Syntheses and antimicrobial activities of a series of new bis-quaternary ammonium compounds.
A series of new bis-quaternary ammonium compounds (bis-QACs), 4,4'-(2,9-dioxadecane) bis(1-alkylpyridinium bromide)s, 3,3'-(2,9-dioxadecane)bis(1-alkylpyridinium bromide)s and 3,3'-(2,7-dioxaoctane)bis(1-decylpyridinium bromide) was synthesized. The compounds were evaluated by their activities against bacteria, molds and yeasts; the activities were expressed as the minimum inhibitory concentrations (MIC) and/or the minimum bactericidal concentrations (MBC). Compound 4,4'-(2,9-dioxadecane) bis(1-decylpyridinium bromide) had MIC values which exceeded those of benzalkoniumchloride and thiabendazole. It was in vitro active against a broad spectrum of Gram-negative and Gram-positive bacteria, against yeasts and some molds, it had high solubility and thermal decomposition temperature. The relationships between structure and biological activity of the tested bis-QACs are discussed.
Kourai
Hiroki
H
Department of Biological Science and Technology, Faculty of Engineering, The University of Tokushima, Japan. kourai3@bio.tokushima-u.ac.jp
Yabuhara
Tadao
T
Shirai
Akihiro
A
Maeda
Takuya
T
Nagamune
Hideki
H
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D005658:Fungi / Q000187:drug effects; D006461:Hemolysis / Q000187:drug effects; D006801:Humans; D006863:Hydrogen-Ion Concentration; D066298:In Vitro Techniques; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D000644:Quaternary Ammonium Compounds / Q000138:chemical synthesis* / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D013696:Temperature
D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D007202:Indicators and Reagents; D000644:Quaternary Ammonium Compounds