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

ABSTRACT: 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.

SUBMITTER: Lahaye D

PROVIDER: S-EPMC2111292 | biostudies-literature | 2007 Nov

REPOSITORIES: biostudies-literature

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

Lahaye Dorothée D 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

Bioorganic & medicinal chemistry 20070819 22

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 ...[more]

PMID: 17822908

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