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

Maciel, Elisabete; Neves, Bruno Miguel; Santinha, Deolinda; Reis, Ana; Domingues, Pedro; Cruz, Maria Teresa; Pitt, Andrew R.; Spickett, Corinne M.; Domingues, M. Rosário M.

doi:10.1016/j.abb.2014.02.002

Cited by 20 publications

(21 citation statements)

References 36 publications

(43 reference statements)

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“…Lipids containing the phosphoserine headgroup can be selectively detected by a neutral loss of 87 amu, and this has been applied for the detection of native PSs and PSs containing an oxidized fatty acyl chain (72). However, it has also been observed that the amine moiety of the headgroup is susceptible to oxidation, leading to formation of glycerophosphoacetic acid (GPAA).…”

Section: Application Of Targeted Ms Methods For Oxidized Phospholipidsmentioning

confidence: 99%

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Oxidative Lipidomics Coming of Age: Advances in Analysis of Oxidized Phospholipids in Physiology and Pathology

Spickett

Pitt

2015

Antioxidants & Redox Signaling

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Significance: Oxidized phospholipids are now well recognized as markers of biological oxidative stress and bioactive molecules with both pro-inflammatory and anti-inflammatory effects. While analytical methods continue to be developed for studies of generic lipid oxidation, mass spectrometry (MS) has underpinned the advances in knowledge of specific oxidized phospholipids by allowing their identification and characterization, and it is responsible for the expansion of oxidative lipidomics. Recent Advances: Studies of oxidized phospholipids in biological samples, from both animal models and clinical samples, have been facilitated by the recent improvements in MS, especially targeted routines that depend on the fragmentation pattern of the parent molecular ion and improved resolution and mass accuracy.

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Section: Application Of Targeted Ms Methods For Oxidized Phospholipidsmentioning

confidence: 99%

“…Alternative selective scanning procedures for this modification to the head group have been reported, involving a neutral loss of 58 amu or scanning for precursor ions of m/z 137.1, and used to detect PS oxidation in keratinocytes subjected to radical oxidation in vitro (Fig. 9) (72).…”

Section: Application Of Targeted Ms Methods For Oxidized Phospholipidsmentioning

confidence: 99%

Oxidative Lipidomics Coming of Age: Advances in Analysis of Oxidized Phospholipids in Physiology and Pathology

Spickett

Pitt

2015

Antioxidants & Redox Signaling

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“…These modifications were observed for the first time in a study in which oxidation of PS was carried out in vitro through the Fenton reaction (Maciel et al, ). Later on, the oxidation of PS polar head to terminal acetic acid was found to occur in human keratinocytes treated with AAPH (Maciel et al, ). Similarly, in vitro irradiation of PE standards with white light in the presence of cationic porphyrins as photosensitizers (photo‐oxidation) led to oxidative deamination of the ethanolamine group, with the generation of the polar head modified as terminal acetaldehyde (Fig.…”

Section: Chemistry Of Apl Modificationsmentioning

confidence: 99%

“…The structural characterization of APL bearing an oxidized polar head group is a poorly explored topic that should deserve more attention. These molecules were found to be pro‐inflammatory factors in peripheral blood (Silva et al, ) and were detected in keratinocytes treated with the oxidant AAPH (Maciel et al, ). APL oxidative modifications of the polar head were characterized by negative ion mode MS/MS for ox‐PS.…”

Section: Ms‐based Strategies For the Analysis Of Apl Modificationsmentioning

confidence: 99%

“…Maciel et al () reported a PIS approach for the detection of ox‐PS derivatives in keratinocytes subjected to in vitro radical oxidation with AAPH. The authors studied the fragmentation of ox‐PS with polar head modified as GPAA (Figures A and ) by MS/MS in negative ion mode, observing the formation of the reporter ion at m/z 137.1 (HOPO 3 CH 2 COO ‐ ).…”

Section: Ms‐based Strategies For the Analysis Of Apl Modificationsmentioning

confidence: 99%

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Mass spectrometry strategies to unveil modified aminophospholipids of biological interest

Colombo

Domingues

2018

Mass Spectrometry Reviews

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The biological functions of modified aminophospholipids (APL) have become a topic of interest during the last two decades, and distinct roles have been found for these biomolecules in both physiological and pathological contexts. Modifications of APL include oxidation, glycation, and adduction to electrophilic aldehydes, altogether contributing to a high structural variability of modified APL. An outstanding technique used in this challenging field is mass spectrometry (MS). MS has been widely used to unveil modified APL of biological interest, mainly when associated with soft ionization methods (electrospray and matrix‐assisted laser desorption ionization) and coupled with separation techniques as liquid chromatography. This review summarizes the biological roles and the chemical mechanisms underlying APL modifications, and comprehensively reviews the current MS‐based knowledge that has been gathered until now for their analysis. The interpretation of the MS data obtained by in vitro‐identification studies is explained in detail. The perspective of an analytical detection of modified APL in clinical samples is explored, highlighting the fundamental role of MS in unveiling APL modifications and their relevance in pathophysiology.

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The non‐enzymatic oxidation of phosphatidylethanolamine and phosphatidylserine and their intriguing roles in inflammation dynamics and diseases

Santos,

Melo,

Maurício

et al. 2024

FEBS Letters

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Phosphatidylethanolamine (PE) and phosphatidylserine (PS), along with phosphatidylcholine (PC), are key phospholipids (PL) in cell membranes and lipoproteins, prone to oxidative modifications. Their oxidized forms, OxPE and OxPS, play significant roles in inflammation and immune response. This review explores their structural oxidative changes under non‐enzymatic conditions and their roles in physiological and pathological contexts, influencing inflammation, and immunity. Specific oxidations of PE and PS significantly alter their physicochemical properties, leading to enhanced biological functions, reduced activity, or inactivation. OxPE may show pro‐inflammatory actions, similar to well‐documented OxPC, while the OxPS pro‐inflammatory effects are less noted. However, OxPS and OxPE have also shown an antagonistic effect against lipopolysaccharides (LPS), suggesting a protective role against exacerbated immune responses, similar to OxPC. Further research is needed to deepen our understanding of these less‐studied OxPL classes. The role of OxPE and OxPS in disease pathogenesis remains largely unexplored, with limited studies linking them to Alzheimer's disease, diabetes, rheumatoid arthritis, traumatic brain injury, and skin inflammation. These findings highlight the potential of OxPE and OxPS as biomarkers for disease diagnosis, monitoring, and therapeutic targeting.

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

Cited by 20 publications

References 36 publications

Oxidative Lipidomics Coming of Age: Advances in Analysis of Oxidized Phospholipids in Physiology and Pathology

Oxidative Lipidomics Coming of Age: Advances in Analysis of Oxidized Phospholipids in Physiology and Pathology

Mass spectrometry strategies to unveil modified aminophospholipids of biological interest

The non‐enzymatic oxidation of phosphatidylethanolamine and phosphatidylserine and their intriguing roles in inflammation dynamics and diseases

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