Relationship between uptake of p-hydroxybenzoic acid esters by Escherichia coli and antibacterial activity.
The relationship between the uptake and antimicrobial activity of p-hydroxybenzoic acid esters (parabens) was studied using Escherichia coli. The uptake into bacterial cells and the antibacterial activity of parabens were logarithmically proportional to the carbon number of the alkyl group from methyl to butyl paraben. The free energy change for the transfer of the methylene group of parabens from the aqueous to the cell phase was less than that obtained from the n-hexane and n-octanol-water partition systems. This demonstrates that the hydrophilicity of the cells is larger than n-hexane and n-octanol. The uptake of hydrophobic ethyl benzoate was less than that of the more hydrophilic butyl paraben possessing a phenolic hydroxyl group. Parabens may thus be incorporated into cells by both hydrophobic and hydrophilic interactions. The apparent concentration of parabens in the bacterial cells required to produce the same antibacterial activity decreased logarithmically with an increasing carbon number of the alkyl group. The dependence of the antibacterial activity of parabens on the alkyl chain length may thus be concluded to be due to the alkyl group, not only for uptake into bacterial cells but also for accumulation or concentration on biological receptors after incorporation into the cells.
Fukahori
M
M
Central Research Laboratories, Zeria Pharmaceutical Co., Ltd., Saitama, Japan.
Akatsu
S
S
Sato
H
H
Yotsuyanagi
T
T
D002473:Cell Wall / Q000378:metabolism; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D015169:Colony Count, Microbial; D003593:Cytoplasm / Q000378:metabolism; D004926:Escherichia coli / Q000187:drug effects* / Q000378:metabolism* / Q000648:ultrastructure; D007700:Kinetics; D008826:Microbial Sensitivity Tests; D010226:Parabens / Q000378:metabolism* / Q000494:pharmacology*; D011310:Preservatives, Pharmaceutical / Q000378:metabolism* / Q000494:pharmacology*
D010226:Parabens; D011310:Preservatives, Pharmaceutical