Metabolism of quaternary ammonium compounds. II. Microautoradiographic studies on the effect of CCl4 on the intralobular distribution of tritiated BTTB in mice liver.
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Animals↗
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[Molecular rigidity of ammonium compounds as a necessary condition for selective action on skeletal muscle cholinoreceptors].
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Animals↗
Neuromuscular blocking activities of some steroidal mono and bis-quaternary ammonium compounds with special reference to NN'-dimethylconessine.
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Action Potentials↗
[The effect of quaternary ammonium compounds on the hydrolysis of various substrates that is catalyzed by specific and nonspecific cholinesterases].
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Acetylcholine↗
Metabolism of quaternary ammonium compounds. I. Binding of tropane alkaloids to rat liver lysosomes.
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Acid Phosphatase↗
Biliary excretion of some penicillins, quaternary ammonium compounds and tertiary amines, including aspects on mechanisms for their excretion.
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Acetates↗
[Kinetics of the ammonium compound inhibition of the hydrolysis of various substrates by cholinesterase from the visual ganglia of the squid].
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Acetylcholine↗
Different modes of blockade by p-phenylene-polymethylene bis-ammonium compounds of the nicotinic acetylcholine receptor channel in skeletal muscle cells of mice.
The structure-activity relationships of five newly synthesized p-phenylene-polymethylene bis-ammonium (PMBA: C6H4[(CH2)nN+R3]2) compounds were investigated on the blockade of the nicotinic acetylcholine receptor (nAChR) channel. The cell-attached patch clamp configuration was used to measure single-channel currents in the endplate region of single flexor digitorum brevis muscle cells of adult mice. The bis-trimethylammonium compounds PMBA-1 (n = 4, R = CH3) and PMBA-23 (n = 6, R = CH3) produced channel opening above 0.3 microM and open channel blockade above 10 and 3 microM, respectively. The bis-triethylammonium compounds PMBA-43 (n = 1, R = CH2CH3) and PMBA-24 (n = 6, R = CH2CH3) showed no channel opening action, but PMBA-21 (n = 4, R = CH2CH3) opened channels weakly at 3 and 10 microM. These bis-triethylammonium compounds exerted different blocking actions on acetylcholine-activated channel currents. Above 10 microM PMBA-43, like tetraethylammonium, blocked open channels by decreasing the mean open time by rapid partial closing of the channel during the open-phase. At 10 microM, PMBA-21 blocked open and closed channels by decreasing the opening frequency by means of an irregular sequence of short pulses. At 0.3 microM, PMBA-24 blocked closed or nonconducting channels by decreasing the opening frequency without producing changes in mean open time. These results indicate that by lengthening the distance between two nitrogen atoms in the bis-triethylammonium group of PMBA, open channel blockade changes to closed channel blockade.(ABSTRACT TRUNCATED AT 250 WORDS)
Animals↗
Site of action of certain antibacterial heterocyclic quaternary ammonium compounds.
The site of action of related mono- and bis-quinaldinium compounds was investigated in Staphylococcus aureus and Bacillus megaterium. The effects of these compounds on cell morphology and on protoplast formation and fragility were studied, and the distribution of C(14)-labeled quinaldinium compound in cell fractions was measured. The latter studies showed that a major part of the quaternary compound penetrates the cell, leaving a very small quantity associated with the cell wall. Similar antibacterial effects were seen with both the mono- and bis-quinaldinium compounds studied, and these effects were comparable with antibacterial properties of known cationic surface-active antibacterial agents.
Anti-Bacterial Agents↗
New quaternary ammonium compounds with adrenomimetic action.
Quaternary salts of two triesters of p-dimethylaminothiophenol and phosphoric acid or thiophosphoric acid have effects similar to epinephrine on blood pressure, heart rate, and the nictitating membrane of the anesthetized cat. Two analogous compounds derived from phenol are depressor. None is a potent anticholinesterase. Further investigation is desirable because of the possibility of a relatively specific action on sympathetic ganglia.
Adrenergic Agonists↗
[The optimization of the availability of homologous quaternary ammonium compounds. 2. In vitro studies on the partition of homologous benzilic acid esters of dimethyl-(2-hydroxyethyl)-alkylammonium bromides].
The partition of homologous quaternary esters of benzilic acid is studied in a modified three-phase model according to Schulmann (water-n-octanol-water). The logarithms of the partition coefficients of the compounds increase linearly with increasing alkyl chain. The rate determining step for the interphase transport of hydrophilic compound is the diffusion through the organic diffusion layer. The rate constants for the transfer from the aqueous to the organic phase increase linearly with the corresponding partition coefficient, whereas the rate constants for the reverse reaction are not influenced. With increasing chain length the diffusion through the aqueous diffusion layer becomes rate determining for the interphase transport. Thus the rate constants for the transfer from the aqueous to the organic phase are independent of partition coefficients. The rate constants for the reverse transfer are inversely proportional to the corresponding partition coefficients. The half-lives of the transfer of the homologous compounds under sink conditions show a minimum between the heptyl and octyl derivative. The equilibration time decreases with increasing agitation, concentration and temperature. The significance of the results for biological problems is discussed.
Benzilates↗
[Role of the hydrophobicity of monoquaternary ammonium compounds in the mechanism of their curariform action].
The lengthening of the alkyl radical at the quaternary nitrogen atom (from -C2H5 to -C20H41) in the series of alkyltrimethylammonium compounds was found to lead to a gradually growing hydrophobicity of the compound. A change in the mechanism responsible for the myoparalytic action of the compound is due to a mounting degree of hydrophobicity. With the methyl group in the molecule of tetramethylammonium replaced with polyalicyclic radicals (bornyl, adamantyl) the compound, acting after a non-depolarizing type, possess a greater degree of hyrophobicity than do substances of the depolarizing type.
Alkylation↗
[Antibacterial activity of disinfectant solutions containing quaternary ammonium compounds for the storage of surgical instruments].
A survey conducted among the health managements and dispensary services of all Italian hospitals showed that disinfectants containing quaternary ammonium salts were most commonly used for the disinfection and storage of surgical instruments (66% of frequencies). It was therefore decided to run in vitro tests on the bactericidal activity of some of the more frequently used substances containing one or more of these salts as their active principle. Five were therefore examined against 8 hospital and 4 lab strains, namely three aqueous solution: 1% benzalkonium chloride plus 1% ethylbenzalkonium chloride; 0.6% alkyldimethylbenzylammonium chloride, plus 0.185% diisobutylphenoxyethoxyethylbenzyl ammonium chloride monohdydrate and 0.133% diisobutylcresoxyethoxydimethylbenzyl ammonium chloride monohydrate; 0.1% dodecylbenzylammonium-N-diethyl alcohol chloride; and two alcoholic solutions: 0.1% alkyldimethylbenzylammonium chloride; 0.25% benzalkonium chloride (F.U.).
Bacteria↗
Effect of chain length on critical micelle formation and protein binding of quaternary ammonium compounds.
The micelle formation tendency (log 1/CMC)) of a series of alkyldimethylbenzylammonium compounds is shown to be linearly dependent on the alky chain length, indicating no curling of the side chain up to C19. Protein binding of these charged molecules on the primary binding site for sulfaethiodole is shown to be parabolically dependent on the chain length with an optimal chain length around C16.
Binding Sites↗
HPLC analysis of commercial alkyl and aryl quaternary ammonium compounds used in organoclay type rheological additives.
Mixtures of aliphatic and aromatic "quats" can be qualitatively identified in a one step chromatographic run. After separation on a strong cation exchange column, the eluted components are detected using a UV and RI detector system in series. The quaternaries present in organoclays (e.g., BENTONE type products) can also be identified by prior destruction of the silicate with hydrofluoric acid followed by chromatography of the residual quat fluorides.
Aluminum Silicates↗
[Sensitivity of the cholinoreceptive membrane of Lymnaea stagnalis neurons to mono- and bisquaternary ammonium compounds].
The depolarizing potency of polymethylene-bis-trimethylammonium and alkyl-trimenthylammonium compounds with 3-10 methylene groups was studied on the identified giant central neurons of gastropod mollusc Limnaea stagnalis using intracellular microelectrode technique. The bisquaternary salts with 4-7 methylene groups were inactive while the mononitrogen analogues showed cholinomimetic activity. The similar results were obtained by other authors on Vertebrate skeletal muscles with substances studied. The possible explanations of this fact are suggested.
Animals↗
[Studies on the absorption of benzilic acid esters of homologous dimethyl-(2-hydroxyethyl)-alkylammonium bromides through buccal mucosa. 5th communication: On optimum bioavailability of homologous quaternary ammonium compounds (author's transl)].
Distribution studies in vitro predict increasing absorption rates in vivo with increasing distribution coefficients up to a limiting value. Buccal absorption tests with homologous, quaternary cholinesterbromides of benzilic acid do not confirm this hypothesis. The reasons could be the rather hydrophilic properties of the mucosal membranes and thus adsorption of drug to the mucosa. The evaluation of results with undissociated homologous carboxylic acids, however, shows a good correlation between the prediction from in vitro studies and the buccal absorption test.
Absorption↗
Quaternary ammonium compounds efficiently inhibit Plasmodium falciparum growth in vitro by impairment of choline transport.
Hemicholinium 3, decamethonium, and decyltrimethylammonium previously have been demonstrated to be efficient inhibitors, with 50% inhibitory concentrations of 4 X 10(-6), 10(-6), and 7 X 10(-7) M, respectively. We show that lengthening of the alkyl chain of decyltrimethylammonium by successive additions of two carbon atoms up to hexadecyltrimethylammonium results in a very low 50% inhibitory concentration of 5 X 10(-7) M for dodecyltrimethylammonium. Furthermore, hemicholinium 3 and decamethonium exerted their antiplasmodial activity, regardless of the developmental stage of the parasite, whereas decyltrimethylammonium was particularly lethal for the mature forms. After infected erythrocytes with radioactive choline were supplied, the determination of the water-soluble choline-containing compounds, as well as the assay of choline kinase activity, showed that the specific inhibition of phosphatidylcholine biosynthesis is related to the impairment of choline entry into erythrocytes. Thus, the impairment of the transport of choline, a natural polar head group of phospholipids, appears to be lethal for Plasmodium falciparum in vitro and could be a reasonable approach for a new malaria chemotherapy.
Animals↗