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Redox properties and human serum albumin binding of nitro-oleic acid

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F68081707%3A_____%2F19%3A00509880" target="_blank" >RIV/68081707:_____/19:00509880 - isvavai.cz</a>

  • Alternative codes found

    RIV/61989592:15110/19:73595256 RIV/60076658:12310/19:43899433

  • Result on the web

    <a href="https://doi.org/10.1016/j.redox.2019.101213" target="_blank" >https://doi.org/10.1016/j.redox.2019.101213</a>

  • DOI - Digital Object Identifier

    <a href="http://dx.doi.org/10.1016/j.redox.2019.101213" target="_blank" >10.1016/j.redox.2019.101213</a>

Alternative languages

  • Result language

    angličtina

  • Original language name

    Redox properties and human serum albumin binding of nitro-oleic acid

  • Original language description

    Nitro-fatty acids modulate inflammatory and metabolic stress responses, thus displaying potential as new drug candidates. Herein, we evaluate the redox behavior of nitro-oleic acid (NO2-OA) and its ability to bind to the fatty acid transporter human serum albumin (HSA). The nitro group of NO2-OA underwent electrochemical reduction at 0.75 V at pH 7.4 in an aqueous milieu. Based on observations of the R-NO2 reduction process, the stability and reactivity of NO2-OA was measured in comparison to oleic acid (OA) as the negative control. These electrochemically-based results were reinforced by computational quantum mechanical modeling. DFT calculations indicated that both the C9-NO2 and C10-NO2 positional isomers of NO2-OA occurred in two conformers with different internal angles (69 degrees and 110 degrees) between the methyl- and carboxylate termini. Both NO2-OA positional isomers have LUMO energies of around 0.7 eV, affirming the electrophilic properties of fatty acid nitroalkenes. In addition, the binding of NO2-OA and OA with HSA revealed a molar ratio of similar to 7:1 [NO2-OA]: [HSA]. These binding experiments were performed using both an electrocatalytic approach and electron paramagnetic resonance (EPR) spectroscopy using 16-doxyl stearic acid. Using a Fe(DTCS)(2) spin-trap, EPR studies also showed that the release of the nitro moiety of NO2OA resulted in the formation of nitric oxide radical. Finally, the interaction of NO2-OA with HSA was monitored via Tyr and Trp residue electro-oxidation. The results indicate that not only non-covalent binding but also NO2-OA-HSA adduction mechanisms should be taken into consideration. This study of the redox properties of NO2-OA is applicable to the characterization of other electrophilic mediators of biological and pharmacological relevance.

  • Czech name

  • Czech description

Classification

  • Type

    J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database

  • CEP classification

  • OECD FORD branch

    10608 - Biochemistry and molecular biology

Result continuities

  • Project

    Result was created during the realization of more than one project. More information in the Projects tab.

  • Continuities

    P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Others

  • Publication year

    2019

  • Confidentiality

    S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Data specific for result type

  • Name of the periodical

    Redox Biology

  • ISSN

    2213-2317

  • e-ISSN

  • Volume of the periodical

    24

  • Issue of the periodical within the volume

    JUN 2019

  • Country of publishing house

    NL - THE KINGDOM OF THE NETHERLANDS

  • Number of pages

    12

  • Pages from-to

    101213

  • UT code for WoS article

    000471255400042

  • EID of the result in the Scopus database