Relation between structure and antimicrobial activity of 2-(N,N,N-trialkylammonio)alkyl hydrogen phosphates.
A series of phosphobetaines [2-(N,N,N-trialkylammonio)alkyl hydrogen phosphates], having different alkyl chains and a methylene bridge separating the phosphate and ammonio group, was investigated in order to provide a new antimicrobial agent. Maximal activity was obtained with the compound having a hexadecyl group as a long-chained alkyl group, two methyl groups as short-chained alkyl groups, and a dimethylene bridge as an intercharge distance. In contrast, sodium 2-(N-hexadecyl-N-methylamino)ethyl hydrogen phosphate, 2-(N-hexadecyl-N,N-dimethylammonio)-1-hydroxyethyl iodide, and N-octadecyl-N,N-dimethylammonio acetate showed decreased activity, indicating that the presence of a phosphobetaine moiety was essential for activity. Thus, 2-(N-hexadecyl-N,N-dimethylammonio)ethyl hydrogen phosphate has been found to possess strong antimicrobial activity and a broad antimicrobial spectrum against nine kinds of bacteria (e.g., fungi, yeast, gram-negative and gram-positive bacteria), which are comparable with those of chlorhexidine digluconate.
Tsubone
K
K
Kanebo, Ltd., Cosmetics Laboratory, Kanagawa, Japan.
Uchida
N
N
Ito
Y
Y
D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents / Q000737:chemistry* / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D001622:Betaine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D005658:Fungi / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D009943:Organophosphorus Compounds / Q000737:chemistry* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D015003:Yeasts / Q000187:drug effects
D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D009943:Organophosphorus Compounds; D001622:Betaine