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Complementation of SOD-deficientEscherichia coliby manganese porphyrin mimics of superoxide dismutase activity

Authors
Journal
Free Radical Biology and Medicine
0891-5849
Publisher
Elsevier
Publication Date
Volume
37
Issue
3
Identifiers
DOI: 10.1016/j.freeradbiomed.2004.04.040
Keywords
  • Mn(Iii) Alkylpyridyl-
  • Diethylimidazolyl-
  • Methoxyethylpyridyl-
  • And Methoxyethylimidazolylporphyrins
  • Superoxide Dismutase Mimics
  • Sod-Deficiente. Coli
  • Complementation Of Sod Defect
  • Free Radicals
Disciplines
  • Chemistry

Abstract

Abstract Cationic Mn(III) porphyrins substituted on the methine bridge carbons ( meso positions) with N-alkylpyridinium or N,N′-diethylimidazolium groups have been prepared and characterized, both chemically and as SOD mimics. The ortho tetrakis N-methylpyridinium compound was substantially more active than the corresponding para isomer. This ortho compound also exhibited a more positive redox potential and greater ability to facilitate the aerobic growth of a SOD-deficient Escherichia coli. Analogs with longer alkyl side chains and with methoxyethyl side chains, as well as with N,N′-diethylimidazolium and N,N′-dimethoxyethylimidazolium groups on the meso positions, have been prepared in anticipation of greater penetration of the cells due to greater lipophilicity. We now report that the more lipophilic compounds were effective at complementing the SOD-deficient E. coli at lower concentrations than were needed with the less lipophilic compounds. The greater efficacy of the more lipophilic compounds was achieved at the cost of greater toxicity that became apparent when these compounds were applied at higher concentrations.

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