The Antibacterial Action of Surface Active Cations

Abstract

The antibacterial action of surface-active cations was reported by Hartmann and Kiigi (1928) on the basis of observations made by Doerr. Domagk (1935) gave a detailed description of the bacteriological properties of a very potent member of this group. Notwithstanding the considerable attention which these discoveries aroused, as shown by the number of investigations reported in the literature, apparently no attempt has been made to relate the antibacterial action of surface-active cations to that of other types of toxic cations.The observations on the reversibility of the antibacterial effect of the surfaceactive cations, and on the protective action on bacteria exerted by relatively harmless cations against the action of toxic cations, which are described in this paper, indicate that there is a close relationship between the antibacterial behavior of metallic and dye cations and that of surface-active cations. It appears that the basis for the antibacterial action of all these cations can be satisfactorily described in terms of a cationic exchange by the bacteria. It is not claimed that this concept explains the ultimate mechanism of the antibacterial action, but nevertheless it probably is a necessary step in this direction and makes possible the elimination of other proposals which have been put forward.The most striking example of the reversibility of the antibacterial action has been presented by Engelhardt (1922), although the reversibility of the action of mercuric chloride on bacteria was already known (Geppert, 1889; Siupfle alnd Miiller, 1920). Engelhardt demonstrated that Staphylococcus aureus remained viable after a two-hour exposure to 1 % mercuric chloride, when thereafter the poison was removed by washing. When hydrogen sulphide was used for detoxication, even the effects of a 72-hour exposure to 1 % mercuric chloride proved reversible. Similar results were obtained with anthrax spores.Simon and Wood (1914), adopted Ehrlich's conception of a combination between the antibacterial agent and some of the nutriceptors of the bacteria as the basis for the inhibiting action of basic dyes and assumed the existence of acidic groups in the structure of the bacterial organism with which the ammonium groups of the inhibiting dyes would unite. The cell dies, according to them, because a sufficient number of its nutriceptors have been thrown out of actioln, bringing about its starvation or inability to multiply.

Correlation between Antibacterial Power and Chemical Structure of Higher Alkyl Ammonium Ions

“…Just as in the case of the benzotriazolium derivatives (Valko and DuBois, 1944) with which, in agreement with Rawlins et al (1943), we could not reproduce Westphal's (1940a, 1940b) results,' here again we found that the di-n-octyl derivatives were not superior to the hexadecyl or dodecyl homologs, as Kuhn, Jerchel, and Westphal (1940) claim.…”

“…It is obvious that the determination of the average chemical composition is of no value in the control of these materials, and fractionation methods have to be used for their chemical control. At the same time, the results indicate that the determining factor in the antibacterial activity is not the average composition of a mixed micelle but the independent contribution of each single component, except in the special cases where competitive effects (Valko and DuBois, 1944) come into play. Our results, as presented in tables 3 to 10, clearly demonstrate that maximum antibacterial potency is not reached with the same chain length of the high molecular aliphatic chain in various homologous series.…”

Mixtures of Quaternary Ammonium Compounds and Long-chain Fatty Acids as Antifungal Agents

“…Frequent references are found in the literature emphasizing the synergistic or antagonistic effect of a particular substance upon the biological activity of other, chemically unrelated compounds. In the case of the germicides, it has been shown by Domagk (1935), Baker, Harrison, and Miller (1941), Valko and DuBois (1944), and many others that cationic and anionic detergents will neutralize each other. Such reversal of the activity of quaternary ammonium compounds have been demonstrated with soaps, sodium taurochoate, sodium lauryl sulfate, suramin sodium and many other anionic agents.…”

Determination of Benzalkonium Chloride by Chemical Ionization Mass Spectroscopy

“…I C6H5CH2-N-R C1-L AH3 J I activity of the mixture (1)(2)(3). The current methods of identification of benzalkonium chloride solutions according to the USP (4), rely upon titrimetric analysis of total alkyl benzyldimethylammonium chloride based upon potassium iodate equivalents.…”