Hypochlorous acid and nitrite react to nitryl chloride (NO2Cl)

Stable Identifier
R-HSA-6788974
Type
Reaction [transition]
Species
Homo sapiens
Compartment
phagocytic vesicle lumen
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Hypochlorous acid and nitrite react to nitryl chloride (NO2Cl)
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Nitrated and chlorinated proteins were found in bacteria phagocytosed by polymorphonuclear cells, suggesting a host–defense mechanism mediated by reactive nitrogen and chlorine species (Evans TJ et al. 1996; Hazen SL et al. 1996). Hypochlorous acid (HOCl) was shown to react with nitrite NO2(-) to form nitryl chloride (NO2Cl) (Eiserich JP et al. 1996). NO2Cl formation by activated human neutrophils in the presence of added NO2(-) has been also demonstrated (Eiserich JP et al. 1998). The addition of HOCl to isolated DNA or cells in the presence of NO2(-) results in increased cytosine chlorination and DNA oxidation compared with DNA or cells in the absence ofadded NO2(-) (Whiteman M et aal. 1999; Spencer JP et al. 2000). NO2Cl was also capable of nitrating, chlorinating, and dimerizing phenolic compounds such as tyrosine (Jacob JS et al. 1996; Eiserich JP et al. 1996, 1998). These studies have emphasized the potential toxic effects of nitrite and HOCl-reaction products. However, NO2(-) has also been reported to inhibit the antimicrobial activity of HOCl and MPO (van Dalen CJ et al. 2000;Marcinkiewicz J et al. 2000).

Literature References
PubMed ID Title Journal Year
8702599 Formation of nitrating and chlorinating species by reaction of nitrite with hypochlorous acid. A novel mechanism for nitric oxide-mediated protein modification

Eiserich, JP, Cross, CE, Jones, AD, Halliwell, B, van der Vliet, A

J. Biol. Chem. 1996
9450756 Formation of nitric oxide-derived inflammatory oxidants by myeloperoxidase in neutrophils

Eiserich, JP, Hristova, M, Cross, CE, Jones, AD, Freeman, BA, Halliwell, B, van der Vliet, A

Nature 1998
Participants
Input
Output
Participant Of
hasEvent
Authored
Shamovsky, V  (2018-10-23)
Reviewed
Nüsse, O  (2018-11-07)
Created
Shamovsky, V  (2015-07-29)