Amphiphilic amine-N-oxides with aliphatic alkyl chain act as efficient superoxide dismutase mimics, antioxidants and lipid peroxidation blockers in yeast
Language English Country United States Media print
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
16821718
DOI
10.1007/bf02932163
Knihovny.cz E-resources
- MeSH
- Antioxidants pharmacology MeSH
- Dimethylamines pharmacology MeSH
- Membrane Fluidity drug effects MeSH
- Membrane Lipids chemistry metabolism MeSH
- Oxidative Stress MeSH
- Paraquat toxicity MeSH
- Lipid Peroxidation drug effects MeSH
- Saccharomyces cerevisiae drug effects enzymology MeSH
- Superoxide Dismutase chemistry genetics metabolism MeSH
- tert-Butylhydroperoxide toxicity MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Antioxidants MeSH
- Dimethylamines MeSH
- Membrane Lipids MeSH
- Paraquat MeSH
- Superoxide Dismutase MeSH
- tert-Butylhydroperoxide MeSH
Amphiphilic 3-(alkanoylamino)propyldimethylamine-N-oxides with different length of the alkyl chain, i.e. different hydrophilic-lipophilic balance, act in micromolar concentrations as SOD mimics by lifting the inhibition of aerobic growth caused by SOD deletions in Saccharomyces cerevisiae. They also enhance the survival of sod mutants of S. cerevisiae exposed to the hydrophilic superoxide-generating prooxidant paraquat and the amphiphilic hydroperoxide-producing tert-butylhydroperoxide (TBHP), and largely prevent TBHP-induced peroxidation of isolated yeast plasma membrane lipids. Unlike the SOD-mimicking effect, the magnitude of these effects depends on the alkyl chain length of the amine-N-oxides, which incorporate into S. cerevisiae membranes, causing fluidity changes in both the hydrophilic surface part of the membrane and the membrane lipid matrix. Unlike wild-type strains, the membranes of sod mutants were found to contain polyunsaturated fatty acids; the sensitivity of the mutants to lipophilic pro-oxidants was found to increase with increasing content of these acids. sod mutants are useful in assessing pro- and antioxidant properties of different compounds.
See more in PubMed
Environ Sci Technol. 1988 Jan 1;22(1):77-82 PubMed
Folia Microbiol (Praha). 2002;47(2):145-51 PubMed
Mol Cell Biochem. 2005 Aug;276(1-2):175-81 PubMed
Free Radic Biol Med. 2003 Jan 15;34(2):177-85 PubMed
Z Naturforsch C J Biosci. 2002 Mar-Apr;57(3-4):344-7 PubMed
Pharmacol Res Commun. 1982 Feb;14(2):113-20 PubMed
Acta Biochim Pol. 2005;52(3):679-84 PubMed
Arch Biochem Biophys. 1995 Sep 10;322(1):291-4 PubMed
Free Radic Biol Med. 1996;20(6):843-52 PubMed
Folia Microbiol (Praha). 2003;48(6):754-60 PubMed
Folia Microbiol (Praha). 2005;50(1):24-30 PubMed
Z Naturforsch C J Biosci. 2001 Sep-Oct;56(9-10):878-85 PubMed
Free Radic Biol Med. 1998 Nov 1;25(7):832-8 PubMed
J Biol Chem. 1989 Jul 5;264(19):11131-5 PubMed
Free Radic Res. 1996 Aug;25(2):109-15 PubMed
J Agric Food Chem. 2001 Aug;49(8):3638-43 PubMed
Nucleic Acids Res. 1996 Jul 1;24(13):2519-24 PubMed
Free Radic Biol Med. 1997;22(7):1165-74 PubMed
Arch Biochem Biophys. 1997 Jul 15;343(2):225-33 PubMed
Indian J Exp Biol. 1990 May;28(5):430-3 PubMed
J Biol Chem. 1996 Oct 18;271(42):26149-56 PubMed
Methods Enzymol. 1988;157:513-28 PubMed
Chem Phys Lipids. 1996 Jan 25;79(1):55-63 PubMed
Free Radic Res. 2004 Nov;38(11):1159-65 PubMed
J Biol Chem. 1987 Dec 15;262(35):16871-9 PubMed
