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At least 667 records · Page 37Linked to original sources
PubMed1989

[Effectiveness of new quarternary ammonium chloride compounds against selected bacteria and fungi. XXI. Synthesis of alkoxymethyl-3,4-dimethyl- pyridine and 1-ethyloxymethyl-3-alkylthiomethylimidazole chlorides].

Syntheses and antibacterial properties of alkoxymethyl-3,4-dimethylpyridinium chlorides and 1-ethyloxymethyl-3-alkylthiomethylimidazolium chlorides are described. Alkoxymetgyl-3,4-dimethylpyridinium chlorides were synthetized by reacting 3,4-dimethylpyridine with chloromethyl alkyl ethers, while 1-ethyloxymethyl-3-alkylthiomethylimidazolium chlorides were obtained in reactions of 1-ethyloxymethylimidazol with chloromethyl alkyl sulfides. Antibacterial properties of the obtained compounds were tested on 13 strains of bacteria and fungi. Strong bacteriostatic activity was found to be displayed by iminium chlorides with octyloxymethyl, decyloxymethyl, octylthiomethyl and decylthiomethyl groups.

Anti-Bacterial Agents↗
PubMed1986

Effect of lipophilic cations on thiamine transport system in isolated rat hepatocytes.

The effect of lipophilic cations such as triphenylmethylphosphonium, tetraphenylphosphonium and tetraphenylarsonium in addition to dibenzyldimethylammonium on thiamine transport in isolated rat hepatocytes was studied. Lipophilic cations at the concentration 10 microM almost completely inhibited thiamine uptake. Kinetic studies showed that these compounds were competitive inhibitors with a very high affinity. These results suggest that lipophilic cations in addition to quaternary ammonium compounds also share a common binding site for thiamine in isolated rat hepatocytes.

Animals↗
PubMed1997

Submicellar complexes may initiate the fungicidal effects of cationic amphiphilic compounds on Candida albicans.

The killing of Candida albicans by a series of amphiphilic quaternary ammonium compounds (QACs) with different hydrocarbon chain lengths was closely related to the binding of the compounds to the cells and damage of the cell membranes. The membrane damage was measured as the level of release of the UV-absorbing material into the medium in which the cells were suspended and as the level of uptake of propidium iodide in individual cells by flow cytometry. It was shown that of the compounds tested, hexadecyltrimethylammonium bromide (cetyltrimethylammonium bromide [CTAB]) bound most efficiently. Tetradecyl betainate chloride (B14), tetradecanoylcholine bromide (C14), tetradecyltrimethylammonium bromide (TTAB), and dodecyltrimethylammonium bromide (DTAB) followed and had declining degrees of binding efficiency. The proportion of CTAB bound was almost total at concentrations up to the critical micelle concentration (CMC) of the compound, whereas that of B14 was somewhat smaller. For the two remaining tetradecyl compounds (C14 and TTAB), still smaller proportions were bound at low concentrations, but the proportions rose disproportionally at increasing concentrations to a distinct maximum at concentrations of 0.2 to 0.5 times the CMC. We propose that interfacial micelle-like aggregates are formed at the cell surface as a step in the binding process. An analogous, but less conspicuous, maximum was seen for DTAB. Thus, great differences in the binding affinity of QACs with different hydrocarbon chains at different concentrations to C. albicans were observed. These differences were related to the CMC of the compound. In contrast, the binding of TTAB to Salmonella typhimurium 395 MS was almost total at low as well as high concentrations until saturation was attained, indicating fundamental differences between binding to the yeast and binding to gram-negative bacteria. The importance of lipid-type complexes or aggregates to the antifungal effect of membrane-active substances are discussed.

Antifungal Agents↗