Selektive Synthese von neuartigen Chlorinen für die Photodynamische Therapie

Abstract

From Deuteroporphyrin through partial synthesis derived chlorins were taken in this work as starting products for the synthesis of regioisomeric formylchlorins, crown ether- and estron-chlorin adducts. The cis- trans- stereoisomeric chlorins can be through appropriate protonating conditions interconverted. The difference in the bathochromic shift of the UV/Vis bands of the formylchlorins were investigated and qualitatively interpreted on the basis of similar in the literature described phenomena. The binding through esterification of an enantiomeric estron derivative to the propionic side chains of a racemic chlorin yields two through open column chromatography separable optical active diastereomers which can be deployed as fluorescence pigments and photosensibilisators for the tumor detection and/or destruction. The binding through amidation of crown ether to the propionic side chains of a chlorin produce derivatives which could be of interest for a variety of host-guest relations concerning molecular recognition and catalysis. The last part of the work deals with the novel enzymatic and catalytic oxidation of deuteroporphyrin to chlorins and oxochlorins which should carry significant consequences for the biosynthesis and synthesis of similar natural hydroporphyrins.