PMID- 9597770
OWN - NLM
STAT- MEDLINE
DCOM- 19980604
LR  - 20181016
IS  - 1076-5174 (Print)
IS  - 1076-5174 (Linking)
VI  - 33
IP  - 4
DP  - 1998 Apr
TI  - Quantitative analysis of 1,3-butadiene-induced DNA adducts in vivo and in vitro 
      using liquid chromatography electrospray ionization tandem mass spectrometry.
PG  - 363-76
AB  - 1,3-Butadiene (BD) is a high volume industrial chemical which is known as a 
      multi-site rodent carcinogen and is classified as a probable human carcinogen. 
      Covalent interactions of the reactive epoxy metabolites of BD with DNA lead to 
      the formation of DNA adducts which may cause mutations and tumor formation. In 
      the present work, liquid chromatography/electrospray ionization tandem mass 
      spectrometry (LC/ESI-MS/MS) was employed for analyses of BD-induced DNA adducts 
      in vitro and in vivo. Selected reaction monitoring (SRM) using the fragmentation 
      of the [M + H]+ ions of the adducts to the corresponding protonated nucleobases 
      under collision-induced dissociation was performed. Quantitation was based on 
      isotope dilution with 13C- and 15N-labeled internal standards. The methods were 
      applied in vitro [calf thymus DNA and TK6 cell cultures treated with epoxy 
      metabolites of BD, 3,4-epoxy-1-butene (EB) and diepoxybutane (DEB)] and in vivo 
      [DNA isolated from tissues of BD-exposed laboratory animals]. Two regioisomers of 
      N-7-EB-guanine adducts, N-7-(2-hydroxy-3-buten-1-yl)guanine (N-7-EB-Gua I) and 
      N-7-(1-hydroxy-3-buten-2-yl)guanine (N-7-EB-Gua II) and two N-3-EB-adenine 
      isomers, N-3-(2-hydroxy-3-buten-1-yl)adenine and 
      N-3-(1-hydroxy-3-buten-2-yl)adenine (N-3-EB-Ade I and II), were found in 
      EB-exposed samples. N-7-(2',3',4'-trihydroxybut-1'-yl)guanine (N-7-THB-Gua), 
      N6-(2',3',4'-trihydroxybut-1'-yl)adenine (N6-THB-Ade), and 
      N-3-(2',3',4'-trihydroxybut-1'-yl)adenine (N-3-THB-Ade) were detected in 
      DEB-treated DNA. DNA isolated from liver and lung of rats and mice exposed to 
      1250 ppm BD for 2 weeks contained both regioisomers of N-7-EB-Gua and N-3-EB-Ade, 
      as well as N-7-THB-Gua and N6-THB-Ade. The methods developed in this work provide 
      the means to study accumulation, repair and dose-response relationships of BD-DNA 
      adducts in vivo. Although less sensitive than gas chromatography/electron capture 
      negative ionization high-resolution mass spectrometry (GC/ECNI-HRMS), 
      LC/ESI(+)-MS/MS in the SRM mode is extremely useful for analysis of BD-DNA 
      adducts, which are not amenable to GC and derivatization owing to the presence of 
      several adjacent polar functional groups. Using LC/ESI-MS/MS and isotope 
      dilution, multiple structurally diverse BD-DNA adducts can be analyzed 
      simultaneously in the same sample with minimal sample preparation.
FAU - Tretyakova NYu
AU  - Tretyakova NYu
AD  - Department of Environmental Sciences and Engineering, University of North 
      Carolina, Chapel Hill 27599-7400, USA.
FAU - Chiang, S Y
AU  - Chiang SY
FAU - Walker, V E
AU  - Walker VE
FAU - Swenberg, J A
AU  - Swenberg JA
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
PL  - England
TA  - J Mass Spectrom
JT  - Journal of mass spectrometry : JMS
JID - 9504818
RN  - 0 (Butadienes)
RN  - 0 (DNA Adducts)
RN  - 0 (Epoxy Compounds)
RN  - 0 (Mutagens)
RN  - 478ERR5NKR (3,4-epoxy-1-butene)
RN  - 60OB65YNAB (diepoxybutane)
RN  - 9007-49-2 (DNA)
RN  - JSD5FGP5VD (1,3-butadiene)
SB  - IM
MH  - Animals
MH  - Butadienes/*pharmacology
MH  - Cattle
MH  - Cells, Cultured
MH  - Chromatography, Gas/methods
MH  - Chromatography, Liquid/*methods
MH  - DNA/analysis/drug effects
MH  - DNA Adducts/*analysis
MH  - Epoxy Compounds/pharmacology
MH  - Humans
MH  - Hydrolysis
MH  - Lymphocytes/chemistry/drug effects
MH  - Mass Spectrometry/*methods
MH  - Mice
MH  - Mice, Inbred Strains
MH  - Mutagens/*pharmacology
MH  - Rats
MH  - Rats, Inbred F344
EDAT- 1998/05/23 02:16
MHDA- 2000/06/22 10:00
CRDT- 1998/05/23 02:16
PHST- 1998/05/23 02:16 [pubmed]
PHST- 2000/06/22 10:00 [medline]
PHST- 1998/05/23 02:16 [entrez]
AID - 10.1002/(SICI)1096-9888(199804)33:4<363::AID-JMS643>3.0.CO;2-E [pii]
AID - 10.1002/(SICI)1096-9888(199804)33:4<363::AID-JMS643>3.0.CO;2-E [doi]
PST - ppublish
SO  - J Mass Spectrom. 1998 Apr;33(4):363-76. doi: 
      10.1002/(SICI)1096-9888(199804)33:4<363::AID-JMS643>3.0.CO;2-E.