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Semisynthetic Analogs of the Antibiotic Fidaxomicin—Design, Synthesis, and Biological Evaluation

Andrea Dorst, Regina Berg, Christoph G. W. Gertzen, Daniel Schäfle, Katja Zerbe, Myriam Gwerder, Simon D. Schnell, Peter Sander, Holger Gohlke, Karl Gademann

2020ACS Medicinal Chemistry Letters25 citationsDOIOpen Access PDF

Abstract

infections (CDI). Among the main limitations for this compound, its low water solubility impacts further clinical uses. We report on the synthesis of new fidaxomicin derivatives based on structural design and utilizing an operationally simple one-step protecting group-free preparative approach from the natural product. An increase in solubility of up to 25-fold with largely retained activity was observed. Furthermore, hybrid antibiotics were prepared that show improved antibiotic activities.

Topics & Concepts

FidaxomicinAntibioticsMedicinePharmacologyMicrobiologyBiologyVancomycinBacteriaGeneticsStaphylococcus aureusCancer therapeutics and mechanismsMicrobial Natural Products and BiosynthesisAntibiotics Pharmacokinetics and Efficacy