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Assaying the antioxidant and radical scavenging properties of aliphatic mono- and Di-N-oxides in superoxide dismutase-deficient yeast and in a chemiluminescence test

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Abstract

The antioxidative action of amphiphilic mono-(alkanoylamino) ethyldimethylamine-N-oxides (EDA), di-N-oxides 1,1-bis{[2-(N,N-dimethylamino)ethyl]amido}alkane-di-N-oxides (MEDA) and 1,1-bis {[3-(N,N-dimethylamino)propyl]amido}alkane-di-N-oxides (MPDA) with a 12- and 14-membered acyl chain againsttert-butylhydroperoxide (TBHP)-produced peroxyl and paraquat (PQ)-generated superoxide radicals was determined in superoxide dismutase-deficient mutants ofSaccharomyces cerevisiae, and, in parallel, in a chemical assay based on chemiluminescence changes caused in a luminol system by peroxyl radicals generated from the azo-compound 2,2′-azobis(2-amidinopropane dihydrochloride) (AAPH). At 30 µmol/L, the shorter-chain compounds did not affect strain survival while longer-chain ones, in some cases, lowered the survival ofsod2 andsod1 sod2 cells. Whether nontoxic or medium-toxic, allN-oxides protected thesod strains against the toxic effect of PQ and TBHP, the protection being stronger with the di-N-oxides. The survival was lowered only by 14-MPDA in the TBHP-exposedsod2 mutant. Membrane lipids isolated from all strains were protected against TBHP-induced peroxidation by both mono- and di-N-oxides, the protection being dependent on the alkyl chain length. Mono-N-oxides were again less active than di-N-oxides with the same alkyl chains, the antiperoxidative activity being also dependent on lipids isolated from the individual mutants. In the chemiluminescence assay, the IC50 value of theN-oxides for scavenging of radicals generated from AAPH generally decreased (i.e. the scavenging efficiency increased) with increasing chain length and was the highest in MEDA.

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Abbreviations

AAPH:

2,2′-azobis(2-amidinopropane) dihydrochloride

IC50 :

antioxidant concentration that reduces luminol luminescence to 50 %

EDA:

2-(alkanoylamino)ethyldimethylamine-N-oxides;see Fig. 1

MEDA:

1,1-bis{[2-(N,N-dimethylamino)ethyl]amido}alkane-di-N-oxides;see Fig. 1

MPDA:

1,1-bis{[3-(N,N-dimethylamino)propyl]amido}alkane-di-N-oxides;see Fig. 1

PDA:

3-(alkanoylamino)propyldimethylamine-N-oxides;see Fig. 1

PQ:

paraquat

ROS:

reactive oxygen species

SOD:

superoxide dismutase (EC 1.15.1.1)

SUV:

small unilamellar vesicles

TBA:

thiobarbituric acid

TBHP:

tert-butylhydroperoxide

TBRS:

thiobarbituric acid-reactive substances

TMA-DPH:

N,N,N-trimethyl-4-(6-phenyl-1,3,5-hexatrien-1-y1)phenylammonium 4-toluenesulfonate

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Authors and Affiliations

  1. Faculty of Biotechnology, Wrocław University, 51-148, Wrocław, Poland

    A. Krasowska & A. Murzyn

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

    A. Piasecki

  3. 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. Murzyn
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  4. K. Sigler
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Corresponding author

Correspondence to A. Krasowska.

Additional information

This work was supported by thePolish Committee for Scientific Research (grant 3 T09B 075 27), by theWrocław University (grant 2483/W/IGIM), by theMinistry of Education, Youth and Sports of the Czech Republic (Research Center 1M0570), and by theInstitutional Research Concept AV 0Z 5020 0510.

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Krasowska, A., Piasecki, A., Murzyn, A. et al. Assaying the antioxidant and radical scavenging properties of aliphatic mono- and Di-N-oxides in superoxide dismutase-deficient yeast and in a chemiluminescence test. Folia Microbiol 52, 45–51 (2007). https://doi.org/10.1007/BF02932137

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  • DOI: https://doi.org/10.1007/BF02932137

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