Synthesis, Anti-Inflammatory Activity, and Docking Simulation of a Novel Styryl Quinolinium Derivative
Stilbenes, like resveratrol, are natural small molecules with several applications in the treatment of chronic illnesses, diabetes, and neurological and cardiovascular conditions. Considering the molecular structure of stilbenes and the biological activities of resveratrol, we investigated the synth...
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2024-12-01
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| author | Mina Todorova Rumyana Bakalska Mehran Feizi-Dehnayebi Ghodsi Mohammadi Ziarani Mina Pencheva Kirila Stojnova Miglena Milusheva Paraskev Nedialkov Emiliya Cherneva Tsonko Kolev Stoyanka Nikolova |
| author_facet | Mina Todorova Rumyana Bakalska Mehran Feizi-Dehnayebi Ghodsi Mohammadi Ziarani Mina Pencheva Kirila Stojnova Miglena Milusheva Paraskev Nedialkov Emiliya Cherneva Tsonko Kolev Stoyanka Nikolova |
| author_sort | Mina Todorova |
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| description | Stilbenes, like resveratrol, are natural small molecules with several applications in the treatment of chronic illnesses, diabetes, and neurological and cardiovascular conditions. Considering the molecular structure of stilbenes and the biological activities of resveratrol, we investigated the synthesis and biological activity of a novel styryl quinolinium (SQ) derivative. The SQ was synthesized using the alkylation of lepidine and methyl 4-methylbenzenesulfonate and further Knoevenagel condensation with 2-hydroxy naphthaldehyde. Its structure was determined using NMR, IR, Raman, UV-Vis, and MS. The current trend of research has shifted toward the synthesis of novel SQ as resveratrol’s analog. Therefore, its anti-inflammatory and antioxidant activities were evaluated. The compound exerted very good anti-inflammatory effects in preventing albumin denaturation, which were confirmed by ex vivo immunohistochemical studies. Density functional theory (DFT) analyses were conducted on the SQ structure to gain detailed insights into its active sites, energy gap, quantum properties, and electronic behavior. The biological evaluation of the compound was completed, assessing its antioxidant potential using DPPH radical scavenging assay. In addition, molecular docking simulations were utilized to assess the SQ compound’s potential inhibitory effect on human serum albumin (HSA). |
| format | Article |
| id | doaj-art-ff38f095314b4579ac4a711f59e5e893 |
| institution | Kabale University |
| issn | 2076-3417 |
| language | English |
| publishDate | 2024-12-01 |
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| spelling | doaj-art-ff38f095314b4579ac4a711f59e5e8932025-01-10T13:15:02ZengMDPI AGApplied Sciences2076-34172024-12-0115128410.3390/app15010284Synthesis, Anti-Inflammatory Activity, and Docking Simulation of a Novel Styryl Quinolinium DerivativeMina Todorova0Rumyana Bakalska1Mehran Feizi-Dehnayebi2Ghodsi Mohammadi Ziarani3Mina Pencheva4Kirila Stojnova5Miglena Milusheva6Paraskev Nedialkov7Emiliya Cherneva8Tsonko Kolev9Stoyanka Nikolova10Department of Organic Chemistry, Faculty of Chemistry, University of Plovdiv, 4000 Plovdiv, BulgariaDepartment of Organic Chemistry, Faculty of Chemistry, University of Plovdiv, 4000 Plovdiv, BulgariaDepartment of Organic Chemistry, Faculty of Chemistry, Alzahra University, Tehran 19938-93973, IranDepartment of Organic Chemistry, Faculty of Chemistry, Alzahra University, Tehran 19938-93973, IranDepartment of Medical Physics and Biophysics, Faculty of Pharmacy, Medical University of Plovdiv, 4002 Plovdiv, BulgariaDepartment of General and Inorganic Chemistry with Methodology of Chemistry Education, Faculty of Chemistry, University of Plovdiv, 4000 Plovdiv, BulgariaDepartment of Organic Chemistry, Faculty of Chemistry, University of Plovdiv, 4000 Plovdiv, BulgariaDepartment of Pharmacognosy, Faculty of Pharmacy, Medical University of Sofia, 1000 Sofia, BulgariaDepartment of Chemistry, Faculty of Pharmacy, Medical University of Sofia, 2 Dunav Str., 1000 Sofia, BulgariaInstitute of Molecular Biology “R. Tsanev”, Bulgarian Academy of Sciences, Acad. G. Bonchev Str, bl. 21, 1113 Sofia, BulgariaDepartment of Organic Chemistry, Faculty of Chemistry, University of Plovdiv, 4000 Plovdiv, BulgariaStilbenes, like resveratrol, are natural small molecules with several applications in the treatment of chronic illnesses, diabetes, and neurological and cardiovascular conditions. Considering the molecular structure of stilbenes and the biological activities of resveratrol, we investigated the synthesis and biological activity of a novel styryl quinolinium (SQ) derivative. The SQ was synthesized using the alkylation of lepidine and methyl 4-methylbenzenesulfonate and further Knoevenagel condensation with 2-hydroxy naphthaldehyde. Its structure was determined using NMR, IR, Raman, UV-Vis, and MS. The current trend of research has shifted toward the synthesis of novel SQ as resveratrol’s analog. Therefore, its anti-inflammatory and antioxidant activities were evaluated. The compound exerted very good anti-inflammatory effects in preventing albumin denaturation, which were confirmed by ex vivo immunohistochemical studies. Density functional theory (DFT) analyses were conducted on the SQ structure to gain detailed insights into its active sites, energy gap, quantum properties, and electronic behavior. The biological evaluation of the compound was completed, assessing its antioxidant potential using DPPH radical scavenging assay. In addition, molecular docking simulations were utilized to assess the SQ compound’s potential inhibitory effect on human serum albumin (HSA).https://www.mdpi.com/2076-3417/15/1/284styryl quinoliniumsynthesisin silicoanti-inflammatoryalbumin denaturationimmunohistochemical analysis |
| spellingShingle | Mina Todorova Rumyana Bakalska Mehran Feizi-Dehnayebi Ghodsi Mohammadi Ziarani Mina Pencheva Kirila Stojnova Miglena Milusheva Paraskev Nedialkov Emiliya Cherneva Tsonko Kolev Stoyanka Nikolova Synthesis, Anti-Inflammatory Activity, and Docking Simulation of a Novel Styryl Quinolinium Derivative Applied Sciences styryl quinolinium synthesis in silico anti-inflammatory albumin denaturation immunohistochemical analysis |
| title | Synthesis, Anti-Inflammatory Activity, and Docking Simulation of a Novel Styryl Quinolinium Derivative |
| title_full | Synthesis, Anti-Inflammatory Activity, and Docking Simulation of a Novel Styryl Quinolinium Derivative |
| title_fullStr | Synthesis, Anti-Inflammatory Activity, and Docking Simulation of a Novel Styryl Quinolinium Derivative |
| title_full_unstemmed | Synthesis, Anti-Inflammatory Activity, and Docking Simulation of a Novel Styryl Quinolinium Derivative |
| title_short | Synthesis, Anti-Inflammatory Activity, and Docking Simulation of a Novel Styryl Quinolinium Derivative |
| title_sort | synthesis anti inflammatory activity and docking simulation of a novel styryl quinolinium derivative |
| topic | styryl quinolinium synthesis in silico anti-inflammatory albumin denaturation immunohistochemical analysis |
| url | https://www.mdpi.com/2076-3417/15/1/284 |
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