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Protein modifications by electrophilic lipoxidation products: Adduct formation, chemical strategies and tandem mass spectrometry for their detection and identification

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  • The post-translational modification of proteins by electrophilic oxylipids is emerging as an important mechanism that contributes to the complexity of proteomes. Enzymatic and non-enzymatic oxidation of biological lipids results in the formation of chemically diverse electrophilic carbonyl compounds, such as 2-alkenals and 4-hydroxy alkenals, epoxides and eicosanoids with reactive cyclopentenone structures. These lipoxidation products are capable of modifying proteins. Originally considered solely as markers of oxidative insult, more recently the modifications of proteins by lipid peroxidation products are being recognized as a new mechanism of cell signaling with relevance to redox homeostasis, adaptive response and inflammatory resolution. The growing interest in protein modifications by reactive oxylipid species necessitates the availability of methods that are capable of detecting, identifying and characterizing these protein adducts in biological samples with high complexity. However, the efficient analysis of these chemically diverse proteins presents a considerable analytical challenge. We first provide an introduction into the chemistry and biological relevance of the protein adduction by electrophilic lipoxidation products. We then provide an overview of tandem mass spectrometry approaches that have been developed in recent years for the interrogation of protein modifications by electrophilic oxylipid species.
  • Keywords: Ion mobility mass spectrometry, Collision induced dissociation, HSAB theory, Electron transfer dissociation, HNE, Electrophilic lipoxidation products, Electron capture dissociation, Aldehyde-reactive probe
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  • Vasil'ev, Y. V., Tzeng, S. C., Huang, L. and Maier, C. S. (2014), Protein modifications by electrophilic lipoxidation products: Adduct formation, chemical strategies and tandem mass spectrometry for their detection and identification. Mass Spectrometry Reviews, 33: 157–182. doi:10.1002/mas.21389
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  • 33
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  • 3
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  • Work described in this contribution was supported by the National Institutes of Health Grants R01AG025372, S10RR025628 and P30ES000210. YVV is supported by the National Science Foundation under Grant No. 0924027, the National Institutes of Health under Grant No. R01RR026275 and a grant from OSU RERF.
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