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 +0.3V 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 Mn(III)/Mn(II) reduction potentials has been characterized, and the superoxide dismutase activity of the compounds has been examined.
Lahaye
Dorothée
D
Department of Chemistry, North Carolina State University, Raleigh, NC 27695, USA.
Muthukumaran
Kannan
K
Hung
Chen-Hsiung
CH
Gryko
Dorota
D
Rebouças
Júlio S
JS
Spasojević
Ivan
I
Batinić-Haberle
Ines
I
Lindsey
Jonathan S
JS
D002384:Catalysis; D045304:Cytochromes c / Q000737:chemistry; D015195:Drug Design; D004563:Electrochemistry; D004579:Electron Transport; D004789:Enzyme Activation / Q000187:drug effects; D008051:Lipid Bilayers / Q000737:chemistry; D008345:Manganese / Q000737:chemistry*; D008665:Metalloporphyrins / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D012995:Solubility; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013482:Superoxide Dismutase / Q000737:chemistry*; D013481:Superoxides / Q000737:chemistry