Antimicrobial Activity of Copper(II), Nickel(II) and Zinc(II) Complexes with Semicarbazone and Thiosemicarbazone Ligands Derived from Substituted Salicylaldehydes
Antibiotic resistance is a problem repeatedly reported by health authorities. Metalloantibiotics, i.e., biologically active compounds containing one or more metal ions, can be an important resource in the fight against bacteria and fungi. Here, we report the results obtained with a panel of copper(I...
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2025-05-01
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| author | Alessio Zavaroni Luca Rigamonti Franco Bisceglie Mauro Carcelli Giorgio Pelosi Giovanna Angela Gentilomi Dominga Rogolino Francesca Bonvicini |
| author_facet | Alessio Zavaroni Luca Rigamonti Franco Bisceglie Mauro Carcelli Giorgio Pelosi Giovanna Angela Gentilomi Dominga Rogolino Francesca Bonvicini |
| author_sort | Alessio Zavaroni |
| collection | DOAJ |
| description | Antibiotic resistance is a problem repeatedly reported by health authorities. Metalloantibiotics, i.e., biologically active compounds containing one or more metal ions, can be an important resource in the fight against bacteria and fungi. Here, we report the results obtained with a panel of copper(II), nickel(II) and zinc(II) complexes with thiosemicarbazone, semicarbazone and acylhydrazone ligands on <i>Staphylococcus aureus</i>, <i>Escherichia coli</i> and <i>Candida albicans</i>, taken as model systems of human pathogens. To increase the solubility in water, the sulfonic group was introduced on some of the ligands, isolating them as sodium salts (NaH<sub>2</sub>L4-NaH<sub>2</sub>L7). Complexes <b>1</b>–<b>14</b> were isolated, fully characterized and the X-ray structures of <b>11</b>, <b>12</b> and <b>13</b> were obtained. While all the ligands have no antimicrobial activity, the copper(II) complexes <b>1</b> and <b>4</b> and the nickel(II) complex <b>2</b>, obtained from thiosemicarbazone ligands, showed good activity, in particular against <i>S. aureus</i>; these complexes were investigated in depth, calculating their respective IC<sub>50</sub> values (4.2 μM, 3.5 μM and 61.8 μM, respectively). It should be noted that nickel(II) complex <b>2</b> does not show hemolytic activity and has a favorable SI value. While all the copper(II) complexes completely degraded the plasmid DNA in presence of H<sub>2</sub>O<sub>2</sub>, nickel(II) complex <b>2</b> cleaved the plasmid DNA leading to the formation of the relaxed nicked conformation, thus suggesting a different mechanism of action. |
| format | Article |
| id | doaj-art-ccb827e7a95a43a0b3327680e700e7d4 |
| institution | OA Journals |
| issn | 1420-3049 |
| language | English |
| publishDate | 2025-05-01 |
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| series | Molecules |
| spelling | doaj-art-ccb827e7a95a43a0b3327680e700e7d42025-08-20T02:33:02ZengMDPI AGMolecules1420-30492025-05-013011232910.3390/molecules30112329Antimicrobial Activity of Copper(II), Nickel(II) and Zinc(II) Complexes with Semicarbazone and Thiosemicarbazone Ligands Derived from Substituted SalicylaldehydesAlessio Zavaroni0Luca Rigamonti1Franco Bisceglie2Mauro Carcelli3Giorgio Pelosi4Giovanna Angela Gentilomi5Dominga Rogolino6Francesca Bonvicini7Department of Chemistry, Life Sciences and Environmental Sustainability, University of Parma, Parco Area delle Scienze 17/A, 43124 Parma, ItalyDipartimento di Scienze Chimiche e Geologiche, Università degli Studi di Modena e Reggio Emilia, Via G. Campi 103, 41125 Modena, ItalyDepartment of Chemistry, Life Sciences and Environmental Sustainability, University of Parma, Parco Area delle Scienze 17/A, 43124 Parma, ItalyDepartment of Chemistry, Life Sciences and Environmental Sustainability, University of Parma, Parco Area delle Scienze 17/A, 43124 Parma, ItalyDepartment of Chemistry, Life Sciences and Environmental Sustainability, University of Parma, Parco Area delle Scienze 17/A, 43124 Parma, ItalyDepartment of Pharmacy and Biotechnology, University of Bologna, Via Massarenti 9, 40138 Bologna, ItalyDepartment of Chemistry, Life Sciences and Environmental Sustainability, University of Parma, Parco Area delle Scienze 17/A, 43124 Parma, ItalyDepartment of Pharmacy and Biotechnology, University of Bologna, Via Massarenti 9, 40138 Bologna, ItalyAntibiotic resistance is a problem repeatedly reported by health authorities. Metalloantibiotics, i.e., biologically active compounds containing one or more metal ions, can be an important resource in the fight against bacteria and fungi. Here, we report the results obtained with a panel of copper(II), nickel(II) and zinc(II) complexes with thiosemicarbazone, semicarbazone and acylhydrazone ligands on <i>Staphylococcus aureus</i>, <i>Escherichia coli</i> and <i>Candida albicans</i>, taken as model systems of human pathogens. To increase the solubility in water, the sulfonic group was introduced on some of the ligands, isolating them as sodium salts (NaH<sub>2</sub>L4-NaH<sub>2</sub>L7). Complexes <b>1</b>–<b>14</b> were isolated, fully characterized and the X-ray structures of <b>11</b>, <b>12</b> and <b>13</b> were obtained. While all the ligands have no antimicrobial activity, the copper(II) complexes <b>1</b> and <b>4</b> and the nickel(II) complex <b>2</b>, obtained from thiosemicarbazone ligands, showed good activity, in particular against <i>S. aureus</i>; these complexes were investigated in depth, calculating their respective IC<sub>50</sub> values (4.2 μM, 3.5 μM and 61.8 μM, respectively). It should be noted that nickel(II) complex <b>2</b> does not show hemolytic activity and has a favorable SI value. While all the copper(II) complexes completely degraded the plasmid DNA in presence of H<sub>2</sub>O<sub>2</sub>, nickel(II) complex <b>2</b> cleaved the plasmid DNA leading to the formation of the relaxed nicked conformation, thus suggesting a different mechanism of action.https://www.mdpi.com/1420-3049/30/11/2329metalloantibioticsacylhydrazonethiosemicarbazoneantimicrobial activitycytotoxicityhemolytic properties |
| spellingShingle | Alessio Zavaroni Luca Rigamonti Franco Bisceglie Mauro Carcelli Giorgio Pelosi Giovanna Angela Gentilomi Dominga Rogolino Francesca Bonvicini Antimicrobial Activity of Copper(II), Nickel(II) and Zinc(II) Complexes with Semicarbazone and Thiosemicarbazone Ligands Derived from Substituted Salicylaldehydes Molecules metalloantibiotics acylhydrazone thiosemicarbazone antimicrobial activity cytotoxicity hemolytic properties |
| title | Antimicrobial Activity of Copper(II), Nickel(II) and Zinc(II) Complexes with Semicarbazone and Thiosemicarbazone Ligands Derived from Substituted Salicylaldehydes |
| title_full | Antimicrobial Activity of Copper(II), Nickel(II) and Zinc(II) Complexes with Semicarbazone and Thiosemicarbazone Ligands Derived from Substituted Salicylaldehydes |
| title_fullStr | Antimicrobial Activity of Copper(II), Nickel(II) and Zinc(II) Complexes with Semicarbazone and Thiosemicarbazone Ligands Derived from Substituted Salicylaldehydes |
| title_full_unstemmed | Antimicrobial Activity of Copper(II), Nickel(II) and Zinc(II) Complexes with Semicarbazone and Thiosemicarbazone Ligands Derived from Substituted Salicylaldehydes |
| title_short | Antimicrobial Activity of Copper(II), Nickel(II) and Zinc(II) Complexes with Semicarbazone and Thiosemicarbazone Ligands Derived from Substituted Salicylaldehydes |
| title_sort | antimicrobial activity of copper ii nickel ii and zinc ii complexes with semicarbazone and thiosemicarbazone ligands derived from substituted salicylaldehydes |
| topic | metalloantibiotics acylhydrazone thiosemicarbazone antimicrobial activity cytotoxicity hemolytic properties |
| url | https://www.mdpi.com/1420-3049/30/11/2329 |
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