Fragmentation Patterns of DNA-Benzo(a)pyrene Diol Epoxide Adducts Characterized by Nanoflow LC/Quadrupole Time-of-Flight Mass Spectrometry

Details

• Personal Author:
  Law B ; Lewis, Daniel M. ; Marshall WD ; Wang JJ
• Description:
  Polycyclic aromatic hydrocarbons are a pervasive and abundant class of environmental and workplace pollutants. Formation of covalent DNA adducts has been considered to be a useful dosimeter or molecular biomarker for assessing the exposure to such pollutants. The establishment of prospective models for the formation of DNA adducts may help to understand the mechanisms of the effects. To identify the DNA adducts in this study, the fragmentation patterns of DNA-benzo(a)pyrene diol epoxide adducts were characterized by nanoflow liquid chromatography (LC) coupled to hybrid quadrupole orthogonal acceleration time-of-flight mass spectrometry (Q-TOF-MS). In the experiment, the DNA adducts were synthesized by reaction of calf thymus DNA with anti-benzo(a)pyrene-r-7,t-8-dihydrodiol-t-9,10-epoxide(+/-) (anti-BPDE). The major adducts of N2-deoxyguanosine-benzo(a)pyrene-7,8-dihydrodiol-9,10-epoxide (N2-dG-BPDE), N6-deoxyadenosine-benzo(a)pyrene-7,8-dihydrodiol-9,10-epoxide (N6-dA-BPDE), N4-deoxycytidine-benzo(a)pyrene-7,8-epoxide (N4-dC-BPDE), and N3-deoxythymidine-benzo(a)pyrene-7,8-dihydrodiol-9,10-epoxide adduct (N3-dT-BPDE) were identified by electrospray positive ionization with TOF-MS/MS scan mode. The results of this study demonstrated that the approach that utilizes collision-induced dissociation leading to a characteristic fragmentation pattern offers a distinct advantage for identification and elucidation of molecular structural features of the DNA adducts. The fragmentation patterns established in this study may be applied to identify DNA adducts in biological systems. [Description provided by NIOSH]
• Subjects:
  Benzopyrenes Biomarkers Chromatography Hydrocarbons Mass Spectrometry Occupational Health Polycyclic Aromatic Hydrocarbons Safety
• Keywords:
  Analytical-models Chromatographic-analysis DNA-adducts Mass-spectrometry Molecular-biology Molecular-structure Polycyclic-aromatic-hydrocarbons
• ISSN:
  1387-3806
• Document Type:
  Text
• Genre:
  Journal Article
• Place as Subject:
  OSHA Region 3 ; West Virginia
• CIO:
  National Institute for Occupational Safety and Health (NIOSH)
• Division:
  HELD - Health Effects Laboratory Division
• Topic:
  Workplace Safety & Health
• Location:
  North America
• Pages in Document:
  45-55
• Volume:
  230
• Issue:
  1
• NIOSHTIC Number:
  nn:20032137
• Citation:
  Int J Mass Spectrom 2003 Nov; 230(1):45-55
• Contact Point Address:
  National Institute for Occupational Safety and Health, Heath Effects Laboratory Division,1095 Willowdale Road, Morgantown, WV 26505
• Email:
  juw9@cdc.gov
• CAS Registry Number:
  Benzo[a]pyrene (CAS RN 50-32-8) ; Benzo[a]pyrene-7,8-dihydrodiol (CAS RN 13345-25-0)
• Federal Fiscal Year:
  2004
• Peer Reviewed:
  True
• Source Full Name:
  International Journal of Mass Spectrometry
• Collection(s):
  National Institute for Occupational Safety and Health
• Main Document Checksum:
  urn:sha-512:2f7426530a48af842aee01fd30e178612400bdaf347fee8438c5b92b66ac333c05f623d45ccaa94ea1bd0829509501d25848561e1203ab4ed927fb003ed47ec5
• Download URL:
  https://stacks.cdc.gov/view/cdc/186185/cdc_186185_DS1.pdf
• File Type:
  [PDF - 492.86 KB ]