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PubMed1977

Iodination of Escherichia coli with chloramine T: selective labeling of the outer membrane lipoprotein.

Iodination of Escherichia coli cells with chloramine T preferentially labels the free and murein-bound forms of the outer membrane lipoprotein. Iodination for 15 s at 15 degrees C labels the two forms of the lipoprotein almost exclusively, whereas iodination for 60 s at 25 degrees C also labels the other major outer membrane proteins. Chloramine T iodination is a rapid, simple technique for labeling the outer membrane lipoprotein.

Arginine↗
PubMed1981

Occupational asthma due to inhalation of chloramine-T. I. Clinical observations and inhalation-provocation studies.

Respiratory symptoms developed in 5 patients who were exposed to chloramine-T, a potent disinfectant used in cleaning butcheries, kitchens, and operating theaters. Skin tests, performed in 4 patients, showed an immediate type of wheal and flare reaction followed by a late-type infiltrative reaction. In 3 patients, inhalation tests with chloramine-T were done. 1 patient showed asthmatic bronchial obstruction, immediately after inhalation, followed by a late-type asthmatic reaction after some hours. 2 patients only exhibited late-type reactions, 4-8 h after challenge. The late bronchial response lasted for several hours or even days and was accompanied by leukocytosis in all 3 patients and a slight fever in 1 patient. No evidence of alveolar involvement appeared. Pre-challenge inhalation of cromoglycate in 1 patient ameliorated the late response considerably.

Administration, Intranasal↗
PubMed1981

A model of decreased functional alpha-1-proteinase inhibitor. Pulmonary pathology of dogs exposed to chloramine T.

The objective of this study was to develop an animal model representative of chronic human alpha-1-proteinase inhibitor deficiency. Eight dogs were treated with a mild oxidizing agent, chloramine T, with varying regimens for 3--27 wk. The capacity of the serum to inhibit both trypsin and elastase was examined and found to respond differently. Although immunologically determined levels of protease inhibitor did not change, the ability of serum to inhibit elastase in an in vitro assay decreased in direct response to chloramine T treatment. The trypsin inhibitory capacity was less affected. Emphysemalike alterations in lung morphology were observable when histologic sections were evaluated both subjectively and objectively by mean linear intercept measurements. The data suggest that this model parallels the emphysema associated with the genetic alpha-1-proteinase inhibitor deficiency in man.

Animals↗
PubMed2003

Hypochlorite scavenging activity of hydroxycinnamic acids evaluated by a rapid microplate method based on the measurement of chloramines.

Scavengers of hypochlorite (XOCl) could have beneficial effects in diseases in which this oxidant plays a pathogenic role. It has been reported that ferulic acid and chlorogenic acid, the quinic ester of caffeic acid, are good hypochlorite scavengers, but a systematic evaluation of the naturally occurring hydroxycinnamic acids (HCAs), which these substances belong to, has not been performed yet. Thus, in this work we studied, by two different in-vitro methods, the antioxidant activity of five HCAs: p-coumaric acid, ferulic acid, sinapinic acid, caffeic acid and chlorogenic acid. The methods applied in this study were based on the oxidation of human serum albumin (HSA) by XOCl, a new microplate method based on the measurement of chloramines and a previously described carbonyl assay. Firstly, lysine-derived chloramines, in the presence or absence of the HCAs, were detected using 5-thio-2-nitrobenzoic acid (TNB), measuring the absorbance at 415 nm by a microplate reader. To remove excess XOCl, Trolox, a known XOCl scavenger, was added before TNB. Secondly, lysine-derived carbonyls, in the presence or absence of the HCAs, were detected by using 2,4-dinitrophenylhydrazine. Hydroxycinnamic acids appeared active (caffeic >/= sinapinic > chlorogenic congruent with ferulic > p-coumaric acid) by both methods, suggesting possible pharmacological applications for these compounds, which are present at high concentrations in the plant kingdom.

Chloramines↗
PubMed1982

Organic N-chloramines: chemistry and toxicology.

The stability of aqueous solutions of organic N-chloramines, suspected of contaminating chlorinated water, has been studied. Two factors influence the decomposition of solutions of N-chloropiperidine and N-chlorodiethylamine: a spontaneous decomposition and photodecomposition. Since solutions of these compounds are relatively long-lived, a need for an analytical method for their identification is discussed. A new method is described which involves reaction of organic N-chloramines with arenesulfinic acid salts. The method gives high yields of stable arenesulfonamides. Several toxicological studies of N-chloropiperidine are described. The compound is mutagenic by Ames assay in Salmonella typhimurium strain TA 100 and does not require metabolic activation as indicated in a total body fluids analysis using C57BL/J6 mice. N-Chloropiperidine was subjected to a modified in vitro cell transformation assay using diploid fibroblast cells from Syrian hamster fetuses. A maximum number of foci of 4 per dish was observed at a seeding of 5 X 10(3) cells/60 mm dish. Under similar conditions, MNNG-induced foci ranged from 4 to 7 per dish.

Animals↗
PubMed2003

The relationship between disinfection by-product formation and structural characteristics of humic substances in chloramination.

The influence of structural characteristics of humic substances on disinfection by-product (DBP) formation was investigated for seven humic substances isolated from aquatic and terrestrial sources. The structural characterizations included 13C nuclear magnetic resonance (13C NMR) spectroscopy and ultraviolet (UV) spectroscopy. The aqueous humic substances were chloraminated at pH 7.0 and 8.5, with and without the presence of the bromide ion, and analyzed for total organic halogen (TOX), trihalomethanes (THMs), and haloacetic acids (HAAs). Aromatic contents determined by 13C NMR and differential UV absorbance at 254 nm statistically correlated with TOX formation for the humic substances investigated at p < 0.08. In contrast, a lack of correlation was observed for THM and HAA formation and these parameters. This paper also compiles relevant literature and discusses the contrasting reaction response of DBP precursor material to chlorination and chloramination.

Chloramines↗
PubMed1999

Secondary radicals derived from chloramines of apolipoprotein B-100 contribute to HOCl-induced lipid peroxidation of low-density lipoproteins.

Oxidation of low-density lipoproteins (LDL) is thought to contribute to atherogenesis. Although there is increasing evidence for a role of myeloperoxidase-derived oxidants such as hypochlorite (HOCl), the mechanism by which HOCl modifies LDL remains controversial. Some studies report the protein component to be the major site of attack, whereas others describe extensive lipid peroxidation. The present study addresses this controversy. The results obtained are consistent with the hypothesis that radical-induced oxidation of LDL's lipids by HOCl is a secondary reaction, with most HOCl consumed via rapid, non-radical reaction with apolipoprotein B-100. Subsequent incubation of HOCl-treated LDL gives rise to lipid peroxidation and antioxidant consumption in a time-dependent manner. Similarly, with myeloperoxidase/H2O2/Cl- (the source of HOCl in vivo), protein oxidation is rapid and followed by an extended period of lipid peroxidation during which further protein oxidation does not occur. The secondary lipid peroxidation process involves EPR-detectable radicals, is attenuated by a radical trap or treatment of HOCl-oxidized LDL with methionine, and occurs less rapidly when the lipoprotein was depleted of alpha-tocopherol. The initial reaction of low concentrations of HOCl (400-fold or 800-fold molar excess) with LDL therefore seems to occur primarily by two-electron reactions with side-chain sites on apolipoprotein B-100. Some of the initial reaction products, identified as lysine-residue-derived chloramines, subsequently undergo homolytic (one-electron) reactions to give radicals that initiate antioxidant consumption and lipid oxidation via tocopherol-mediated peroxidation. The identification of these chloramines, and the radicals derived from them, as initiating agents in LDL lipid peroxidation offers potential new targets for antioxidative therapy in atherogenesis.

Apolipoprotein B-100↗
PubMed2001

Chlorination of N-acetyltyrosine with HOCl, chloramines, and myeloperoxidase-hydrogen peroxide-chloride system.

N-acetyl-L-tyrosine (N-acTyr), with the alpha amine residue blocked by acetylation, can mimic the reactivity of exposed tyrosyl residues incorporated into polypeptides. In this study chlorination of N-acTyr residue at positions 3 and 5 in reactions with NaOCl, chloramines and the myeloperoxidase (MPO)-H2O2-Cl- chlorinating system were invesigated. The reaction of N-acTyr with HOCl/OCl- depends on the reactant concentration ratio employed. At the OCl-/N-acTyr (molar) ratio 1:4 and pH 5.0 the chlorination reaction yield is about 96% and 3-chlorotyrosine is the predominant reaction product. At the OCl-/N-acTyr molar ratio 1:1.1 both 3-chlorotyrosine and 3,5-dichlorotyrosine are formed. The yield of tyrosine chlorination depends also on pH, amounting to 100% at pH 5.5, 91% at pH 4.5 and 66% at pH 3.0. Replacing HOCl/OCl- by leucine/chloramine or alanine/chloramine in the reaction system, at pH 4.5 and 7.4, produces trace amount of 3-chlorotyrosine with the reaction yield of about 2% only. Employing the MPO-H2O2-Cl- chlorinating system at pH 5.4, production of a small amount of N-acTyr 3-chloroderivative was observed, but the reaction yield was low due to the rapid inactivation of MPO in the reaction system. The study results indicate that direct chlorination of tyrosyl residues which are not incorporated into the polypeptide structure occurs with excess HOCl/OCl- in acidic media. Due to the inability of the myeloperoxidase-H2O2-Cl- system to produce high enough HOCl concentrations, the MPO-mediated tyrosyl residue chlorination is not effective. Semistable amino-acid chloramines also appeared not effective as chlorine donors in direct tyrosyl chlorination.

Chloramines↗
PubMedDate not supplied

[Chemiluminescence in oxidation of luminol by chloramine derivatives of biogenic compounds].

Chloramine derivatives of amino acids induce chemiluminescence of a luminol solution. The chemiluminescence is more prolonged than the emission of luminol produced by hypochlorite. Persistent chemiluminescence also appears under the action of hypochlorite on a mixture of luminol and amino acids. It is assumed that the chemiluminescence of luminol in suspensions of stimulated phagocytes may be associated with its oxidation by chloramines.

Chloramines↗
PubMedDate not supplied

[Kinetic characteristics of luminol chemiluminescence caused by chloramine compounds].

The decaying part of the kinetic curves of luminol chemiluminescence (0.02 mM) induced by N-chlorphenylalanine is approximated by an exponential dependence, which varies insignificantly as chloramine concentration is changed from 0.2 to 0.7 mM. On the whole, the chemiluminescence of luminol is a result of its oxidation, which occurs in three stages with the formation of two intermediate products. N-Chlorphenylalanine is involved in the process at the initial stage. The reciprocal of the time the luminescence reaches a maximum increases linearly with the growth of N-chlorphenylalanine concentration. According to the calculations using the equations that reflect three stages of luminol conversion in the presence of excess chloramine, the rate constant for the initial stage is about 10(3) l/(mol.min). The rate constant for one stage of the conversion of luminol oxidation product is approximately 0.2 min-1, and the rate constant of the other is severalfold greater. Luminol chemiluminescence induced by low concentrations of N,N-dichlortaurine is more durable. Probably, it is composed of two types of emission one of which slowly decays.

Alanine↗
PubMedDate not supplied

Bronchial asthma due to sensitization to chloramine T.

Chloramine T, an organic, highly reactive derivative of chlorine with potent bactericidal properties, is used as a disinfectant in the food industry. Described as an occupational sensitizer in 1945 for the first time, it produces late or dual asthma, occasionally accompanied by fever and leukocytosis, which is mediated by IgE. We present the case of a male dairy worker who, after 4 years of exposure to the product, developed rhinitis and asthma. Skin tests with chloramine T were positive at a concentration of 10 mg/ml, while all other allergens tested negative. RAST detected specific IgE at 12 PRU and bronchial provocation induced immediate and late bronchoconstriction.

Asthma↗
PubMed2004

Effects of chlorine and chloramines on earthy and musty odors in drinking water.

Water treatment plants in the US may operate under the assumption that chlorine masks earthy and musty odors from geosmin and 2-methylisoborneol (MIB) in drinking water. To test this hypothesis, we evaluated the effects of chlorine and chloramines on geosmin and MIB by two sensory analysis approaches--a statistical Pairwise Comparison Test, and Flavor Profile Analysis (FPA). All Pairwise Ranking test statistics were significant (p<0.05); we conclude that panelists can differentiate minor differences in geosmin and MIB concentrations in a Pairwise Comparison Test even in the presence of chlorine. FPA appeared to be more challenging in discerning subtle differences in concentrations of geosmin or MIB than did the Pairwise Comparison Test, and the presence of chlorine (0.5-20 mg/L) and chloramines (3-24 mg/L) confused the panelists (i.e showed a larger error in the intensity of response reported by the panel), but did not necessarily mask geosmin or MIB.

Camphanes↗
PubMedDate not supplied

[Chemiluminescence of the polymorphonuclear leukocytes-luminol system in the presence of biogenic chloramines].

It was demonstrated that N-chlorphenylalanine and other chloramines strengthen sharply chemiluminescence in the polymorphonuclear leukocytes (PML)-luminol system without special activation of cells. The intensity of chemiluminescence is higher than the intensity of luminol solution emission induced by N-chlorphenylalanine. But it was nearly equal to chemiluminescence intensity of a mixture of luminol, N-chlorphenylalanine and 20-30 nM H2O2. The increase in chemiluminescence in the PML-luminol system in the presence of N-chlorphenylalanine is not related to PML activation but is the result of direct oxidation of luminol by N-chlorphenylalanine. Chloramine derivatives of amino acids and taurine at final concentrations of 0.01-0.1 mM do not suppress luminol chemiluminescence in suspension of PML stimulated by phorbol-12-myristate-13-acetate. At the same time, hypochlorite inhibits sharply luminol emission induced by stimulated cells.

Alanine↗
PubMed1991

[The activity of formaldehyde, glutardialdehyde, peracetic acid, chloramine T (N-chlor-4-toluolsulfonamide), m-cresol, ethanol and benzyldimethyldodecylammonium bromide against bacteria which are found in coagulated blood. (Model studies for chemical disinfection of instruments].

The experiments were performed using frosted glass as carrier with its surface being contaminated with whole blood containing Staphylococcus aureus as test organism. At the time of sampling, a heparin preparation was added to the blood to prevent premature coagulation. After addition of the staphylococci, coagulation was initiated by means of a heparin antagonist. 10, 25, 50, 100, and 150 microliters, respectively, of the blood were homogeneously spread on rectangular test areas of 10 x 20 mm. After the blood had coagulated, each of the test objects was placed in 15 ml of the solution (20 degrees C) containing the active ingredient tested for 60 min. After that, the test objects were removed from the disinfectant and, in order to inactivate any adhering active components, treated with a neutralizing solution of suitable composition. The number of viable germs (colony-forming units) was determined quantitatively. The blood samples were ground together with quartz sand. Aliquots of the diluted suspensions were mixed with molten agar medium. The plates then were incubated at 37 degrees C over a period of 14 days. The relative number of viable germs (N/No) per test object was calculated from the number of colonies. Plotting of the microbicidal effects obtained (log N/No] versus the concentration of the active substance (see Figs. 1-3) yielded curves differing in some characteristics as e.g. curvature, slope of the lower curve section (log N/No). less than -3), concentration range according to the layer thickness of the contamination. To visualize the reduction of the efficacy of the respective disinfectants caused by blood, the concentrations of active components were determined which are necessary to achieve a microbicidal effect of log (N/No) = -4. These concentrations were plotted versus the amounts of blood per test area (Fig. 4). The resulting curve for formaldehyde was slightly U-shaped. With a raising amount of blood, the concentration required slightly decreased in the beginning and increased again from an amount of ca. 100 microliter blood per test area. For all other active substances, the required concentration of these substances increased with the amount of blood used. The curve obtained for ethanol exhibited the lowest slope. The slope of the curves increased in the following order: ethanol, m-cresol, peracetic acid, chloramine T, glutardialdehyde, benzyldimethyldodecylammoniumbromide. The curves for chloramine T and glutardialdehyde nearly paralleled each other.(ABSTRACT TRUNCATED AT 400 WORDS)

Animals↗
PubMed1987

[Action of chloramine-T on the processes of sodium channel activation and inactivation in neuroblastoma cells].

Effect of chloramine-T, the specific reagent on methionine residues, on gating of sodium channels was studied in neuroblastoma cell membrane. After the chloramine treatment the inactivation became slower, incomplete and the steepness of its voltage dependence considerably decreased; the inactivation curve was shifted towards depolarization. Time course of activation did not change. The activation curve shifted towards negative potentials, its slope being insignificantly decreased. Effective charge of activation as determined from the limiting logarithmic slope of the activation decreased by a factor of 1.17. Possible explanations of the phenomena observed are discussed.

Animals↗
PubMed1988

[Chloramine T solution for intraoperative peritoneal lavage. A statistical analysis].

An analysis and statistical evaluation of 1,157 cases of wound healing produced evidence to the effect that the rate of wound healing disorders could be substantially reduced by prophylactic peritoneal lavage, using 0.1 per cent chloramine-T solution. That reduction was from nine to 2.6 per cent in the author's cases. - In the context of perforations (n = 186), therapeutic peritoneal lavage, using chloramine-T, proved clearly superior to washing with physiological salt solution in coping with wound healing disorders. Here, the rate of such disorders was reduced from 22.4 to 8.3 per cent, and it dropped further to 4.5 per cent in those cases of perforation in which additional lavage was applied to the surgical wound proper.

Abdomen↗
PubMed1977

Chloramines, an aggravating factor in the anemia of patients on regular dialysis treatment.

In two dialysis centres in the same city, with a total of 56 patients on regular dialysis treatment, it has been shown that the tap water used for the production of the dialysate contains chloramines. Total chlorine concentration and percentage of chloramines varies from 0.5 to 1.1 ppm and from 40 to 95 per cent. There in a high percentage of Heinz bodies in the patients' erythrocytes, and incubation of red cells in vitro with the dialysate raises the methaemoglobin concentration and alters the hexose-monophosphate shunt. The patients' mean haematocrit improved from 23.13 +/- 4.41 SD to 25.93 +/- 5.17 SD (p less than 0.0025) with the administration of ascorbic acid, 500 mg given intravenously once a week, but an unexpected transitory increase of the total chlorine to 3.5 ppm resulted in a serious decline of the mean haematocrit to 20.80 +/- 5.22 SD (p less than 0.0001). Ascorbic acid added to the dialysate at a concentration of 1.7 mg/dl produced a great improvement in the anaemia and the almost total disappearance of Heinz bodies from the patients' red cells.

Anemia↗