Design and synthesis of manganese porphyrins with tailored lipophilicity: Investigation of redox properties and superoxide dismutase activity

Thirteen new manganese porphyrins and two porphodimethenes bearing one to three different substituents at the meso positions in a variety of architectures have been synthesized. The substituents employed generally are (i) electron-withdrawing to tune the reduction potential to the desirable range (near +0.3 V vs NHE), and/or (ii) lipophilic to target the interior of lipid bilayer membranes and/or the blood–brain barrier. The influence of the substituents on the MnIII/MnII reduction potentials has been characterized, and the superoxide dismutase activity of the compounds has been examined.

Thirteen manganese porphyrins and two porphodimethenes bearing diverse substituents (electron-withdrawing, lipophilic, polar) in distinct patterns at the meso positions have been prepared, characterized electrochemically and evaluated as potential superoxide dismutase mimics.Figure optionsDownload as PowerPoint slide