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• W2034768329 abstract "F2-isoprostanes diclofenac cyclo-oxygenase TO THE EDITOR UVB irradiation of the skin induces a complex cascade of acute inflammation, characterized by erythema, edema, and immunosuppression and is according to chronic exposure subsequently linked to the initiation and progression of skin cancer (Matsumura and Ananthaswamy, 2004Matsumura Y. Ananthaswamy H.N. Toxic effects of ultraviolet radiation on the skin.Toxicol Appl Pharmacol. 2004; 195: 298-308Crossref PubMed Scopus (762) Google Scholar). The role of inflammatory mediators in skin diseases is of critical importance. This includes the release of cytokines, NO, and oxidized arachidonic acid derivatives (Reilly et al., 2000Reilly D.M. Parslew R. Sharpe G.R. Powell S. Green M.R. Inflammatory mediators in normal, sensitive and diseased skin types.Acta Derm Venereol. 2000; 80: 171-174Crossref PubMed Scopus (71) Google Scholar; Rhodes et al., 2001Rhodes L.E. Belgi G. Parslew R. McLoughlin L. Clough G.F. Friedmann P.S. Ultraviolet-B-induced erythema is mediated by nitric oxide and prostaglandin E2 in combination.J Invest Dermatol. 2001; 117: 880-885Crossref PubMed Google Scholar). The so-called eicosanoid lipid mediators are formed by two main pathways: enzymatically and non-enzymatically. Inflammatory stimuli induce the liberation of arachidonic acid from membrane phospholipids and the formation of prostaglandins, which are generated by cyclo-oxygenase (COX) isoenzymes and are blocked by non-steroidal anti-inflammatory drugs. Prostaglandins are known as bioactive products with vasoregulatory properties acting in a synergistic or antagonistic manner. Whereas PGE2 mediates vasodilatation, PGF2α is responsible for vasoconstriction. The non-enzymatical pathway of arachidonic acid oxidation includes free radical mechanisms and synthesis of F2-isoprostanes (F2-IsoPs), which are mostly bound to the backbone of phospholipids (Morrow et al., 1992Morrow J.D. Awad J.A. Boss H.J. Blair I.A. Roberts L.J. Non-cyclooxygenase-derived prostanoids (F2-isoprostanes) are formed in situ in phospholipids.Proc Natl Acad Sci (USA). 1992; 89: 10721-10725Crossref PubMed Scopus (640) Google Scholar). F2-IsoPs are a novel group of prostaglandin-like compounds with potent biological activities, as evidenced by their pulmonary and renal vasoconstrictive effects (Lawson et al., 1999Lawson J.A. Rokach J. FitzGerald G.A. Isoprostanes: formation, analysis and use as indices of lipid peroxidation in vivo.J Biol Chem. 1999; 274: 24441-24444Crossref PubMed Scopus (342) Google Scholar). Several studies have indicated associations between isoprostanes and severe inflammatory conditions (Basu, 2004Basu S. Isoprostanes: novel bioactive products of lipid peroxidation.Free Radic Res. 2004; 38: 105-122Crossref PubMed Scopus (188) Google Scholar). Although F2-IsoPs are preferentially formed non-enzymatically, a COX-dependent generation can not be excluded (Klein et al., 1996Klein T. Reutter F. Schweer H. Seyberth H.W. Nüsing R.M. Generation of the isoprostane 8-epi-prostaglandin F2α in vitro and in vivo via the cyclooxygenases.J Pharmacol Exp Ther. 1996; 282: 1658-1665Google Scholar; Lawson et al., 1999Lawson J.A. Rokach J. FitzGerald G.A. Isoprostanes: formation, analysis and use as indices of lipid peroxidation in vivo.J Biol Chem. 1999; 274: 24441-24444Crossref PubMed Scopus (342) Google Scholar). Therefore, F2-IsoPs are not only biomarkers of lipid peroxidation and potential in vivo indicators of oxidant stress in various clinical conditions, but also mediators of acute inflammation (Basu, 2004Basu S. Isoprostanes: novel bioactive products of lipid peroxidation.Free Radic Res. 2004; 38: 105-122Crossref PubMed Scopus (188) Google Scholar; Montuschi et al., 2004Montuschi P. Barnes P.J. Roberts L.J. Isoprostanes: markers and mediators of oxidative stress.FASEB J. 2004; 18: 1791-1800Crossref PubMed Scopus (548) Google Scholar). Diclofenac (DCLF) belongs to the most common non-steroidal anti-inflammatory drugs used for the treatment of pain and inflammation. DCLF (2-[(2,6-dichlorophenyl)amino] phenyl-acetate) non-selectively inhibits COX-1 and COX-2, which both catalyze prostaglandin synthesis (Hickey et al., 2001Hickey E.J. Raje R.R. Reid V.E. Gross S.M. Ray S.D. Diclofenac induced in vivo nephrotoxicity may involve oxidative stress-mediated massive genomic DNA fragmentation and apoptotic cell death.Free Radic Biol Med. 2001; 31: 139-152Crossref PubMed Scopus (160) Google Scholar). It was the aim of our study to test the hypotheses that1.low-dose UVB irradiation influences the concentrations of F2-IsoPs and prostaglandins in vitro in human HaCaT keratinocytes and in vivo in the interstitial fluid of the dermis and this could be a dose-dependent action.2.application of non-toxic concentrations of DCLF can lower the levels of enzymatically and of non-enzymatically formed lipid mediators as well.3.HaCaT keratinocytes may serve as a suitable in vitro model to reflect UVB- and DCLF-induced alterations of lipid mediators in vivo. In this study, we showed early evidence that in HaCaT keratinocytes both F2-IsoPs and PGF2α can reliably be quantified by gas chromatography–mass spectrometry (negative ion chemical ionization–selected ion monitoring (Table 1a) and that their concentrations were dose-dependently enhanced with low-dose UVB irradiation between 30 and 100 mJ/cm2 (Figure 1). 8-iso-PGF2α as marker of non-enzymatic arachidonic acid oxidation exclusively reflects phospholipid-bound F2-IsoPs, because (i) it occurred in HaCaT keratinocytes completely in the esterified and not in the free form (experiments according to Wiswedel et al., 2004Wiswedel I. Hirsch D. Kropf S. Gruening M. Pfister E. Schewe T. et al.Flavanol-rich cocoa drink lowers plasma F2-isoprostane concentrations in humans.Free Radic Biol Med. 2004; 37: 411-421Crossref PubMed Scopus (136) Google Scholar) and (ii) no 8-iso-PGF2α was released and detected in the cell-free supernatant (Quist et al., 2006Quist S.R. Simmel F. Wiswedel I. Neubert R. Gollnick H. Influence of green and black tea, epigallocatechin-3-gallate and theaflavin on prostanoid synthesis in vitro and in vivo using microdialysis.Proceedings of the 13th Biennial Congress of the International Society for Free Radical Research – SFRR. Medimond, Davos, Switzerland2006: pp 293-297Google Scholar). Concerning 9α,11α-PGF2α, it can be assumed that the main part represents COX-catalyzed generation. This was derived from the predominant occurrence in the free and non-esterified form (about 77%) and by the considerable release of PGF2α in the supernatant (Quist et al., 2006Quist S.R. Simmel F. Wiswedel I. Neubert R. Gollnick H. Influence of green and black tea, epigallocatechin-3-gallate and theaflavin on prostanoid synthesis in vitro and in vivo using microdialysis.Proceedings of the 13th Biennial Congress of the International Society for Free Radical Research – SFRR. Medimond, Davos, Switzerland2006: pp 293-297Google Scholar). COX-derived PGE2 was not detectable in HaCaT cells, but was completely released in the supernatant (Table 1a). The UVB-induced enhancement of PGE2 was definitely more pronounced compared with the other mediators.Table 1aLevels of F2-isoprostanes/prostaglandins in HaCaT keratinocytes and supernatants – Influence of UVB irradiation and DCLF8-iso-PGF2α9α,11α-PGF2αPGE2(pmol/mg protein in HaCaTs)(pmol/mg protein in HaCaTs)(pmol/ml supernatant)Non-irradiated cells0.23±0.030.50±0.060.21±0.08(n=26)(n=22)(n=3)UVB (30 mJ/cm2)0.35±0.061.21±0.2862.5±18.8(n=19)(n=17)(n=3)UVB (30 mJ/cm2)0.32±0.070.95±0.03*n.d.+2.5 μm DCLF(n=6)(n=6)UVB (30 mJ/cm2)0.23±0.05**For 8-iso-PGF2a, UVB+5µm DCLF is significantly different from UVB (P<0.05). In the case of 9a,11a-PGF2a, UVB+2.5µm DCLF as well as UVB+5µm DCLF are significantly different vs UVB (P=0.010 and 0.004); Student's t-test.0.79±0.18*0.25±0.05+5.0 μm DCLF(n=6)(n=6)(n=3)DCLF, diclofenac; n.d., not determined.Values are means±SEM for HaCaT cells and±SD for supernatants. Values of non-irradiated and UVB-irradiated HaCaT keratinocytes (30 mJ/cm2) are identical with those of Figure 1.* *For 8-iso-PGF2a, UVB+5 µm DCLF is significantly different from UVB (P<0.05). In the case of 9a,11a-PGF2a, UVB+2.5 µm DCLF as well as UVB+5 µm DCLF are significantly different vs UVB (P=0.010 and 0.004); Student's t-test. Open table in a new tab DCLF, diclofenac; n.d., not determined. Values are means±SEM for HaCaT cells and±SD for supernatants. Values of non-irradiated and UVB-irradiated HaCaT keratinocytes (30 mJ/cm2) are identical with those of Figure 1. In Figure 1, it is shown that 8-iso-PGF2α concentrations were slightly and more continuously increased up to 100 mJ/cm2, whereas 9α,11α-PGF2α concentrations already reached a maximum at 50 mJ/cm2 with a more than fivefold enhancement compared with the non-irradiated control values and dropped down thereafter to about half-maximum levels. The decrease of PGF2α in HaCaTs may reflect the enhanced release in the supernatant as shown by Quist et al., 2006Quist S.R. Simmel F. Wiswedel I. Neubert R. Gollnick H. Influence of green and black tea, epigallocatechin-3-gallate and theaflavin on prostanoid synthesis in vitro and in vivo using microdialysis.Proceedings of the 13th Biennial Congress of the International Society for Free Radical Research – SFRR. Medimond, Davos, Switzerland2006: pp 293-297Google Scholar or a partial transformation to the more stable 15-keto-dihydro-PGF2α, which was not analyzed in this study. The different UVB dependence of 8-iso-PGF2α and 9α,11α-PGF2α may be an additional indication for their different origin: free radical-catalyzed or COX-derived. The results correspond to those of Pentland et al., 1990Pentland A.P. Mahoney M. Jacobs S.C. Holtzmann M.J. Enhanced prostaglandin synthesis after ultraviolet injury is mediated by endogenous histamine stimulation. A mechanism for irradiation erythema.J Clin Invest. 1990; 86: 566-574Crossref PubMed Scopus (97) Google Scholar showing fivefold increases of PGF2α and PGE2 in human skin explants following 120 mJ/cm2 UVB irradiation and those of Buckman et al., 1998Buckman S.Y. Gresham A. Hale P. Hruza G. Anast J. Masferrer J. et al.COX-2 expression is induced by UVB exposure in human skin: implication for the development of skin cancer.Carcinogenesis. 1998; 19: 723-729Crossref PubMed Scopus (491) Google Scholar, demonstrating Western blots with sixfold increases of COX-2 protein in cultured human keratinocytes 24 hours following 30 mJ/cm2 UVB exposure. In a next set of experiments, the influence of DCLF on the UVB-induced enhancement of prostanoids was investigated (Table 1a). The DCLF concentrations used in HaCaT keratinocytes were between 1 and 5 μm and a low, but effective, UVB dose of 30 mJ/cm2 was chosen. Concentrations of 1 μm DCLF or less were not effective at all and concentrations of 10 μm and higher were proven to be toxic to HaCaT cell cultures. The UVB-induced increases of 8-iso-PGF2α and of 9α,11α-PGF2α were suppressed by about 35 % with 5 μm DCLF, whereas only that of 9α,11α–PGF2α were suppressed by about 12 % with 2.5 μm DCLF (Table 1a). PGE2 concentrations were followed in the supernatant. In contrast to the mediators before, they were about 300-fold enhanced by UVB and nearly totally reduced to control levels by DCLF (Table 1a). The results obtained with HaCaT keratinocytes in vitro have been qualitatively confirmed using a microdialysis technique, which has been used in human studies for more than 10 years (Stahl et al., 2002Stahl M. Bouw R. Jackson A. Pay V. Human microdialysis.Curr Pharm Biotechnol. 2002; 3: 165-178Crossref PubMed Scopus (50) Google Scholar; Grundmann et al., 2004Grundmann J.U. Wiswedel I. Hirsch D. Gollnick H.P.M. Detection of monohydroxyeicosatetraenoic acids and F2-isoprostanes in microdialysis samples of human UV-irradiated skin by gas chromatography-mass spectrometry.Skin Pharmacol Physiol. 2004; 17: 37-41Crossref PubMed Scopus (23) Google Scholar). Six healthy female volunteers, 18–30 years old, were included in the study after giving their written, informed consent and after approval by the ethics committee of the Medical Faculty, Otto-von-Guericke-University Magdeburg, Germany. The Declarations of Helsinki Principles were followed. Microdialysis allows the “near in vivo” measurement of endogeneous eicosanoid mediators released in the interstitial space of the dermis under control and inflammatory conditions (Table 1b). Whereas UVB- and DCLF-induced alterations of 9α,11α-PGF2α concentrations were not significant, the concentrations of 8-iso-PGF2α and PGE2 were four and 2.7-fold enhanced 24 hours following UVB treatment in comparison with healthy untreated skin. DCLF, topically applied as cream or gel, immediately after UVB irradiation, prevented the generation of an erythema and reduced the levels of 8-iso-PGF2α and PGE2 remarkably (Table 1b). The anti-inflammatory effect of DCLF was more pronounced for the 5% cream than for the 1% gel. As found in HaCaT cells, DCLF did not only influence the prostaglandin, but additionally the isoprostane pathway. The so-called radical scavenging or antioxidant side effects of DCLF were also described by Aruoma and Halliwell, 1988Aruoma O.I. Halliwell B. The iron-binding and hydroxyl radical scavenging action of anti-inflammatory drugs.Xenobiotica. 1988; 18: 459-470Crossref PubMed Scopus (139) Google Scholar and Maffei Facino et al., 1993Maffei Facino R. Carini M. Aldini G. Saibene L. Macciocchi A. Antioxidant profile of nimesulide, indomethacin and diclofenac in phosphatidylcholine liposomes as membrane model.Int J Tissue React. 1993; 15: 225-234PubMed Google Scholar.Table 1bLevels of F2-isoprostanes/prostaglandins in microdialysis samples of human skin – influence of UVB irradiation and treatment with DCLF8-iso-PGF2α9α,11α- PGF2αPGE2(pmol/ml microdialysate)(pmol/ml microdialysate)(pmol/ml microdialysate)Non-irradiated skin0.25±0.110.53±0.250.62±0.14UVB1.00±0.22*P<0.05 vs non-irradiated control0.38±0.281.65±0.23*P<0.05 vs non-irradiated controlUVB+DCLF (1%)0.59±0.09*P<0.05 vs UVB without DCLF.0.62±0.350.97±0.13*P<0.05 vs UVB without DCLF.UVB+DCLF (5%)0.41±0.12*P<0.05 vs UVB without DCLF.0.55±0.300.81±0.12*P<0.05 vs UVB without DCLF.DCLF, diclofenac.Values are means±SEM of n=6 healthy volunteers.UVB irradiation (about 20–40 mJ/cm2) caused the formation of erythema of stages 3–5, which were completely suppressed by DCLF immediately applicated following UVB irradiation. Samples were taken 24 h later; after an additional hour of “baseline” microdialysis for equilibration. Microdialysate samples of about 2 hours have to be combined for triplicate analyses. Differences in the levels of prostanoids are significant for 8-iso-PGF2α and PGE2 according to Student's t-test.* P<0.05 vs non-irradiated control** P<0.05 vs UVB without DCLF. Open table in a new tab DCLF, diclofenac. Values are means±SEM of n=6 healthy volunteers. UVB irradiation (about 20–40 mJ/cm2) caused the formation of erythema of stages 3–5, which were completely suppressed by DCLF immediately applicated following UVB irradiation. Samples were taken 24 h later; after an additional hour of “baseline” microdialysis for equilibration. Microdialysate samples of about 2 hours have to be combined for triplicate analyses. Differences in the levels of prostanoids are significant for 8-iso-PGF2α and PGE2 according to Student's t-test. Prostanoid concentrations measured by gas chromatography–mass spectrometry in this study were on the same level as isoprostane concentrations reported by Karamouzis et al., 2004Karamouzis I. Christoulas K. Grekas D. Giannoulis K. Vamvakoudis E. Mandroukas K. The response of muscle interstitial F2-isoprostane (8-iso-PGF2alpha) during dynamic muscle concentrations in humans.Prostaglandins Leukot Essent Fatty Acids. 2004; 71: 87-90Abstract Full Text Full Text PDF PubMed Scopus (17) Google Scholar in dialysate samples from muscle and PGE2 levels in microdialysates of human skin reported by Fairweather et al., 2004Fairweather I. McGlone F. Reilly D. Rukwied R. Controlled dermal cell damage as human in vivo model for localised pain and inflammation.Inflamm Res. 2004; 53: 118-123Crossref PubMed Scopus (12) Google Scholar. UVB-induced increases of 8-iso-PGF2α were also shown by Schneider et al., 2006Schneider L.A. Bloch W. Kopp K. Hainzl A. Rettberg P. Wlaschek M. et al.8-isoprostane is a dose-related biomarker for photo-oxidative ultraviolet (UV) B damage in vivo: a pilot study with personal UV dosimetry.Br J Dermatol. 2006; 6: 1147-1154Crossref Scopus (27) Google Scholar in human skin biopsies and by Kuhn et al., 2006Kuhn M. Wolber R. Kolbe L. Schnorr O. Sies H. Solar-simulated radiation induces secretion of IL-6 and production of isoprostanes in human skin in vivo.Arch Dermatol Res. 2006; 297: 477-479Crossref PubMed Scopus (18) Google Scholar in suction blister fluid 24 hours post-irradiation. The authors state no conflict of interest. The experimental work was supported by grants of the Federal State of Saxony-Anhalt (FKZ: 3173A/0089 M) and from the BMBF-Forschungsverbundprojekt (FKZ 01ZZ0407). We thank Rita Adolf and Marita Lotzing for excellent technical assistance. Methods. Figure S1. Standard calibration curves for 8-iso-PGF2α and 9α,11α-PGF2α. Download .pdf (.05 MB) Help with pdf files Supplementary Information" @default.
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• W2034768329 title "Effects of UVB Irradiation and Diclofenac on F2-Isoprostane/Prostaglandin Concentrations in Keratinocytes and Microdialysates of Human Skin" @default.
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