. (1971), disc plate methods of microbiological antibiotic assay, App. Microbioll., 22(4): 659-665.
Doan, T.N., dan Tran, D.T. (2011), Synthesis, Antioxidant and Antimicrobial Activities of a Novel Series of Chalcones, Pirazolyc Chalcones, and Allylic Chalcones. Scientific Research, 2: 282-288. DOI: http://dx.doi.org/10.4236/pp.2011.24036
Eze, F.U., Okoro, U.C., Ugwu, D.I., Okafor, S.N. (2019), Biological Activity Evaluation of Some New Benzenesulphonamide Derivatives. Frontiers in Chemistry, Vol.7. 634. DOI: http://dx.doi.org/10.3389/fchem.2019.00634
Fikroh, R. A., Matsjeh, S., & Anwar, C. (2020), Synthesis and anticancer activity of (E)-2’- hydroxy-2-bromo-4,5-dimethoxychalcone against breast cancer (MCF-7) cell line. Molekul, 15(1), 34–39. DOI: https://doi.org/10.20884/1.jm.2020.15.1.558
Kaur, S., Rao, R., and Nanda, S. (2011), Amoxicillin: A Broad Spectrum Antibiotic. International Journal of Pharmacy and Pharmaceutical Sciences, 3(3): 30-37.
Natheer, S. (2012), Evaluation of Antibacterial Activity of Morinda Citrifolia, Vitex Trifolia and Chromolaena Odorata. African Journal of Pharmacy and Pharmacology, Vol. 6. No.11, p. 783-788. DOI: https://doi.org/10.5897/AJPP11.435
Prabawati, S.Y., Khusnuryani, A., dan Khamidinal. (2017), Sintesis Senyawa Calkon Bebas Pelarut Sebagai Zat Antibakteri. ALCHEMY Jurnal Penelitian Kimia, Vol.13, No. 1, Hal. 96-102. DOI: http://dx.doi.org/10.20961/alchemy.v13i1.4324
Prabawati, S.Y., Yuda, K. E., Firdaus, R. C., Sugihati, A. (2022), Green Synthesis of Several Chalcone Derivatives using Grinding Technique. Advanced of Engineering Science. Vol.54. No.08. p.2449-2456.
Prasad, Y.R., Kumar, P.R., Deepti, C.A., and Ramana, M.V. (2006), Synthesis and Antimicrobial Activity of Some Novel Chalcones of 2-hidroxy-1-acetonapthone and 3-acetylcoumarin. E-journal of Chemisry, 3(13): 236-241. DOI: https://doi.org/10.1155/2006/395386
Prestinaci, F., Pezzotti, P., and Pantosti, A. (2015), Antimicrobial resistance: a global multifaceted phenomenon. Pathog. Glob. Health., 109, 309–318. DOI: http://dx.doi.org/10.1179/2047773215Y.0000 000030
Sakkiah, S., Selvaraj,C., Guo, W., Liu, J., Ge, W., Patterson, T. A., Hong, H. (2021), Elucidation of Agonist and Antagonist Dynamic Binding Patterns in ER-? by Integration of Molecular Docking, Molecular Dynamics Simulations and Quantum Mechanical Calculations. Int. J. Mol. Sci. 22(17),9371. DOI:https://doi.org/10.3390/ijms22179371
Saxena, S. dan Gober, C. (2008). Comparative in vitro Antimicrobial Procedural Efficacy for Susceptibility of Staphylococcus aures, Eschechia coli and Pseudomonas species to Chloramphenicol, Ciprofloxacin and Cefaclor. British Journal of Biochemical Science, 65: 178-183. DOI: https://doi.org/10.1080/09674845.2008.11732825
Susanti Vh, E., & Eko Setyowati, W. A. (2018), A Green Synthesis of Chalcones As an Antioxidant and Anticancer. IOP Conference Series: Materials Science and Engineering, 299(1), 1–6. DOI: https://doi.org/10.1088/1757-899X/299/1/012077
Syam, S., Abdelwahab, S.I., Al-Mamary, M.A., dan Mohan, S. (2012), Synthesis of Chalcones with Anticancer Activities. Molecules. 17: 6179-6195. DOI: https://doi.org/10.3390/molecules17066179.
Xu, M., Wu, P., Fan Shen, F., Ji, J., Rakesh, K.P., (2019), Chalcone derivatives and their antibacterial activities: Current development. Bioorganic Chemistry, 91. 103133. DOI: https://doi.org/10.1016/j.bioorg.2019.103133.
DOI: https://doi.org/10.14421/biomedich.2026.151.83-90
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