Synthesis and antibacterial evaluation of some teicoplanin pseudoaglycon derivatives containing alkyl- and arylthiosubstituted maleimides

Abstract

Dedicated to the memory of Professor Maria N Preobrazhenskaya ✠ Bis-alkylthio maleimido derivatives have been prepared from teicoplanin pseudoaglycon by reaction of its primary amino group with N-ethoxycarbonyl bis-alkylthiomaleimides. Some of the new derivatives displayed excellent antibacterial activity against resistant bacteria.

VanZ Reduces the Binding of Lipoglycopeptide Antibiotics to Staphylococcus aureus and Streptococcus pneumoniae Cells

“…Teicoplanin, vancomycin, oritavancin, and chloramphenicol (Sigma-Aldrich, Germany); dalbavancin (MedChemExpress, Sweden); MA79 (Csávás et al, 2015), ERJ390 (Pintér et al, 2009), and SZZS-12 (Szucs et al, 2017); carbenicillin, gentamicin and erythromycin (Duchefa Biochemie, Netherland); vancomycin BODIPY-FL conjugate (Thermo Fisher Scientific, Germany) and fluorescently labeled teicoplanin (Vimberg et al, 2019).…”

“…The ability of the E. faecium vanZ Tei and vanZ g paralogs to confer resistance to glycopeptide antibiotics was tested in S. aureus, which naturally does not encode any proteins of the VanZ superfamily. In particular, we determined the susceptibility of S. aureus RN4220 expressing vanZ Tei and vanZ g to the clinically used glycopeptide antibiotic vancomycin (VAN); the lipoglycopeptide antibiotics teicoplanin (TEI), oritavancin (ORI), and dalbavancin (DALB); and three experimental lipoglycopeptide antibiotics derived from teicoplanin pseudoaglycone: MA79 (Csávás et al, 2015), ERJ390 (Pintér et al, 2009) and SZZS-12 (Szucs et al, 2017; Figure 1). In addition, the non-glycopeptide antibiotics carbenicillin (CARB, cell wall-targeting) gentamicin (GEN, 30S ribosometargeting) and erythromycin (ERY, 50S ribosome-targeting) were used as controls.…”

Synthesis and biological evaluation of lipophilic teicoplanin pseudoaglycon derivatives containing a substituted triazole function

“…These include the conjugation with a squaric acid moiety, isoindole formation and the incorporation of variously substituted maleimides. [10][11][12] Many of these compounds showed good in vitro activity against various bacteria, including VRE, and interestingly, some of them proved to be efficient against different strains of influenza virus.…”

Lipophilic teicoplanin pseudoaglycon derivatives are active against vancomycin- and teicoplanin-resistant enterococci

“…37 The logP calculations for the whole collection of compounds revealed that all of them are lipophilic compounds with logP values close to or 43. Based on the results presented here and in our previous articles, [16][17][18][19][20][21]27,28 it seems that there is no linear correlation between the lipophilicity of glycopeptide antibiotics and their antibacterial activity against VRE strains, but the presence of a hydrophobic moiety on the antibiotic is critical in most cases.…”