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2015 | 60 | 3 | 475-481
Article title

The acid-catalyzed interaction of melanin with nitrite ions. An EPR investigation

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Abstracts
EN
The interaction of synthetic dihydroxyphenylalanine (DOPA) melanin (DM) with nitrite ions, NO2−, in the pH 3.6–7.0 range, has been investigated using electron paramagnetic resonance (EPR). We found that especially at pH <5.5 (from ca. 5.5 to 3.6) the reaction of DM with nitrite generated large quantities of new melanin radicals, which implies the involvement of nitrous acid, HNO2, in the radical formation process. Measurements carried out at constant pH of 3.6 showed that the melanin signal increased together with nitrite concentration, reaching a plateau level which was more than fourfold larger compared to the initial signal amplitude observed in a nitrite-free buffer of the same pH. The effects of nitrite and DM concentrations on the melanin-free radical content were also investigated. It is proposed that the radicals are generated by one electron oxidation of melanin ortho-hydroquinone groups to ortho-semiquinones by HNO2 or related nitrogen oxides such as NO2• radicals. The possible involvement of nitric oxide (•NO) and peroxynitrite (ONOO−) in DM oxidation was also examined. In air-free solutions, nitric oxide per se did not generate melanin radicals; however, in the presence of oxygen a marked increase in the melanin EPR signal intensity was observed. This result is interpreted in terms of the generation of radicals via the oxidation of DM by peroxynitrite. Our findings suggest that melanin can function as a natural scavenger of nitrous acid and some nitrous acid-derived species. This property may be relevant to physiological functions of melanin pigments in vivo.
Keywords
Publisher
Journal
Year
Volume
60
Issue
3
Pages
475-481
Physical description
Dates
published
1 - 7 - 2015
received
1 - 10 - 2014
accepted
30 - 1 - 2015
online
6 - 8 - 2015
References
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Document Type
Publication order reference
YADDA identifier
bwmeta1.element.-psjd-doi-10_1515_nuka-2015-0084
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