title: Quaternary Alkylammonium Conjugates of Steroids: Synthesis, Molecular Structure, and Biological Studies.
abstract: The methods of synthesis as well as physical, spectroscopic (¹H-NMR, 13C-NMR, and FT-IR, ESI-MS), and biological properties of quaternary and dimeric quaternary alkylammonium conjugates of steroids are presented. The results were contrasted with theoretical calculations (PM5 methods) and potential pharmacological properties (PASS). Alkylammonium sterols exhibit a broad spectrum of antimicrobial activity comparable to squalamine.
authors.affiliation: Laboratory of Microbiocides Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Umultowska 89b, 61-614 Poznań, Poland. brycki@amu.edu.pl.
authors.forename: Bogumił
authors.initials: B
authors.lastname: Brycki
authors.affiliation: Laboratory of Microbiocides Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Umultowska 89b, 61-614 Poznań, Poland. koenig@amu.edu.pl.
authors.forename: Hanna
authors.initials: H
authors.lastname: Koenig
authors.affiliation: Laboratory of Microbiocides Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Umultowska 89b, 61-614 Poznań, Poland. tposp@amu.edu.pl.
authors.forename: Tomasz
authors.initials: T
authors.lastname: Pospieszny
mesh_terms: D000818:Animals; D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000494:pharmacology; D001647:Bile Acids and Salts / Q000138:chemical synthesis / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D017550:Spectroscopy, Fourier Transform Infrared; D013256:Steroids / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D000890:Anti-Infective Agents; D001647:Bile Acids and Salts; D000644:Quaternary Ammonium Compounds; D013256:Steroids
keywords: PM5 calculations; bile acids; conjugates; prediction of activity spectra for substances (PASS); quaternary alkylammonium salt; squalamine; sterols