Evaluation of oxidation and glyco-oxidation of 1-palmitoyl-2-arachidonoyl-phosphatidylserine by LC–MS/MS

Maciel, Elisabete; Faria, R.; Santinha, Deolinda; Domingues, M. Rosário M.; Domingues, Pedro

doi:10.1016/j.jchromb.2013.04.009

Cited by 15 publications

(39 citation statements)

References 38 publications

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“…To observe whether PS polar head-group oxidation occurred in HaCaT cells after AAPH incubation, as observed after radical oxidation of PS by hydroxyl radical [10,25], cells were subjected to oxidation with AAPH (30 and 50 mM). The oxidative stimuli used were the same as reported in a previous study that mimicked oxidative stress injury in keratinocytes as a model of inflammation [18].…”

Section: Resultsmentioning

confidence: 99%

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

Maciel

Neves

Santinha

et al. 2014

Archives of Biochemistry and Biophysics

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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

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Section: Resultsmentioning

confidence: 99%

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

Maciel

Neves

Santinha

et al. 2014

Archives of Biochemistry and Biophysics

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“…Adduction of glucose to the polar head with or without further oxidation of the adduct (glycation and glyco‐oxidation) (Ravandi et al, ; Ravandi et al, ; Requena et al, ; Lertsiri et al, ; Pamplona et al, ; Fountain et al, ; Breitling‐Utzmann et al, ; Nakagawa, ; Shoji et al, ; Simões et al, ; Sookwong et al, ; Maciel et al, ,; Annibal et al, );…”

Section: Chemistry Of Apl Modificationsmentioning

confidence: 99%

“…This cleavage leads to the formation of esterified aldehydes, keto‐aldehydes, hydroxy‐aldehydes, carboxylic acids, keto‐carboxylic acids, and hydroxy‐carboxylic acids, named short chain oxidation products (Fig. ) (Gugiu et al, ; Domingues et al, ; Maciel et al, ). When radical‐radical reactions occur, in some cases due to antioxidant molecules, the radical‐based oxidation process reaches the termination phase (Wefers and Sies, ; Tadolini et al, ).…”

Section: Chemistry Of Apl Modificationsmentioning

confidence: 99%

“…The amino group present in the polar head of APL is reactive toward electrophilic moieties as carbonyl groups. In fact, several published works mentioned the reactivity of the amino groups of PE and PS towards glucose and the consequent formation of glycated APL (Ravandi et al, ; Ravandi et al, ; Lertsiri et al, ; Oak et al, ; Nakagawa, ; Simões et al, ; Sookwong et al, ; Maciel et al, ,; Melo et al, ; Annibal et al, ). APL glycation occurs via reaction between the amino group of the APL polar heads and the carbonyl moiety of glucose, initially leading to a Schiff‐base derivative which promptly establishes an equilibrium with the Amadori ketoamine (Simões et al, ; Annibal et al, ).…”

Section: Chemistry Of Apl Modificationsmentioning

confidence: 99%

“…Glycated APL can be further modified if radical driven oxidation occurs during or after the glycation. Both the Schiff‐base and the Amadori derivatives were found to undergo oxidation on the fatty acyl chains and the glycated polar heads when ROS were present, in a process that is identified as glyco‐oxidation, and leads to the production of AGE of APL (Simões et al, ; Melo et al, ; Maciel et al, ,; Simões et al, ; Annibal et al, ). When the radical mechanism involves the polar head glycated as Schiff base, the hydrogen atom on the methylene adjacent to the imine bond is abstracted, leading to peroxyl and alkoxyl radicals.…”

Section: Chemistry 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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Evaluation of oxidation and glyco-oxidation of 1-palmitoyl-2-arachidonoyl-phosphatidylserine by LC–MS/MS

Cited by 15 publications

References 38 publications

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

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

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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