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Synthesis and structure-activity relationship of berkeleylactone A-derived antibiotics.
Malatinský, Tomás; Valachová, Dominika; Pinceková, Lucia; Scherhaufer, David; Olejníková, Petra; Májeková, Magdaléna; Vargová, Jarmila; Gaálová-Radochová, Barbora; Bujdáková, Helena; Nováciková, Jana; Farley, Alistair J M; Berkes, Dusan; Jakubec, Pavol; Kolarovic, Andrej; Caletková, Olga.
Afiliación
  • Malatinský T; Institute of Organic Chemistry, Catalysis and Petrochemistry, Slovak University of Technology, Radlinského 9, 812 37 Bratislava, Slovakia. olga.caletkova@stuba.sk.
  • Valachová D; Institute of Organic Chemistry, Catalysis and Petrochemistry, Slovak University of Technology, Radlinského 9, 812 37 Bratislava, Slovakia. olga.caletkova@stuba.sk.
  • Pinceková L; Institute of Organic Chemistry, Catalysis and Petrochemistry, Slovak University of Technology, Radlinského 9, 812 37 Bratislava, Slovakia. olga.caletkova@stuba.sk.
  • Scherhaufer D; Institute of Organic Chemistry, Catalysis and Petrochemistry, Slovak University of Technology, Radlinského 9, 812 37 Bratislava, Slovakia. olga.caletkova@stuba.sk.
  • Olejníková P; Institute of Biochemistry and Microbiology, Slovak University of Technology, Radlinského 9, 812 37 Bratislava, Slovakia.
  • Májeková M; Institute of Experimental Pharmacology & Toxicology, Centre of Experimental Medicine SAS, Dúbravská cesta 9, 841 04 Bratislava, Slovakia.
  • Vargová J; Department of Microbiology and Virology, Faculty of Natural Sciences, Comenius University in Bratislava, Mlynská dolina, Ilkovicova 6, 842 15 Bratislava, Slovakia.
  • Gaálová-Radochová B; Department of Microbiology and Virology, Faculty of Natural Sciences, Comenius University in Bratislava, Mlynská dolina, Ilkovicova 6, 842 15 Bratislava, Slovakia.
  • Bujdáková H; Department of Microbiology and Virology, Faculty of Natural Sciences, Comenius University in Bratislava, Mlynská dolina, Ilkovicova 6, 842 15 Bratislava, Slovakia.
  • Nováciková J; Central Laboratories, Slovak University of Technology, Radlinského 9, 812 37 Bratislava, Slovakia.
  • Farley AJM; The Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK.
  • Berkes D; Institute of Organic Chemistry, Catalysis and Petrochemistry, Slovak University of Technology, Radlinského 9, 812 37 Bratislava, Slovakia. olga.caletkova@stuba.sk.
  • Jakubec P; Institute of Organic Chemistry, Catalysis and Petrochemistry, Slovak University of Technology, Radlinského 9, 812 37 Bratislava, Slovakia. olga.caletkova@stuba.sk.
  • Kolarovic A; Department of Chemistry, Faculty of Education, Trnava University, Priemyselná 4, 918 43 Trnava, Slovakia.
  • Caletková O; Institute of Organic Chemistry, Catalysis and Petrochemistry, Slovak University of Technology, Radlinského 9, 812 37 Bratislava, Slovakia. olga.caletkova@stuba.sk.
Org Biomol Chem ; 20(39): 7821-7832, 2022 10 12.
Article en En | MEDLINE | ID: mdl-36169622
Berkeleylactone A is a potent 16-membered macrolactone antibiotic, recently isolated from a coculture of Berkeley Pit Lake fungi. Although its antimicrobial activity has already been investigated, little is known about the structure-activity relationship. Based on our previous synthetic studies, a series of berkeleylactone A derivatives were synthesized and evaluated for their in vitro antimicrobial activities against methicillin-sensitive and methicillin-resistant Staphylococcus aureus (MRSA) strains. Our data confirmed the essential role of the embedded conjugated system and suggest a reversible sulfa-protection of the Michael acceptor as a viable option. Structurally simplified achiral macrolactam 8 showed the best inhibitory activity against S. aureus L12 (MRSA) with MIC50 values of 0.39 µg mL-1, 8-fold lower than those of berkeleylactone A. These studies may be of value in the development of more advanced candidates for antibiotic applications.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Staphylococcus aureus Resistente a Meticilina Idioma: En Revista: Org Biomol Chem Asunto de la revista: BIOQUIMICA / QUIMICA Año: 2022 Tipo del documento: Article País de afiliación: Eslovaquia Pais de publicación: Reino Unido
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Staphylococcus aureus Resistente a Meticilina Idioma: En Revista: Org Biomol Chem Asunto de la revista: BIOQUIMICA / QUIMICA Año: 2022 Tipo del documento: Article País de afiliación: Eslovaquia Pais de publicación: Reino Unido