Solvolysis of the bay-region diol epoxides of 7-methylbenz(c)acridine in aqueous solution and effect of DNA
Journal Article
·
· Chemical Research in Toxicology; (USA)
- Univ. of Sydney (Australia)
The hydrolysis of the bay-region syn- and anti-diol epoxides of 7-methylbenz(c)acridine (7MBAC) has been studied in aqueous solution. The rates of reaction have been measured at low ionic strength in the absence and presence of DNA, as a function of pH and temperature, by spectrophotometry and high-pressure liquid chromatography. The major products are the corresponding tetrols, but the syn diastereomer also undergoes rearrangement to a keto diol. The hydrolysis reaction is catalyzed by both acid and DNA and conforms to a mechanism in which a physical association complex is formed between diol epoxide and DNA, followed by two parallel pathways in which the diol epoxide either is hydrolyzed or becomes covalently bound to the DNA. The very small changes (2 nm) in spectroscopic characteristics observed for the covalently bound adduct as compared to the free tetrol suggest that the binding occurs with little intercalation of the compound between the base pairs of DNA.
- OSTI ID:
- 6363465
- Journal Information:
- Chemical Research in Toxicology; (USA), Journal Name: Chemical Research in Toxicology; (USA) Vol. 3:2; ISSN 0893-228X; ISSN CRTOE
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
560300* -- Chemicals Metabolism & Toxicology
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
ACRIDINES
ADDUCTS
AQUEOUS SOLUTIONS
AROMATICS
AZAARENES
AZINES
CARCINOGENS
CHEMICAL REACTIONS
CHROMATOGRAPHY
DECOMPOSITION
DISPERSIONS
DNA ADDUCTS
EPOXIDES
HETEROCYCLIC COMPOUNDS
HYDROLYSIS
LIQUID COLUMN CHROMATOGRAPHY
LYSIS
MIXTURES
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
PH VALUE
PYRIDINES
SEPARATION PROCESSES
SOLUTIONS
SOLVOLYSIS
SPECTROPHOTOMETRY
TEMPERATURE DEPENDENCE
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
ACRIDINES
ADDUCTS
AQUEOUS SOLUTIONS
AROMATICS
AZAARENES
AZINES
CARCINOGENS
CHEMICAL REACTIONS
CHROMATOGRAPHY
DECOMPOSITION
DISPERSIONS
DNA ADDUCTS
EPOXIDES
HETEROCYCLIC COMPOUNDS
HYDROLYSIS
LIQUID COLUMN CHROMATOGRAPHY
LYSIS
MIXTURES
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
PH VALUE
PYRIDINES
SEPARATION PROCESSES
SOLUTIONS
SOLVOLYSIS
SPECTROPHOTOMETRY
TEMPERATURE DEPENDENCE