The First Dimeric Derivatives of the Glycopeptide Antibiotic Teicoplanin
Various dimeric derivatives of the glycopeptide antibiotic teicoplanin were prepared with the aim of increasing the activity of the parent compound against glycopeptide-resistant bacteria, primarily vancomycin-resistant enterococci. Starting from teicoplanin, four covalent dimers were prepared in tw...
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-01-01
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| Series: | Pharmaceuticals |
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| Online Access: | https://www.mdpi.com/1424-8247/15/1/77 |
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| author | Ilona Bereczki Zsolt Szűcs Gyula Batta Tamás Milán Nagy Eszter Ostorházi Katalin E. Kövér Anikó Borbás Pál Herczegh |
| author_facet | Ilona Bereczki Zsolt Szűcs Gyula Batta Tamás Milán Nagy Eszter Ostorházi Katalin E. Kövér Anikó Borbás Pál Herczegh |
| author_sort | Ilona Bereczki |
| collection | DOAJ |
| description | Various dimeric derivatives of the glycopeptide antibiotic teicoplanin were prepared with the aim of increasing the activity of the parent compound against glycopeptide-resistant bacteria, primarily vancomycin-resistant enterococci. Starting from teicoplanin, four covalent dimers were prepared in two orientations, using an α,ω-bis-isothiocyanate linker. Formation of a dimeric cobalt coordination complex of an <i>N</i>-terminal L-histidyl derivative of teicoplanin pseudoaglycone has been detected and its antibacterial activity evaluated. The Co(III)-induced dimerization of the histidyl derivative was demonstrated by DOSY experiments. Both the covalent and the complex dimeric derivatives showed high activity against VanA teicoplanin-resistant enterococci, but their activity against other tested bacterial strains did not exceed that of the monomeric compounds. |
| first_indexed | 2024-03-10T00:44:00Z |
| format | Article |
| id | doaj.art-3da40169d3d543cc84a3002057ef95a6 |
| institution | Directory Open Access Journal |
| issn | 1424-8247 |
| language | English |
| last_indexed | 2024-03-10T00:44:00Z |
| publishDate | 2022-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Pharmaceuticals |
| spelling | doaj.art-3da40169d3d543cc84a3002057ef95a62023-11-23T15:01:42ZengMDPI AGPharmaceuticals1424-82472022-01-011517710.3390/ph15010077The First Dimeric Derivatives of the Glycopeptide Antibiotic TeicoplaninIlona Bereczki0Zsolt Szűcs1Gyula Batta2Tamás Milán Nagy3Eszter Ostorházi4Katalin E. Kövér5Anikó Borbás6Pál Herczegh7Department of Pharmaceutical Chemistry, University of Debrecen, Egyetem tér 1, H-4032 Debrecen, HungaryDepartment of Pharmaceutical Chemistry, University of Debrecen, Egyetem tér 1, H-4032 Debrecen, HungaryDepartment of Organic Chemistry, University of Debrecen, H-4032 Debrecen, HungaryDepartment of Inorganic and Analytical Chemistry, University of Debrecen, H-4032 Debrecen, HungaryDepartment of Medical Microbiology, Semmelweis University, Nagyvárad tér 4, H-1089 Budapest, HungaryDepartment of Inorganic and Analytical Chemistry, University of Debrecen, H-4032 Debrecen, HungaryDepartment of Pharmaceutical Chemistry, University of Debrecen, Egyetem tér 1, H-4032 Debrecen, HungaryDepartment of Pharmaceutical Chemistry, University of Debrecen, Egyetem tér 1, H-4032 Debrecen, HungaryVarious dimeric derivatives of the glycopeptide antibiotic teicoplanin were prepared with the aim of increasing the activity of the parent compound against glycopeptide-resistant bacteria, primarily vancomycin-resistant enterococci. Starting from teicoplanin, four covalent dimers were prepared in two orientations, using an α,ω-bis-isothiocyanate linker. Formation of a dimeric cobalt coordination complex of an <i>N</i>-terminal L-histidyl derivative of teicoplanin pseudoaglycone has been detected and its antibacterial activity evaluated. The Co(III)-induced dimerization of the histidyl derivative was demonstrated by DOSY experiments. Both the covalent and the complex dimeric derivatives showed high activity against VanA teicoplanin-resistant enterococci, but their activity against other tested bacterial strains did not exceed that of the monomeric compounds.https://www.mdpi.com/1424-8247/15/1/77teicoplaninpseudoaglyconesynthesisdimerCo(III) complexDOSY NMR |
| spellingShingle | Ilona Bereczki Zsolt Szűcs Gyula Batta Tamás Milán Nagy Eszter Ostorházi Katalin E. Kövér Anikó Borbás Pál Herczegh The First Dimeric Derivatives of the Glycopeptide Antibiotic Teicoplanin Pharmaceuticals teicoplanin pseudoaglycone synthesis dimer Co(III) complex DOSY NMR |
| title | The First Dimeric Derivatives of the Glycopeptide Antibiotic Teicoplanin |
| title_full | The First Dimeric Derivatives of the Glycopeptide Antibiotic Teicoplanin |
| title_fullStr | The First Dimeric Derivatives of the Glycopeptide Antibiotic Teicoplanin |
| title_full_unstemmed | The First Dimeric Derivatives of the Glycopeptide Antibiotic Teicoplanin |
| title_short | The First Dimeric Derivatives of the Glycopeptide Antibiotic Teicoplanin |
| title_sort | first dimeric derivatives of the glycopeptide antibiotic teicoplanin |
| topic | teicoplanin pseudoaglycone synthesis dimer Co(III) complex DOSY NMR |
| url | https://www.mdpi.com/1424-8247/15/1/77 |
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