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Synthesis and photophysical study of hydrophilic tetrapyridoporphyrazines bearing charged substituents on the periphery
Demuth, Jiří ; Nováková, Veronika (advisor) ; Vávrová, Kateřina (referee)
Charles University in Prague, Faculty of Pharmacy in Hradec Králové Department Department of Biophysics and Physical Chemistry Candidate Jiří Demuth Supervisor Assoc. Prof. Veronika Nováková, PhD. Title of Thesis Synthesis and photophysical study of hydrophilic tetrapyridoporphyrazines bearing charged substituents on the periphery Phthalocyanines are planar organic molecules, which have a metal cation coordinated in their centre. This work deals with their aza-analogues - tetra-3,4-pyridoporphyrazines (TPyPz). TPyPz can absorb light in red part spectrum and then produce singlet oxygen. Due to this ability, they may be used in photodynamic therapy (PDT) of cancer. PDT's mechanism is based on three components: photosensitizer, light and singlet oxygen. Photosensitizer transfers energy of absorbed light to oxygen making, thus, cytotoxic singlet oxygen. The goal of this thesis was to synthesize water soluble TPyPzs absorbing in red part of absorption spectrum. TPyPzs bearing different charged substituents will be compared within the series. The synthesis consisted of preparation of 2-chloro-5,6-dimethylpyridine-3,4-dicarbonitrile (1), which was the starting precursor for other reactions. Nucleophilic substitution of 1 was used for the introducing of various hydrophilic substituents. Prepared precursors...
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