High lipophilicity of meta Mn(III) N-alkylpyridylporphyrin-based superoxide dismutase mimics compensates for their lower antioxidant potency and makes them as effective as ortho analogues in protecting superoxide dismutase-deficient Escherichia coli.
Publication
, Journal Article
Kos, I; Benov, L; Spasojević, I; Rebouças, JS; Batinić-Haberle, I
Published in: J Med Chem
December 10, 2009
Lipophilicity/bioavailibility of Mn(III) N-alkylpyridylporphyrin-based superoxide dismutase (SOD) mimics has a major impact on their in vivo ability to suppress oxidative stress. Meta isomers are less potent SOD mimics than ortho analogues but are 10-fold more lipophilic and more planar. Enhanced lipophilicity contributes to their higher accumulation in cytosol of SOD-deficient Escherichia coli, compensating for their lower potency; consequently, both isomers exert similar-to-identical protection of SOD-deficient E. coli. Thus meta isomers may be prospective therapeutics as are ortho porphyrins.
Duke Scholars
Published In
J Med Chem
DOI
EISSN
1520-4804
Publication Date
December 10, 2009
Volume
52
Issue
23
Start / End Page
7868 / 7872
Location
United States
Related Subject Headings
- Superoxide Dismutase
- Porphyrins
- Oxidation-Reduction
- Organometallic Compounds
- Medicinal & Biomolecular Chemistry
- Manganese
- Isomerism
- Hydrophobic and Hydrophilic Interactions
- Escherichia coli
- Cytosol
Citation
APA
Chicago
ICMJE
MLA
NLM
Kos, I., Benov, L., Spasojević, I., Rebouças, J. S., & Batinić-Haberle, I. (2009). High lipophilicity of meta Mn(III) N-alkylpyridylporphyrin-based superoxide dismutase mimics compensates for their lower antioxidant potency and makes them as effective as ortho analogues in protecting superoxide dismutase-deficient Escherichia coli. J Med Chem, 52(23), 7868–7872. https://doi.org/10.1021/jm900576g
Kos, Ivan, Ludmil Benov, Ivan Spasojević, Júlio S. Rebouças, and Ines Batinić-Haberle. “High lipophilicity of meta Mn(III) N-alkylpyridylporphyrin-based superoxide dismutase mimics compensates for their lower antioxidant potency and makes them as effective as ortho analogues in protecting superoxide dismutase-deficient Escherichia coli.” J Med Chem 52, no. 23 (December 10, 2009): 7868–72. https://doi.org/10.1021/jm900576g.
Kos I, Benov L, Spasojević I, Rebouças JS, Batinić-Haberle I. High lipophilicity of meta Mn(III) N-alkylpyridylporphyrin-based superoxide dismutase mimics compensates for their lower antioxidant potency and makes them as effective as ortho analogues in protecting superoxide dismutase-deficient Escherichia coli. J Med Chem. 2009 Dec 10;52(23):7868–72.
Kos, Ivan, et al. “High lipophilicity of meta Mn(III) N-alkylpyridylporphyrin-based superoxide dismutase mimics compensates for their lower antioxidant potency and makes them as effective as ortho analogues in protecting superoxide dismutase-deficient Escherichia coli.” J Med Chem, vol. 52, no. 23, Dec. 2009, pp. 7868–72. Pubmed, doi:10.1021/jm900576g.
Kos I, Benov L, Spasojević I, Rebouças JS, Batinić-Haberle I. High lipophilicity of meta Mn(III) N-alkylpyridylporphyrin-based superoxide dismutase mimics compensates for their lower antioxidant potency and makes them as effective as ortho analogues in protecting superoxide dismutase-deficient Escherichia coli. J Med Chem. 2009 Dec 10;52(23):7868–7872.
Published In
J Med Chem
DOI
EISSN
1520-4804
Publication Date
December 10, 2009
Volume
52
Issue
23
Start / End Page
7868 / 7872
Location
United States
Related Subject Headings
- Superoxide Dismutase
- Porphyrins
- Oxidation-Reduction
- Organometallic Compounds
- Medicinal & Biomolecular Chemistry
- Manganese
- Isomerism
- Hydrophobic and Hydrophilic Interactions
- Escherichia coli
- Cytosol