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At least 721 records · Page 40Linked to original sources
PubMed1978

Functional group contribution of bile salt molecules to partitioning of a quaternary ammonium N,N-dimethyl derivative of propranolol.

A quaternary ammonium N,N-dimethyl derivative of propranolol was extracted from pH 7.4 phosphate buffer into 1-octanol as ion-pairs with 12 different bile salts. The binding number, n, and the extraction constant, Ke, were determined. To obtain group contribution values of the bile salt molecule from the ion-pair extraction data, multiple linear regression analysis by the Free-Wilson technique was applied. The results showed that the fundamental premise of the functional group's contribution to the ion-pair extraction is valid. The functional groups of counterions contribute to the partitioning of the ammonium compound independently and additively in this system.

Bile Acids and Salts↗
PubMed1979

[Gentamycin activity in combination with etonium in relation to Pseudomonas aeruginosa].

Gentamicin is one of the most effective drugs for treatment of infections caused by Ps. aeruginosa. However, isolation of the strains resistant to the antibiotics was not infrequent. It was shown in the experiments with 40 cultures that the activity of gentamicin against Ps. aeruginosa increased approximately 20 times when it was used in combination with ethonium, a derivative of bis-quaternary ammonium compounds.

Dose-Response Relationship, Drug↗
PubMed1992

The effects of surfactants on the permeability of isolated perfused fish gills to urea.

1. The diffusional transfer capacity of [14C]urea in isolated perfused trout (Oncorhynchus mykiss) gills in the presence of sodium n-dodecylsulphate (SDS), n-dodecyltrimethylammonium bromide (DTAB) and p-t-octylbenzene oxyethylene10 (Triton X-100) has been measured over a range of surfactant concentrations. 2. Urea has been shown to be transported transcellularly through the respiratory cells of the gill secondary lamellae by passive diffusion. Each surfactant was found to markedly increase the rate of diffusion and the diffusional transfer capacity reached a steady-state at a particular surfactant concentration. 3. The steady state flux was increased by surfactant in the sequence DTAB greater than SDS greater than Triton X-100 and the surfactant concentrations in terms of the critical micelle concentration (CMC) at which the diffusional transfer capacities reached limiting values were 0.92 x CMC (SDS), 0.53 x CMC (DTAB) and 2.5 x CMC (Triton X-100). 4. Compared to interactions between isolated epithelial cells and the surfactants, the rates at which the surfactants changed the urea flux were slow, suggesting that the mucus layer plays a significant role in protecting the epithelial cells of the secondary lamellae from disruption. 5. Relative to the other surfactants, DTAB had the most marked effect on both the rate of flux change and on the magnitude of the change, at concentrations which are low relative to the CMC, suggesting a more specific interaction with the negatively charged mucus layer consistent with the toxic effects of quaternary ammonium compounds on aquatic organisms.

Animals↗
PubMed1979

Synthesis and evaluation of benzylfluorenyl and 1-arylethyl quaternary ammonium salts for antimicrobial and antineoplastic activities.

A number of substituted benzyldimethyl-9-fluorenylammonium bromides (II) and 9-benzylfluorenyl-9-trimethylammonium bromides (IV) were synthesized and examined for antimicrobial and anticancer activites. Series IV showed greater antimicrobial activity than Series II while some corresponding acyclic fluorene analogs were bereft of antimicrobial activities. Significant antineoplastic activity was not found in Series II and IIV. Representative fluorenes subjected to a preliminary screen for various pharmacological activities revealed marked anti-inflammatory and analgesic properties coupled with some antihistaminic activities. The acyclic quaternary ammonium compounds demonstrated substantial pressor activites.

Animals↗
PubMed1996

Architecture of the neuronal nicotinic acetylcholine receptor ion channel at the binding site of bis-ammonium blockers.

Structure-activity relationships of 56 pentamethylenbis-ammonium compounds, the blockers of the neuronal nicotinic acetylcholine receptor (nAChR) ion channel, have been studied to estimate the cross-sectional dimensions of the channel pore. The cat superior cervical sympathetic ganglion in situ and isolated guinea pig ileum were used to evaluate the potency of the compounds to block ganglionic transmission. Minimum-energy conformations of each compound were calculated by the molecular mechanics method. A topographic model of the binding site of the blockers was proposed. It incorporates two narrowings, a large and a small one. The small narrowing is located between the large one and the cytoplasmic end of the pore. The cross-sectional dimensions of the large and small narrowings estimated from the dimensions of the blockers are 6.1 x 8.3 A and 5.5 x 6.4 A, respectively, the distance between the narrowings along the pore being approximately 7 A. Most potent blockers would occlude the pore via binding to the channel at the levels of both narrowings. Less potent blockers are either too large or too small to bind to both narrowings simultaneously: large blockers would occlude the pore at the level of large narrowing, while small blockers would pass the large narrowing and occlude the pore at the level of small narrowing only. A comparison of the topographic model with a molecular five-helix bundle model of nAChR pore predicts Serine and Threonine rings to be the most probable candidates for the large and small narrowings, respectively.

Amino Acid Sequence↗
PubMed1976

The antagonism of nicotine-induced cardiovascular responses by DMAE and DEO analogs.

A series of quaternary ammonium compounds cinsisting of 4, 4'-bis-[N-(2, 2-diethoxyethyl)-N, N-dimethylammonioacetyl]-biphenyl dibromide (DMAE) and 4, 4'-bis-[N, N-di(2-ethoxyethyl)-N-methylammonioacetyl]-biphenyl dibromide (DEO) analogs was investigated for selective nicotine antagonism. Each series of compounds contained the monophenyl (MPh.DMAE, MPh.DEO); biphenyl (DMAE, DEO); terphenyl (TPh,DMAE, TPh.DEO); half-molecule (1/2DMAE, 1/2DEO); p-phenyl half-molecule (p-Ph.-1/2DMAE, p-Ph.-1/2DEO) and biphenyl half-molecule (p-BPh.-1/2DMAE, p-BPh.-1/2DEO) analogs. Studies were conducted on isolated spontaneously beating guinea pig atria and anesthetized dogs. Relative potencies of the DMAE and DEO series to antagonize the nicotine (20 mug/ml) induced positive chronotropic effect of the guinea pig atria were determined as follows: DMAE (1.0); TPh.DMAE (0.82); P-Ph.1/2DMAE (0.59); DEO (0.54); MPh.DMAE (0.27); TPh.DEO (0.26); MPh.DEO (0.18); p-Ph.-1/2DEO (0.16); 1/2DMAE (0.03); 1/2DEO (0.02); p-BPh.-1/2DMAE (less than 0.01); p-BPh.-1/2DEO (less than 0.01) and C-6 (0.85). The I50 to antagonize nicotine induced responses by DMAE was 0.13 muM (0.10 mu/ml). Several of the above analogs were studied in the dog and their ability to antagonize nicotine (100 mug/kg) induced positive chronotropic effects were compared with their ability to inhibit transmission through the stellate or the superior cervical ganglia. The I50 doses of the drugs antagonizing nicotine, impairing superior cervical ganglionic transmission and the corresponding fold shifts in the dose--response curves follow: DMAE (120 mug/kg, 3.0 mg/kg, 25); TPh.DMAE (40 mug/kg, 1.10 mg/kg, 30), DEO (45 mug/kg, 1.30 mg/kg, 25) and C-6 (140 mug/kg, 0.42 mg/kg, 0.42 mg/kg, 3.0). These findings are suggestive of the hypothesis that receptors normally activated by endogenously released ACh in the stellate or superior cervical ganglia of the dog may be dissociated from those receptors activated by nicotine which results in an increase in blood pressure or heart rate. Clinical implications are that TPh.DMAE as well as other DMAE analogs may pose less of a problem with hypotension than hexamethonium as a nicotine antagonist.

Animals↗
PubMed1989

Interaction of potassium channel openers and blockers in canine atrial muscle.

1. The possibility that the interaction between potassium channel openers, e.g. cromakalim, pinacidil and nicorandil, and some potassium channel blockers involves a common site was investigated in canine atrial muscle. 2. Cromakalim, pinacidil and nicorandil produced a negative inotropic effect, their pD2 (-log EC50) values being 6.11 +/- 0.07, 5.37 +/- 0.09 and 4.55 +/- 0.07, respectively. 3. The potassium channel blockers, tetraethylammonium (TEA), tetrabutylammonium (TBA), 3,4-diaminopyridine (DAP), CsCl and BaCl2 all produced a positive inotropic effect. 4. The concentration-effect curves for the negative inotropic actions of pinacidil were shifted in a parallel way to the right by low concentrations of TEA, TBA or BaCl2. Maximum responses to pinacidil were depressed by higher concentrations of the blockers. An analysis of the non-competitive antagonism by TEA yielded pKA (-log KA) values of 4.00-4.05 for pinacidil. 5. The concentration-effect curves for cromakalim and nicorandil were shifted by TEA similarly to those for pinacidil, and a similar analysis yielded pKA values of 4.47-4.68 for cromakalim and 3.47-3.74 for nicorandil. 6. The KA values of cromakalim, pinacidil and nicorandil were about 10-30 times greater than their EC50 values, indicating that there are non-linear stimulus-effect relationships between the binding of the three potassium channel openers to their binding sites at potassium channels and their negative inotropic effects. 7. The dissociation constants for TEA could also be estimated from pA2 and pKB values for antagonizing competitively and non-competitively the negative inotropic effects of the three potassium channel openers; they were 3.47-3.89, and did not differ between the potassium channel openers. 8. The concentration-effect curves for the three potassium channel openers were not affected by DAP or CsCl. 9. These results suggest the following: (i) quaternary ammonium compounds like TEA and TBA antagonize the negative inotropic effect of cromakalim, pinacidil and nicorandil by binding to potassium channels, thus preventing binding of the channel openers to the same sites or closely related sites in canine right atrial muscles.

Animals↗
PubMed1986

Intestinal absorption of tetramethylammonium and its derivatives in rats.

The intestinal absorption of tetramethylammonium (TMA) and its derivatives from rat jejunum has been investigated with an in situ loop method and an in vitro everted sac method. At a low concentration, TMA was absorbed rapidly from the in situ intestinal lumen without being metabolized in the tissue and the rate of absorption was dependent upon the concentration used. The profile of TMA absorption included two processes, i.e. saturable and non-saturable. The absorption of TMA was inhibited competitively by analogs that have a N-trimethyl group in their structure. Among them, choline showed the strongest inhibition to TMA absorption. The inhibitory potency of these analogs was related to their chemical structure. Although TMA was not transported into the intracellular fluid of the everted intestine against a concentration gradient, the tissue accumulation of TMA was inhibited by 2,4-dinitrophenol (2,4-DNP), a metabolic inhibitor, and was highly dependent upon the incubation temperature. These findings demonstrate that TMA is absorbed through the rat small intestine by a carrier mediated transport system. An apparent Kt of 0.73 mM and a maximum V of 11.5 nmol/g tissue wet wt/min were determined by an in situ loop method. It was also suggested that the endogenous quaternary ammonium compound, choline, might be absorbed by the same carrier system.

2,4-Dinitrophenol↗
PubMed1998

[Effect of halogenated quaternary ammonium on cultured tumor cells].

This work reports the action of one halogenic quaternary ammonium compound on the in-vitro proliferation of different lines of human cancer cells. IC 50 inhibition growth was observed at a concentration of 2.10(-6) mol and T1 growth at 3.10(-6)-5.10(-5) mol. These results seem to indicate that halogenic quaternary ammoniums present a potent growth inhibitory activity on different cancer cells lines. The presence of a quaternary ammonium group, responsible for some alkylating effect, could explain such a result.

Cell Division↗
PubMed2005

Bridge-linked bis-quaternary ammonium anti-microbial agents: relationship between cytotoxicity and anti-bacterial activity of 5,5'-[2,2'-(tetramethylenedicarbonyldioxy)-diethyl]bis(3-alkyl-4-methylthiazonium iodide)s.

We examined the correlation between the anti-bacterial activity against Escherichia coli and the cytotoxicity of five synthesized bridge types of bis-quaternary ammonium compounds (bis-QACs) as follows: thioether type, 4,4'-(p-xylydithio)bis(1-octylpyridinium iodide) (4DTBP-X,8); amide type, N,N'-tetramethylenebis(1-dodecyl-4-carbamoylpyridinium iodide) (4BCAP-4,12), N,N'-(phenylene)bis(1-octyl-4-carbamoylpyridinium iodide) (4BCAP-P,8); anti-amide type, 4,4'-(tetramethylenedicarbonyldiamino)bis(1-octylpyridinium iodide) (4DCABP-4,8), 4,4'-(phenylenedicarbonyldiamino)bis(1-octylpyridinium iodide) (4DCABP-P,8); ester type, 4,4'-(1,6-hexamethylenedioxydicarbonyl)bis(1-dodecylpyridinium iodide) (4DOCBP-6,12); and an anti-ester type, 5,5'-[2,2'-(tetramethylenedicarbonyldioxy)diethyl]bis(3-alkyl-4-methylthiazolium iodide) (5DEBT-4,n, The letter n indicates the carbon number of the alkyl group). 5DEBT-4,8 showed low cytotoxicity (LD(50)) to human erythrocytes (97+/-6microM) and the NB1RGB cell line (111+/-20microM) and remarkable anti-bacterial activity (MIC) toward E. coli K12 W3110 (7.9microM). Moreover, 5DEBT-4,8 indicated 1144 conformers by global minimum analysis and had two minimum dGW (solvation free energy) points as well as 4DTBP-6,8, which had been previously examined and concluded to be a significant useful anti-bacterial compound.

Anti-Bacterial Agents↗
PubMed2000

Evaluation of the cytotoxic effects of bis-quaternary ammonium antimicrobial reagents on human cells.

The cytotoxic effects of newly synthesized bis-quaternary ammonium compounds (bis-QACs) and benzalkonium chloride were investigated on skin and blood cells, namely normal human epidermal keratinocytes of neonatal foreskin, a normal human skin fibroblast cell line NB1RGB, erythrocytes and a lymphoma cell line JM. The bis-QACs tested were 4, 4'-(1,6-hexamethylenedithio)bis(1-octylpyridinium iodide) (4DTBP-6, 8), N,N'-tetramethylenebis(1-dodecyl-4-carbamoylpyridinium iodide) (4BCAP-4,12), N,N'-hexamethylenebis(1-decyl-4-carbamoylpyridinium iodide) (4BCAP-6,10), 4,4'-(1,4-tetramethylenedicarbonyldiamine) bis (1-decylpyridinium iodide) (4DCABP-4,10), 4,4'-(1, 4-tetramethylenedicarbonyldiamine) bis (1-dodecylpyridinium iodide) (4DCABP-4,12), 4,4'-(1, 4-phenyldicarbonyldiamine)bis(1-dodecylpyridinium iodide) (4DCABP-P, 12), and 4,4'-(1, 6-hexamethylenedioxydicarbonyl)bis(1-dodecylpyridinium iodide) (4DOCBP-6,12). All bis-QACs consisted of two identical alkylpyridinium rings and bridge structure linking rings to each other have a methylene bridge but only 4DCABP-P,12 has a phenyl ring as a bridge. Most of the LD(50) values in acute cytotoxic assays of these bis-QACs tended to be lower than those of benzalkonium chloride. However, the comparison of the antibacterial activity against cytotoxic effects on several human cells revealed that bis-QACs, especially 4DTBP-6,8, have wide concentration ranges showing sufficient antibacterial activity and lower cytotoxic effect on human cells (except for 4DOCBP-6,12), although benzalkonium chloride caused significant human cell damage at the concentrations necessary for antibacterial activity. Moreover, judging from the LD(50) value of 4DTBP-6,8 [67 microM, a 6.7-fold higher concentration than the upper value of MIC] obtained in an artificial human skin model TESTSKIN, 4DTBP-6,8 is thought to be a more effective and safer antiseptic reagent for application to the skin surface than benzalkonium chloride. Taken together, bis-QACs are expected to be a promising new generation of antimicrobial QACs.

Anti-Bacterial Agents↗
PubMed1999

Effect of the alkyl chain length on the anaerobic biodegradability and toxicity of quaternary ammonium based surfactants.

The anaerobic biodegradability and toxicity to methanogenic gas production of different alkyl chain length homologs of quaternary ammonium based surfactants were examinated. Two series of these cationic surfactants were selected: alkyl trimethyl ammonium and alkyl benzyl dimethyl ammonium compounds. A simple anaerobic gas production test containing municipal digester solids as a source of anaerobic bacteria was used. Under the applied methanogenic conditions, the cationic surfactants tested showed a very poor primary biodegradation and no evidence of any extent of ultimate biodegradation was observed. The toxicity of quaternary ammonium based surfactants to methanogenic gas production decreased with increasing the alkyl chain length.

Alkylation↗
PubMed2002

Synthesis and neuromuscular blocking activity of 16beta-N-methylpiperazino steroidal derivatives.

Steroidal quaternary ammonium compounds 12 and 13 with quaternised nitrogen at positions 3 and 16 of the steroidal nucleus in androstane series were synthesised and their neuromuscular blocking activities and ganglion blocking activities were studied using chick biventer and anaesthetised cat as the models. The bisquaternary compounds 12 and 13 have been found to be greater in potency than D-tubocurarine. Acetoxy derivative 13 has been found to be more potent than pipecuronium bromide taking D-tubocurarine as the standard compound indicating the need of acetoxy function at position 16.

Animals↗
PubMed1985

In vitro diagnosis and studies on the mechanism(s) of anaphylactoid reactions to muscle relaxant drugs.

By covalently coupling alcuronium, d-tubocurarine and the pancuronium analogue, vecuronium, and using the resultant complexes in radioimmunoassays with patients' sera, we have found high levels of drug-reactive IgE antibodies in some subjects who reacted to these muscle relaxants. This is the first demonstration of IgE antibodies to such compounds. Assays were also developed for the detection of drug-reactive IgE antibodies to the muscle relaxant drugs succinylcholine, decamethonium and gallamine. They involved the coupling of choline and its ethyl analogue, triethylcholine to activated Sepharose. Results of direct binding and inhibition experiments and correlations with clinical findings demonstrated that the assays are relevant to the detection of succinylcholine-, decamethonium- and gallamine-reactive IgE antibodies in patients who experienced adverse reactions to these drugs. Quantitative inhibition studies revealed that IgE antibodies from most patients cross-reacted with all muscle relaxants tested, other quaternary ammonium compounds and some pharmacologically unrelated drugs including promethazine, morphine, neostigmine and pentolinium. Results showed that the specificities of the IgE antibodies are directed towards quaternary or tertiary ammonium ions on the drugs that bind the antibodies. As these ions occur widely in man's environment in drugs, cosmetics, disinfectants, foods and industrial materials, it seems possible that sensitization of patients may occur without previous exposure to muscle relaxant drugs. Thus, we now have assays that will detect antibodies to all six muscle relaxant drugs --alcuronium, d-tubocurarine, pancuronium, succinylcholine, decamethonium and gallamine-- and, for the first time since the work on penicillins, drug-specific IgE antibodies have been found in large numbers of patients and the allergenic determinants have been identified.

Anaphylaxis↗
PubMed1976

[Inhibition effects of extracellular glucosyltransferase from Streptococcus mutans].

The extracellular, gel-electrophoretically pure glucosyl transferase (GT) of Streptococcus mutans st.227 was incubated with various inhibitors and the synthetic product quantitatively determined. The GT activity was increased with low urea concentration (0.3 - 1.2 M) and inhibited with higher urea molarity. Sodium dodecyl sulfate and quarternary ammonium compounds (detergents) have a clear inhibiting effect starting with 0.005%, while NaF, KSCN, ethylene diamine tetra-acetic acid and sugar alcohols do not have any influence.

Enzyme Inhibitors↗
PubMed2003

The effect of small cations on the positive electrospray responses of proteins at low pH.

Solutions consisting of protein and small molecule mixtures have been subjected to electrospray ionization to study the influence of small molecule/cation components at high concentrations on the electrospray responses of proteins. Emphasis was placed on solutions consisting of equal parts methanol and water and containing 1 vol % acetic acid. The results, therefore, are relevant to low pH solutions with significant organic content, a commonly used set of conditions in electrospray ionization mass spectrometry that tends to denature proteins. A variety of small cations/molecules were selected to sample a range of chemical characteristics. For example, sodium and cesium cations were studied to represent metal ions, tetrabutylammonium and tetramethylammonium cations were studied to represent quaternary ammonium compounds with different surface activities, and octadecylamine and glycine were studied to represent species that compete for protons but have different surface activities. A methodology for measuring relative ion suppression efficiencies was developed and applied for protein ions derived from bovine cytochrome c. The form of the small cation (i.e., metal ion, quaternary ammonium ion, or protonated molecule) did not appear to be a factor in determining the efficiency with which protein ion signals were suppressed. The extent to which ions are expected to concentrate on the surface, however, was the major factor in determining the ion suppression efficiency. Itwas found that the ion suppression efficiency of the most surface active species in this study was comparable to that of a protein on another protein after normalization by charge. These results are particularly relevant to the development of mixture analysis strategies based on ionization and tandem mass spectrometry applied to mixtures of whole proteins.

Algorithms↗