New phosphorus (V) porphyrin derivatives: Synthesis and interactions with DNA.

摘要

Phosphorus (V) porphyrins are of significant interest due to their broad potential applications. They are used for DNA sequence sensing, to construct molecular photoswitches, and as models in photochemistry. Phosphorus (V) porphyrins have been investigated as photosensitizers in DNA binding/cleaving processes due to their strong oxidizing power in the singlet and triplet excited states and the ability to generate singlet oxygen. Because they are promising synthetic photonucleases, they offer potential applications in cancer chemotherapy and molecular biology. The possibility of stable axial derivatization broadens the usefulness of those compounds.; The research is described in six parts: (a) design and synthesis of new phosphorus (V) porphyrins with DNA binding/cleaving properties, and studies of their interactions with DNA, (b) synthesis of a nucleic base derivatized phosphorus (V) porphyrin, (c) diaxial substitution of phosphorus (V) porphyrins with amino acids, (d) successful synthesis of first phosphorus (V) porphyrin diaxially substituted with a peptide: leucine enkephalin-P(V) porphyrin conjugate, (e) design and synthesis of phosphorus (V) porphyrins substituted with crown ethers: derivatives with potential applications in chromatographic analysis and isolation of metals, (f) synthesis of new phosphorus (V) porphyrins and comparison of their interactions with DNA to the previously studied free base porphyrins, bearing analogous substituents in their meso-positions.