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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.
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.