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Synthesis and in vitro antioxidant properties of manganese(III) beta-octabromo-meso-tetrakis(4-carboxyphenyl)porphyrin.

Publication ,  Journal Article
Kachadourian, R; Flaherty, MM; Crumbliss, AL; Patel, M; Day, BJ
Published in: Journal of inorganic biochemistry
July 2003

Manganese(III) meso-tetrakis(4-carboxypheny)porphyrin (MnTBAP) is a readily available and widely used agent to scavenge reactive oxygen species. A major limitation of MnTBAP is its relatively weak potency due to its low metal centered redox potential. The goal of these studies was to prepare a more potent analog of MnTBAP by increasing its redox potential through beta-substitution on the porphyrin ring by bromination. Manganese(III) beta-octabromo-meso-tetrakis(4-carboxyphenyl)porphyrin (MnBr(8)TBAP) was prepared in three steps starting from the methyl ester of the free ligand meso-tetrakis(4-carboxyphenyl)porphyrin, with an overall yield of 50%. The superoxide dismutase (SOD)-like activity of MnBr(8)TBAP (IC(50)=0.7 microM) was the same as manganese(III) meso-tetrakis(N-methylpyridinium-4-yl)porphyrin (MnTM-4-PyP(5+)), while the metal-centered redox potential of the first was considerably higher than the second (E(1/2)=+128 and 0 mV vs. normal hydrogen electrode, respectively). However, a number of these cationic Mn-porphyrins (such as MnTM-4-PyP(5+)) redox-cycle with cytochrome P450 reductase in the presence of oxygen and NADPH whereas MnTBAP and its halogenated analog, MnBr(8)TBAP do not. The enhanced ability of MnBr(8)TBAP to inhibit paraquat- and hypoxia-induced injuries in vitro is also reported. In these in vitro models, in which cationic Mn-porphyrins exhibit very low activity, MnBr(8)TBAP appears to be at least eightfold more active than the non-brominated analog MnTBAP.

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Published In

Journal of inorganic biochemistry

DOI

EISSN

1873-3344

ISSN

0162-0134

Publication Date

July 2003

Volume

95

Issue

4

Start / End Page

240 / 248

Related Subject Headings

  • Superoxide Dismutase
  • Rats
  • Paraquat
  • Oxidation-Reduction
  • NADPH-Ferrihemoprotein Reductase
  • Molecular Structure
  • Metalloporphyrins
  • Lung
  • Lipid Peroxidation
  • Inorganic & Nuclear Chemistry
 

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Kachadourian, R., Flaherty, M. M., Crumbliss, A. L., Patel, M., & Day, B. J. (2003). Synthesis and in vitro antioxidant properties of manganese(III) beta-octabromo-meso-tetrakis(4-carboxyphenyl)porphyrin. Journal of Inorganic Biochemistry, 95(4), 240–248. https://doi.org/10.1016/s0162-0134(03)00135-1
Kachadourian, Remy, Meghan M. Flaherty, Alvin L. Crumbliss, Manisha Patel, and Brian J. Day. “Synthesis and in vitro antioxidant properties of manganese(III) beta-octabromo-meso-tetrakis(4-carboxyphenyl)porphyrin.Journal of Inorganic Biochemistry 95, no. 4 (July 2003): 240–48. https://doi.org/10.1016/s0162-0134(03)00135-1.
Kachadourian R, Flaherty MM, Crumbliss AL, Patel M, Day BJ. Synthesis and in vitro antioxidant properties of manganese(III) beta-octabromo-meso-tetrakis(4-carboxyphenyl)porphyrin. Journal of inorganic biochemistry. 2003 Jul;95(4):240–8.
Kachadourian, Remy, et al. “Synthesis and in vitro antioxidant properties of manganese(III) beta-octabromo-meso-tetrakis(4-carboxyphenyl)porphyrin.Journal of Inorganic Biochemistry, vol. 95, no. 4, July 2003, pp. 240–48. Epmc, doi:10.1016/s0162-0134(03)00135-1.
Kachadourian R, Flaherty MM, Crumbliss AL, Patel M, Day BJ. Synthesis and in vitro antioxidant properties of manganese(III) beta-octabromo-meso-tetrakis(4-carboxyphenyl)porphyrin. Journal of inorganic biochemistry. 2003 Jul;95(4):240–248.
Journal cover image

Published In

Journal of inorganic biochemistry

DOI

EISSN

1873-3344

ISSN

0162-0134

Publication Date

July 2003

Volume

95

Issue

4

Start / End Page

240 / 248

Related Subject Headings

  • Superoxide Dismutase
  • Rats
  • Paraquat
  • Oxidation-Reduction
  • NADPH-Ferrihemoprotein Reductase
  • Molecular Structure
  • Metalloporphyrins
  • Lung
  • Lipid Peroxidation
  • Inorganic & Nuclear Chemistry