Porphyrin—Nucleic Acid Interactions: A Review

Abstract

Research involving three important interactions of synthetic cationic porphyrins with nucleic acids: DNA binding, oxidative-reductive strand scission and photosensitized strand scission, is examined retrospectively. The observation that these porphyrins as a class can associate with DNA by intercalative binding, outside binding and outside binding with self-stacking, i.e., the “three-mode binding model”, is evaluated with regard to supporting data from several studies including recent evidence from NMR spectroscopy. Results from investigations into the “nuclease-like” activity of the metallo-derivatives of this class of porphyrins are surveyed for demonstrations of base specificity and the mechanism of the chemical interaction. The ability of cationic porphyrins to induce photosensitized damage in DNA is also reviewed with an emphasis on their strand scission activity via a singlet oxygen intermediate.