Home LiteratureArticle Details
PMID: 9531471 Published · ppublish English Journal Article Research Support, Non-U.S. Gov't

Measurement of oxidative DNA damage by gas chromatography-mass spectrometry: ethanethiol prevents artifactual generation of oxidized DNA bases.

The Biochemical journal ·Vol. 331 ( Pt 2) ·1998-04-15 ·Pages 365-9

Jenner A, England TG, Aruoma OI, Halliwell B

Abstract

Analysis of oxidative damage to DNA bases by GC-MS enables identification of a range of base oxidation products, but requires a derivatization procedure. However, derivatization at high temperature in the presence of air can cause 'artifactual' oxidation of some undamaged bases, leading to an overestimation of their oxidation products, including 8-hydroxyguanine. Therefore derivatization conditions that could minimize this problem were investigated. Decreasing derivatization temperature to 23 degrees C lowered levels of 8-hydroxyguanine, 8-hydroxyadenine, 5-hydroxycytosine and 5-(hydroxymethyl)uracil measured by GC-MS in hydrolysed calf thymus DNA. Addition of the reducing agent ethanethiol (5%, v/v) to DNA samples during trimethylsilylation at 90 degrees C also decreased levels of these four oxidized DNA bases as well as 5-hydroxyuracil. Removal of guanine from hydrolysed DNA samples by treatment with guanase, prior to derivatization, resulted in 8-hydroxyguanine levels (54-59 pmol/mg of DNA) that were significantly lower than samples not pretreated with guanase, independent of the derivatization conditions used. Only hydrolysed DNA samples that were derivatized at 23 degrees C in the presence of ethanethiol produced 8-hydroxyguanine levels (56+/-8 pmol/mg of DNA) that were as low as those of guanase-pretreated samples. Levels of other oxidized bases were similar to samples derivatized at 23 degrees C without ethanethiol, except for 5-hydroxycytosine and 5-hydroxyuracil, which were further decreased by ethanethiol. Levels of 8-hydroxyguanine, 8-hydroxyadenine and 5-hydroxycytosine measured in hydrolysed calf thymus DNA by the improved procedures described here were comparable with those reported previously by HPLC with electrochemical detection and by GC-MS with prepurification to remove undamaged base. We conclude that artifactual oxidation of DNA bases during derivatization can be prevented by decreasing the temperature to 23 degrees C, removing air from the derivatization reaction and adding ethanethiol.

MeSH Terms
Adenine/analogs & derivatives,analysis Animals Cattle Cytosine/analogs & derivatives,analysis DNA/analysis,chemistry DNA Damage Gas Chromatography-Mass Spectrometry/methods Guanine/analogs & derivatives,analysis Guanine Deaminase/pharmacology Oxidation-Reduction Pentoxyl/analogs & derivatives,analysis Sulfhydryl Compounds/pharmacology Temperature
Chemicals
Sulfhydryl Compounds 8-hydroxyadenine 5-hydroxymethyluracil 8-hydroxyguanine Guanine 5-hydroxycytosine Pentoxyl Cytosine DNA Guanine Deaminase Adenine ethanethiol
Authors & Affiliations
4 authors, click to expand affiliations / ORCID
Jenner A
International Antioxidant and Neurodegenerative Disease Research Centres, Pharmacology Group, University of London, King's College, Manresa Road, London. SW3 6LX, U.K. [email protected]
England T G
Aruoma O I
Halliwell B
References (22)
22 references, click to expand
  1. The measurement of oxidative damage to DNA by HPLC and GC/MS techniques.
    Free Radic Res Commun. 1992;16(2):75-87 PMID: 1321076
  2. Assays for 8-hydroxy-2'-deoxyguanosine: a biomarker of in vivo oxidative DNA damage.
    Free Radic Biol Med. 1991;10(3-4):211-6 PMID: 1650737
  3. Oxidants, antioxidants, and the degenerative diseases of aging.
    Proc Natl Acad Sci U S A. 1993 Sep 1;90(17):7915-22 PMID: 8367443
  4. Quantitative determination of 8-hydroxyguanine and guanine by isotope dilution mass spectrometry.
    Anal Biochem. 1995 Aug 10;229(2):336-44 PMID: 7485992
  5. Damage to DNA by reactive oxygen and nitrogen species: role in inflammatory disease and progression to cancer.
    Biochem J. 1996 Jan 1;313 ( Pt 1):17-29 PMID: 8546679
  6. Determination of 8-oxoguanine in DNA by gas chromatography--mass spectrometry and HPLC--electrochemical detection: overestimation of the background level of the oxidized base by the gas chromatography--mass spectrometry assay.
    Chem Res Toxicol. 1995 Dec;8(8):1039-45 PMID: 8605286
  7. Observation and prevention of an artefactual formation of oxidized DNA bases and nucleosides in the GC-EIMS method.
    Carcinogenesis. 1996 Feb;17(2):347-53 PMID: 8625462
  8. Measurement of oxidized and methylated DNA bases by HPLC with electrochemical detection.
    Biochem J. 1996 Aug 15;318 ( Pt 1):21-3 PMID: 8761446
  9. Oxidative stress, nutrition and health. Experimental strategies for optimization of nutritional antioxidant intake in humans.
    Free Radic Res. 1996 Jul;25(1):57-74 PMID: 8814444
  10. Base modification and strand breakage in isolated calf thymus DNA and in DNA from human skin epidermal keratinocytes exposed to peroxynitrite or 3-morpholinosydnonimine.
    Chem Res Toxicol. 1996 Oct-Nov;9(7):1152-8 PMID: 8902271
  11. What structural features determine repair enzyme specificity and mechanism in chemically modified DNA?
    Chem Res Toxicol. 1997 Jul;10(7):713-32 PMID: 9250405
  12. Oxidative DNA damage in the parkinsonian brain: an apparent selective increase in 8-hydroxyguanine levels in substantia nigra.
    J Neurochem. 1997 Sep;69(3):1196-203 PMID: 9282943
  13. Hypochlorous acid-induced base modifications in isolated calf thymus DNA.
    Chem Res Toxicol. 1997 Nov;10(11):1240-6 PMID: 9403176
  14. Characterization of free radical-induced base damage in DNA at biologically relevant levels.
    Anal Biochem. 1986 Jul;156(1):182-8 PMID: 3017148
  15. Formation of cytosine glycol and 5,6-dihydroxycytosine in deoxyribonucleic acid on treatment with osmium tetroxide.
    Biochem J. 1986 Apr 15;235(2):531-6 PMID: 3741404
  16. Iron ion-dependent modification of bases in DNA by the superoxide radical-generating system hypoxanthine/xanthine oxidase.
    J Biol Chem. 1989 Aug 5;264(22):13024-8 PMID: 2546943
  17. Endogenous carcinogenesis: molecular oncology into the twenty-first century--presidential address.
    Cancer Res. 1989 Oct 15;49(20):5489-96 PMID: 2676144
  18. The role of 8-hydroxyguanine in carcinogenesis.
    Carcinogenesis. 1990 Sep;11(9):1447-50 PMID: 2205403
  19. Gas chromatography-mass spectrometry of free radical-induced products of pyrimidines and purines in DNA.
    Methods Enzymol. 1990;193:842-57 PMID: 2074846
  20. Chemical nature of DNA-protein cross-links produced in mammalian chromatin by hydrogen peroxide in the presence of iron or copper ions.
    Biochemistry. 1991 May 21;30(20):4873-9 PMID: 2036356
  21. Formation of 8-hydroxy(deoxy)guanosine and generation of strand breaks at guanine residues in DNA by singlet oxygen.
    Biochemistry. 1991 Jun 25;30(25):6283-9 PMID: 2059635
  22. Quantitative determination of oxidative base damage in DNA by stable isotope-dilution mass spectrometry.
    FEBS Lett. 1993 Jan 2;315(1):1-6 PMID: 8416801
Article Info
Journal
The Biochemical journal
Abbr.
Biochem J
ISSN
0264-6021
Published
1998-04-15
Pages
365-9
Language
English
Region
England
NLM ID
2984726R
PMCID
PMC1219362
Subset
IM
Analysis Services
Analysis Services

Contact

No. 2 Wenbo Road, Zhangqiu District, Jinan, Shandong

Qilu Normal University · Genelibs Bioinformatics Lab

750 Shunhua Rd, Jinan

2F, Bldg F, University Science Park

Tel: 0531-88819269

WeChat Official Account

Follow our WeChat subscription account for real-time updates and the latest in medical and biological research.


Business Email

E-mail: [email protected]