Activation of dihaloalkanes by glutathione conjugation and formation of DNA adducts
Journal Article
·
· Environ. Health Perspect.; (United States)
Ethylene dibromide (1,2-dibromoethane, EDB) can be activated to electrophilic species by either oxidative metabolism or conjugation with glutathione. Although conjugation is generally a route of detoxication, in this case it leads to genetic damage. The major DNA adduct has been identified as S-(2-(N/sup 7/-guanyl)ethyl)glutathione, which is believed to arise via half-mustard and episulfonium ion intermediates. The adduct has a half-life of about 70 to 100 hr and does not appear to migrate to other DNA sites. Glutathione-dependent DNA damage by EDB was also demonstrated in human hepatocyte preparations. The possible relevance of this DNA adduct to genetic damage is discussed.
- Research Organization:
- Vanderbilt Univ. School of Medicine, Nashville, TN (USA)
- OSTI ID:
- 5129789
- Journal Information:
- Environ. Health Perspect.; (United States), Journal Name: Environ. Health Perspect.; (United States) Vol. 76; ISSN EVHPA
- Country of Publication:
- United States
- Language:
- English
Similar Records
Chemical mechanism involved in the formation of N/sup 7/-guanine adducts from ethylene dibromide via glutathione conjugates
DNA adducts of ethylene dibromide: Aspects of formation and mutagenicity
Comparison of the DNA-alkylating properties and mutagenic responses of a series of S-(2-haloethyl)-substituted cysteine and glutathione derivatives
Conference
·
Fri May 01 00:00:00 EDT 1987
· Fed. Proc., Fed. Am. Soc. Exp. Biol.; (United States)
·
OSTI ID:6068724
DNA adducts of ethylene dibromide: Aspects of formation and mutagenicity
Thesis/Dissertation
·
Mon Dec 31 23:00:00 EST 1990
·
OSTI ID:5579984
Comparison of the DNA-alkylating properties and mutagenic responses of a series of S-(2-haloethyl)-substituted cysteine and glutathione derivatives
Journal Article
·
Wed Oct 31 23:00:00 EST 1990
· Biochemistry; (USA)
·
OSTI ID:5524566
Related Subjects
550201 -- Biochemistry-- Tracer Techniques
560300* -- Chemicals Metabolism & Toxicology
59 BASIC BIOLOGICAL SCIENCES
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
ADDUCTS
ANIMAL CELLS
ANIMALS
CARBON 14 COMPOUNDS
CHEMICAL REACTIONS
DNA ADDUCTS
DRUGS
GLUTATHIONE
HALOGENATED ALIPHATIC HYDROCARBONS
LABELLED COMPOUNDS
LIVER CELLS
MAMMALS
MAN
METABOLIC ACTIVATION
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
OXIDATION
PEPTIDES
POLYPEPTIDES
PRIMATES
PROTEINS
PURIFICATION
RADIOPROTECTIVE SUBSTANCES
RISK ASSESSMENT
SOMATIC CELLS
VERTEBRATES
560300* -- Chemicals Metabolism & Toxicology
59 BASIC BIOLOGICAL SCIENCES
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
ADDUCTS
ANIMAL CELLS
ANIMALS
CARBON 14 COMPOUNDS
CHEMICAL REACTIONS
DNA ADDUCTS
DRUGS
GLUTATHIONE
HALOGENATED ALIPHATIC HYDROCARBONS
LABELLED COMPOUNDS
LIVER CELLS
MAMMALS
MAN
METABOLIC ACTIVATION
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
OXIDATION
PEPTIDES
POLYPEPTIDES
PRIMATES
PROTEINS
PURIFICATION
RADIOPROTECTIVE SUBSTANCES
RISK ASSESSMENT
SOMATIC CELLS
VERTEBRATES