Measurement of styrene-oxide cysteine adducts in hemoglobin by selective catalytic reduction

Details

• Personal Author:
  Doane-Setzer P ; Rappaport SM ; Smith MT ; Ting D ; Woodlee J
• Description:
  Alkylating agents, either direct-acting or generated in vivo, form an important class of environmental mutagens and carcinogens. These agents are characterized by their ability to bind covalently to nucleophilic sites in proteins and DNA. Due to the long life time of red blood cells and the stability of protein adducts, Ehrenberg and coworkers first (Calle man 1978; Osterman-Golkar 1976) proposed the use of hemoglobin (Hb) as a dosimeter for alkylation in vivo. Since then, several methods have been devised to detect hemoglobin adducts (Bryant 1987; Calleman 1978; Farmer 1980; Neumann 1984). Here, we report an alternative method that is sensitive, specific and relatively simple. It is based on the well known desulfurization by Raney nickel (Ra-Ni) (Pettit 1962; Pizey 1974), in which the carbon-sulphur bond formed by the alkylating agent and cysteine is selectively cleaved and at least one new carbon-hydrogen bond is formed. Pachecka et al. (Pachecka 1979) demonstrated that when styrene-7,8-oxide-glutathione adducts were refluxed with Ra-Ni in ethanol, 1-phenylethanol (1-PE) and 2-phenylethanol (2-PE) were produced. This reaction between cysteine-bound styrene oxide and Ra-Ni is shown in Figure 1. We utilized this reaction to determine the amount of cysteine-bound styrene-7,8-oxide (SO) which reacted with Hb in vitro and in vivo. [Description provided by NIOSH]
• Subjects:
  Animals Carcinogens DNA Energy Metabolism Epoxy Resins Hazardous Substances Laboratories Men Mutagens Occupational Health Radiation Dosimeters Safety Styrene

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• Keywords:
  Alkylating-agents Chemical-binding Deoxyribonucleic-acids DNA-adducts Dosimetry Drugs Epoxy-compounds Erythrocytes Humans In-vitro-study In-vivo-study Laboratory-animals Metabolism Oxidation-reduction-reactions Proteins Red-blood-cells Styrenes Toxic-effects

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• ISSN:
  0065-2598
• Document Type:
  Text
• Funding:
  Grant
• Genre:
  Journal Article
• Place as Subject:
  California ; North Carolina ; OSHA Region 4 ; OSHA Region 9
• CIO:
  National Institute for Occupational Safety and Health (NIOSH)
• Topic:
  Workplace Safety & Health
• Location:
  North America
• Volume:
  283
• NIOSHTIC Number:
  nn:20041064
• Citation:
  Adv Exp Med Biol 1991 Jan; 283:837-841
• Contact Point Address:
  S. M. Rappaport, Dept. of Biomedical and Environmental Health Sciences, School of Public Health, University of California, Berkeley, CA 94720
• CAS Registry Number:
  (S)-1-Phenylethanol (CAS RN 1445-91-6) ; Glutathione (CAS RN 70-18-8) ; L-(+)-Cysteine (CAS RN 52-90-4) ; Nickel (CAS RN 7440-02-0) ; Phenylethanol (CAS RN 1321-27-3) ; Styrene (CAS RN 100-42-5) ; Styrene oxide (CAS RN 96-09-3)
• Federal Fiscal Year:
  1991
• Performing Organization:
  University of North Carolina, Chapel Hill
• Peer Reviewed:
  True
• Start Date:
  19860929
• Source Full Name:
  Advances in Experimental Medicine and Biology
• End Date:
  19931227
• Collection(s):
  National Institute for Occupational Safety and Health
• Main Document Checksum:
  urn:sha-512:de2c99da3dd055a7117e0a15afa4eb5f4c36288347a39fb2d39bf507acf59a08669da50e79b40b750f5e09d4dfa25bf35c2a2a4f47d92a3b9a752baa7de792c8
• Download URL:
  https://stacks.cdc.gov/view/cdc/193722/cdc_193722_DS1.pdf
• File Type:
  [PDF - 223.73 KB ]