Biological evaluation of Schiff bases containing dopamine as antibacterial/antifungal and potential Anti COVID-19 agents: Design, synthesis, characterization, molecular docking studies, and ADME properties

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dc.authoridOzdemir Ozmen, ummuhan/0000-0001-9161-9367
dc.contributor.authorUnlu, Ayse
dc.contributor.authorOzmen, Ummuhan Ozdemir
dc.contributor.authorAlyar, Saliha
dc.contributor.authorOzturk, Ali
dc.contributor.authorAlyar, Hamit
dc.contributor.authorGunduzalp, Ayla Balaban
dc.date.accessioned2024-11-07T13:34:40Z
dc.date.available2024-11-07T13:34:40Z
dc.date.issued2023
dc.departmentNiğde Ömer Halisdemir Üniversitesi
dc.description.abstractIn this study, Schiff bases containing dopamine were synthesized and their antimicrobial activities were investigated in vitro. What makes this study unique is the use of dopamine as a starting compound, which has not been previously explored for the synthesis of Schiff bases with acetophenone substituents. These newly synthesized compounds exhibit important pharmacological properties, and their structures have been thoroughly characterized using elemental analysis, 1H NMR, 13C NMR, and FT-IR methods. In the next phase of the study, we evaluated the antimicrobial activities of these dopamine Schiff bases against seven different bacterial and fungal isolates. Remarkably, one compound, 5NO2-afdop, demonstrated exceptionally high antibacterial activity (MIC: 0.078 & mu;g/ml) against Gram-positive bacteria, namely Staphylococcus aureus and Staphylococcus epidermis. Its activity was even superior to that of the reference drugs sulfisoxazole and sulfamethoxazole (MIC: 0.312 & mu;g/ml). This finding highlights the potential of the synthesized compound as a promising antimicrobial agent. Moreover, in-silico studies, the 5NO2-afdop compound shows comparable activity against the major protease of SARS-CoV2, the virus responsible for the COVID-19 pandemic. To assess the drug-likeness of all synthesized compounds, we employed the five Lipinski rules and conducted ADME predictions. These analyses provided valuable insights into the compounds' pharmacological profiles, suggesting their potential as drug candidates.. Additionally, molecular docking studies shed light on the interactions between the synthesized compounds and their target proteins. Notably, 5NO2-afdop exhibited the strongest antibacterial activity against the S. aureus protein (PDB ID: 4FGD) and displayed promising antiviral activity against the SARS-CoV-2 major protease (PDB ID: 5R80). These docking results further support the potential of 5NO2-afdop as a dual-action compound with antibacterial and antiviral properties.
dc.identifier.doi10.1016/j.molstruc.2023.136318
dc.identifier.issn0022-2860
dc.identifier.issn1872-8014
dc.identifier.scopus2-s2.0-85166485922
dc.identifier.scopusqualityQ2
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2023.136318
dc.identifier.urihttps://hdl.handle.net/11480/16110
dc.identifier.volume1293
dc.identifier.wosWOS:001052911400001
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherElsevier
dc.relation.ispartofJournal of Molecular Structure
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_20241106
dc.subjectDopamine Schiff bases
dc.subjectADME
dc.subjectMolecular docking
dc.subjectAntimicrobial activities
dc.subjectSARS-CoV-2
dc.titleBiological evaluation of Schiff bases containing dopamine as antibacterial/antifungal and potential Anti COVID-19 agents: Design, synthesis, characterization, molecular docking studies, and ADME properties
dc.typeArticle

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