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Amphiphilic Porphyrins as Possible Photodynamic Therapy Sensitizers: A Rational versus Statistical Synthesis of Tetraphenylporphyrins bearing fluoro and carboxy substituents
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About Amphiphilic Porphyrins As Possible Photodynamic
Although photodynamic therapy with porphyrinic pigments as photosensitizers has emerged as promising modality for disease treatment, there remains a great need for the preparation of more selective sensitizers. Thus, the synthesis of amphiphilic porphyrins bearing fluoro and carboxy substituents was attempted. The most successful were the synthesis of three para-phenyl substituted tetraphenylporphyrins (TPPs) using both rational and statistical methodology. The porphyrins of greatest interest, where carboxy and fluoro substituents were placed at the para positions of opposite or adjacent phenyl rings, were either not obtained or only in small yields. However, 5,10,15-tri(4-fluorophenyl)-20(4-carboxyphenyl)porphyrin was synthesized in higher yields. To derive information on the factors that govern the permeation of this porphyrin across cell membrane mimics and its localization patters, it was allowed to diffuse into unilamellar vesicles at pH 2,7 and 10. The porphyrin incorporated in vesicles only to a small extent at pH 10 demonstrating that a proper amphiphilicity balance is required for porphyrins to incorporate into cell membrane mimics.
