Literature DB >> 17822908

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

Dorothée Lahaye1, Kannan Muthukumaran, Chen-Hsiung Hung, Dorota Gryko, Júlio S Rebouças, Ivan Spasojević, Ines Batinić-Haberle, Jonathan S Lindsey.   

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.

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Year:  2007        PMID： 17822908      PMCID： PMC2111292          DOI： 10.1016/j.bmc.2007.07.015

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN： 0968-0896            Impact factor:   3.641


  71 in total

1.  Calixphyrins: Novel Macrocycles at the Intersection between Porphyrins and Calixpyrroles This work was supported by the National Institutes of Health (CA-68682, GM-58907, and TW-00682 to J.L.S.), the National Science Foundation (CHE-9725399 to J.L.S. and CHE-9807702 to V.L. for the purchase of the Nonius Kappa CCD), the Howard Hughes Foundation (V.K. and J.L.S.), the Grant Agency of the Czech Republic (No. 203/97/1099 to V.K.), the Ministry of Education (No. VS-97135 and Project CEZ: J19/98: 223400008 to V.K.), and the Howard Hughes Medical Institute (74195-541101 to V.K.).

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3.  Mitochondrial reactive oxygen species in mice lacking superoxide dismutase 2: attenuation via antioxidant treatment.

Authors:  Karl J Morten; Brian A C Ackrell; Simon Melov
Journal:  J Biol Chem       Date:  2005-12-02       Impact factor: 5.157

4.  Synthesis of Linear Amphipathic Porphyrin Dimers and Trimers: An Approach to Bilayer Lipid Membrane Spanning Porphyrin Arrays.

Authors:  Norikazu Nishino; Richard W. Wagner; Jonathan S. Lindsey
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7.  Catalytic scavenging of peroxynitrite by isomeric Mn(III) N-methylpyridylporphyrins in the presence of reductants.

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Journal:  Chem Res Toxicol       Date:  1999-05       Impact factor: 3.739

8.  Rational syntheses of porphyrins bearing up to four different meso substituents.

Authors:  P D Rao; S Dhanalekshmi; B J Littler; J S Lindsey
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9.  A salen-manganese catalytic free radical scavenger inhibits type 1 diabetes and islet allograft rejection.

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  16 in total

1.  Peroxynitrite formation in nitric oxide-exposed submitochondrial particles: detection, oxidative damage and catalytic removal by Mn-porphyrins.

Authors:  Valeria Valez; Adriana Cassina; Ines Batinic-Haberle; Balaraman Kalyanaraman; Gerardo Ferrer-Sueta; Rafael Radi
Journal:  Arch Biochem Biophys       Date:  2012-11-08       Impact factor: 4.013

2.  A new SOD mimic, Mn(III) ortho N-butoxyethylpyridylporphyrin, combines superb potency and lipophilicity with low toxicity.

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Journal:  Free Radic Biol Med       Date:  2012-02-13       Impact factor: 7.376

3.  Methoxy-derivatization of alkyl chains increases the in vivo efficacy of cationic Mn porphyrins. Synthesis, characterization, SOD-like activity, and SOD-deficient E. coli study of meta Mn(III) N-methoxyalkylpyridylporphyrins.

Authors:  Artak G Tovmasyan; Zrinka Rajic; Ivan Spasojevic; Julio S Reboucas; Xin Chen; Daniela Salvemini; Huaxin Sheng; David S Warner; Ludmil Benov; Ines Batinic-Haberle
Journal:  Dalton Trans       Date:  2011-03-08       Impact factor: 4.390

4.  Impact of electrostatics in redox modulation of oxidative stress by Mn porphyrins: protection of SOD-deficient Escherichia coli via alternative mechanism where Mn porphyrin acts as a Mn carrier.

Authors:  Júlio S Rebouças; Gilson DeFreitas-Silva; Ivan Spasojević; Ynara M Idemori; Ludmil Benov; Ines Batinić-Haberle
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Review 5.  Superoxide dismutase mimics: chemistry, pharmacology, and therapeutic potential.

Authors:  Ines Batinić-Haberle; Júlio S Rebouças; Ivan Spasojević
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6.  Detailed mechanism of the autoxidation of N-hydroxyurea catalyzed by a superoxide dismutase mimic Mn(III) porphyrin: formation of the nitrosylated Mn(II) porphyrin as an intermediate.

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7.  Orally available Mn porphyrins with superoxide dismutase and catalase activities.

Authors:  Rosalind A Rosenthal; Karl D Huffman; Leslie W Fisette; Christy A Damphousse; Wyeth B Callaway; Bernard Malfroy; Susan R Doctrow
Journal:  J Biol Inorg Chem       Date:  2009-06-06       Impact factor: 3.358

8.  Lipophilicity of potent porphyrin-based antioxidants: comparison of ortho and meta isomers of Mn(III) N-alkylpyridylporphyrins.

Authors:  Ivan Kos; Júlio S Rebouças; Gilson DeFreitas-Silva; Daniela Salvemini; Zeljko Vujaskovic; Mark W Dewhirst; Ivan Spasojević; Ines Batinić-Haberle
Journal:  Free Radic Biol Med       Date:  2009-04-08       Impact factor: 7.376

9.  Acid-base and electrochemical properties of manganese meso(ortho- and meta-N-ethylpyridyl)porphyrins: voltammetric and chronocoulometric study of protolytic and redox equilibria.

Authors:  Tin Weitner; Ivan Kos; Zoran Mandić; Ines Batinić-Haberle; Mladen Biruš
Journal:  Dalton Trans       Date:  2013-10-01       Impact factor: 4.390

10.  Pure manganese(III) 5,10,15,20-tetrakis(4-benzoic acid)porphyrin (MnTBAP) is not a superoxide dismutase mimic in aqueous systems: a case of structure-activity relationship as a watchdog mechanism in experimental therapeutics and biology.

Authors:  Júlio S Rebouças; Ivan Spasojević; Ines Batinić-Haberle
Journal:  J Biol Inorg Chem       Date:  2007-11-29       Impact factor: 3.358
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