Synthesis of 5-[4ʹ-(phenoxydimethylenoxy)-phenyl]-10,15,20-tris(N-methylpyridinium-3ʹ-yl)porphyrin Triiodide and the Study of its Interaction with Representative Oligonucleotides poly[d(AT)2] and poly[d(GC)2]

Abstract: Porphyrins and their analogues, due to their unique physicochemical properties, have a wide range of applications. Synthetic tetraarylporphyrins with an asymmetric substituent system are of particular interest. In this regard, an asymmetric porphyrin was synthesized, containing a phenyl fragment on the periphery of the porphyrin macrocycle. Subsequent quaternization of the compound with methyl iodide was carried out in order to obtain water-soluble porphyrin. Its structure was confirmed by 1H NMR spectroscopy and MALDI-TOF spectrometry. The photochemical properties and structural features of the complexation of synthesized porphyrin with representative oligonucleotides poly[d(AT)2] and poly[d(GC)2] have been studied. According to the results obtained, the studied compound forms a highly stable complex with poly[d(GC)2] by the intercalation mechanism. In the case of poly[d(AT)2], porphyrin binds in the minor groove.