title: The effect of complexation of 3-formylrifamycin SV macrocyclic ether derivatives with metal cations and small nitrogen-containing organic molecules on antibacterial activity against S. aureus and S. epidermidis.
abstract: Spectroscopic studies of ether rifamycins (1-9) have shown that all these compounds tend to be zwitterions with different localizations of intramolecularly transferred proton, which influences their solubility and logP values. According to ESI MS studies, rifamycins 3 and 4 form complexes with Li(+) or Na(+), while the other ones (7-9) coordinate small organic molecules, which can be further replaced by Na(+) cation. Biological assays revealed that the use of 7-9 in the form of complexes with small organic molecules improves their antibacterial potency as a result of changed: logP, solubility and binding mode with bacterial RNA polymerases.
authors.affiliation: Faculty of Chemistry, A. Mickiewicz University, Umultowska 89b, 61-614 Poznan, Poland. Electronic address: piotrp@amu.edu.pl.
authors.forename: Piotr
authors.initials: P
authors.lastname: Przybylski
authors.affiliation: Faculty of Chemistry, A. Mickiewicz University, Umultowska 89b, 61-614 Poznan, Poland.
authors.forename: Krystian
authors.initials: K
authors.lastname: Pyta
authors.affiliation: Faculty of Chemistry, A. Mickiewicz University, Umultowska 89b, 61-614 Poznan, Poland.
authors.forename: Dominika
authors.initials: D
authors.lastname: Czerwonka
authors.affiliation: Department of Genetics and Pharmaceutical Microbiology, University of Medical Sciences, Święcickiego 4, 60-781 Poznan, Poland.
authors.forename: Marcelina M
authors.initials: MM
authors.lastname: Kubicka
authors.affiliation: Department of Genetics and Pharmaceutical Microbiology, University of Medical Sciences, Święcickiego 4, 60-781 Poznan, Poland; Institute of Human Genetics, Polish Academy of Science, Strzeszynska 32, 60-479 Poznan, Poland.
authors.forename: Marzena
authors.initials: M
authors.lastname: Gajecka
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D004987:Ethers / Q000737:chemistry* / Q000494:pharmacology; D008094:Lithium / Q000737:chemistry / Q000494:pharmacology; D047028:Macrocyclic Compounds / Q000737:chemistry* / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D009584:Nitrogen / Q000737:chemistry*; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D012294:Rifamycins / Q000737:chemistry / Q000494:pharmacology; D012964:Sodium / Q000737:chemistry / Q000494:pharmacology; D013211:Staphylococcus aureus / Q000187:drug effects*; D013212:Staphylococcus epidermidis / Q000187:drug effects*; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D004987:Ethers; D047028:Macrocyclic Compounds; D009942:Organometallic Compounds; D012294:Rifamycins; C038966:3-formylrifamycin SV; D008094:Lithium; D012964:Sodium; D009584:Nitrogen
keywords: Antibacterial; Bacterial RNA polymerases; Complexes; LogP; Rifamycin antibiotics; Solubility