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PubMed1999

The effect of blood on the antiviral activity of sodium hypochlorite, a phenolic, and a quaternary ammonium compound.

OBJECTIVE: To assess the virucidal activity of three disinfectants (sodium hypochlorite, a phenolic, and a quaternary ammonium compound) in the presence and absence of blood. METHODS: Disinfectants at varying concentrations (hypochlorite: 5,000, 500, or 50 ppm; phenolic: 1:10 or 1:128 dilution; quaternary ammonium compound: 1:10 or 1:128 dilution) were added to either saline or whole blood (final concentration, 80% or 20% blood) and mixed. Test organisms included an attenuated vaccine strain of poliovirus type 1 (prototype for relatively resistant hydrophilic viruses) and herpes simplex virus (HSV) type 1 (prototype for relatively susceptible lipophilic viruses). Virus was added to create a viral-blood suspension. Viral survival was tested at room temperature at the following times: 0, 15 seconds, 30 seconds, 1 minute, 2 minutes, 5 minutes, and 10 minutes. A neutralizer stopped the reaction, and virus was assayed using a plaque technique. RESULTS: In the absence of blood, complete inactivation of HSV was achieved within 30 seconds with 5,000 (1:10 dilution of bleach) and 500 (1:100 dilution of bleach) ppm chlorine, 1:10 and 1:128 diluted phenolic (use dilution), and 1:10 and 1:128 diluted quaternary ammonium compound (use dilution). In the presence of 80% blood, only 5,000 ppm hypochlorite, 1:10 phenolic, and 1:10 or 1:128 quaternary ammonium compound were effective. In the absence of blood, complete inactivation of polio was achieved within 30 seconds by 5,000 and 500 ppm chlorine and 1:10 quaternary ammonium compound. In the presence of 80% blood, no solution tested was capable of completely inactivating poliovirus within 10 minutes. CONCLUSIONS: Our data suggest that, in the absence of visible blood, environmental surfaces may be disinfected with a diluted hypochlorite solution (1:10 or 1:100), a phenolic, or a quaternary ammonium compound. Based on our studies using HSV, which has similar susceptibilities to disinfectants as human immunodeficiency virus (HIV), phenolics at their use dilution and 1:100 diluted hypochlorite are unlikely to inactivate HIV or hepatitis B virus reliably in the presence of blood. Hypochlorite at a final concentration of 5,000 ppm (1:10 dilution) should be used to decontaminate blood spills, but, even after decontamination, care should be used to avoid sharps injuries.

Blood↗
PubMed2006

Syntheses and antimicrobial activities of a series of new bis-quaternary ammonium compounds.

A series of new bis-quaternary ammonium compounds (bis-QACs), 4,4'-(2,9-dioxadecane) bis(1-alkylpyridinium bromide)s, 3,3'-(2,9-dioxadecane)bis(1-alkylpyridinium bromide)s and 3,3'-(2,7-dioxaoctane)bis(1-decylpyridinium bromide) was synthesized. The compounds were evaluated by their activities against bacteria, molds and yeasts; the activities were expressed as the minimum inhibitory concentrations (MIC) and/or the minimum bactericidal concentrations (MBC). Compound 4,4'-(2,9-dioxadecane) bis(1-decylpyridinium bromide) had MIC values which exceeded those of benzalkoniumchloride and thiabendazole. It was in vitro active against a broad spectrum of Gram-negative and Gram-positive bacteria, against yeasts and some molds, it had high solubility and thermal decomposition temperature. The relationships between structure and biological activity of the tested bis-QACs are discussed.

Anti-Bacterial Agents↗
PubMedDate not supplied

Relationship between nasal absorption and physicochemical properties of quaternary ammonium compounds.

The present study was undertaken to investigate the in situ nasal absorption of a series of tetraethylammonium chloride-related aliphatic quaternary ammonium compounds in rats and its relationship with their physicochemical properties (molecular weight and partition coefficient). All of the ten quaternary ammonium compounds examined were found to be absorbed through the nasal mucosa of rats. The nasal absorption rates of ethyltrimethyl-ammonium iodide and tetraethylammonium chloride, with the lowest molecular weight, were the highest, and those of tetra-n-butylammonium chloride and tetra-n-propylammonium bromide, with high molecular weight, were much lower. Thus, there was a tendency that the nasal absorption rates of quaternary ammonium compounds in rats decreased with an increase in their molecular weight. A physicochemical study has shown that there was a linear relationship between the molecular weight of the ten quaternary ammonium compounds and their partition coefficient, thereby suggesting an increase in lipophilicity with the molecular weight. In addition, there was a good correlation between the extent of the nasal absorption of the quaternary ammonium compounds studied and their molecular weight or partition coefficient. These data suggest that there is a reciprocal relationship between the membrane transport of quaternary ammonium compounds in the nasal mucosa and their lipophilic character. In conclusion, it seems likely that quaternary ammonium compounds are predominantly absorbed from the nasal mucosa of the rat through waterfilled channels or pores rather than through the lipid membrane.

Absorption↗
PubMed2006

Correlation between the bacterioclastic action of a bis-quaternary ammonium compound and outer membrane proteins.

Bis-quaternary ammonium compounds (bis-QACs) have the ability to cause a rapid and abundant leakage of the turbid materials from cells, and such a bacterioclastic ability leads to a potent bactericidal activity. In order to clarify the detailed mechanism of the bactericidal action of bis-QACs, the correlation between the bacterioclastic action of 4,4'-(1,6-hexamethylenedithio)bis(1-octylpyridinium bromide) (4DTBP-6,8) and the leakage of outer membrane pore protein E (OmpE) was investigated. Using the antiserum against a fusion protein consisting of GST and the OmpE protein of Escherichia coli encoded by the ompE gene, it was seen that the leakage of OmpE from E. coli cells was caused by treatment with low concentrations (much lower than the critical vesiculation concentration) of 4DTBP-6,8. Furthermore, it was confirmed that 4DTBP-6,8 caused an increase in the turbidity of the cell suspension of Klebsiella pneumoniae, Salmonella typhimurium and Serratia marcescences, and led to the leakage of several proteins which have a high percentage of homology with OmpE of E. coll. By immunoelectron microscopy investigation, it was revealed that the vesiculation from E. coli treated with 4DTBP-6,8 contains OmpE. In addition, the bacteriolytic action of 4DTBP-6,8 was investigated. The results suggested that the lysis of cells by bis-QACs was not an enzymatic action such as that by autolysin but a physical bacterioclastic action. Judging from these results, it is suggested that the leakage of OmpE is one of the major bacterioclastic actions of bis-QACs, and deals the bacterial cells a fatal blow.

Anti-Bacterial Agents↗
PubMed2001

Plasmid-borne smr gene causes resistance to quaternary ammonium compounds in bovine Staphylococcus aureus.

Resistance to quaternary ammonium compounds (QAC) in staphylococci is common in hospital environments and has been described in the food industry. Little is known about staphylococcal QAC resistance associated with animal disease, although such disinfectants are widely used in veterinary medicine. In order to investigate the occurrence of QAC resistance in staphylococci isolated from QAC-exposed animals, 32 penicillin- and tetracycline-resistant and 23 penicillin- and tetracycline-susceptible Staphylococcus aureus isolates collected from milk from cows with mastitis during a 4-year period were selected for QAC susceptibility studies and genetic characterization. The isolates originated from four different herds that used a common pasture with a joint milking parlor in the summer. During the pasture season, a teat cream containing the QAC cetyltrimethylammonium bromide had been used daily for more than 10 years for mastitis control. Three of the penicillin- and tetracycline-resistant isolates, which were recovered from three different cows during a 20-month period, were resistant to QAC. Plasmid analysis, PCR, and DNA sequencing revealed a novel plasmid of 2,239 bp containing the smr gene. The plasmid, designated pNVH99, has similarities to small, smr-containing staphylococcal plasmids previously found in human and food isolates. pNVH99 is a new member of the pC194 family of rolling-circle replication plasmids. The three QAC-resistant isolates, as well as 28 of the 29 remaining penicillin- and tetracycline-resistant isolates, were indistinguishable by pulsed-field gel electrophoresis. The study indicates that the occurrence and spread of QAC-resistant S. aureus among dairy cows may be a problem that needs further investigation.

Amino Acid Sequence↗
PubMed1989

Inhibitory effects of quaternary ammonium compounds on lysosomal degradation of endogenous proteins.

The effects of quaternary ammonium compounds on the degradation of endogenous proteins in isolated lysosomes were studied. Proteolysis was assayed by measuring the trichloroacetic acid-soluble radioactivity in the lysosomes which had been labeled in vivo with 14C-leucine. p-Biphenylmethyl-(dl-tropyl-alpha-tropinium)bromide (BTTB), at concentrations higher than 0.85 mM, was found to inhibit the lysosomal proteolysis stoichiometrically. Other quaternary ammonium compounds, such as N-methylatropinium bromide (NMA), cetyltrimethylammonium bromide (CTAB), tubocurarine and gallamine, were also examined in the presence or absence of Triton X-100 which is able to destroy the lysosomal membranes. Of these four compounds, NMA was the most effective proteolysis inhibitor, showing 25% inhibition for intact lysosomes at a concentration of 1 mM of the compound. When these compounds were assayed after Triton X-100 treatment of the lysosomes, the effects of all the drugs were augmented, suggesting that they, after accumulation in the lysosomes, act through direct interactions with lysosomal proteases. This was supported by a kinetic analysis of the action of NMA on cathepsin B, a typical lysosomal protease.

Animals↗
PubMed1989

Effects of quaternary ammonium compounds on the degradation of lipids in lysosomes.

We have examined effects of quaternary ammonium compounds on the in vitro degradation of endogenous lipids in isolated lysosomes. The degree of lipid degradation was assessed by determining hydrolysis products of labeled lipid. Lipolysis was inhibited by quaternary ammonium compounds. The degrees of inhibition were as follows: ethidium bromide greater than N-methylatropinium bromide (NMA) greater than tubocurarine. The inhibition of lipolysis by these quaternary ammonium compounds is not necessarily correlated with the differences in their polarities, molecular weight or structures. The degradation of three phospholipid classes was inhibited by NMA with phosphatidylcholine the most vulnerable. The effect of NMA on the hydrolysis of [14C]dipalmitoylphosphatidylcholine (phospholipid) by lysosomal soluble proteins was also examined. The effect of NMA on phospholipase A1 was assessed by the formation of lysophosphatidylcholine, and that on phospholipase C was assessed as the sum of mono- and diglyceride formations. The action of NMA on the phospholipid degradation was similar to that of cationic amphiphilic drugs, but it differed somewhat from that of chloroquine for each enzyme. From these results, it was concluded that one of the inhibitory mechanisms of phospholipid degradation by NMA was the direct interaction between NMA and phospholipase A1 or C.

Animals↗
PubMed1986

Induction of contact dermatitis in guinea pigs by quaternary ammonium compounds: the mechanism of antigen formation.

Eight quaternary ammonium compounds were tested for their ability to induce contact dermatitis in guinea pigs by using a modified Freund's complete adjuvant test together with the guinea pig maximization test. Only two quaternary ammonium salts of the eight tested could be designated as strong allergens. These two active substances were shown to be capable of stable association with membrane lipids in forming immunogenic complexes. This surface complexation phenomenon was confirmed by using a spin-labeled quaternary ammonium salt which competed for binding sites at the surface of epidermal cells in vivo. Electron spin resonance was used to demonstrate that stable "ion-pairs" are formed between binding sites and the two allergenic preservatives. Furthermore, information was obtained on the kinetics of immunogenic complex formation as well as on the position and orientation of the quaternary ammonium ion at the cell surface.

Allergens↗
PubMed1977

Simplified detection of quaternary ammonium compounds by gas chromatography.

An analytical method for the measurement of quaternary ammonium compounds in biological fluids has been developed. Samples are prepared by forming the corresponding iodides, which are extracted and isolated. The residue is taken into n-hexane or into water and part of the solution obtained is injected onto the gas chromatograph where thermal degradation takes place. The methyl iodide released is measured by a 63Ni electron capture detector. This method is quite sensitive and detects with good reliability and reproducibility as little as 10(-14) mole quaternary ammonium compound.

Body Fluids↗
PubMed1985

Effect of a phenyl group in quaternary ammonium compounds on thiamine uptake in isolated rat hepatocytes.

The inhibitory effect of a phenyl group in quaternary ammonium compounds on thiamine uptake in isolated rat hepatocytes was investigated. The phenyltrimethylammonium ion was a more potent inhibitor than the tetramethylammonium ion, while the dibenzyldimethylammonium ion was the most potent inhibitor of thiamine uptake among those compounds examined. A kinetic study showed that this compound was a competitive inhibitor. The cetyltrimethylammonium ion was a less effective inhibitor than the benzyltrimethylammonium ion, and the palmitoylcholine ion was a weak inhibitor. These results indicate that the lipophilicity of a quaternary ammonium compound is not always correlated with its affinity for thiamine-carrier binding, but the presence of a phenyl group plays a significant role in affinity. The inhibitory effect of the series of (CH3)3N+ (CH2)nC6H5 (n = 0-6) compounds on thiamine uptake in isolated rat hepatocytes was studied. The maximal inhibitory activity occurred at n = 5. These results suggest that the phenyl group in a quaternary ammonium compound has a specific interaction with the thiamine-binding site in rat liver plasma membrane.

Animals↗
PubMed1983

[The effect of new quaternary ammonium compounds on bacteria and fungi. 5: Synthesis of 3-methyl-n-alkylthiomethylpyridinium-, 1-methyl-3-n-alkylthiomethylimidazolium- and 1-ethyl-3-n-alkylthioimidazolinium chloride].

Synthesis of some chlorides indicated in headline and their antibacterial properties was described. Synthesis of quaternary pyridine and imidazoline chlorides was performed by reaction of chloromethyl-n-alkylthioether with 3-methylpyridine or 1-methyl- and 1-ethylimidazole. Antibacterial properties of obtained compounds was tested on 13 strains of bacteria and fungi. Chlorides with dodecyl radical indicated the best antibacterial activity.

Anti-Bacterial Agents↗