Detection of phosphatidylserine with a modified polar head group in human keratinocytes exposed to the radical generator AAPH

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Phosphatidylserine (PS) is preferentially located in the inner leaflet of the cell membrane, and translocation of PS oxidized in fatty acyl chains to the outside of membrane has been reported as signaling to macrophage receptors to clear apoptotic cells. It was recently shown that PS can be oxidized in serine moiety of polar head-group. In the present work, a targeted lipidomic approach was applied to detecting OxPS modified at the polar head-group in keratinocytes that were exposed to the radical generator AAPH. Glycerophosphoacetic acid derivatives (GPAA) were found to be the major oxidation products of OxPS modified at the polar head-group during oxidation induced by AAPH-generated radicals, similarly to previous observations for the oxidation induced by OH radical. The neutral loss scan of 58Da and a novel precursor ion scan of m/z 137.1 (HOPO3CH2COOH) allowed the recognition of GPAA derivatives in the total lipid extracts obtained from HaCaT cells treated with AAPH. The positive identification of serine head group oxidation products in cells under controlled oxidative conditions opens new perspectives and justifies further studies in other cellular environments in order to understand fully the role of PS polar head-group oxidation in cell homeostasis and disease.


  • Detection of phosphatidylserine with a modified polar head group

    Rights statement: NOTICE: this is the author’s version of a work that was accepted for publication in Archives of biochemistry and biophysics. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Maciel, E, Neves, BM, Santinha, D, Reis, A, Domingues, P, Cruz, MT, Pitt, AR, Spickett, CM & Domingues, MRM, 'Detection of phosphatidylserine with a modified polar head group in human keratinocytes exposed to the radical generator AAPH' Archives of biochemistry and biophysics, vol. 548 (2014) DOI

    Accepted author manuscript, 763 KB, PDF-document


Original languageEnglish
Pages (from-to)38–45
Number of pages8
JournalArchives of Biochemistry and Biophysics
Early online date20 Feb 2014
Publication statusPublished - 15 Apr 2014


  • phosphatidylserine, keratinocytes, AAPH, oxidative stress, mass spectrometry, shotgun lipidomic

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