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Conjugation of butadiene diepoxide with glutathione yields DNA adducts in vitro and in vivo.
Chem Res Toxicol
March 2012
Department of Biochemistry and Center in Molecular Toxicology, Vanderbilt University School of Medicine, 638 Robinson Research Building, 2200 Pierce Avenue, Nashville, Tennessee 37232-0146, USA.
1,2,3,4-Diepoxybutane (DEB) is reported to be the most potent mutagenic metabolite of 1,3-butadiene, an important industrial chemical and environmental pollutant. DEB is capable of inducing the formation of monoalkylated DNA adducts and DNA-DNA and DNA-protein cross-links. We previously reported that DEB forms a conjugate with glutathione (GSH) and that the conjugate is considerably more mutagenic than several other butadiene-derived epoxides, including DEB, in the base pair tester strain Salmonella typhimurium TA1535 [Cho et al.
View Article and Find Full Text PDFStereospecific activation of the procarcinogen benzo[a]pyrene: a probe for the active sites of the cytochrome P450 superfamily.
Biochemistry
May 1995
Department of Pharmacology, University of Rochester, New York 14642, USA.
It has been established previously that the sterochemistry of epoxidation of the procarcinogen benzo[a]pyrene determines the potency of the ultimate carcinogen. Herein we report that seven human P450s, five rodent P450s, and two bacterial P450s all convert B[a]P to the most potent carcinogenic often differ in both regioselectivity and stereoselectivity. This is likely due to the large size of the substrate molecule and its constraints in the active sites.
View Article and Find Full Text PDFIridoids and an Alkaloid from Oxera morieri1.
Planta Med
February 1991
Département de Pharmacognosie de l'Université René Descartes, URA au C.N.R.S. n° 484, Faculté des Sciences Pharmaceutiques et Biologiques, 4 avenue de l'Observatoire, F-75006 Paris, France.
A novel monoterpene alkaloid, oxerine, has been isolated from the aerial parts of OXERA MORIERI. Its structure 7 has been elucidated on the basis of its spectral data and its sterochemistry established by its synthesis, using harpagide as starting material. Five iridoids and verbascoside have also been isolated from the plant material.
View Article and Find Full Text PDFChemotaxonomic implications of the venom chemistry of someMonomorium "antarcticum" populations.
J Chem Ecol
December 1988
Laboratory of Chemistry, National Heart, Lung, and Blood Institute, 20892, Bethesda, Maryland.
A comparative analysis of the venom alkaloids produced by ants in the genusMonomorium (= Chelaner) collected on North Island and South Island, New Zealand, has been undertaken. All of the ants producetrans-2, 5-dialkylpyrrolidines along with 3,5-dialkylpyrrolizidines. The structures and sterochemistry of the novel alkaloidstrans-2-butyl-5-(8-nonenyl) pyrrolidine, (5E,8Z)-3,5-di(5-hexenyl)pyrrolizidine, and (5Z,8E)-3-methyl-5-(8-nonenyl)pyrrolizidine were established by unambiguous synthesis.
View Article and Find Full Text PDFTwo different tetracyclic chromophoric analogues of actinomycin D have been synthesized by engaging two chromophoric DNA-binding functions in actinomycin D, i.e., 2-amino and 3-oxo, into either a 1,4-oxazin-2-one or an oxazole ring system.
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