Liquid chromatography–tandem mass spectrometry of phosphatidylserine advanced glycated end products

Maciel, Elisabete; Silva, Raquel Nunes da; Simões, Cláudia; Melo, Tânia; Ferreira, Rita; Domingues, Pedro; Domingues, M. Rosário M.

doi:10.1016/j.chemphyslip.2013.05.005

Cited by 11 publications

(29 citation statements)

References 27 publications

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“…Recently, there have been studies on detection of oxidized PS by targeted MS approaches (70,71,131,135). 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).…”

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

101

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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%

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

Spickett

Pitt

2015

Antioxidants & Redox Signaling

101

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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%

“…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%

“…APL are prone to be modified by oxidation (Domingues et al, ; Simões et al, ; Maciel et al, ; Melo et al, ), glycation (Simões et al, ; Maciel et al, ; Melo et al, ; Annibal et al, ), and reactive molecules such as electrophilic aldehydes (Bernoud‐Hubac et al, ; Bacot et al, ). These changes in native APL may occur under physiological and pathological conditions through non‐enzymatic reactions with reactive oxygen species (ROS), glucose, and other carbonyl compounds, or through enzyme‐catalyzed reactions, generating a vast number of differently modified derivatives which display several biological functions.…”

Section: Introductionmentioning

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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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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Liquid chromatography–tandem mass spectrometry of phosphatidylserine advanced glycated end products

Cited by 11 publications

References 27 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

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

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