In a homologous series of N-(n-alky1)diethanolamines antimicrobial activity was related to surface activity and increasing octanol-water partition coefficient. Maximum activity was exhibited by the dodecyl-, tetradecyl-and hexadecyl-derivatives. Dodecyldiethanolamine (DDE) displayed a broad spectrum of activity. Towards Escherichiu coli NCIB8277, its bacteriostatic and bactericidal activity increased as the degree of protonation lessened, and may have been influenced by the formation of micelles. Uptake of DDE by washed suspensions of E. coli was more rapid and more extensive at pH 7.0 than pH 4.0. Within this pH range, bacterial uptake, the octanol-water partition coefficient (lipid solubility) and the proportion of unprotonated DDE all increased. Uptake isotherms at pH values in the range 4.0 to 8.0 are interpreted as signifying different uptake mechanisms for the protonated and unprotonated forms.
I N T R O D U C T I O NN-(n-dodecy1)diethanolamine (DDE) is bacteriostatic and bactericidal towards Escherichia coli. We have previously shown (Lambert & Smith, 1976) that at pH 7.0 DDE was taken up by whole cells in less than 3 min, resulting in the rapid leakage of potassium ions and the cessation of glucose oxidation. Sphaeroplast suspensions in isotonic media were destabilized. Nucleotide leakage from whole cells was biphasic, corresponding to an initial loss of low molecular weight pool metabolites (within 10 min) followed by slower efflux of rRNA breakdown products (extending over 3 h) due to the drug-induced activation of latent RNAase I activity (Lambert & Smith, 1977).These observations support the conclusion that DDE is a membrane-active (Hamilton, 1971) antimicrobial agent. In the present paper we compare the antimicrobial activity of homologous N-(n-alky1)diethanolamines and describe the effect of pH on the activity and uptake of DDE. A preliminary report of this investigation has appeared (Lambert & Smith, 1974). No other publications have been found that refer to the antimicrobial activity of the alkyldiethanolamines, although Persianov et al.
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