Relative reactivity of lysine and other peptide-bound amino acids to oxidation by hypochlorite

Nightingale, Zachary D; Lancha, Antônio Herbert; Handelman, Samuel K.; Dolnikowski, Gregory G.; Busse, Scott C.; Dratz, Edward A.; Blumberg, Jeffrey B.; Handelman, Garry J.

doi:10.1016/s0891-5849(00)00262-8

Cited by 60 publications

(48 citation statements)

References 33 publications

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“…Laingam et al (2011) studied the ability of the N-chloramines of several amino acids to induce micronuclei in mammalian cells. As suggested by the results of Nightingale et al (2000) with the ε-amino group of lysine, ethanolamine and α-acetyllysine formed significant amounts of dichloramine at equivalent molar concentrations with chlorine, whereas only monochloramines were observed with glycine, ε-acetyllysine, and histidine. Thus, α-amino groups are much less likely to form dichloramines at physiological pH than those which are not adjacent to a carboxyl group.…”

Section: Toxicological Evaluation Of N-halaminesmentioning

confidence: 80%

“…While the initial formation of N-chloramines is more rapid when the amino group is α to a carboxyl function, the formation of the initial N-chloro group on an amine without an α-carboxyl group facilitates addition of the second N-chloro group (Nightingale et al, 2000). As a consequence, the N-chloro groups on the epsilon amino groups of lysine in proteins appear to be responsible for the production of nitrogen-centered free radicals that play a role in inactivation of the proteins (Hawkins and Davies, 1999 …”

Section: Toxicological Evaluation Of N-halaminesmentioning

confidence: 99%

See 1 more Smart Citation

Potential carcinogenic hazards of non-regulated disinfection by-products: Haloquinones, halo-cyclopentene and cyclohexene derivatives, N-halamines, halonitriles, and heterocyclic amines

Bull¹,

et al. 2011

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Drinking water disinfectants react with natural organic material (NOM) present in source waters used for drinking water to produce a wide variety of by-products. Several hundred disinfection by-products (DBPs) have been identified, but none have been identified with sufficient carcinogenic potency to account for the cancer risks projected from epidemiological studies. In a search for DBPs that might fill this risk gap, the present study projected reactions of chlorine and chloramine that could occur with substructures present in NOM to produce novel by-products. A review of toxicological data on related compounds, supplemented by use of a quantitative structure toxicity relationship (QSTR) program TOPKAT® identified chemicals with a high probability of being chronically toxic and/or carcinogenic among 489 established and novel DBPs. Classes of DBPs that were specifically examined were haloquinones (HQs), related halo-cyclopentene and cyclohexene (HCP&H) derivatives, halonitriles (HNs), organic N-chloramines (NCls), haloacetamides (HAMs), and nitrosamines (NAs). A review of toxicological data available for quinones suggested that HQs and HCP&H derivatives appeared likely to be of health concern and were predicted to have chronic lowest observed adverse effect levels (LOAELs) in the low μg/kg day-1 range. Several HQs were predicted to be carcinogenic. Some have now been identified in drinking water. The broader class of HNs was explored by considering current toxicological data on haloacetonitriles and extending this to halopropionitriles. 2,2-Dichloropropionitrile has been identified in drinking water at low concentrations, as well as the more widely recognized haloacetonitriles. The occurrence of HAMs has been previously documented. The very limited toxicological data on HAMs suggests that this class would have toxicological potencies similar to the dihaloacetic acids. Organic N-halamines are also known to be produced in drinking water treatment and have biological properties of concern, but no member has ever been characterized toxicologically beyond bacterial or in vitro studies of genotoxicity. The documented formation of several nitrosamines from secondary amines from both natural and industrial sources prompted exploration of the formation of additional nitrosamines. N-Diphenylnitrosamine was identified in drinking waters. Of more interest, however, was the formation of phenazine (and subsequently N-chorophenazine) in a competing reaction. These are the first heterocyclic amines that have been identified as chlorination by-products. Consideration of the amounts detected of members of these by-product classes and their probable toxicological potency suggest a prioritization for obtaining more detailed toxicological data of HQs > HCP&H derivatives > NCls > HNs. Based upon a ubiquitous occurrence and virtual lack of in vivo toxicological data, NCls are the most difficult group to assign a priority as potential carcinogenic risks. This analysis indicates that research on the general problem of DBPs re...

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Section: Toxicological Evaluation Of N-halaminesmentioning

confidence: 80%

Section: Toxicological Evaluation Of N-halaminesmentioning

confidence: 99%

Potential carcinogenic hazards of non-regulated disinfection by-products: Haloquinones, halo-cyclopentene and cyclohexene derivatives, N-halamines, halonitriles, and heterocyclic amines

Bull¹,

et al. 2011

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“…HOCl and -OCl have been reported to react with a wide variety of biological molecules such as proteins (Hawkins andDavies, 1998 and1999;Hazell et al, 1993 and1994), amino acids (Nightingale et al, 2000), peptides (Heinecke et al, 1993), lipids (Spickett et al, 2000), and DNA (Prutz, 1998) at physiological pH conditions. The CI atom in HOCl and -OCl b ehaves as Cl+, a strong electrophile, and combines with a pair of electrons in parts of the substrate that have high electron densities (Wojtowicz, 1979).…”

Section: Oxidizing Reactionmentioning

confidence: 99%

“…The CI atom in HOCl and -OCl b ehaves as Cl+, a strong electrophile, and combines with a pair of electrons in parts of the substrate that have high electron densities (Wojtowicz, 1979). Among biological molecules, the C=C double bond, peptide bond (amide bond) , amino groups, and thiol groups are susceptible to the electrophilic attack of Cl+ (Nightingale et al, 2000;Pereira et al, 1973;Winterbourn and Brennan, 1997). The CI atom is reduced to the chloride ion (Cl-) as it accepts two electrons.…”

Section: Oxidizing Reactionmentioning

confidence: 99%

Mechanisms of Actions of Sodium Hypochlorite in Cleaning and Disinfection Processes

2006

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Sodium hypochlorite (NaOCI) is the most widely used disinfectant in the food industry despite the increasing availability of other disinfectants.Sodium hypochlorite fulfills many requirements as the ideal disinfectant and furthermore it has an excellent cleaning action. The effectiveness of sodium hypochlorite in the cleaning and disinfection processes depends on the concentration of available chlorine and the pH of the solution. Hypochlorous acid (HOCI) is a weak acid and dissociates to the hypochlorite ion (-OCI) and proton (H+) depending on the solution pH. It is generally believed that HOCI is the active species in the germicidal action, whereas the concentration of -OCI is a key factor determining the cleaning efficiency. This implies that the optimal pH region of the germicidal activity of sodium hypochlorite differs from that of its cleaning activity. This paper describes the theory and practice of the cleaning and disinfecting operations based on the use of sodium hypochlorite solution.

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“…2). Since the UV absorption of HSA at 280 nm is mainly due to the absorption of aromatic amino acids tryptophan (Trp) and tyrosine (Tyr; Peters, 1996), which are subject to oxidation by XOCl (Nightingale et al, 2000;Kettle, 1996), we speculated that the decrease of the AUC of peak 2 in Fig. 2(A-C) was due to the oxidation of these two amino acids.…”

Section: Discussionmentioning

confidence: 99%

Development of a new assay for the screening of hypochlorous acid scavengers based on reversed‐phase high‐performance liquid chromatography

Gatto

Firuzi

Agostino

et al. 2002

Biomedical Chromatography

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A new assay for the screening of hypochlorite/hypochlorous acid (XOCl) scavengers, based on the reversed-phase high performance liquid chromatographic analysis of human serum albumin (HSA, 0.2% in 100 mM sodium phosphate, pH 7), before and after oxidation by XOCl (1.6 mM), was developed. XOCl induced a significant decrease of the area under the chromatographic peak of HSA at 280 nm due to the oxidation of the aromatic amino acids tryptophan and tyrosine, as suggested by the literature and by the chromatographic analyses and the electrochemical study performed here. The assay was validated by testing known XOCl scavengers such as ascorbic acid, cysteine, glutathione, S-methylglutathione and alpha-lipoic acid and other antioxidants such as carnosine and chlorogenic acid, which inhibited the oxidation of HSA. Quantitative activities were calculated using an original formula based on the changes of the area of the albumin peak. Electrochemical data collected here in a homogeneous medium showed that the anodic potentials of the antioxidants tested are less positive (ascorbic acid, chlorogenic acid and cysteine) or similar (alpha-lipoic acid) compared with those of the aromatic residues (tryptophan and tyrosine) of HSA oxidized by XOCl. However, as expected, carnosine, glutathione and S-methylglutathione were inactive at a glassy-carbon, gold or platinum electrode.

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Relative reactivity of lysine and other peptide-bound amino acids to oxidation by hypochlorite

Cited by 60 publications

References 33 publications

Potential carcinogenic hazards of non-regulated disinfection by-products: Haloquinones, halo-cyclopentene and cyclohexene derivatives, N-halamines, halonitriles, and heterocyclic amines

Potential carcinogenic hazards of non-regulated disinfection by-products: Haloquinones, halo-cyclopentene and cyclohexene derivatives, N-halamines, halonitriles, and heterocyclic amines

Mechanisms of Actions of Sodium Hypochlorite in Cleaning and Disinfection Processes

Development of a new assay for the screening of hypochlorous acid scavengers based on reversed‐phase high‐performance liquid chromatography

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