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Phototoxikologie Der Kaliumkanal-Blocker Psora-3 Und Psora-4: in Vitro-Untersuchungen Zur Photoirritation, Photokarzinogenität Und Photoallergenität

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Phototoxikologie Der Kaliumkanal-Blocker Psora-3 Und Psora-4: in Vitro-Untersuchungen Zur Photoirritation, Photokarzinogenität Und Photoallergenität Phototoxikologie der Kaliumkanal-Blocker Psora-3 und Psora-4: In vitro-Untersuchungen zur Photoirritation, Photokarzinogenität und Photoallergenität Dissertation zur Erlangung des Doktorgrades der Mathematisch-Naturwissenschaftlichen Fakultät der Christian-Albrechts-Universität zu Kiel vorgelegt von Carsten Wilhelm Bode Kiel 2004 Referent: Prof. Dr. Wolfram Hänsel Korreferenten: Prof. Dr. Dieter Heber Prof. Dr. Hans-Jürgen Duchstein, Hamburg Tag der mündlichen Prüfung: 10. November 2004 Zum Druck genehmigt: 10. November 2004 Prof. Dr. Jürgen Grotemeyer (Dekan) Meinen Eltern „Mad dogs and Englishmen go out in the midday sun“ Sir Noël Pierce Coward (1899-1973) Inhaltsverzeichnis I 1 Einleitung .......................................................................................................... 1 1.1 Zielsetzung................................................................................................... 5 1.2 Untersuchte Verbindungen .......................................................................... 6 1.3 Furocumarine............................................................................................... 8 1.3.1 Psoralene .............................................................................................. 9 1.3.1.1 Psoralen ............................................................................................. 9 1.3.1.2 Bergaptol ............................................................................................ 9 1.3.1.3 Bergapten......................................................................................... 10 1.3.1.4 Xanthotoxol....................................................................................... 10 1.3.1.5 Xanthotoxin....................................................................................... 10 1.3.1.6 Trioxsalen......................................................................................... 11 1.3.1.7 Isopimpinellin.................................................................................... 11 1.3.1.8 Imperatorin ....................................................................................... 11 1.3.1.9 5-Benzyloxypsoralen ........................................................................ 12 1.3.1.10 Bergamottin ...................................................................................... 12 1.3.2 Phytophotodermatitis........................................................................... 12 2 Photosensibilisierung .................................................................................... 17 2.1 Klassifizierung der Photosensibilisierung ................................................... 19 2.2 Vorkommen von Photosensibilisatoren...................................................... 21 2.3 Mechanismus der Photosensibilisierung .................................................... 26 2.4 Sonnenstrahlung........................................................................................ 29 2.5 Photosensibilisierung als therapeutischer Effekt........................................ 35 2.5.1 PUVA-Therapie ................................................................................... 36 2.5.2 Extrakorporale Photopherese.............................................................. 36 2.5.3 Photodynamische Therapie................................................................. 37 2.6 Historische Aspekte der Photosensibilisierung .......................................... 41 II Inhaltsverzeichnis 3 Arzneistoffentwicklung und Photosensibilisierung .................................... 43 3.1 Regulatorische Anforderungen .................................................................. 43 3.1.1 Europäische Richtlinie ......................................................................... 44 3.1.2 Amerikanische Richtlinie ..................................................................... 46 3.2 Sonstige Empfehlungen ............................................................................. 48 4 Materialien....................................................................................................... 51 4.1 Chemikalien ............................................................................................... 51 4.2 Verbrauchsgegenstände ............................................................................ 52 4.3 Geräte ........................................................................................................ 53 4.3.1 Zentrifugation....................................................................................... 53 4.3.2 UV-Vis-Spektroskopie ......................................................................... 53 4.3.3 Fluoreszenz-Spektroskopie ................................................................. 53 4.3.4 Strahlungsquellen................................................................................ 53 4.3.4.1 Heraeus Original Hanau Fluotest ..................................................... 53 4.3.4.2 Philips Sunlamp TL 36 D 25/09N...................................................... 53 4.3.4.3 Dr. Hönle Sonnensimulator SOL-500 ............................................... 54 4.3.4.4 Atlas MTS Suntest CPS+ .................................................................. 55 4.3.5 Sonstige Geräte................................................................................... 56 5 Photophysikalische Untersuchungen........................................................... 57 5.1 Photophysikalische Eigenschaften der Psoralene ..................................... 57 5.2 Absorptionseigenschaften.......................................................................... 60 5.2.1 Methode .............................................................................................. 60 5.2.2 Ergebnisse .......................................................................................... 60 5.3 Fluoreszenzeigenschaften ......................................................................... 62 5.3.1 Methode .............................................................................................. 62 5.3.2 Ergebnisse .......................................................................................... 62 5.4 Diskussion.................................................................................................. 64 Inhaltsverzeichnis III 6 Photochemische Untersuchungen................................................................ 65 6.1 Photoproduktion von Singulett-Sauerstoff.................................................. 65 6.1.1 Eigenschaften des Singulett-Sauerstoffs............................................. 65 6.1.2 Reaktionen von Singulett-Sauerstoff mit biologischen Molekülen ....... 67 6.1.2.1 Reaktionen mit Aminosäuren und Proteinen .................................... 68 6.1.2.2 Reaktionen mit Nukleosiden und DNA ............................................. 74 6.1.2.3 Reaktionen mit Lipiden ..................................................................... 76 6.1.2 Photoproduktion von Singulett-Sauerstoff durch Psoralene ................ 84 6.1.2.1 Methode ........................................................................................... 84 6.1.2.2 Ergebnisse........................................................................................ 86 6.1.2.3 Diskussion ........................................................................................ 88 6.2 Photoproduktion von Superoxidradikalanionen.......................................... 89 6.2.1 Eigenschaften von reaktiven Sauerstoff-Spezies (ROS) ..................... 90 6.2.2 Reaktionen von ROS mit biologischen Molekülen............................... 92 6.2.2.1 Reaktionen mit Aminosäuren und Proteinen .................................... 92 6.2.2.2 Reaktionen mit Nukleosiden und DNA ............................................. 94 6.2.2.3 Reaktionen mit Lipiden ..................................................................... 98 6.2.2 Photoproduktion von Superoxidradikalanionen durch Psoralene ...... 102 6.2.2.1 Methode ......................................................................................... 102 6.2.2.2 Ergebnisse...................................................................................... 105 6.2.2.3 Diskussion ...................................................................................... 107 6.3 Quervernetzung von DNA ........................................................................ 109 6.3.1 Photoaddition von Psoralenen an DNA ............................................. 110 6.3.2 Phasenübergangsverhalten von DNA ............................................... 113 6.3.3 Quervernetzung von DNA durch Psoralene ...................................... 115 6.3.3.1 Methode ......................................................................................... 115 6.3.3.2 Ergebnisse...................................................................................... 117 6.3.3.3 Diskussion ...................................................................................... 120 IV Inhaltsverzeichnis 6.4 Photolyse von Membranen ...................................................................... 122 6.4.1 Aufbau von Biomembranen ............................................................... 122 6.4.2 Photoreaktionen von Psoralenen mit Membrankomponenten ........... 124 6.4.3 Photohämolyse von porcinen Erythrozyten ....................................... 126 6.4.3.1 Methode ........................................................................................
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