title: Lipophosphonoxins: new modular molecular structures with significant antibacterial properties.
abstract: Novel compounds termed lipophosphonoxins were prepared using a simple and efficient synthetic approach. The general structure of lipophosphonoxins consists of four modules: (i) a nucleoside module, (ii) an iminosugar module, (iii) a hydrophobic module (lipophilic alkyl chain), and (iv) a phosphonate linker module that holds together modules i-iii. Lipophosphonoxins displayed significant antibacterial properties against a panel of Gram-positive species, including multiresistant strains. The minimum inhibitory concentration (MIC) values of the best inhibitors were in the 1-12 μg/mL range, while their cytotoxic concentrations against human cell lines were significantly above this range. The modular nature of this artificial scaffold offers a large number of possibilities for further modifications/exploitation of these compounds.
authors: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic v.v.i., Flemingovo nám. 2, 166 10 Prague 6, Czech Republic. rejman@uochb.cas.cz
authors: Dominik
authors: D
authors: Rejman
authors: Alžbeta
authors: A
authors: Rabatinová
authors: António R
authors: AR
authors: Pombinho
authors: Soňa
authors: S
authors: Kovačková
authors: Radek
authors: R
authors: Pohl
authors: Eva
authors: E
authors: Zborníková
authors: Milan
authors: M
authors: Kolář
authors: Kateřina
authors: K
authors: Bogdanová
authors: Otakar
authors: O
authors: Nyč
authors: Hana
authors: H
authors: Sanderová
authors: Tomáš
authors: T
authors: Látal
authors: Petr
authors: P
authors: Bartůněk
authors: Libor
authors: L
authors: Krásný
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D017209:Apoptosis / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D002478:Cells, Cultured; D024901:Drug Resistance, Multiple, Bacterial; D015672:Erythroid Precursor Cells / Q000166:cytology / Q000187:drug effects; D005312:Fetal Blood; D006094:Gram-Positive Bacteria / Q000187:drug effects; D006801:Humans; D057927:Hydrophobic and Hydrophilic Interactions; D008826:Microbial Sensitivity Tests; D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D063065:Organophosphonates / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D009705:Nucleosides; D063065:Organophosphonates