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Reactions of Cosmetic UV Filters Towards Skin Proteins

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Reactions of Cosmetic UV Filters Towards Skin Proteins Investigations on (photo) reactions of cosmetic UV filters towards skin proteins Dissertation zur Erlangung des Doktorgrades der Naturwissenschaften (Dr. rer. nat.) Fakultät Naturwissenschaften Universität Hohenheim Institut für Lebensmittelchemie vorgelegt von Constanze Stiefel aus Leonberg 2014 Dekan: Prof. Dr. Heinz Breer 1. berichtende Person, 1. Prüfer: Prof. Dr. Wolfgang Schwack 2. berichtende Person, 2. Prüfer: Prof. Dr. Gertrud Morlock 3. Prüfer: Prof. Dr. Heinz-Dieter Isengard Eingereicht am: 07.10.2014 Mündliche Prüfung am: 17.02.2015 Die vorliegende Arbeit wurde am 02.02.2015 von der Fakultät Naturwissenschaften der Uni- versität Hohenheim als „Dissertation zur Erlangung des Doktorgrades der Naturwissenschaf- ten“ angenommen. Danksagungen Ganz herzlich möchte ich mich bei all jenen bedanken, die zum guten Gelingen dieser Arbeit beigetra- gen haben: Prof. Dr. Wolfgang Schwack für das spannende Thema dieser Arbeit, die stete Diskussionsbe- reitschaft und Erreichbarkeit bei jeglichen Fragenstellungen, die beständige Hilfe während des gesamten Publikationsprozesses sowie die Möglichkeit einer flexiblen Einteilung der Arbeit, so dass die Fertigstellung der Dissertation parallel zum bereits begonnenen Arbeitsverhältnis problemlos möglich war Prof. Dr. Gerda Morlock für die Übernahme des Mitberichts, die stete Bereitschaft zum wis- senschaftlichen Austausch und die stets aufbauenden und inspirierenden Gespräche Prof. Dr. Heinz-Dieter Isengard für die Bereitschaft, als 3. Prüfer zur Verfügung zu stehen Sylvia Maître, Lilli Sawitzki und Yen-Thi Hai Nguyen, die mich bei meiner experimentellen Arbeit unterstützt haben bei allen Mitarbeitern des Instituts für Lebensmittelchemie für eine wirklich tolle Zeit und vie- le schöne gemeinsame Erlebnisse und Erinnerungen Ein ganz besonderer Dank gilt meinen Eltern, die immer für mich da sind, mich stets unterstützen, motivieren und fördern und ohne die das Gelingen dieser Arbeit nicht möglich gewesen wäre; meinem Freund Frank für seine ruhige und besonnene Art und seine stete Unterstützung; meiner Patentante Bruni und ihrem Mann Herbert, die extra zum Strand gefahren sind, um mir Sand und Meerwasser von der Ostsee zu schicken; all meinen guten Freunden, die mich immer wieder motiviert und während der ganzen Zeit begleitet haben und mich nie haben vergessen lassen, dass man den Computer irgendwann auch mal ausschalten kann. Table of contents I PHOTOPROTECTION IN CHANGING TIMES – UV FILTER EFFICACY AND SAFETY, SENSITIZATION PROCESSES AND REGULATORY ASPECTS .....................1 SYNOPSIS ............................................................................................................................................. 1 GENERAL INTRODUCTION .................................................................................................................... 1 STRUCTURE OF THE HUMAN SKIN ........................................................................................................ 3 NATURAL SUNLIGHT ............................................................................................................................ 5 Positive effects ................................................................................................................................ 6 Negative effects ............................................................................................................................... 7 UVB radiation ............................................................................................................................................ 7 UVA radiation ............................................................................................................................................ 9 Squamous cell and basal cell carcinoma .................................................................................................... 9 Malignant melanoma ............................................................................................................................... 11 NATURAL PHOTOPROTECTION OF THE SKIN ...................................................................................... 12 UV filter substances ...................................................................................................................... 14 Legal requirements and recommendations ............................................................................................... 14 Inorganic UV filters ................................................................................................................................. 20 Organic UV filters .................................................................................................................................... 22 DEVELOPMENT OF ALLERGIC AND PHOTOALLERGIC REACTIONS ...................................................... 26 Skin sensitization test methods ...................................................................................................... 27 REFERENCES ...................................................................................................................................... 33 AIM AND STRUCTURE OF THE WORK ................................................................................................. 65 II RAPID SCREENING METHOD TO STUDY THE REACTIVITY OF UV FILTER SUBSTANCES TOWARDS SKIN PROTEINS BY HIGH-PERFORMANCE THIN- LAYER CHROMATOGRAPHY ..............................................................................................69 SYNOPSIS ........................................................................................................................................ 69 RÉSUMÉ ........................................................................................................................................... 69 INTRODUCTION ............................................................................................................................. 70 MATERIALS AND METHODS ....................................................................................................... 71 Synthesis of 4-methylbenzylidene camphor (4-MBC) .................................................................. 72 Standard solutions ......................................................................................................................... 72 High performance thin-layer chromatography (HPTLC) .............................................................. 72 Irradiation ...................................................................................................................................... 73 Solar simulator ......................................................................................................................................... 73 Natural sunlight ........................................................................................................................................ 73 Reactions of UV filters on the HPTLC plates ............................................................................... 73 RESULTS AND DISCUSSION ........................................................................................................ 73 Concept of the study ...................................................................................................................... 73 Ketones and diketones (BP-3, HMBS, BM-DBM, 3-BC, 4-MBC) .............................................. 77 Esters (EHMC, EHS, OCR, OD-PABA, EHT, DEBT) ................................................................ 79 I CONCLUSION ................................................................................................................................. 81 ACKNOWLEDGEMENTS .............................................................................................................. 81 REFERENCES .................................................................................................................................. 82 III REACTIONS OF COSMETIC UV FILTERS WITH SKIN PROTEINS: MODEL STUDIES OF KETONES WITH PRIMARY AMINES .........................................................86 ABSTRACT ...................................................................................................................................... 86 INTRODUCTION ............................................................................................................................. 86 MATERIALS AND METHODS ....................................................................................................... 87 High-performance liquid chromatography (HPLC) ...................................................................... 88 HPLC-Electrospray ionization mass spectrometry (LC/ESI-MS) ................................................. 88 Spectroscopy ................................................................................................................................. 88 Thermal reaction of UV filters with amines .................................................................................. 89 Photoreaction of UV filters in the presence of amines .................................................................. 89 Isolation of reaction products ........................................................................................................ 89 Reaction products isolated from batches at 80 °C for three hours ................................................ 90 BP-3 ........................................................................................................................................................
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