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[The effect of affinity on the type of action of ammonium compounds on skeletal muscle cholinoreceptors].

The dependence of the mode of action (agonist or antagonist) of ammonium compounds on the acetylcholine receptors (AcR) of frog skeletal muscles on their affinity for AcR was studied in experiments on musculus rectus abdominis of Rana temporaria frogs. The mode of action of the compounds proved to be dependent on the degree of the affinity and on the character of their intermolecular interactions with the receptors. The affinity of compounds of the polymethylene-bis-trimethylammonium series is determined by electrostatic and hydrophobic interaction with the AcR. In this case compounds with a low affinity constant (Ka) are poor antagonists, compounds with high Ka are strong antagonists, and compounds with intermediate Ka are partly agonists. Compounds whose affinity is determined not only by the electrostatic and hydrophobic but also by the dipole-dipole interaction (series D compounds) are pure and strong agonists.

Animals↗

Interaction of quaternary ammonium compounds with acetylcholinesterase: characterization of the active site.

The relation of the structure of 31 quaternary ammonium compounds (28 inhibitors; 3 substrate analogues) with their effects on the activity of acetylcholinesterase (EC 3.1.1.7; AChE) was studied. The compounds were structurally related to the natural substrate acetylcholine (ACh). All bear a trimethylammonium moiety as cationic head. The inhibitors include a variety of functional groups instead of an electrophilic ester group, making these substances suitable to probe the esteratic subsite. The inhibition constants and Km values were determined in kinetic experiments under steady state conditions (pH-stat method). Most of the substances acted as reversible, competitive inhibitors with KI in the range of 10(-6)-10(-3) M. The substrate analogues had Km values between (1.2-2.2) X 10(-4) M. The data allow the following main conclusions: (1) The quaternary trimethylammonium group of ACh is of high importance for substrate binding to AChE. It mediates association at the anionic site. (2) A poorer contribution to binding (two orders of magnitude lower) is attributable to the apolar methylene chain in ACh. It can be related to a hydrophobic interaction of the hydrocarbon chain at a region neighbouring the anionic site. (3) The ester group (both C = O and O) does not contribute to substrate binding. It is only responsible for reactivity.

Acetylcholinesterase↗

Isolation and determination of quaternary ammonium compounds by means of amberlite XAD-columns and thin layer chromatography.

The potentials of XAD-columns for the isolation of quaternary ammonium compounds from aqueous media have been investigated. When adequate amounts of counter ions (perchlorate, chloride, phosphate, nitrate) were added to the aqueous sample, to the column pretreatment fluid and to the aqueous washing fluid, most quaternary compounds investigated were retained on the column and could be recovered by elution with methanol. This approach proved also suitable for urine. Quantitation of quaternaries isolated in this way from urine samples could be performed on silicagel thin layer plates through visualization with iodine, followed by densitometric evaluation. For decamethonium detection limits were 0.1 micrograms/ml. Recoveries at the 1 micrograms/ml level were between 80--90% with variation coefficients of less than 10%.

Chromatography, Ion Exchange↗

Involvement of sialic acid in high-affinity binding of quaternary ammonium compounds by brush border membrane from rat intestine.

As one approach to clarify the absorption mechanisms of quaternary ammonium compounds (QACs), their binding characteristics have been studied using brush border membrane vesicles isolated from rat small intestine and liposomes composed of phospholipid and GM3 ganglioside. The binding of propantheline was significantly decreased when the vesicles were pretreated with neuraminidase. Propantheline and methochlorpromazine bound to the liposomes, the binding for the latter drug being significantly greater than that for propantheline. When GM3, isolated from rat small intestine, was incorporated into the liposomes their binding capacity for both drugs increased significantly. It is suggested that the binding of QACs to the lipid layer and sialic acid play a role in the high binding of drugs to the intestinal brush border membrane. Furthermore, a sensitive and reproducible high-performance liquid chromatographic method for sialic acid has been developed.

Animals↗

Synergistic effect of heartwood extractives and quaternary ammonium compounds on termite resistance of treated wood.

This study evaluates the synergistic effect of wood extractives and quaternary ammonium compounds (QACs) on the resistance to termites of several treated wood species. Wood specimens from different natural durability classes were extracted with either hot water alone or hot water + ethanol/benzene. The extracted and unextracted wood specimens were treated with either didecyldimethylammonium tetrafluoroborate (DBF) or commercial didecyldimethylammonium chloride (DDAC) solutions and then exposed to subterranean termites, Coptotermes formosanus Shiraki, for 3 weeks under laboratory conditions. The results showed that extractives of the heartwood portions of the wood species contributed to increased resistance against termite attack in the presence of either DBF or DDAC wood preservatives. The synergistic effect of wood extractives and DBF was much clearer with Pseudotsuga menziesii (Mirbel) Franco and Tsuga heterophylla Sarg wood samples. Further studies are needed for a better understanding of the synergism between wood extractives and either DBF or DDAC using both the sapwood and heartwood portions of the same wood species.

Animals↗

Correlation between resistance of Pseudomonas aeruginosa to quaternary ammonium compounds and expression of outer membrane protein OprR.

The adaptation mechanism of Pseudomonas aeruginosa ATCC 10145 to quaternary ammonium compounds (QACs) was investigated. A P. aeruginosa strain with adapted resistance to QACs was developed by a standard broth dilution method. It was revealed that P. aeruginosa exhibited remarkable resistance to N-dodecylpyridinium iodide (P-12), whose structure is similar to that of a common disinfectant, cetylpyridinium chloride. Adapted resistance to benzalkonium chloride (BAC), which is commonly used as a disinfectant, was also observed in P. aeruginosa. Moreover, the P-12-resistant strain exhibited cross-resistance to BAC. Analysis of the outer membrane protein of the P-12-resistant strain by two-dimensional polyacrylamide gel electrophoresis showed a significant increase in the level of expression of a protein (named OprR) whose molecular mass was approximately 26 kDa. The actual function of OprR is not yet clear; however, OprR was expected to be an outer membrane-associated protein with homology to lipoproteins of other bacterial species, according to a search of the National Center for Biotechnology Information website with the BLAST program by use of the N-terminal sequence of OprR. A correlation between the level of expression of OprR and the level of resistance of P. aeruginosa to QACs was observed by using a PA2800 gene knockout mutant derived from the P-12-resistant strain. The knockout mutant recovered susceptibility not only to P-12 but also to BAC. These results suggested that OprR significantly participated in the adaptation of P. aeruginosa to QACs, such as P-12 and BAC.

Adaptation, Physiological↗

Conformation and biological activity of hydroxy-phenyl-ammonium compounds.

Ab initio (STO-3G) and semiempirical (NDDO) quantum chemical methods were applied to some hydroxy-phenyl-ammonium compounds to investigate their conformational structure. It is demonstrated that the theoretical conformational analysis in combination with experimentally measured activity data of a small number of compounds may serve as a useful tool to optimize the biological active conformation, which does not correspond to the blobal minimum conformation in this group of molecules.

Chemical Phenomena↗

Gastrointestinal absorption of quaternary ammonium compounds correlated to their binding to small intestinal brush border membrane in rat.

The relationship between absorption of quaternary ammonium compounds (QACs) from rat intestine and their in-vitro binding to isolated brush-border membrane has been examined, using a series of n-alkyltrimethylammoniums. The binding of these QACs gradually increased with each extension of unbranched hydrocarbon chain from octyltrimethylammonium to tetradecyltrimethylammonium. However, hexyltrimethylammonium and heptyltrimethylammonium failed to bind to the membrane. On the other hand, the disappearance of these QACs from rat jejunal loop also increased with the length of hydrocarbon chain over the range of 8.9 to 71.3%. A good correlation was found between binding to the brush-border membrane and disappearance from jejunal loop. From these results, it was suggested that the size of the hydrophobic part of a QAC molecule was a principal determinant of both absorption and membrane binding, and that the absorption of QACs with an appropriate sized hydrophobic part, was closely associated with the degree of binding to the membrane.

Animals↗