Ionic Liquid-Assisted Fabrication of Bioactive Heterogeneous Magnetic Nanocatalyst with Antioxidant and Antibacterial Activities for the Synthesis of Polyhydroquinoline Derivatives
Antibacterial materials have obtained much attention in recent years due to the presence of hazardous agents causing oxidative stress and observation of pathogens. However, materials with antioxidant and antibacterial activities can cause toxicity due to their low biocompatibility and safety profile...
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MDPI AG
2022-03-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/5/1748 |
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| author | Shefa Mirani Nezhad Ehsan Nazarzadeh Zare Azimeh Davarpanah Seied Ali Pourmousavi Milad Ashrafizadeh Alan Prem Kumar |
| author_facet | Shefa Mirani Nezhad Ehsan Nazarzadeh Zare Azimeh Davarpanah Seied Ali Pourmousavi Milad Ashrafizadeh Alan Prem Kumar |
| author_sort | Shefa Mirani Nezhad |
| collection | DOAJ |
| description | Antibacterial materials have obtained much attention in recent years due to the presence of hazardous agents causing oxidative stress and observation of pathogens. However, materials with antioxidant and antibacterial activities can cause toxicity due to their low biocompatibility and safety profile, urging scientists to follow new ways in the synthesis of such materials. Ionic liquids have been employed as a green and environmentally solvent for the fabrication of electrically conductive polymers. In the present study, an antibacterial poly(<i>p</i>-phenylenediamine)@Fe<sub>3</sub>O<sub>4</sub> (P<i>p</i>PDA@Fe<sub>3</sub>O<sub>4</sub>) nanocomposite was fabricated using [HPy][HSO<sub>4</sub>] ionic liquid. The chemical preparation of P<i>p</i>PDA@Fe<sub>3</sub>O<sub>4</sub> nanocomposite was initiated through the oxidative polymerization of <i>p</i>-phenylenediamine by ammonium persulfate in the presence of [HPy][HSO<sub>4</sub>]. The P<i>p</i>PDA@Fe<sub>3</sub>O<sub>4</sub> nanocomposite exhibited antibacterial properties against Gram-negative (<i>Escherichia coli</i>) and Gram-positive (<i>Bacillus subtilis</i>) bacteria. The P<i>p</i>PDA@Fe<sub>3</sub>O<sub>4</sub> nanocomposite was employed as a heterogeneous nanocatalysis for one-pot synthesis of polyhydroquinoline derivatives using aromatic aldehyde, dimedone, benzyl acetoacetate, and ammonium acetate. Polyhydroquinoline derivatives were synthesized in significant yields (90–97%) without a difficult work-up procedure in short reaction times. Additionally, P<i>p</i>PDA@Fe<sub>3</sub>O<sub>4</sub> nanocatalyst was recycled for at least five consecutive catalytic runs with a minor decrease in the catalytic activity. In this case, 11 derivatives of polyhydroquinoline showed in vitro antioxidant activity between 70–98%. |
| first_indexed | 2024-03-09T20:28:25Z |
| format | Article |
| id | doaj.art-ae7633c68a834ee2a0220be83d785d6d |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T20:28:25Z |
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| series | Molecules |
| spelling | doaj.art-ae7633c68a834ee2a0220be83d785d6d2023-11-23T23:29:09ZengMDPI AGMolecules1420-30492022-03-01275174810.3390/molecules27051748Ionic Liquid-Assisted Fabrication of Bioactive Heterogeneous Magnetic Nanocatalyst with Antioxidant and Antibacterial Activities for the Synthesis of Polyhydroquinoline DerivativesShefa Mirani Nezhad0Ehsan Nazarzadeh Zare1Azimeh Davarpanah2Seied Ali Pourmousavi3Milad Ashrafizadeh4Alan Prem Kumar5School of Chemistry, Damghan University, Damghan 36716-41167, IranSchool of Chemistry, Damghan University, Damghan 36716-41167, IranSchool of Chemistry, Damghan University, Damghan 36716-41167, IranSchool of Chemistry, Damghan University, Damghan 36716-41167, IranFaculty of Engineering and Natural Sciences, Sabanci University, Orta Mahalle, Üniversite Caddesi No. 27, Orhanlı, Tuzla 34956, TurkeyCancer Science Institute of Singapore and Department of Pharmacology, Yong Loo Lin School of Medicine, National University of Singapore, Singapore 117599, SingaporeAntibacterial materials have obtained much attention in recent years due to the presence of hazardous agents causing oxidative stress and observation of pathogens. However, materials with antioxidant and antibacterial activities can cause toxicity due to their low biocompatibility and safety profile, urging scientists to follow new ways in the synthesis of such materials. Ionic liquids have been employed as a green and environmentally solvent for the fabrication of electrically conductive polymers. In the present study, an antibacterial poly(<i>p</i>-phenylenediamine)@Fe<sub>3</sub>O<sub>4</sub> (P<i>p</i>PDA@Fe<sub>3</sub>O<sub>4</sub>) nanocomposite was fabricated using [HPy][HSO<sub>4</sub>] ionic liquid. The chemical preparation of P<i>p</i>PDA@Fe<sub>3</sub>O<sub>4</sub> nanocomposite was initiated through the oxidative polymerization of <i>p</i>-phenylenediamine by ammonium persulfate in the presence of [HPy][HSO<sub>4</sub>]. The P<i>p</i>PDA@Fe<sub>3</sub>O<sub>4</sub> nanocomposite exhibited antibacterial properties against Gram-negative (<i>Escherichia coli</i>) and Gram-positive (<i>Bacillus subtilis</i>) bacteria. The P<i>p</i>PDA@Fe<sub>3</sub>O<sub>4</sub> nanocomposite was employed as a heterogeneous nanocatalysis for one-pot synthesis of polyhydroquinoline derivatives using aromatic aldehyde, dimedone, benzyl acetoacetate, and ammonium acetate. Polyhydroquinoline derivatives were synthesized in significant yields (90–97%) without a difficult work-up procedure in short reaction times. Additionally, P<i>p</i>PDA@Fe<sub>3</sub>O<sub>4</sub> nanocatalyst was recycled for at least five consecutive catalytic runs with a minor decrease in the catalytic activity. In this case, 11 derivatives of polyhydroquinoline showed in vitro antioxidant activity between 70–98%.https://www.mdpi.com/1420-3049/27/5/1748magnetic catalystionic liquidbioactiveantioxidantantibacterialpolyhydroquinoline derivatives |
| spellingShingle | Shefa Mirani Nezhad Ehsan Nazarzadeh Zare Azimeh Davarpanah Seied Ali Pourmousavi Milad Ashrafizadeh Alan Prem Kumar Ionic Liquid-Assisted Fabrication of Bioactive Heterogeneous Magnetic Nanocatalyst with Antioxidant and Antibacterial Activities for the Synthesis of Polyhydroquinoline Derivatives Molecules magnetic catalyst ionic liquid bioactive antioxidant antibacterial polyhydroquinoline derivatives |
| title | Ionic Liquid-Assisted Fabrication of Bioactive Heterogeneous Magnetic Nanocatalyst with Antioxidant and Antibacterial Activities for the Synthesis of Polyhydroquinoline Derivatives |
| title_full | Ionic Liquid-Assisted Fabrication of Bioactive Heterogeneous Magnetic Nanocatalyst with Antioxidant and Antibacterial Activities for the Synthesis of Polyhydroquinoline Derivatives |
| title_fullStr | Ionic Liquid-Assisted Fabrication of Bioactive Heterogeneous Magnetic Nanocatalyst with Antioxidant and Antibacterial Activities for the Synthesis of Polyhydroquinoline Derivatives |
| title_full_unstemmed | Ionic Liquid-Assisted Fabrication of Bioactive Heterogeneous Magnetic Nanocatalyst with Antioxidant and Antibacterial Activities for the Synthesis of Polyhydroquinoline Derivatives |
| title_short | Ionic Liquid-Assisted Fabrication of Bioactive Heterogeneous Magnetic Nanocatalyst with Antioxidant and Antibacterial Activities for the Synthesis of Polyhydroquinoline Derivatives |
| title_sort | ionic liquid assisted fabrication of bioactive heterogeneous magnetic nanocatalyst with antioxidant and antibacterial activities for the synthesis of polyhydroquinoline derivatives |
| topic | magnetic catalyst ionic liquid bioactive antioxidant antibacterial polyhydroquinoline derivatives |
| url | https://www.mdpi.com/1420-3049/27/5/1748 |
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