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«MODULATION OF POLYAMINE METABOLISM AS A CHEMOPREVENTIVE STRATEGY OF PHYTOCHEMICALS IN A CELL CULTURE MODEL OF COLORECTAL CANCERS Dissertation zur ...»

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Ursolsäure steigert die Aktivität der Spermin/Spermidin Acetyltransferase in kolorektalen Karzinomzellen über einen PPARγ-vermittelten Signaltransduktionsweg Jahrestagung der Mitteldeutschen Gesellschaft für Gastroenterologie, Bad Nauheim, May 5-7, 2005

12. Ulrich, S., Wolter, F., Loitsch, S., Stein, J.

PPARγ as a molecular target for chemopreventive effects of polyphenol Resveratrol; Gastroenterology 2005; 128(4), Suppl. 2 Digestive Disease Week, Chicago, IL, May 14-19, 2005

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The phytoalexin resveratrol induces inhibition of ornithine decarboxylase via a ceramide signaling pathway; Gastroenterology 2005; 128(4), Suppl. 2 Digestive Disease Week, Chicago, IL, May 14-19, 2005

14. Ulrich, S., Wolter, F., Loitsch, S., Stein, J.

PPARγ fungiert als molekulares Target in der Resveratrol-vermittelten Modulation des Polyaminstoffwechsels; Akt Ern Med 2005; 30(3):173 Nutrition 2005, Geneva, June 2-4, 2005

15. Ulrich, S., Hagos, M., Loitsch, S., Stein, J.

Ursolsäure steigert die Aktivität der Spermin/Spermidin Acetyltransferase in kolorektalen Karzinomzellen über einen PPARγ-vermittelten Signaltransduktionsweg; Akt Ern Med 2005; 30(3):173 Nutrition 2005, Geneva, June 2-4, 2005

16. Ulrich, S., Huwiler, A., Wolter, F., Loitsch, S., Stein, J.

PPARγ as a molecular target for chemopreventive effects of polyphenol Resveratrol ZAFES symposium “Biologicals-Presence and Perspectives”, Frankfurt/Main, September 9, 2005

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18. Ulrich, S., Jung, B., Loitsch, S., Hagos, M., Stein, J.

Chemopreventive properties of ursolic acid in colorectal cancers;

Z Gastroenterol 2005; 43(8): 916

60. Jahrestagung der Deutschen Gesellschaft für Verdauungs- und Stoffwechselkrankheiten, Köln, September 14-17, 2005

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21. Ulrich, S., Jung, B., Buettner, S., Stein, J Molecular characterization of the chemopreventive activity of pentacyclic triterpene ursolic acid; Gastroenterology 2006; 130 (4) Suppl. 2 Digestive Disease Week, Los Angeles, CA, May 20-25, 2006

22. Ulrich, S., Turan, Y, Stein, J.

Omega-3-fatty acids inhibit the proliferation of colorectal cancer cells – Evidence for PPARγ independent mechanisms; Gastroenterology 2006;

130 (4) Suppl. 2 Digestive Disease Week, Los Angeles, CA, May 20-25, 2006

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26. Ulrich, S., Buettner, S., Stein, J., Molecular characterization of the anti-angiogenic properties of the pentacyclic triterpene ursolic acid 14th International AEK Cancer Congress, Frankfurt am Main, February 28 – March 2,

27. Ulrich, S., Kampan, W., Stein, J., (2007) Resveratrol sensitizes colorectal cancer cells to oxaliplatin-induced cell growth inhibition 14th International AEK Cancer Congress, Frankfurt am Main, February 28 – March 2,

28. Ulrich, S., Huwiler, A., Loitsch, S., Schmidt, H., Stein, J.

De novo ceramide biosynthesis is involved in resveratrol-induced inhibition of ornithine decarboxylase activity 14th International AEK Cancer Congress, Frankfurt am Main, February 28 – March 2,

29. Ulrich, S., Kampan, W., Stein, J. Resveratrol sensitizes colorectal cancer cells to oxaliplatin-induced cell growth inhibition;

Gastroenterology 2007; 132(4), Suppl. 2 Digestive Disease Week, Washington, DC, May 19-24, 2007

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Digestive Disease Week, Washington, DC, May 19-24, 2007

31. Ulrich, S., Huwiler, A., Loitsch, S., Schmidt, H., Stein, J.

De novo ceramide biosynthesis is involved in resveratrol-induced inhibition of ornithine decarboxylase activity; Gastroenterology 2007;

132(4), Suppl. 2 Digestive Disease Week, Washington, DC, May 19-24, 2007

32. Ulrich, S., Büttner, S., Stein, J.

Molekulare Charakterisierung anti-angiogener Eigenschaften des pentacyclischen Triterpens Ursolsäure Z Gastroenterol 45(8):773

62. Jahrestagung der Deutschen Gesellschaft für Verdauungs- und Stoffwechselkrankheiten, Bochum, September 12-15, 2007

33. Shastri, Y., Hoepffner, N., Tessmer, A., Ulrich, S., Schröder, O., Stein, J.

New introducer PEG-Gastropexy does not need prophylactic antibiotics:

Prospective randomised double blind placebo controlled study Z Gastroenterol 45(8):787

62. Jahrestagung der Deutschen Gesellschaft für Verdauungs- und Stoffwechselkrankheiten, Bochum, September 12-15, 2007 Frankfurt, den 26.09.2007

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EIDESSTATTLICHE ERKLÄRUNG

Ich erkläre: Ich habe die vorgelegte Dissertation selbstständig und ohne unerlaubte fremde Hilfe und nur mit den Hilfen angefertigt, die ich in der Dissertation angegeben habe. Alle Textstellen, die wörtlich oder sinngemäß aus veröffentlichten Schriften entnommen sind, und alle Angaben, die auf mündlichen Auskünften beruhen, sind als solche kenntlich gemacht. Bei den von mir durchgeführten und in der Dissertation erwähnten Untersuchungen habe ich die Grundsätze guter wissenschaftlicher Praxis, wie sie in der „Satzung der Justus-Liebig-Universität Gießen zur Sicherung guter wissenschaftlicher Praxis“ niedergelegt sind, eingehalten.

Teile der vorliegenden Arbeit wurden in folgenden Publikationsorganen

veröffentlicht:





I. ULRICH, S., LOITSCH, S., RAU O., VON KNETHEN, A., BRÜNE, B., SCHUBERTZSILAVECZ, M., STEIN, J. (2006) Peroxisome-Proliferator activated receptor γ as a molecular target of resveratrol-induced modulation of polyamine metabolism. Cancer Res 66(14): 7348-54.

II. ULRICH, S., HUWILER, A., LOITSCH, S., SCHMIDT, H., STEIN J. (2007) De novo ceramide biosynthesis is assaociated with resveratrol-induced inhibition of ornithine decarboxylase activity. Biochem Pharmacol 74(2):281-9 III. ULRICH, S., JUNG, B., LOITSCH, S., KAMPAN, W., STEIN, J. (2007) Ursolic acid induces apoptosis through PPARγ mediated SSAT-activation in colon cancer cells. (submitted) IV. WOLTER, F., ULRICH, S., STEIN, J. (2004) Molecular mechanisms of the chemopreventive effetcs of resveratrol and its analogs in colorectal cancer: key role of polyamines. J Nutr 134(12): 3219-22. Review V. ULRICH, S., WOLTER, F., STEIN, J. (2005) Molecular mechanisms of the chemopreventive effects of resveratrol and its analogs in carcinogenesis.

Mol Nutr Food Res 49(5): 452-61. Review

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ABGRENZUNGSERKLÄRUNG

Frau Dipl. oec.troph. Sandra Ulrich hat die dem Promotionsamt des Fachbereichs Ernährungswissenschaften der Justus Liebig Universität Gießen

vorgelegte Arbeit mit dem Titel:

„MODULATION OF POLYAMINE METABOLISM AS A CHEMOPREVENTIVE STRATEGY OF

PHYTOCHEMICALS IN A CELL CULTURE MODEL OF COLORECTAL CANCERS”

als kumulative Dissertation verfasst.

Der Arbeit liegen folgende Veröffentlichungen zugrunde:

I. ULRICH, S., LOITSCH, S., RAU O., VON KNETHEN, A., BRÜNE, B., SCHUBERTZSILAVECZ, M., STEIN, J. (2006) Peroxisome-Proliferator activated receptor γ as a molecular target of resveratrol-induced modulation of polyamine metabolism. Cancer Res 66(14): 7348-54.

II. ULRICH, S., HUWILER, A., LOITSCH, S., SCHMIDT, H., STEIN J. (2007) De novo ceramide biosynthesis is assaociated with resveratrol-induced inhibition of ornithine decarboxylase activity. Biochem Pharmacol 74(2):281-9 III. ULRICH, S., JUNG, B., LOITSCH, S., KAMPAN, W., STEIN, J. (2007) Ursolic acid induces apoptosis through PPARγ mediated SSAT-activation in colon cancer cells. (submitted) IV. WOLTER, F., ULRICH, S., STEIN, J. (2004) Molecular mechanisms of the chemopreventive effetcs of resveratrol and its analogs in colorectal cancer: key role of polyamines. J Nutr 134(12): 3219-22. Review V. ULRICH, S., WOLTER, F., STEIN, J. (2005) Molecular mechanisms of the chemopreventive effects of resveratrol and its analogs in carcinogenesis.

Mol Nutr Food Res 49(5): 452-61. Review Frau Bettina Jung hat im Rahmen ihrer Doktorarbeit im Fachbereich Medizin der J.W. Goethe Universität (unter Betreung von Frau Sandra Ulrich)

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verschiedene Versuche mit dem Triterpen Ursolsäure durchgeführt, die allesamt von Frau Sandra Ulrich wiederholt und verifiziert wurden.

Die dominant-negative PPARγ wurde freundlicherweise von Herrn Dr. V.K.

Chatterjee (Department of Medicine, University of Cambridge, Addenbrooke’s Hospital, Cambridge, United Kingdom) zur Verfügung gestellt und von Sandra Ulrich unter Anleitung von Herrn Dr. Stefan Loitsch in Caco-2-Zellen stabil transfiziert.

Die intrazelluläre Ceramidmessung wurde in Zusammenarbeit mit Frau Prof.

Andrea Huwiler und Herrn Dr. Helmut Schmidt durchgeführt, wobei die Probenvorbereitung von Frau Sandra Ulrich durchgeführt wurde.

Die Messung der PPARγ Liganden-Aktivierung erfolgte in Zusammenarbeit mit der Arbeitsgruppe von Prof. Schubert-Zsilavecz, wo das Modell des Gal4PPARγ Fusions-Rezeptors von Herrn Dr. Oliver Rau etabliert wurde Weitere Versuche zur Messung der PPARγ-Aktivierung wurden von Frau Sandra Ulrich in der Arbeitsgruppe von Prof. Bernhard Brüne in Zusammenarbeit mit Dr. Andreas Knethen durchgeführt.

Prof. Dr. Dr. J. Stein hat die Manuskripte kritisch Korrektur gelesen und in Diskussionen hilfreiche Ideen für weitere Versuche geliefert.

Sandra Ulrich ANHANG I Research Article Peroxisome Proliferator–Activated Receptor ; as a Molecular Target of Resveratrol-Induced Modulation of Polyamine Metabolism Sandra Ulrich, Stefan M. Loitsch, Oliver Rau, Andreas von Knethen, Bernhard Brune, ¨ Manfred Schubert-Zsilavecz, and Jurgen M. Stein ¨ First Department of Internal Medicine-ZAFES; 2Institute of Pharmaceutical Chemistry ZAFES; and 3Institute of Biochemistry I ZAFES, Johann Wolfgang Goethe University, Frankfurt am Main, Germany

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Figure 1. Cell counts and cell proliferation of HCT-116 cells 24, 48, and 72 hours after incubation without (control) or with resveratrol (30-200 Amol/L).

Resveratrol leads to a conspicuous dose- and time-dependent reduction of cell counts as well as an inhibition of cell proliferation.

Columns, mean (n = 8); bars, SE. ***, P 0.001.

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Figure 2. Activity of SSAT in Caco-2-wild type cells in comparison with transfected Caco-2-empty vector and Caco-2-dnPPARg cells after incubation with resveratrol (50-100 Amol/L) for 24 hours.

Resveratrol leads to a significant increase both in Caco-2-wild type and Caco-2-empty vector cells. However, no effects could be observed when PPARg-mediated functions are suppressed.

Columns, mean (n = 4); bars, SE. Values not sharing a letter differ significantly (P 0.05).

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Transfection Assay Gal4-PPAR; Transactivation Assay The following plasmids were used for transfection: pcDNA3 (Invitrogen), Plasmids. The Gal4-fusion receptor plasmid pFA-CMV-PPARg-LBD, as an empty vector for control transfection, and plasmid pcDNA3- containing hinge region and the LBD of PPARg, was constructed by PPARgL468A/E471A, a dominant-negative double mutant, which was kindly integrating cDNA fragment obtained from PCR amplification of human provided by V.K. Chatterjee (Department of Medicine, University of monocytes into the SmaI/XbaI (Promega) sites of the pFA-CMV vector Cambridge, Addenbrooke’s Hospital, Cambridge, United Kingdom; ref. 22). (Stratagene). The cDNA fragment contained bps 610-1,518 (NM_015869) of These constructs were transfected into subconfluent Caco-2 cells with the PPARg coding sequence. Frame and sequence of the fusion receptors

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were verified by sequencing. As reporter plasmids, we used pFR-Luc (Stratagene). For normalizing of transfection efficacy, we used pRL-SV40 (Promega).

Transfection. Cos7 cells were seeded at 30,000 per well in a 96-well plate. After 24 hours, transfection was carried out using Lipofectamine 2000 according to the protocol of the manufacturer. Transfection mixes contained 0.8 AL LF2000, 280 ng pFR-Luc, 2 ng pRL-SV40, and 14 ng of the PPARg fusion receptor plasmid for each well. Four hours after transfection, medium was changed to DMEM without phenol red– containing 100 units/mL penicillin, 100 Ag/mL streptomycin, 2 mmol/L glutamine, 1 mmol/L sodium pyruvate, appropriate concentration of test substance, and 0.1% DMSO, testing each concentration in triplicate wells.

Cells were incubated overnight and assayed for reporter gene activity with the Dual-Glo Luciferase Assay system. Luminescence of both luciferases was measured in GENiosPro Luminometer (Tecan). Each assay was repeated at least thrice.

Calculations. Luciferase activity for all assays was corrected by subtracting background activity obtained from nontransfected controls.

Relative light units were calculated by dividing firefly light units by renilla light units. Activation factors are gained by dividing mean values of relative light units for each concentration of agonist by mean relative light unit values of the DMSO control. Relative activation is calculated by dividing activation factors by the maximum activation factor. Calculation of EC50 values was done using the four-parameter logistic regression function of SigmaPlot2001 (SPSS, Inc.) using the mean of relative activation for each tested concentration of at least three determinations.

Statistics The data are expressed as means F SE of at least three independent experiments. ANOVA was done when more than two groups were compared, and when significant (P 0.05), multiple comparisons were done with the Turkey test. P 0.05 was considered to be significant.

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