Development of an LC-ESI(-)-MS/MS method for the simultaneous quantification of 35 isoprostanes and isofurans derived from the major n3- and n6-PUFAs

Rund, Katharina M.; Ostermann, Annika I.; Kutzner, Laura; Galano, Jean‐Marie; Oger, Camille; Vigor, Claire; Wecklein, Sabine; Seiwert, Nina; Durand, Thierry; Schebb, Nils Helge

doi:10.1016/j.aca.2017.11.002

Cited by 82 publications

(128 citation statements)

References 54 publications

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“…For example, when Yang et al developed a method for murine sera and BALF oxylipin profiling, for 8, 9 EET the weaker transition 319.2/123 was chosen, because the stronger transition 319.2/167 overlaps with the transition 319.2/167 for 11, 12 EET [101]. Also, to increase the sensibility of the MS method, the optimization of MS operating conditions should be carried out for each individual compound [15,69,103,131,164]. By the careful selection of transitions, it is possible to optimize sensitivity and selectivity so that the overall sensitivity will improve several times [85,101].…”

Section: Lc-ms/msmentioning

confidence: 99%

“…Immunoassay, thin layer chromatography (TLC), HPLC with a diode array or fluorescent detector and capillary electrophoresis with a photodiode array detector were used to analyze oxylipins [13][14][15][16][17][18][19]. However, a very similar structure, limited stability and extremely low concentrations of oxylipins in the tissues impose some restrictions on these methods.…”

Section: Introductionmentioning

confidence: 99%

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Methods of the Analysis of Oxylipins in Biological Samples

et al. 2020

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Oxylipins are derivatives of polyunsaturated fatty acids and due to their important and diverse functions in the body, they have become a popular subject of studies. The main challenge for researchers is their low stability and often very low concentration in samples. Therefore, in recent years there have been developments in the extraction and analysis methods of oxylipins. New approaches in extraction methods were described in our previous review. In turn, the old analysis methods have been replaced by new approaches based on mass spectrometry (MS) coupled with liquid chromatography (LC) and gas chromatography (GC), and the best of these methods allow hundreds of oxylipins to be quantitatively identified. This review presents comparative and comprehensive information on the progress of various methods used by various authors to achieve the best results in the analysis of oxylipins in biological samples.

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Section: Lc-ms/msmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Methods of the Analysis of Oxylipins in Biological Samples

et al. 2020

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“…PGE 2 , 17(R)‐RvD1, and 15(R)‐LXA 4 were quantified in colon tissues by means of LC‐MS/MS as described before . The lower limits of quantification for 17(R)‐RvD1 and 15(R)‐LXA4 were 0.7 and 1 fmol/mg tissue, respectively.…”

Section: Methodsmentioning

confidence: 99%

Effects of chronic low‐dose aspirin treatment on tumor prevention in three mouse models of intestinal tumorigenesis

et al. 2020

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Although early detection and treatment of colorectal cancer (CRC) have improved, it remains a significant health‐care problem with high morbidity and mortality. Data indicate that long‐term intake of low‐dose aspirin reduces the risk of CRC; however, the mechanisms underlying this chemopreventive effect are still unclear. Different mouse models for inflammation‐associated, sporadic, and hereditary CRC were applied to assess the efficacy and mechanism of low‐dose aspirin on tumor prevention. An initial dosing study performed in healthy mice indicates that aspirin at a dose of 25 mg/kg/d has a similar pharmacodynamic effect as low‐dose aspirin treatment in human subjects (100 mg/d). Chronic low‐dose aspirin treatment suppresses colitis‐associated and to a lesser extent spontaneous tumorigenesis in mice. Aspirin's antitumor effect is most pronounced in a preventive approach when aspirin administration starts before the tumor‐initiating genotoxic event and continues for the duration of the experiment. These effects are not associated with alterations in cell proliferation, apoptosis, or activation of signaling pathways involved in CRC. Aspirin‐induced reduction in tumor burden is accompanied by inhibition of thromboxane B2 formation, indicating reduced platelet activation. Aspirin treatment also results in decreased colonic prostaglandin E2 formation and tumor angiogenesis. With respect to colitis‐triggered tumorigenesis, aspirin administration is associated with a reduction in inflammatory activity in the colon, as indicated by decreased levels of pro‐inflammatory mediators, and tumor‐associated iNOS‐positive macrophages. Our results suggest that low‐dose aspirin represents an effective antitumor agent in the context of colon tumorigenesis primarily due to its well‐established cyclooxygenase inhibition effects.

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“…Standards of regioisomeric cis-epoxy-PUFA (mixture of R,S-and S,Renantiomers), isoprostane 15-F 2t -IsoP and the deuterated internal standards (IS) 2 H 4 -15-F 2t -IsoP ( 2 H 4 -8-iso-PGF 2α ), 2 H 11 -5(R,S)-5-F 2t -IsoP ( 2 H 11 -( ± )5-iPF 2a -VI), 2 H 4 -9(10)-EpOME, 2 H 11 -14(15)-EpETrE were purchased from Cayman Chemicals (local distributor: Biomol, Hamburg, Germany). Other IsoP and IsoF standards from the biologically relevant PUFA α-linolenic acid (18:3n3, ALA), ARA, eicosapentaenoic acid (20:5n3, EPA), adrenic acid (22:4n6, AdA), docosapentaenoic acid (22:5n6, DPA n6 ), docosahexaenoic acid (22:6n3, DHA) [27] were synthesized according to our chemical strategies already described in the literature [28][29][30][31][32].…”

Section: Chemicalsmentioning

confidence: 99%

“…HCT-116 human colorectal carcinoma cells, Caki-2 human kidney carcinoma cells and HepG2 human liver carcinoma cells were grown in 10 cm dishes and incubated with 50 μM and 200 μM of t-BOOH (Sigma Aldrich, Schnelldorf, Germany) for 30 min, 1 h and 2 h. The cells were harvested using trypsin as described and the cell pellets were stored at -80°C until analysis [27]. Cell pellets typically contained 5 × 10 6 (HCT-116), 4 × 10 6 (Caki-2) and 20 × 10 6 (HepG2) cells.…”

Section: Cell Culture Assaymentioning

confidence: 99%

Formation of trans-epoxy fatty acids correlates with formation of isoprostanes and could serve as biomarker of oxidative stress

Rund

Heylmann

Seiwert

et al. 2019

Prostaglandins & Other Lipid Mediators

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In mammals, epoxy-polyunsaturated fatty acids (epoxy-PUFA) are enzymatically formed from naturally occurring all-cis PUFA by cytochrome P450 monooxygenases leading to the generation of cis-epoxy-PUFA (mixture of R,S-and S,R-enantiomers). In addition, also non-enzymatic chemical peroxidation gives rise to epoxy-PUFA leading to both, cis-and trans-epoxy-PUFA (mixture of R,R-and S,S-enantiomers). Here, we investigated for the first time trans-epoxy-PUFA and the trans/cis-epoxy-PUFA ratio as potential new biomarker of lipid peroxidation. Their formation was analyzed in correlation with the formation of isoprostanes (IsoP), which are commonly used as biomarkers of oxidative stress. Five oxidative stress models were investigated including incubations of three human cell lines as well as the in vivo model Caenorhabditis elegans with tert-butyl hydroperoxide (t-BOOH) and analysis of murine kidney tissue after renal ischemia reperfusion injury (IRI). A comprehensive set of IsoP and epoxy-PUFA derived from biologically relevant PUFA (ARA, EPA and DHA) was simultaneously quantified by LC-ESI(-)-MS/ MS. Following renal IRI only a moderate increase in the kidney levels of IsoP and no relevant change in the trans/cis-epoxy-PUFA ratio was observed. In all investigated cell lines (HCT-116, HepG2 and Caki-2) as well as C. elegans a dose dependent increase of both, IsoP and the trans/cis-epoxy-PUFA ratio in response to the applied t-BOOH was observed. The different cell lines showed a distinct time dependent pattern consistent for both classes of autoxidatively formed oxylipins. Clear and highly significant correlations of the trans/cis-epoxy-PUFA ratios with the IsoP levels were found in all investigated cell lines and C. elegans. Based on this, we suggest the trans/cis-epoxy-PUFA ratio as potential new biomarker of oxidative stress, which warrants further investigation.

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Development of an LC-ESI(-)-MS/MS method for the simultaneous quantification of 35 isoprostanes and isofurans derived from the major n3- and n6-PUFAs

Cited by 82 publications

References 54 publications

Methods of the Analysis of Oxylipins in Biological Samples

Methods of the Analysis of Oxylipins in Biological Samples

Effects of chronic low‐dose aspirin treatment on tumor prevention in three mouse models of intestinal tumorigenesis

Formation of trans-epoxy fatty acids correlates with formation of isoprostanes and could serve as biomarker of oxidative stress

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