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The First Dimeric Derivatives of the Glycopeptide Antibiotic Teicoplanin.

ABSTRACT: 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 N-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.

SUBMITTER: Bereczki I

PROVIDER: S-EPMC8779952 | biostudies-literature | 2022 Jan

REPOSITORIES: biostudies-literature

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The First Dimeric Derivatives of the Glycopeptide Antibiotic Teicoplanin.

Bereczki Ilona I Szűcs Zsolt Z Batta Gyula G Nagy Tamás Milán TM Ostorházi Eszter E Kövér Katalin E KE Borbás Anikó A Herczegh Pál P

Pharmaceuticals (Basel, Switzerland) 20220108 1

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 ...[more]

PMID: 35056134

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