title: Long-chain alkanoylcholines, a new category of soft antimicrobial agents that are enzymatically degradable.
abstract: A new category of amphiphilic hydrolyzable quaternary ammonium compounds with rapid and high levels of antimicrobial activity was studied. The compounds, alkanoylcholines with hydrocarbon chains of 10 to 14 carbon atoms, are hydrolyzed by butyrylcholine esterase, which is present in human serum and mucosal membranes. The hydrolysis products are common components of human metabolism. Alkanoylcholines were tested and found to be active against gram-negative and gram-positive bacteria as well as yeasts. The microbicidal activities of the alkanoylcholines were comparable to the activities of the stable quaternary ammonium compounds of corresponding chain length and increased with an increasing number of carbon atoms. The compounds were also found to be hydrolyzed by enzymes present in certain microorganisms. The degradation was achieved after reaching the microbicidal effect.
authors.affiliation: Department of Clinical Bacteriology, Göteborg University, Sweden.
authors.forename: B
authors.initials: B
authors.lastname: Ahlström
authors.forename: M
authors.initials: M
authors.lastname: Chelminska-Bertilsson
authors.forename: R A
authors.initials: RA
authors.lastname: Thompson
authors.forename: L
authors.initials: L
authors.lastname: Edebo
mesh_terms: D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents / Q000737:chemistry / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D002091:Butyrylcholinesterase / Q000494:pharmacology; D002794:Choline / Q000031:analogs & derivatives*; D006868:Hydrolysis / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D013329:Structure-Activity Relationship; D015003:Yeasts / Q000187:drug effects
chemical_list: D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D002091:Butyrylcholinesterase; D002794:Choline