title: Rapid partial degradation of DDT by a cytochrome P-450 model system.
abstract: Heme compounds, in combination with a reducing agent and oxygen, can express various activities of cytochrome P-450 enzymes. In the present study it was found that a mixture of hemin and excess cysteine was able to degrade the insecticide DDT partially. The major products were three water-soluble, non-toxic conjugates of DDT metabolites with cysteine which had lost two or three of the five chlorine atoms of DDT per molecule and whose structures were elucidated by gas chromatography/mass spectrometry. In 0.05 M NH4HCO3, pH 7.7/ethanol (5:6, by vol.), the degradation reaction catalyzed by the hemin-cysteine model system was at least 8 x 10(4) times faster than the uncatalyzed reaction. In the presence of a designed 24-residues polypeptide or beta-casein, two DDT-binding proteins, an additional fourfold increase in the rate of DDT degradation was observed. Although the concentrations of DDT and cysteine occurring in an organism would be expected to be lower than those in the experiments described, the formation of water-soluble conjugates of DDT metabolites with cysteine (and other amino acids) could also play a role in metabolism and excretion of DDT in vivo.
authors.affiliation: Biochemisches Institut, Universität Zürich, Switzerland.
authors.forename: H
authors.initials: H
authors.lastname: Langen
authors.forename: T
authors.initials: T
authors.lastname: Epprecht
authors.forename: M
authors.initials: M
authors.lastname: Linden
authors.forename: T
authors.initials: T
authors.lastname: Hehlgans
authors.forename: B
authors.initials: B
authors.lastname: Gutte
authors.forename: H R
authors.initials: HR
authors.lastname: Buser
mesh_terms: D001665:Binding Sites; D001673:Biodegradation, Environmental / Q000187:drug effects; D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D003545:Cysteine / Q000494:pharmacology; D003577:Cytochrome P-450 Enzyme System / Q000378:metabolism*; D003634:DDT / Q000378:metabolism*; D003633:Dichlorodiphenyl Dichloroethylene / Q000378:metabolism; D003632:Dichlorodiphenyldichloroethane / Q000378:metabolism; D008401:Gas Chromatography-Mass Spectrometry; D006427:Hemin / Q000494:pharmacology; D006863:Hydrogen-Ion Concentration; D008962:Models, Theoretical; D010084:Oxidation-Reduction; D012997:Solvents
chemical_list: D012997:Solvents; D003633:Dichlorodiphenyl Dichloroethylene; D006427:Hemin; D003577:Cytochrome P-450 Enzyme System; D003634:DDT; D003545:Cysteine; D003632:Dichlorodiphenyldichloroethane