Advancing Target Identification of Nitrated Phospholipids in Biological Systems by HCD Specific Fragmentation Fingerprinting in Orbitrap Platforms

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2020 May 7

PMID 32369981

Citations 5

Authors

Bruna Neves

Sofia Duarte

Pedro Domingues

Dolores Perez-Sala

Maria Manuel Oliveira

Maria do Rosario Domingues

Tania Melo

Affiliations

Soon will be listed here.

Abstract

Nitrated phospholipids have recently been detected and and associated with beneficial health effects. They were identified and quantified in biological samples by lipidomics methodologies using liquid chromatography-collision-induced dissociation (CID) tandem mass spectrometry (MS/MS) acquired with the linear ion trap mass spectrometer. Only a few studies have used higher-energy collision dissociation (HCD)-MS/MS in high-resolution Orbitraps to characterize nitrated phosphatidylserines and nitrated cardiolipins, highlighting the marked differences in the fragmentation patterns when using CID or HCD fragmentation methods. In this study, we aimed to evaluate the fragmentation of nitrated phosphatidylcholine and nitrated phosphatidylethanolamine species under HCD-MS/MS. We studied the effect of normalized collision energy (NCE) in the fragmentation pattern to identify the best acquisition conditions and reporter ions to detect nitrated phospholipids. The results showed that the intensity of the typical neutral loss of nitrous acid (HNO) diminishes with increasing NCE, becoming non-detectable for a higher NCE. Thus, the loss of HNO could not be the most suitable ion/fragment for the characterization of nitrated phospholipids under HCD. In HCD-MS/MS new fragment ions were identified, corresponding to the nitrated fatty acyl chains, NO-RCOO, (NO-RCOOH-HO + H), and (NO-RCOOH + H), suggested as potential reporter ions to detect nitrated phospholipids when using the HCD-MS/MS lipidomics analysis.

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References

Melo T, Marques S, Ferreira I, Cruz M, Domingues P, Segundo M . New Insights into the Anti-Inflammatory and Antioxidant Properties of Nitrated Phospholipids. Lipids. 2018; 53(1):117-131. DOI: 10.1002/lipd.12007. View

WEINMAN E, CHAIKOFF I, ENTENMAN C, DAUBEN W . Turnover rates of phosphate and fatty acid moieties of plasma phospholipids. J Biol Chem. 1950; 187(2):643-9. View

Hinneburg H, Stavenhagen K, Schweiger-Hufnagel U, Pengelley S, Jabs W, Seeberger P . The Art of Destruction: Optimizing Collision Energies in Quadrupole-Time of Flight (Q-TOF) Instruments for Glycopeptide-Based Glycoproteomics. J Am Soc Mass Spectrom. 2016; 27(3):507-19. PMC: 4756043. DOI: 10.1007/s13361-015-1308-6. View

Schopfer F, Khoo N . Nitro-Fatty Acid Logistics: Formation, Biodistribution, Signaling, and Pharmacology. Trends Endocrinol Metab. 2019; 30(8):505-519. PMC: 7121905. DOI: 10.1016/j.tem.2019.04.009. View

Neves B, Domingues P, Oliveira M, Domingues M, Melo T . Profile of Phosphatidylserine Modifications under Nitroxidative Stress Conditions Using a Liquid Chromatography-Mass Spectrometry Based Approach. Molecules. 2019; 24(1). PMC: 6337642. DOI: 10.3390/molecules24010107. View

Perez-Sala D, Oeste C, Martinez A, Carrasco M, Garzon B, Canada F . Vimentin filament organization and stress sensing depend on its single cysteine residue and zinc binding. Nat Commun. 2015; 6:7287. PMC: 4458873. DOI: 10.1038/ncomms8287. View

Wang M, Wang C, Han R, Han X . Novel advances in shotgun lipidomics for biology and medicine. Prog Lipid Res. 2015; 61:83-108. PMC: 4733395. DOI: 10.1016/j.plipres.2015.12.002. View

Milic I, Griesser E, Vemula V, Ieda N, Nakagawa H, Miyata N . Profiling and relative quantification of multiply nitrated and oxidized fatty acids. Anal Bioanal Chem. 2015; 407(19):5587-602. DOI: 10.1007/s00216-015-8766-3. View

Han X, Gross R . Shotgun lipidomics: electrospray ionization mass spectrometric analysis and quantitation of cellular lipidomes directly from crude extracts of biological samples. Mass Spectrom Rev. 2004; 24(3):367-412. DOI: 10.1002/mas.20023. View

10.

Chiva C, Sabido E . HCD-only fragmentation method balances peptide identification and quantitation of TMT-labeled samples in hybrid linear ion trap/orbitrap mass spectrometers. J Proteomics. 2013; 96:263-70. DOI: 10.1016/j.jprot.2013.11.013. View

11.

Pluskal T, Castillo S, Villar-Briones A, Oresic M . MZmine 2: modular framework for processing, visualizing, and analyzing mass spectrometry-based molecular profile data. BMC Bioinformatics. 2010; 11:395. PMC: 2918584. DOI: 10.1186/1471-2105-11-395. View

12.

Jones L . Chemistry and biology of biomolecule nitration. Chem Biol. 2012; 19(9):1086-92. DOI: 10.1016/j.chembiol.2012.07.019. View

13.

Lima E, Di Mascio P, Rubbo H, Abdalla D . Characterization of linoleic acid nitration in human blood plasma by mass spectrometry. Biochemistry. 2002; 41(34):10717-22. DOI: 10.1021/bi025504j. View

14.

Melo T, Domingues P, Ferreira R, Milic I, Fedorova M, Santos S . Recent Advances on Mass Spectrometry Analysis of Nitrated Phospholipids. Anal Chem. 2016; 88(5):2622-9. DOI: 10.1021/acs.analchem.5b03407. View

15.

Almeida R, Pauling J, Sokol E, Hannibal-Bach H, Ejsing C . Comprehensive lipidome analysis by shotgun lipidomics on a hybrid quadrupole-orbitrap-linear ion trap mass spectrometer. J Am Soc Mass Spectrom. 2014; 26(1):133-48. DOI: 10.1007/s13361-014-1013-x. View

16.

Rubbo H, Trostchansky A, ODonnell V . Peroxynitrite-mediated lipid oxidation and nitration: mechanisms and consequences. Arch Biochem Biophys. 2008; 484(2):167-72. DOI: 10.1016/j.abb.2008.11.007. View

17.

BLIGH E, Dyer W . A rapid method of total lipid extraction and purification. Can J Biochem Physiol. 1959; 37(8):911-7. DOI: 10.1139/o59-099. View

18.

Anjos S, Feiteira E, Cerveira F, Melo T, Reboredo A, Colombo S . Lipidomics Reveals Similar Changes in Serum Phospholipid Signatures of Overweight and Obese Pediatric Subjects. J Proteome Res. 2019; 18(8):3174-3183. DOI: 10.1021/acs.jproteome.9b00249. View

19.

Colombo S, Melo T, Martinez-Lopez M, Carrasco M, Domingues M, Perez-Sala D . Phospholipidome of endothelial cells shows a different adaptation response upon oxidative, glycative and lipoxidative stress. Sci Rep. 2018; 8(1):12365. PMC: 6097988. DOI: 10.1038/s41598-018-30695-0. View

20.

Koivusalo M, Haimi P, Heikinheimo L, Kostiainen R, Somerharju P . Quantitative determination of phospholipid compositions by ESI-MS: effects of acyl chain length, unsaturation, and lipid concentration on instrument response. J Lipid Res. 2001; 42(4):663-72. View