trans-1,2-dihydro-1,2-naphthalenediol

03/15/2020 - "The method described here is the first example of facile quantitation of an intact human dihydrodiol metabolite of any PAH with three or more aromatic rings and will be applicable in clinical and molecular epidemiology studies of PAH metabolism and cancer susceptibility."
03/01/1999 - "Tumor-initiating activity of (-)-(11R,12R)-DB[a,l]P-dihydrodiol, which is the metabolic precursor of the (-)-anti-(11R,12S)-dihydrodiol (13S,14R)-epoxide, was exceptionally higher than the corresponding effect of (+)-(11S,12S)-DB[a,l]P-dihydrodiol, the metabolic precursor of (+)-syn-(11S,12R)-dihydrodiol (13S,14R)-epoxide. "
11/01/1994 - "The tumor-initiating activity of the two diolepoxides in mouse skin was compared to that of DB[a,l]P-11,12-dihydrodiol and the parent DB[a,l]P. "
05/01/1993 - "At 4 nmol DB[a,l]P-11,12-dihydrodiol elicited only benign tumors in 36% of mice. "
05/01/1993 - "At 1 nmol, DB[a,l]P induced 2.6 tumors/mouse, whereas DB[a,l]P-11,12-dihydrodiol and DMBA induced 0.17 and 0.29 tumors/mouse respectively. "

04/01/1986 - "Could these drugs, by inhibiting trans-dihydrodiol oxidation, potentiate the initiation of chemical carcinogenesis? "
01/01/1982 - "These results, together with parallel metabolic studies, suggest that the formation of bay region dihydrodiol epoxides may not be the major activation mechanism in benzofluoranthene tumorigenesis."
03/01/1983 - "Correlation of dihydrodiol and phenol metabolites with organ susceptibility to carcinogenesis in Sprague-Dawley and long-Evans rats."
11/01/2008 - "The much greater catalytic efficiency of retinal reduction compared to PAH trans-dihydrodiol metabolism suggests AKR1B10 may play a greater role in lung carcinogenesis through dysregulation of retinoic acid homeostasis than through oxidation of PAH trans-dihydrodiols."
12/13/2002 - "Synthesis of dihydrodiol metabolites implicated in the mechanism of carcinogenesis of phenanthro[4,3-b][1]benzothiophene and phenanthro[3,4-b][1]benzothiophene, the polycyclic sulfur heterocycles with a "Fjord" structure."

04/01/1996 - "Based on these results, it was concluded that the prevention of the naphthalene cataract probably results from inhibition of the conversion of naphthalene dihydrodiol to 1,2-dihydroxynaphthalene and that the effect of the ARIs cannot be explained by their inhibition of the dihydrodiol dehydrogenase activity of aldose reductase."
01/01/1992 - "In order to study the direct effects of naphthalene metabolites on the lens, we established an in vitro 'naphthalene cataract' model system by exposing rat lens to naphthalene dihydrodiol (2.5 x 10(5) M) containing medium for 48 hr. Under these conditions, we analysed several biochemical parameters including the glutathione level, protein mixed disulfides, protein patterns on SDS-gels, active transport, NA+/K(+)-ATPase activities and the measurement of naphthalene metabolites in the cultured lenses. "

07/01/1985 - "Mass spectral analysis of the dehydration products of the oxygen-18-containing trans-dihydrodiol metabolites indicated that 7-Cl-BA 3S,4R-epoxide and 7-Cl-BA 8R,9S-epoxide were the predominant enantiomeric intermediates."
04/15/1979 - "elegans also oxidized dibenzofuran to 2- and 3-hydroxydibenzofuran under conditions that would not lead to the dehydration of the trans-dihydrodiol. "
12/01/1998 - "The dihydrodiol undergoes a characteristic acid-catalyzed dehydration to produce phenols. "
11/01/1993 - "coli strain expressing the structural genes of naphthalene 1,2-dioxgenase from Pseudomonas sp. NCIB 9816-4. 3-Hydroxycarbazole is presumed to result from the dehydration of an unstable cis-dihydrodiol."
04/01/1983 - "Mass spectral analysis of the acid-catalyzed dehydration products of the dihydrodiol indicated that the naphthalene dihydrodiol forms via the addition of water at the C-2 position of naphthalene-1,2-oxide. "

09/28/2007 - "1,4-DFBcPh and its dihydrodiol were subjected to metabolism, and the amount of DNA binding in human breast cancer MCF-7 cells was assessed. "
09/01/2002 - "DNA binding of DB[a,l]P in human mammary carcinoma MCF-7 and human P450-expressing Chinese hamster V79 cell lines was previously shown to occur preferentially with metabolically generated fjord region DB[a,l]P-11,12-dihydrodiol 13,14-epoxides (DB[a,l]PDE). "
04/08/2005 - "Here we show that 7,12-dimethylbenz[a]anthracene-trans-3,4-dihydrodiol rapidly induces mammary cancer by repeated subcutaneous injection in a high proportion of female Sprague-Dawley rats without malignancies at the site of injection, whereas its more lipid soluble diacetate derivative induced injection site sarcomas in addition to distal mammary cancers. "