1,2,3-Triazole-gold(I)-triethylposphine derivatives active against resistant Gram-positive pathogens

Mathieu Michaut; Alexandre Steffen; Jean-Marie Contreras; Christophe Morice; Isabelle J Schalk; Patrick Plésiat; Gaëtan L A Mislin

doi:10.1016/j.bmcl.2021.127879

1,2,3-Triazole-gold(I)-triethylposphine derivatives active against resistant Gram-positive pathogens

Bioorg Med Chem Lett. 2021 May 15:40:127879. doi: 10.1016/j.bmcl.2021.127879. Epub 2021 Feb 24.

Authors

Mathieu Michaut¹, Alexandre Steffen¹, Jean-Marie Contreras¹, Christophe Morice¹, Isabelle J Schalk², Patrick Plésiat³, Gaëtan L A Mislin⁴

Affiliations

¹ Prestwick Chemical, PC SAS, 220 Boulevard Gonthier d'Andernach, 67400 Illkirch-Graffenstaden, France.
² CNRS, UMR7242 Biotechnologie et Signalisation Cellulaire, 300 Boulevard Sébastien Brant, 67400 Illkirch-Graffenstaden, France; Université de Strasbourg, Institut de Recherche de l'Ecole de Biotechnologie de Strasbourg (IREBS), 67400 Illkirch-Graffenstaden, France; Interdisciplinary Thematic Institute for Innovative Vectorization (ITI InnoVec), Université de Strasbourg, 67000 Strasbourg, France.
³ Laboratoire de Bactériologie, UMR 6249 CNRS Chrono-Environnement, UFR Santé, Université Bourgogne Franche-Comté, 25000 Besançon, France.
⁴ CNRS, UMR7242 Biotechnologie et Signalisation Cellulaire, 300 Boulevard Sébastien Brant, 67400 Illkirch-Graffenstaden, France; Université de Strasbourg, Institut de Recherche de l'Ecole de Biotechnologie de Strasbourg (IREBS), 67400 Illkirch-Graffenstaden, France; Interdisciplinary Thematic Institute for Innovative Vectorization (ITI InnoVec), Université de Strasbourg, 67000 Strasbourg, France. Electronic address: mislin@unistra.fr.

PMID: 33636306
DOI: 10.1016/j.bmcl.2021.127879

Abstract

Innovative organogold(I) antibacterial compounds were synthesized by click chemistry with triethylphosphine-gold(I) azides and an alkyne derivative. The resulting organo-gold(I) compounds exhibit high levels of antibacterial activity against Gram-positive pathogens, with particularly low MICs against Clostridium difficile.

Keywords: Antibiotic; Azide-alkyne Huisgen cycloaddition; Clostridium difficile; Enterococcus sp.; Gold(I) complex; Staphylococcus sp..

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkynes / chemistry
Anti-Bacterial Agents / chemistry*
Anti-Bacterial Agents / pharmacology
Azides / chemistry
Catalysis
Click Chemistry
Clostridioides difficile
Cycloaddition Reaction
Drug Discovery
Drug Resistance
Enterococcus / drug effects
Escherichia coli / drug effects
Humans
Microbial Sensitivity Tests
Organogold Compounds / chemistry*
Organogold Compounds / pharmacology
Phosphines / chemistry*
Phosphines / pharmacology
Staphylococcus / drug effects
Triazoles / chemistry*
Triazoles / pharmacology

Substances

Alkynes
Anti-Bacterial Agents
Azides
Organogold Compounds
Phosphines
Triazoles
triethyl phosphine gold