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PubMed2003

Validation of the chloramine-T induced oxidation of human serum albumin as a model for oxidative damage in vivo.

PURPOSE: The validity of using chloramine-T as a model compound for mimicing oxidative stress was examined using human serum albumin (HSA) as a model. Important sites of oxidation were studied by mild treatment with chloramine-T and by mutating 34Cys for a serine (C34S). METHODS: High-performance liquid chromatography (HPLC) combined with fluorescence detection to confirm the validity of chloramine-T as an oxidizing agent was used. Oxidized amino acid residues were detected by reaction with 5,5'-dithiobis(2-nitro benzoic acid), digestion with cyanogen bromide, followed by capillary electrophoresis. Protein conformation was examined by spectroscopic techniques. RESULTS: From the HPLC analysis of human serum, the validity of using chloramine-T as an oxidizing agent was confirmed. At low chloramine-T concentrations (CT0.1-HSA, CT1-HSA), 34Cys and Met residues were oxidized, at medium concentrations (CT10-HSA), the tryptophan residue also appeared to be oxidized, and at the highest concentration (CT50-HSA), the net charge of Site II of HSA was found to be more negative. The two highest levels of oxidation of HSA (CT10-HSA, CT50-HSA) resulted in conformational changes with an increased exposure of hydrophobic regions, decreased high-affinity bindings of warfarin and ketoprofen and a reduced esterase-like activity. The latter protein also has a shorter plasma half-life and an increased liver clearance. CONCLUSIONS: We succeeded in imitating oxidative damage to HSA using chloramine-T and the findings show that Site II is more affected than Site I and 34Cys, when HSA is exposed to oxidative stress.

Animals↗
PubMed2002

Reaction of protein chloramines with DNA and nucleosides: evidence for the formation of radicals, protein-DNA cross-links and DNA fragmentation.

Stimulated phagocyte cells produce the oxidant HOCl, via the release of the enzyme myeloperoxidase and hydrogen peroxide. HOCl is important in bacterial cell killing, but excessive or misplaced generation can damage the host tissue and may lead to the development of certain diseases such as cancer. The role of HOCl in the oxidation of isolated proteins, DNA and their components has been investigated extensively, but little work has been performed on the protein-DNA (nucleosome) complexes present in eukaryotic cell nuclei. Neither the selectivity of damage in such complexes nor the possibility of transfer of damage from the protein to DNA or vice versa, has been studied. In the present study, kinetic modelling has been employed to predict that reaction occurs predominantly with the protein and not with the DNA in the nucleosome, using molar HOCl excesses of up to 200-fold. With 50-200-fold excesses, 50-80% of the HOCl is predicted to react with histone lysine and histidine residues to yield chloramines. The yield and stability of such chloramines predicted by these modelling studies agrees well with experimental data. Decomposition of these species gives protein-derived, nitrogen-centred radicals, probably on the lysine side chains, as characterized by the EPR and spin-trapping experiments. It is shown that isolated lysine, histidine, peptide and protein chloramines can react with plasmid DNA to cause strand breaks. The protection against such damage afforded by the radical scavengers Trolox (a water-soluble alpha-tocopherol derivative) and 5,5-dimethyl-1-pyrroline-N-oxide suggests a radical-mediated process. The EPR experiments and product analyses have also provided evidence for the rapid addition of protein radicals, formed on chloramine decomposition, to pyrimidine nucleosides to give nucleobase radicals. Further evidence for the formation of such covalent cross-links has been obtained from experiments performed using (3)H-lysine and (14)C-histidine chloramines. These results are consistent with the predictions of the kinetic model and suggest that histones are major targets for HOCl in the nucleosome. Furthermore, the resulting protein chloramines and the radicals derived from them may act as contributing agents in HOCl-mediated DNA oxidation.

Animals↗
PubMed1988

Chemical modification of tryptophanase by chloramine T: a possible involvement of the methionine residue in enzyme activity.

Tryptophanase purified from Escherichia coli B/1t7-A was irreversibly inactivated by chloramine T (sodium N-chloro-p-toluenesulfonamide). The mode of inactivation was rather complex and did not follow pseudo-first-order kinetics. The inactivation of the apoenzyme was much faster than that of the holoenzyme. The Km value for the synthetic substrate S-o-nitrophenyl-L-cysteine (SOPC) increased concomitantly with the modification. In contrast, the Km value for the coenzyme, pyridoxal 5'-phosphate (PLP), was not altered. L-Serine, another substrate, and L-alanine, a competitive inhibitor, protected the enzyme from inactivation. Determination of SH groups in the enzyme protein with 5,5'-dithiobis(2-nitrobenzoic acid) (DTNB) showed that modification of two SH groups per enzyme subunit resulted in a complete inactivation. When the enzyme was subjected to chloramine T-modification following the SH group modification with DTNB, further inactivation was still observed, even after the addition of dithiothreitol. The SH-blocked enzyme preparation thus obtained, however, exhibited less pH dependency of inactivation by chloramine T than that of the native enzyme. The amino acid analysis of the chloramine T-modified enzyme showed that modification of four or five methionine residues among the 16 residues per subunit proceeded concomitantly with the complete inactivation. Modification of the enzyme with chloramine T quenched the absorption peak near 500 nm, characteristic of a quinoidal structure formed by labilization of the alpha-proton. These results suggest the possibility that chloramine T modifies not only the SH groups, but also methionine residues important for the catalytic activity of the enzyme.(ABSTRACT TRUNCATED AT 250 WORDS)

Amino Acids↗
PubMed1984

Irreversible modification of sodium channel inactivation in toad myelinated nerve fibres by the oxidant chloramine-T.

The effects of externally applied chloramine-T on the excitability of single toad myelinated nerve fibres were studied. Chloramine-T is a mild oxidant which reacts specifically with the cysteine and methionine residues of proteins. Chloramine-T prolongs the action potential of a single myelinated fibre by more than 1000-fold. This effect is concentration- and time-dependent; higher concentrations and longer incubation times increase prolongation. Under voltage-clamp conditions, sodium channel inactivation is markedly inhibited by chloramine-T while sodium channel activation remains normal. Prolonged depolarization of the membrane leads to a maintained sodium current. The maintained sodium currents show activation kinetics, dependence on membrane potential, and reversal potentials which are similar to those of normal, inactivating sodium currents in untreated fibres. Both the maintained and the peak sodium currents are equally inhibited by tetrodotoxin. After partial removal of sodium inactivation by brief exposures to chloramine-T, the voltage dependence of the steady-state sodium current inactivation (h infinity) is shifted in the depolarized direction by about 20 mV, even after correction for the non-inactivating component contributed by the maintained current. The phenomena described here imply that cysteine or methionine residues are critical for the sodium channel inactivation processes. The two different modifications of inactivation, its removal shown by the maintained current, and the shift in the voltage-dependence of the remaining inactivatable channels, reveal that at least two separate residues are modified by chloramine-T.

Action Potentials↗
PubMed1979

Asthma due to industrial use of chloramine.

Seven brewery workers developed asthmatic symptoms after using chloramine (chloramine-T) powder as a sterilising agent. They gave positive weal and flare reactions to skin-prick tests with solutions of chloramine at strengths that caused no reactions in unexposed controls. The symptoms did not recur once the men had been removed from areas in which chloramine was handled. As well as causing irritant effects, inhaling dry or liquid aerosols of chloramine may cause sensitisation, with workers being prone to allergic asthma on reexposure. In view of this, measures should be taken to ensure that chloramine is not inhaled.

Adult↗
PubMed1981

Occupational asthma due to inhalation of chloramine-T. II. Demonstration of specific IgE antibodies.

In the sera of patients who developed asthmatic symptoms after exposure to chloramine-T, specific IgE antibodies are demonstrated by a polystyrene tube radioimmunoassay. These antibodies are directed against human serum albumin treated with chloramine-T. Specific antibodies of subclasses IgG1, IgG3 and IgG4 were not found. Histamine release in response to chloramine-T-treated human serum albumin was demonstrated using the peripheral blood leukocytes of one of the patients. To define the antigenic determinant to which the specific IgE antibodies are directed, radioimmunoassay and radioimmunoassay-inhibition studies were performed using several autologous and heterologous chloramine-T-treated proteins. Moreover, the inhibition capacities of chloramine-T and structurally related compounds were also determined. The results of these experiments indicate that the antigenic determinant is formed, at least in part, by the p-toluenesulfonyl group of the chloramine-T molecule.

Adult↗
PubMed2003

Effects of chloramines and sodium hypochlorite on carious dentin.

In chemo-mechanical caries removal procedures, chloramines are typically used for chemical softening of carious dentin. However, the specific effect of chloramines to be compared to sodium hypochlorite has not been sufficiently clarified. In present study, the effect of chloramines used in the Carisolv-system on carious dentin mechanical properties and morphology were investigated, using Vickers hardness test and scanning electron microscopy (SEM). Sections of permanent teeth with dentin caries were treated with chloramines, prepared by mixing amino acids (glutamic acid, lysine, and leucine) with sodium hypochlorite or with sodium hypochlorite alone or with purified water. There was a tendency that the application of the sodium hypochlorite solution softened the sound dentin and/or inner layer of carious dentin more than the application of the chloramines solution did. In SEM observations, the application of chloramines resulted in opening dentinal tubules in the outer layer of carious dentin: Occluded dentinal tubules were seen after sodium hypochlorite application. There is a possibility that the amino acids in the Carisolv-system decrease the aggressive effect of sodium hypochlorite on sound dentin and/or inner layer of carious dentin and also would enhance the disrupting effect on degenerated collagen in carious dentin outer layer.

Cariostatic Agents↗
PubMed1989

[Sensitivity to antibiotics and the disinfectant chloramine of Staphylococci isolated from healthy and sick persons].

Five hundred and twenty seven strains of Staphylococcus aureus with massive contamination of at least 10(3) when estimated quantitatively were tested for their sensitivity to antibiotics and chloramine B. The staphylococcal strains were isolated from patients, air and stock of rooms in medical institutions, from medical personnel and healthy persons having no long-term contacts with hospital media i. e. from pregnant women and workers of confectionery plants. Among the isolates there were strains simultaneously sensitive to antibiotics and chloramine B (16.6 per cent), sensitive to antibiotics but resistant to chloramine B (5.5 per cent), resistant to antibiotics but sensitive to chloramine B (63.1 per cent) and resistant to antibiotics and chloramine B (15.3 per cent). Staphylococci resistant simultaneously to antibiotics and chloramine B were isolated from the persons of all the groups and from the air and stock of the rooms in the medical institutions. This showed the necessity of controlling sensitivity or staphylococci circulating in hospital media not only to antibiotics but also to disinfectants for providing more efficient prophylaxis of intrahospital infections.

Chloramines↗
PubMed1979

High pressure liquid chromatographic determination of chloramine-T in food.

A high pressure liquid chromatographic (HPLC) method for determining chloramine-T (N-chloro-N-sodium-p-toluenesulfonadmie) in foods such as ice cream, minced meat, and shrimp is described. Deproteinized samples are treated with sulfite to convert chloramine-T to p-toluenesulfonamide (p-TSA) and extracted, and HPLC analysis is performed on concentrated extracts. Sample extracts are chromatographed on a reverse phase 10 micrometers Lichrosorb RP-18 column with acetonitrile-water (190), and quantitated by an ultraviolet detector (220 nm) and digital integrator. The relationship between recorded peak area and concentration was linear to 0.600 micrograms p-TSA/microL. The detection limit was 2.5 ng pTSA/microL, corresponding to a chloramine-T concentration of 0.8 mg/kg in samples. Recoveries of added chloramine-T were 88% for ice cream, 73% for minced meat, and 51% for shrimp. Precision data indicate a relative standard deviation of 1.54 and 2.14% for the complete analysis of ice cream with levels of 15 and 63 mg chloramine-T/kg (n = 5 determinations), respectively. The HPLC method was applied to chloramine-T determinations in 62 ice cream, 25 minced meat, and 25 shrimp samples.

Animals↗
PubMed1978

Prevention of chloramine-induced hemolysis in dialyzed patients.

Chloramines, compounds made up of chlorine and ammonia, when present in tap water used for dialysis cause methemoglobinemia and hemolysis. Ascorbic acid addition has been reported to effectively neutralize chloramines in vitro and in patients dialyzed with the single batch dialysis delivery system. We extended these observations to patients dialyzed with the proportioning dialysis delivery system where exposure time of ascorbic acid to chloramines is shorter. This may be important since we found that the half time of the reaction between ascorbic acid and chloramines is 4 minutes. Red cell oxidant sensitivity in 15 patients was assessed by incubating red cells with ascorbate-cyanide and measuring methemoglobin which averaged 2.17 +/- 0.42 g/100 ml (SEM) before dialysis and 2.87 +/- 0.52 g/100 ml after dialysis (NS). Reduced glutathione (GSH) levels were also measured as an index of red cell oxidant damage. GSH decreased from a mean of 7.40 +/- 0.59 micromoles/g Hb before dialysis to 6.98 +/- 0.52 micronmoles/g Hb after dialysis (P less than 0.01). In 2 patients there was no change in 51Cr red cell survival when dialyzed on either the proportioning system or other chloramine free systems. We conclude that addition of ascorbic acid to neutralize chloramines in tap water is also effective when using the proportioning dialysis delivery system.

Adult↗
PubMedDate not supplied

Formation of free cyanide and cyanogen chloride from chloramination of publicly owned treatment works secondary effluent: laboratory study with model compounds.

The potential generation of cyanide species in wastewater upon chlorination in the presence of residual ammonia (resulting in chloramine formation) was investigated in experiments with synthetic solutions and publicly owned treatment works (POTW) secondary effluent. This study demonstrated that low concentrations (approximately 5 to 25 microg/L as cyanide) of cyanogen chloride (CNCI), a highly toxic cyanide species not measured in total or free cyanide analyses, could be detected as a result of chloramination reactions in POTW secondary effluent. The potential for chloramination of nitrogen-bearing organic compounds to yield CNCl and/or free cyanide was demonstrated in experiments with synthetic solutions spiked with selected precursor organics: L-serine, benzene, catechin, and humic acid. The amino acid L-serine yielded the largest concentrations of CNCI upon chloramination. Additionally, detectable cyanide (approximately 10 microg/L) was observed in solutions of L-serine and in POTW secondary effluent that was chloraminated followed by dechlorination to prevent destruction of any free cyanide produced. Thus, chlorination of POTW secondary effluent containing residual ammonia can lead to chloramination of organic compounds and the resulting production of CNCl and free cyanide.

Ammonia↗
PubMed1994

Differential inactivation of rabbit and yeast triosephosphate isomerase: effect of oxidations produced by chloramine-T.

Triosephosphate isomerase from rabbit has 5 Cys and 2 Met, while triosephosphate isomerase from yeast has 2 Cys (present in the rabbit enzyme in equivalent positions) and no Met. Since chloramine-T oxidizes Cys and Met, we determined the effect it has on the activity and structure of both enzymes. The activity of triosephosphate isomerase from rabbit was more sensitive to chloramine-T than that of the yeast enzyme (under conditions where the rabbit isomerase was completely inactive, the yeast enzyme exhibited approximately 50% activity). An initial effect of chloramine-T on triosephosphate isomerase was the oxidation of Cys and the formation of catalytically active acidic isoforms. For the yeast isomerase, the two processes were slower. Our data suggest that oxidation of Cys 126, which is conserved in all of the studied species, does not abolish catalysis. Chloramine-T also oxidized the two Met of the rabbit enzyme. At ratios of 50 chloramine-T/monomer, circular dichroism studies showed that the rabbit enzyme, but not that from yeast, underwent extensive alterations of tertiary and secondary structures. This was accompanied by formation of stable dimers, whose cross-linking was not through disulfide bonds. Studies of dimer formation at various enzyme concentrations showed that cross-linking was between monomers of the same dimer. Under conditions that led to cross-linking, rabbit triosephosphate isomerase took up 2.7 mol of 3H from NaB3H4/mol dimer, and the yeast enzyme incorporated only 0.4 mol of 3H. Thus cross-linking was most likely via a Schiff base. The results revealed the points whose modification caused inactivation of the rabbit enzyme.

Animals↗
PubMed1991

Atopic allergy to chloramine-T and the demonstration of specific IgE antibodies by the radioallergosorbent test.

Chloramine-T is a small molecular oxidizing agent that has been widely used as a disinfectant since the beginning of this century. It is generally used in a 5% solution but it is also supplied in powder form. Sporadic case reports of immediate-type sensitization to this agent associated with symptoms of asthma, rhinitis and urticaria have appeared during recent decades. In one of the reports, specific IgE antibodies in sera of four patients who developed asthmatic symptoms after exposure to chloramine-T were demonstrated using a radioimmuno-assay. Three cases of bronchial asthma in workers who had handled chloramine-T powder are described in the present report. Positive skin-prick test reactions to chloramine-T were observed and specific IgE antibodies to human serum albumin treated with chloramine-T were detected using the classic radioallergosorbent (RAST) technique in all three patients.

Adult↗
PubMed2005

A sensitive and selective assay for chloramine production by myeloperoxidase.

We describe a new assay for the chlorination activity of myeloperoxidase and detection of chloramines. Chloramines were detected by using iodide to catalyze the oxidation of either 3,3',5,5'-tetramethylbenzidine (TMB) or dihydrorhodamine to form strongly absorbing or fluorescent products, respectively. With TMB as little as 1 muM taurine chloramine could be detected. The sensitivity of the dihydrorhodamine assay was about 10-fold greater. The chlorination activity of myeloperoxidase was measured by trapping hypochlorous acid with taurine and subsequently using iodide to promote the oxidation reactions of the accumulated taurine chloramine. A similar approach was used to detect hypochlorous acid production by stimulated human neutrophils. Iodide-dependent catalysis distinguished N-chloramines from N-bromamines. This allows for discrimination between heme peroxidases that generate either hypochlorous acid or hypobromous acid. The assay has distinct advantages over existing assays for myeloperoxidase with regard to sensitivity, specificity, and its ease and versatility of use.

Benzidines↗
PubMed2002

Hydrogen peroxide-induced apoptosis of HL-60 human leukemia cells is mediated by the oxidants hypochlorous acid and chloramines.

We set out to identify whether HOCl, which is generated from H(2)O(2) /MPO/Cl(-), is a proximal mediator of H(2)O(2) programmed cell death in the HL-60 human leukemia cell. We found that authentic HOCl induces apoptosis in the HL-60 cell. Both the addition of methionine, an HOCl scavenger, and the removal of Cl(-) from the medium to prevent the formation of HOCl inhibited H(2)O(2)-induced apoptosis. HL-60 cells underwent apoptosis when exposed to HOCl in full medium, which gives rise to chloramines by the reaction of HOCl with amine groups, but not by HOCl in the amine-free HBSS, in which HOCl but not chloramines can be detected. Authentic chloramines induced apoptosis in this cell line in a concentration-dependent manner and at concentrations lower than HOCl. Full medium exposed to HOCl for 24 h would support methionine noninhibitable apoptosis, but did not react with 2-nitro-5-thiobenzoic acid (TNB), raising the possibility that the final inducer is a nonoxidant formed from HOCl and chloramines. We conclude that the signal for apoptosis induced by H(2)O(2) in the MPO-containing HL-60 cell involves the reaction of the diffusible oxidant HOCl with amines producing chloramines and a subsequent non-TNB-reactive product.

Apoptosis↗
PubMed2003

Two simple methods for the estimation of albendazole and its dosage forms using chloramine-T.

Two simple, rapid and reliable methods for the determination of albendazole are described. Both methods involve the use of chloramine-T as the oxidimetric reagent. In the titrimetric method, a known excess of chloramine-T is added to an acidified solution of sample, and after a specified time, the residual oxidant is determined iodometrically. Spectrophotometric procedure also involves the addition of a measured excess of chloramine-T in buffer medium of pH 2.70+/-0.1 and after the reaction is ensured to be complete, the surplus oxidant is determined by a well established colour reaction involving metol and primary arylamine that results in charge-transfer complex measurable at 520 nm. In both methods, the amount of chloramine-T corresponds to the drug content. Reaction conditions were examined and optimised. Titrimetry is based on a 1:3 stoichiometric reaction between albendazole and chloramine-T and is applicable in the range of 1-15 mg. In spectrophotometry, the absorbance was found to decrease linearly with increasing concentration of albendazole, which is corroborated by the calculated correlation coefficient value of -0.9998. The system obeys Beer's law for 2.5-25 microg x ml(-1) of albendazole. The molar absorptivity and Sandell sensitivity were calculated to be 6.24 x 10(3) l mol(-1) cm(-1) and 42.54 ng cm(-2), respectively. The limits of detection and quantification were calculated to be 1.15 and 3.83 microg x ml(-1), respectively. The proposed methods were successfully applied to the determination of albendazole in commercially available dosage forms. The reliability of the assays was established by parallel determination by the official method and recovery studies.

Albendazole↗
PubMed2001

Improved radioiodination of biomolecules using exhaustive Chloramine-T oxidation.

To improve standardization in analytical reagents we investigated Chloramine-T radioiodination (125I) of several biomolecules based on the use of a single amount of the oxidizing agent Chloramine-T as the limiting reagent being exhausted during the course of the reaction. Whenever the labeling yield resulted in less than one atom 125I/molecule, a second amount of the oxidizing agent was added. Thereafter, the integrity of the various biomolecules was assessed using radioimmunoassays, radioreceptor binding assays, or radioimmunometric assays. Purification yields were done by gel permeation (56% +/- 19%, n=230) or by precipitation with trichloroacetic acid (59% +/- 19%, n=230). Specific activity (117 +/- 61 MBq/nmol) and the degree of iodine incorporation (1.4 +/- 0.8 atoms of 125I/molecule) were achieved after 300 sec of incubation. A second addition of Chloramine-T resulted in an increased labeling yield of all biomolecules tested by a mean factor of 1.8 +/- 0.9. After the second addition of Chloramine-T, we observed for some biomolecules a significant (p<0.001) decreased effect in biological performance. In conclusion, the use of Chloramine-T as a limiting reagent resulted in molecules with appropriate immunological and biological performance. In general, tracers were minimally damaged and assessment of the shelf life as well as storing conditions showed the usefulness of the standardization of biomolecule labeling.

Animals↗
PubMed1996

Chloramine removal from water used in hemodialysis.

Several outbreaks of hemolysis in hemodialysis patients have occurred when chloramines in the public water supply have not been adequately removed by the dialysis unit's water purification system. Chloramines are not removed by reverse osmosis or deionization, and need to be either adsorbed by filtration through granular activated carbon (GAC) or neutralized by chemical reduction by ascorbic acid (vitamin C) added to the dialysate. Chloramine levels in the incoming water can fluctuate unpredictably, and failures of both systems have occurred when chloramines have exhausted their capacity. The medical and technical issues associated with both methods are explored in detail. Safety depends on critical care in the design of the system and rigorous testing more than once daily. Most dialysis units now depend on GAC filters, two of which should be placed in series so that chloramine breakthrough can be detected after the first one, before the second one fails. Comprehensive standards in force in California have not yet been applied universally.

Blood↗