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Wolfgang Pfau, H. Schmeiser, M. Wiessler (1991)
N6-adenyl arylation of DNA by aristolochic acid II and a synthetic model for the putative proximate carcinogen.Chemical research in toxicology, 4 5
H. Schmeiser, J. Janssen, J. Lyons, H. Scherf, W. Pfau, A. Buchmann, C. Bartram, M. Wiessler (1990)
Aristolochic acid activates ras genes in rat tumors at deoxyadenosine residues.Cancer research, 50 17
J. Cosyns, M. Jadoul, J. Squifflet, F. Wese, C. Strihou (1999)
Urothelial lesions in Chinese-herb nephropathy.American journal of kidney diseases : the official journal of the National Kidney Foundation, 33 6
M. Stiborová, E. Frei, M. Wiessler, H. Schmeiser (2001)
Human enzymes involved in the metabolic activation of carcinogenic aristolochic acids: evidence for reductive activation by cytochromes P450 1A1 and 1A2.Chemical research in toxicology, 14 8
S. Chen, K. Wu, D. Zhang, M. Sherman, R. Knox, C. Yang (1999)
Molecular characterization of binding of substrates and inhibitors to DT-diaphorase: combined approach involving site-directed mutagenesis, inhibitor-binding analysis, and computer modeling.Molecular pharmacology, 56 2
M. Reddy, K. Randerath (1986)
Nuclease P1-mediated enhancement of sensitivity of 32P-postlabeling test for structurally diverse DNA adducts.Carcinogenesis, 7 9
M. Montano, B. Katzenellenbogen (1997)
The quinone reductase gene: a unique estrogen receptor-regulated gene that is activated by antiestrogens.Proceedings of the National Academy of Sciences of the United States of America, 94 6
J. Vanherweghem, C. Tielemans, Jonathan Simon, M. Depierreux (1995)
Chinese herbs nephropathy and renal pelvic carcinoma.Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association, 10 2
A. Jaiswal, P. Burnett, M. Adesnik, O. McBride (1990)
Nucleotide and deduced amino acid sequence of a human cDNA (NQO2) corresponding to a second member of the NAD(P)H:quinone oxidoreductase gene family. Extensive polymorphism at the NQO2 gene locus on chromosome 6.Biochemistry, 29 7
M. Ichikawa, T. Nishino, A. Ichikawa (1992)
Subcellular localization of xanthine oxidase in rat hepatocytes: high-resolution immunoelectron microscopic study combined with biochemical analysis.The journal of histochemistry and cytochemistry : official journal of the Histochemistry Society, 40
Hongwei Chen, A. Lum, A. Seifried, L. Wilkens, L. Marchand (1999)
Association of the NAD(P)H:quinone oxidoreductase 609C-->T polymorphism with a decreased lung cancer risk.Cancer research, 59 13
W. Pfau, D. Phillips (1991)
Improved reversed-phase high-performance liquid chromatographic separation of 32P-labelled nucleoside 3',5'-bisphosphate adducts of polycyclic aromatic hydrocarbons.Journal of chromatography, 570 1
H. Schmeiser, K. Schoepe, M. Wiessler (1988)
DNA adduct formation of aristolochic acid I and II in vitro and in vivo.Carcinogenesis, 9 2
A. Hajos, G. Winston (1991)
Dinitropyrene nitroreductase activity of purified NAD(P)H-quinone oxidoreductase: role in rat liver cytosol and induction by Aroclor-1254 pretreatment.Carcinogenesis, 12 4
Y. Yamazoe, T. Zenser, D. Miller, F. Kadlubar (1988)
Mechanism of formation and structural characterization of DNA adducts derived from peroxidative activation of benzidine.Carcinogenesis, 9 9
C. Yang, Y. Tu, D. Koop, M. Coon (1985)
Metabolism of nitrosamines by purified rabbit liver cytochrome P-450 isozymes.Cancer research, 45 3
J. Vanherweghem (1998)
Misuse of herbal remedies: the case of an outbreak of terminal renal failure in Belgium (Chinese herbs nephropathy)Journal of alternative and complementary medicine, 4 1
P. Dauber-Osguthorpe, V. Roberts, D. Osguthorpe, Jon Wolff, Moniqe Genest, A. Hagler (1988)
Structure and energetics of ligand binding to proteins: Escherichia coli dihydrofolate reductase‐trimethoprim, a drug‐receptor systemProteins: Structure, 4
Young-Heum Chae, T. Thomas, F. Guengerich, P. Fu, K. El-Bayoumy (1999)
Comparative metabolism of 1-, 2-, and 4-nitropyrene by human hepatic and pulmonary microsomes.Cancer research, 59 7
J. Vanherweghem, C. Tielemans, D. Abramowicz, M. Depierreux, R. Vanhaelen-fastre, M. Vanhaelen, M. Dratwa, C. Richard, D. Vandervelde, D. Verbeelen, M. Jadoul (1993)
Rapidly progressive interstitial renal fibrosis in young women: association with slimming regimen including Chinese herbsThe Lancet, 341
H. Schmeiser, Christian Bieter, M. Wiessler, C. Strihou, J. Cosyns (1996)
Detection of DNA adducts formed by aristolochic acid in renal tissue from patients with Chinese herbs nephropathy.Cancer research, 56 9
M. Vanhaelen, R. Vanhaelen-fastre, P. But, J. Vanherweghem (1994)
Identification of aristolochic acid in Chinese herbsThe Lancet, 343
J. Robertson, H. Chen, D. Nebert (1986)
NAD(P)H:menadione oxidoreductase. Novel purification of enzyme cDNA and complete amino acid sequence, and gene regulation.The Journal of biological chemistry, 261 33
K. Wiechelman, R. Braun, J. Fitzpatrick (1988)
Investigation of the bicinchoninic acid protein assay: identification of the groups responsible for color formation.Analytical biochemistry, 175 1
R. Gupta, K. Earley (1988)
32P-adduct assay: comparative recoveries of structurally diverse DNA adducts in the various enhancement procedures.Carcinogenesis, 9 9
R. Felsted, A. Chu, S. Chaykin (1973)
Purification and properties of the aldehyde oxidases from hog and rabbit livers.The Journal of biological chemistry, 248 7
F. Bernstein, T. Koetzle, G. Williams, E. Meyer, M. Brice, J. Rodgers, T. Singh, T. Shimanouchi, M. Tasumi (1977)
The Protein Data Bank: a computer-based archival file for macromolecular structures.Journal of molecular biology, 112 3
H. Schmeiser, B. Pool, M. Wiessler (1984)
Mutagenicity of the two main components of commercially available carcinogenic aristolochic acid in Salmonella typhimurium.Cancer letters, 23 1
M. Stiborová, E. Frei, H. Schmeiser, M. Wiessler, J. Hradec (1990)
Mechanism of formation and 32P-postlabeling of DNA adducts derived from peroxidative activation of carcinogenic non-aminoazo dye 1-phenylazo-2-hydroxynaphthalene (Sudan I).Carcinogenesis, 11 10
Joëlle Nortier, Marie Martinez, H. Schmeiser, V. Arlt, C. Bieler, M. Pétein, Michel Depierreux, Luc Pauw, D. Abramowicz, Pierre Vereerstraeten, J. Vanherweghem (2000)
Urothelial carcinoma associated with the use of a Chinese herb (Aristolochia fangchi)The New England journal of medicine, 342 23
M. Stiborová, B. Asfaw, E. Frei, H. Schmeiser, M. Wiessler (1995)
Benzenediazonium ion derived from Sudan I forms an 8-(phenylazo)guanine adduct in DNA.Chemical research in toxicology, 8 4
C. Violon (1997)
Belgian (Chinese herb) nephropathy: why?Journal de pharmacie de Belgique, 52 1
Lars Ernster (1967)
[56] DT diaphoraseMethods in Enzymology, 10
C. Bieler, M. Stiborová, M. Wiessler, J. Cosyns, C. Strihou, H. Schmeiser (1997)
32P-post-labelling analysis of DNA adducts formed by aristolochic acid in tissues from patients with Chinese herbs nephropathy.Carcinogenesis, 18 5
H. Schmeiser, E. Frei, M. Wiessler, M. Stiborová (1997)
Comparison of DNA adduct formation by aristolochic acids in various in vitro activation systems by 32P-post-labelling: evidence for reductive activation by peroxidases.Carcinogenesis, 18 5
G. Morris, D. Goodsell, R. Halliday, R. Huey, W. Hart, R. Belew, A. Olson (1998)
Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy functionJournal of Computational Chemistry, 19
M. Stiborová, E. Frei, A. Breuer, M. Wiessler, H. Schmeiser (2001)
Evidence for reductive activation of carcinogenic aristolochic acids by prostaglandin H synthase -- (32)P-postlabeling analysis of DNA adduct formation.Mutation research, 493 1-2
M. Stiborová, E. Frei, A. Breuer, C. Bieler, H. Schmeiser (1999)
Aristolactam I a metabolite of aristolochic acid I upon activation forms an adduct found in DNA of patients with Chinese herbs nephropathy.Experimental and toxicologic pathology : official journal of the Gesellschaft fur Toxikologische Pathologie, 51 4-5
S. Bauer, P. Howard (1991)
Kinetics and cofactor requirements for the nitroreductive metabolism of 1-nitropyrene and 3-nitrofluoranthene by rabbit liver aldehyde oxidase.Carcinogenesis, 12 9
H. Schmeiser, A. Dipple, M. Schurdak, E. Randerath, K. Randerath (1988)
Comparison of 32P-postlabeling and high pressure liquid chromatographic analyses for 7,12-dimethylbenz[a]anthracene--DNA adducts.Carcinogenesis, 9 4
W. Pfau, H. Schmeiser, M. Wiessler (1990)
Aristolochic acid binds covalently to the exocyclic amino group of purine nucleotides in DNA.Carcinogenesis, 11 2
P. Fu (1990)
Metabolism of nitro-polycyclic aromatic hydrocarbons.Drug metabolism reviews, 22 2-3
M. Stiborová, M. Hájek, H. Vošmiková, E. Frei, H. Schmeiser (2001)
Isolation of DT-Diaphorase [NAD(P)H Dehydrogenase (Quinone)] from Rat Liver Cytosol: Identification of New Enzyme Substrates, Carcinogenic Aristolochic AcidsCollection of Czechoslovak Chemical Communications, 66
S. Swaminathan, J. Hatcher (1986)
Xanthine oxidase-mediated mutagenicity of the bladder carcinogen 4-nitrobiphenyl.Mutation research, 172 1
P. Joseph, Ye-yang Xu, A. Jaiswal (1996)
Non‐enzymatic and enzymatic activation of mitomycin C: Identification of a unique cytosolic activityInternational Journal of Cancer, 65
David Ross, J. Kepa, S. Winski, H. Beall, A. Anwar, D. Siegel (2000)
NAD(P)H:quinone oxidoreductase 1 (NQO1): chemoprotection, bioactivation, gene regulation and genetic polymorphisms.Chemico-biological interactions, 129 1-2
C. Pritsos (2000)
Cellular distribution, metabolism and regulation of the xanthine oxidoreductase enzyme system.Chemico-biological interactions, 129 1-2
J. Cosyns, M. Jadoul, J. Squifflet, P. Cangh, C. Strihou (1994)
Urothelial malignancy in nephropathy due to Chinese herbsThe Lancet, 344
P. Joseph, T. Xie, Y. Xu, A. Jaiswal (1994)
NAD(P)H:quinone oxidoreductase1 (DT-diaphorase): expression, regulation, and role in cancer.Oncology research, 6 10-11
C. Ritter, R. Decker, D. Malejka-giganti (2000)
Reductions of nitro and 9-Oxo groups of environmental nitrofluorenes by the rat mammary gland in vitro.Chemical research in toxicology, 13 8
M. Stiborová, Fernando Rc, H. Schmeiser, E. Frei, W. Pfau, M. Wiessler (1994)
Characterization of DNA adducts formed by aristolochic acids in the target organ (forestomach) of rats by 32P-postlabelling analysis using different chromatographic procedures.Carcinogenesis, 15 6
W. Schulz, A. Krummeck, I. Rösinger, P. Eickelmann, C. Neuhaus, Thomas Ebert, B. Schmitz-Dräger, H. Sies (1997)
Increased frequency of a null-allele for NAD(P)H: quinone oxidoreductase in patients with urological malignancies.Pharmacogenetics, 7 3
C. Strihou, M. Martínez‐Maldonado (1998)
Chinese herbs nephropathy or the evils of nature.American Journal of Kidney Diseases, 32
T. Watanabe, H. Kaji, M. Takashima, T. Kasai, J. Lewtas, T. Hirayama (1997)
Metabolic activation of 2- and 3-nitrodibenzopyranone isomers and related compounds by rat liver S9 and the effect of S9 on the mutational specificity of nitrodibenzopyranones.Mutation research, 388 1
Aristolochic acid (AA), a naturally occurring nephrotoxin and rodent carcinogen, has recently been associated with the development of urothelial cancer in humans. Understanding which enzymes are involved in AA activation and/or detoxication is important in the assessment of an individual susceptibility to this natural carcinogen. We examined the ability of enzymes of rat renal and hepatic cytosolic fractions to activate AA to metabolites forming DNA adducts by the nuclease P1-enhanced version of the 32 P-postlabeling assay. Cytosolic fractions of both these organs generated AA-DNA adduct patterns reproducing those found in renal tissues from humans exposed to AA. 7-(Deoxyadenosin- N 6 -yl)aristolactam I, 7-(deoxyguanosin- N 2 -yl)aristolactam I and 7-(deoxyadenosin- N 6 -yl)aristolactam II were identified as AA-DNA adducts formed from AAI and 7-(deoxyguanosin- N 2 -yl)aristolactam II and 7-(deoxyadenosin- N 6 -yl)aristolactam II were generated from AAII by hepatic cytosol. Qualitatively the same AA-DNA adduct patterns were observed, although at lower levels, upon incubation of AAs with renal cytosol. To define the role of cytosolic reductases in the reductive activation of AA, we investigated the modulation of AA-DNA adduct formation by cofactors, specific inducers or selective inhibitors of the cytosolic reductases, DT-diaphorase, xanthine oxidase (XO) and aldehyde oxidase. The role of the enzymes in AA activation was also investigated by correlating the DT-diaphorase- and XO-dependent catalytic activities in cytosolic sample with the levels of AA-DNA adducts formed by the same cytosolic sample. On the basis of these studies, we attribute most of the cytosolic activation of AA to DT-diaphorase, although a role of cytosolic XO cannot be ruled out. With purified DT-diaphorase, the participation of this enzyme in the formation of AA-DNA adducts was confirmed. The binding orientation of AAI in the active site of DT-diaphorase was predicted by computer modeling based on published X-ray structures. The results presented here are the first report demonstrating a reductive activation of carcinogenic AAs by DT-diaphorase. Key words AA, aristolochic acid; AAI, 8-methoxy-6-nitro-phenanthro-(3,4- d )-1,3-dioxolo-5-carboxylic acid; AAII, 6-nitro-phenanthro-(3,4- d )-1,3-dioxolo-5-carboxylic acid; Ah receptor, aryl hydrocarbon receptor; CT-DNA, calf thymus DNA; dAp, deoxyadenosine 3′-monophosphate; dGp, deoxyguanosine 3′-monophosphate; dA-AAI, 7-(deoxyadenosin- N 6 -yl)aristolactam I; dA-AAII, 7-(deoxyadenosin- N 6 -yl)aristolactam II; dG-AAI, 7-(deoxyguanosin- N 2 -yl) aristolactam I; dG-AAII, 7-(deoxyguanosin- N 2 -yl) aristolactam II; K s , apparent dissociation constant; PB, phenobarbital; PEI, polyethylenimine; RAL, relative adduct labeling; XO, xanthine oxidase. © Oxford University Press « Previous | Next Article » Table of Contents This Article Carcinogenesis (2002) 23 (4): 617-625. doi: 10.1093/carcin/23.4.617 » Abstract Free Full Text (HTML) Free Full Text (PDF) Free Classifications Carcinogenesis Services Article metrics Alert me when cited Alert me if corrected Find similar articles Similar articles in Web of Science Similar articles in PubMed Add to my archive Download citation Request Permissions Citing Articles Load citing article information Citing articles via CrossRef Citing articles via Scopus Citing articles via Web of Science Citing articles via Google Scholar Google Scholar Articles by Stiborová, M. 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Carcinogenesis – Oxford University Press
Published: Apr 1, 2002
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