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Amphiphilic amine-N-oxides with aliphatic alkyl chain act as efficient superoxide dismutase mimics, antioxidants and lipid peroxidation blockers in yeast

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Abstract

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 inSaccharomyces cerevisiae. They also enhance the survival ofsod mutants ofS. cerevisiae exposed to the hydrophilic superoxide-generating prooxidant paraquat and the amphiphilic hydroperoxide-producingtert-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 intoS. 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 ofsod 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.

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Abbreviations

HLB:

hydrophilic-lipophilic balance

LPO:

lipid peroxidation

NBD-PE:

N-(7-nitrobenz-2-oxa-1,3diazol-yl)-1,2-dihexadecanoyl-sn-glycero-3-phosphoethanolamine, triethylammonium salt

PDA:

3-(alkanolyamino)propyldimethylamine-N-oxide

PUFA:

oligounsaturated fatty acids

PCR:

polymerase chain reaction

ROS:

reactive oxygen species

SOD:

superoxide dismutase (EC 1.15.1.1)

SUV:

small unilamellar vesicles

TBHP:

tert-butylhydroperoxide

TBRS:

2-thiobarbituric acid-reactive substances

TMA-DPH:

N,N,N-trimethyl-4-(6-phenyl-1,3,5-hexatrien-1-yl)phenylammonium 4-toluenesulfonate

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Authors and Affiliations

  1. Institute of Genetics and Microbiology, Wrocław University, 51-148, Wrocław, Poland

    A. Krasowska & A. Polinceusz

  2. Institute of Organic and Polymer Technology, Wrocław University of Technology, 50-370, Wrocław, Poland

    A. Piasecki

  3. Department of Food Science and Nutrition, Medical University of Wrocław, 50-140, Wrocaw, Poland

    A. Prescha

  4. Institute of Microbiology, Academy of Sciences of the Czech Republic, 142 20, Prague, Czechia

    K. Sigler

Authors
  1. A. Krasowska
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  2. A. Piasecki
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  3. A. Polinceusz
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  4. A. Prescha
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  5. K. Sigler
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Corresponding author

Correspondence to A. Krasowska.

Additional information

This work was supported byPolish Committee for Scientific Research grant 3 T09B 075 27, byWrocław University grant 2483/W/IGIM,Czech Ministry of Education Research Centre 1M0570, and by theInstitutional Research Concept AV 0Z 5020 0510.

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Krasowska, A., Piasecki, A., Polinceusz, A. et al. Amphiphilic amine-N-oxides with aliphatic alkyl chain act as efficient superoxide dismutase mimics, antioxidants and lipid peroxidation blockers in yeast. Folia Microbiol 51, 99–107 (2006). https://doi.org/10.1007/BF02932163

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  • DOI: https://doi.org/10.1007/BF02932163

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