CHEMICAL RESEARCH IN TOXICOLOGY
VOL.. 12 , NO. 1 , JANUARY 1999
Dihydrodiol Dehydrogenases and Polycyclic Aromatic 1 Trevor M. Penning,*
Hydrocarbon Activation: Generation of Reactive and Redox Michael E. Burczynski,
Active o-Quinones Chien-Fu Hung, Kirsten D. McCoull,
Nisha T. Palackal, and
Laurie S. Tsuruda
ARTICLES
Synthesis, Isolation, and Characterization of the Adduct 19 Stanley L. Hazen, Jozsef Heller,
Formed in the Reaction ofp-Hydroxyphenylacetaldehyde Fong-Fu Hsu, Andre (TAvignon, and
with the Amino Headgroup of Phosphatidylethanolamine and Jay W. Heinecke*
Phosphatidylserine
Peroxidase-Catalyzed Pro- versus Antioxidant Effects of 28 Billy W. Day,* Vladimir A. Tyurin,
4-Hydroxytamoxifen: Enzyme Specificity and Biochemical Yulia Y. Tyurina, Mei Liu,
Sequelae Judy A. Facey, Gianfranca Carta,
Elena R. Kisin,
Raghvendra K. Dubey, and
Valerian E. Kagan
Photosensitization of Guanine-Specific DNA Damage by 38 Clarke Stevenson and
2-Phenylbenzimidazole and the Sunscreen Agent R. Jeremy H. Davies*
2-Phenylbenzimidazole-5-sulfonic Acid
Identification of an Ethenoformyl Adduct Formed in the 46 Tony Munter, Frank Le Curieux,
Reaction of the Potent Bacterial Mutagen • Rainer Sjoholm, and Leif Kronberg*
3-Chloro-4-(dichloromethyl)-5-hydroxy-2(5J:0-furanone with
Guanosine
Regiochemistry of Nucleophilic Attack by the Guanine 2-Amino 53 George P. Ford* and Jon W. Thompson
Group at the Ring Positions of Nitrenium Ions Derived from
Carcinogenic Polycyclic Arylamines and Nitroarenes:
Molecular Orbital Calculations and Simple Models
Analysis of Highly Polar DNA Adducts Formed in SENCAR 60 Suryanarayana V. Vulimiri,*
Mouse Epidermis Following Topical Application of Wanda Baer-Dubowska,
Dibenz[OJ ] anthracene Ronald G. Harvey, Jin-Tao Zhang, and
John DiGiovanni
Synthesis, Characterization, and Quantitation of a 68 Frederick A. Beland,*
4-Aminobiphenyl-DNA Adduct Standard Daniel R. Doerge, Mona I. Churchwell,
Miriam C. Poirier,
Bernadette Schoket, and
M. Matilde Marques
Detection of Monocyclic Aromatic Amines, Possible Mammary 78 Lillian S. DeBruin,
Carcinogens, in Human Milk Janusz B. Pawliszyn, and
P. David Josephy*
Nitration of Unsaturated Fatty Acids by Nitric Oxide-Derived 83 Valerie B. O'Donnell, Jason P. Eiserich^
Reactive Nitrogen Species Peroxynitrite, Nitrous Acid, Phillip H. Chumley,
Nitrogen Dioxide, and Nitronium Ion Michael J. Jablonsky,
N. Rama Krishna, Marion Kirk,
Stephen Barnes,
Victor M. Darley-Usmar, and
Bruce A. Freeman*
(32)P-Postlabeling Analysis of DNA Adducts of Styrene 7,8-Oxide 93 Michael Otteneder, Erwin Eder, and
at the Opposition of Guanine Werner K. Lutz*
Observation of a New Nonfluorescent 100 Mark L. Kearley,* Arti Patel,
Malondialdehyde-Acetaldehyde-Protein Adduct by (13)C NMR Jim Chien, and Dean J. Tuma
Spectroscopy
Detection of Concomitant Formation of O(6)-Carboxymethyl- and 106 Kathryn L. Harrison, Rebekah Jukes,
O(6) -Methyl-2'-deoxyguanosine in DNA Exposed to Nitrosated Donald P. Cooper, and
Glycine Derivatives Using a Combined Immunoaffmity/HPLC David E. G. Shuker*
Method
_____________________________________
Chemical Research in Toxicology
vol. 12 , no. 2 , february 1999
PERSPECTIVE
Development of Cancer Chemopreventive Agents: Oltipraz as a 113 Thomas W. Kensler,*
Paradigm John D. Groopman, Thomas R. Sutter,
Thomas J. Curphey, and
Bill D. Roebuck
COMMUNICATIONS
Synthesis of DNA Oligonucleotidesr Containing Site-Specifically 127 Lijuan Wang, Thomas E. Spratt,
Incorporated O(6)-[4-0xo-4-(3-pyridyl)butyl]guanine and Their Anthony E. Pegg, and
Reaction with O(6)-Alkylguanine-DNA Alkyltransferase Lisa A. Peterson*
Effect of . NO on the Decomposition of Peroxynitrite: Reaction 132 Sara Goldstein,* Gidon Czapski,
of N(2)O(3) with ONOO - Johan Lind, and Gabor Merenyi
ARTICLES
Inhibition of Skeletal Sarcoplasmic Reticulum Ca(2+)-ATPase 137 Masanori Kiyose, Chang-il Lee, and
Activity by Deferoxamine Nitroxide Free Radical Eiichiro Okabe*
Sequence Context Modulation of Translesion Synthesis at a 144 Dominique Y. Burnouf,*
Single JV-2-Acetylaminofluorene Adduct Located within a Roman Miturski, and
Mutation Hot Spot Robert P. P. Fuchs
4-Hydroxytamoxifen Gives DNA Adducts by Chemical 151 Martin R. Osborne,* Warren Davis,
Activation, but Not in Rat Liver Cells Alan J. Hewer, lan R. Hardcastle, and
David H. Phillips
Detection of Adducts of Bromobenzene 3,4-Oxide with Rat 159 Elizabeth M. Rombach and
Liver Microsomal Protein Sulfhydryl Groups Using Specific Robert P. Hanzlik*
Antibodies
Stereoselective Metabolism of Nicotine and Tobacco-Specific 164 Neil Trushin and Stephen S. Hecht*
N-Nitrosamines to 4-Hydroxy-4-(3-pyridyl)butanoic Acid in Rats
Quantitation of4-0xo-4-(3-pyridyl)butanoic Acid and 172 Stephen S. Hecht,*
Enantiomers of 4-Hydroxy-4-(3-pyridyl)butanoic Acid in Human Dorothy K. Hatsukami,
Urine: A Substantial Pathway of Nicotine Metabolism Leo E. Bonilla, and
J. Bradley Hochalter
Nitroreduction of 4-Nitropyrene Is Primarily Responsible for 180 Young-Heum Chae, Ben-Yi Ji,
DNA Adduct Formation in the Mammary Gland of Female CD Jyh-Ming Lin, Peter P. Fu,
Rats Bongsup P. Cho, and
Karam EI-Bayoumy*
UV-B-Induced Photooxidation of Vitamin E in Mouse Skin 187 Kimberly Kramer-Stickland,
Ed S. Krol, and Daniel C. Liebler*
Bolea of Human Hepatic Cytochrome P450(s) 2C9 and 3A4 in the 192 Wei Tang,* Ralph A. Steams,
Metabolic Activation of Diclofenac Regina W. Wang,
Shuet-Hing L. Chiu, and
Thomas A. Baillie
Synthesis of the Equine Estrogen Metabolites 2-Hydroxyequilin 200 Fagen Zhang and Judy L. Bolton*
and 2-Hydroxyequilenin
The Mfijor Metabolite of Equilin, 4-Hydroxyequilin, Autoxidizes 204 Fagen Zhang, Yumei Chen,
to an o-Quinone Which Isomerizes to the Potent Cytotoxin Emily Pisha, Li Shen, Yansan Xiong,
4-Hydroxyequilenin-o-quinone Richard B. van Breemen, and
Judy L. Bolton*
Metabolic Activation of Diclofenac by Human Cytochrome P450 214 Sijiu Shen, Michael R. Marchick,
8A4; Role of 5-Hydroxydiclofenac Margaret R. Davis,
George A. Doss, and Lance R. Pohl*
___________________________________
Chemical Research in Toxicology
VOLUME 12, NUMBER 6, JUNE 1999
ARTICLES__________________________________________________________________________________
Modulation of the Toxicity and Macromolecular Binding of 467 Joseph Wiemels, John K. Wiencke,
Benzene Metabolites by NAD(P)H:Quinone Oxidoreductase in Andrea Varykoni, and
Transfected HL-60 Cells Martyn T. Smith*
A Simple and Sensitive Method for in Vitro Quantitation of 476 Didier Boturyn,
Abasic Sites in DNA Jean-Francois Constant,*
Eric Defrancq, Jean Lhomme,
Alain Barbin, and Christopher P. Wild
The Nutritional Supplement Chromium(lll) Tris(picolinate) 483 J. Kristopher Speetjens,
Cleaves DNA Rachel A. Collins,
John B. Vincent,* and
Stephen A. Woski*
Procainamide, a Drug Causing Lupus, Induces Prostaglandin H 488 Carsten Goebel, Christoph Vogel,
Synthase-2 and Formation of T Cell-Sensitizing Drug Marly Wulferink, Stephanie Mittmann,
Metabolites in Mouse Macrophages Bernhardt Sachs, Sabine Schraa,
Josef Abel, Gisela Degen,
Jack Uetrecht, and Ernst Gleichmann*
Mutagenicity of Site-Specifically Located 1,n(2)-Ethenoguanine 501 Susumu Akasaka and
in Chinese Hamster Ovary Cell Chromosomal DNA F. Peter Guengerich*
Studies on the Pyrrolinone Metabolites Derived from the 508 Xin Liu, Lunyi Zang,
Tobacco Alkaloid l-Methyl-2-(3-pyridinyl)pyrrole (b-Nicotyrine) Cornelis J. Van der Schyf,
Kazuo Igarashi, Kay Castagnoli, and
Neal Castagnoli, Jr.*
DNA Damage in Deoxynucleosides and Oligonucleotides 513 Samar Burney, Jacquin C. Niles,
Treated with Peroxynitrite Peter C. Dedon,* and
Steven R. Tannenbaum*
Glutathione-Dependent Generation of Reactive Oxygen Species 521 Giuseppe Galati, Tom Chan,
by the Peroxidase-Catalyzed Redox Cycling of Flavonoids Bin Wu, and Peter J. O'Brien*
Reaction of Peroxynitrite with Melatonin: A Mechanistic 526 Houwen Zhang,
Study Giuseppe L. Squadrito,* Rao Uppu, and
William A. Pryor*
Reactions of B-Carotene with Cigarette Smoke Oxidants. 535 Daniel L. Baker, Ed S. Krol,
Identification ofCarotenoid Oxidation Products and Neil Jacobsen, and Daniel C. Liebler*
Evaluation of the Prooxidant/Antioxidant Effect
Mammalian Cells Expressing Escherichia coli 544 Nieves Abril and Geoffrey P. Margison*
O(6)-Alkylguanine-DNA Alkyltransferases Are Hypersensitive to
Dibromoalkanes
____________________________________________
Chemical Resealc In Toxicology
VOLUME 12, NUMBER 7, JULY 1999
EDITORIAL
In Memoriam Anthony Dipple 553
COMMUNICATIONS
Design, Synthesis, and Characterization of 555 Rob C. A. Onderwater,
7-Methoxy-4-(aminomethyl)coumarin as a Novel and Selective Jennifer Venhorst,
Cytochrome P450 2D6 Substrate Suitable for High-Throughput Jan N. M. Commandeur, and
Screening Nico P. E. Vermeulen*
Metabolism of Arsenic in Primary Cultures of Human and Rat 560 Miroslav Styblo,* Luz M. Del Razo,
Hepatocytes • Edward L. LeCluyse,
Geraldine A. Hamilton,
Changqing Wang,
William R. Cullen, and
David J. Thomas
ARTICLES
Molecular Dosimetry of N-7 Guanine Adduct Formation in Mice 566 Hasan Koc, Natalia Y. Tretyakova,
and Rats Exposed to 1,3-Butadiene Vernon E. Walker,
Rogene F. Henderson, and
James A. Swenberg*
Quantitative Particle-Induced X-ray Emission Imaging of Rat 575 Kevin K. Divine, Johnnye L. Lewis,
Olfactory Epithelium Applied to the Permeability of Rat Patrick G. Grant, and Graham Bench*
Epithelium to Inhaled Aluminum
Inactivation of Cytochrome P450 2EI by Benzyl Isothiocyanate 582 Rosa L. Moreno, Ute M. Kent,
Kimberly Hodge, and
Paul F. Hollenberg*
Nuclear Targeting and Nuclear Retention of 588 Dylan J. Taatjes, David J. Fenick, and
Anthracycline-Formaldehyde Conjugates Implicates DNA Tad H. Koch*
Covaleiit Bonding in the Cytotoxic Mechanism of
Anthracyclines
Origins of Conformational Differences between Cis and Trans 597 Xiao-Ming Xie,
DNA Adducts Derived from Enantiomeric anti-Benzo[a]Pyrene • Nicholas E. Geacintov,* and
Diol Epoxides Suse Broyde*
Metabolism of Genistein by Rat and Human Cytochrome P450s 610 Elizabeth S. Roberts-Kirchhoff,*
Jan R. Crowley,
Paul F. Hollenberg, and Hyesook Kim
Detoxification of Methyiglyoxal by the Nucleophilic Bidentate, 617 Gail P. Ferguson, Sonya VanPatten,
Phenylacylthiazolium Bromide Richard Bucala, and YousefAI-Abed*
____________________________________________
Chemical Research in toxicology
VOLUME 12, NUMBER 8, AUGUST 1999
Characterization of the Reactivity, Regioselectivity, and ´679 Thomas S. Moll and Adnan A. Elfarra*
Stereoselectivity of the Reactions of Butadiene Monoxide with
Valinamide and the N-Terminal Valine of Mouse and Rat
Hemoglobin
2,2',3,3',6,6'-Hexachlorobiphenyl Hydroxylation by Active Site 690 Stephen C. Waller, You Ai He,
Mutants of Cytochrome P450 2BI and 2BII Greg R. Harlow, You Qun He,
Eugene A. Mash, and
James R. Halpert*
Cytotoxicity and DNA Interaction of the Enantiomers of 700 Moana Tercel,* Michael A. Gieseg,
6-Amino-3-(chloromethyl)-l-[(5,6,7-trimethoxyindol-2-yl)car- Jared B. Milbank, Maruta Boyd,
bonyl]indoline (Amino-seco-CI-TMI) Jun-Yao Fan, L. Karin Tan,
William R. Wilson, and
William A. Denny
Site-Specific Synthesis of Aflatoxin Bi Adducts within an 707 Wendelyn R. Jones,
Oligodeoxyribonucleotide Containing the Human p53 Codon David S. Johnston, and
249 Sequence Michael P. Stone*
Alkylation of Human Serum Albumin by Sulfur Mustard in 715 Daan Noort,* Albert G. Hulst,
Vitro and in Vivo: Mass Spectrometric Analysis of a Cysteine Leo P. A. de Jong, and
Adduct as a Sensitive Biomarker of Exposure Hendrik P. Benschop
A Gas Chromatography/Electron Capture/Negative Chemical 722 Kuen-Yuh Wu, Nova Scheller,
lonization High-Resolution Mass Spectrometry Method for Asoka Ranasinghe, Ten-Yang Yen,
Analysis of Endogenous and Exogenous Ramiah Sangaiah, Roger Giese, and
JV7-(2-Hydroxyethyl)guanine in Rodents and Its Potential for James A. Swenberg*
Human Biological Monitoring
Metabolism of Carbon Tetrachloride to Trichloromethyl 730 Detcho A. Stoyanovsky and
Radical: An ESR and HPLC-EC Study Arthur I. Cederbaum*
Relationship between Surface Properties and Cellular 737 Bice Fubini,* Giovanna Zanetti, Responses to Crystalline Silica: Studies with Heat-Treated Serena Altilia, Roberta Tiozzo, Cristobalite
Dominique Lison, and
Umberto Saffiotti
_______________________________________
CHEMICAL RESEARCH IN TOXICOLOGY
VOLUME 12, NUMBER 9, SEPTEMBER 1999
EDITORIAL
Defining Molecular Toxicology: A Perspective 747 James L. Stevens, Lawrence J. Marnett
ARTICLES
Synthesis and Structure Determination of the Adducts Formed 749 Kai-Ming Li, Jaeman Byun,
by Electrochemical Oxidation of Dibenzo[a,Z]pyrene in the Michael L. Gross, Dan Zamzow,
Presence of Adenine Ryszard Jankowiak,
Eleanor G. Rogan, and
Ercole L. Cavalieri*
Structure Elucidation of the Adducts Formed by Fjord-Region 758 Kai-Ming Li, Mathai George,
Dibenzo[a,l]pyrene 11,12-Dihydrodiol 13,14-Epoxides and Michael L. Gross, Albrecht Seidel,
Deoxyadenosine Andreas Luch, Ele anor G. Rogan, and
Ercole L. Cavalieri*
Spectral and Conformational Analysis of Deoxyadenosine 768 Ryszard Jankowiak,*
Adducts Derived from syn- and anti-Dibenzo[a,l]pyrene Dial Cheng-Huang Lin, Dan Zamzow,
Epoxides; Fluorescence Studies Kenneth P. Roberts, Kai-Ming Li, and
Gerald J. Small
Structure Elucidation of the Adducts Formed by Fjord Region 778 Kai-Ming Li, Mathai George,
Dibenzo[a,Z]pyrene-ll,12-dihydrodiol 13,14-Epoxides with Michael L. Gross, Cheng-Huang Lin,
Deoxyguanosine Ryszard Jankowiak, Gerald J. Small,
Albrecht Seidel, Heiko Kroth,
Eleanor G. Rogan, and
Ercole L. Cavalieri*
Preparation, Isolation, and Characterization of 789 Prabu Devanesan, Freek Ariese,
Dibenzo[a,Z]pyrene Dial Epoxide—Deoxyribonucleoside Ryszard Jankowiak, Gerald J. Small,
Monophosphate Adducts by HPLC and Fluorescence Eleanor G. Rogan, and
Line-Narrowing Spectroscopy Ercole L. Cavalieri*
A Novel Method for the Isolation and Identification of Stable 796 Prabu Devanesan, Freek Ariese,
DNA Adducts Formed by Dibenzo[a,lpyrene and Ryszard Jankowiak, Gerald J. Small,
Dibenzo[a,l]pyrene 11,12-Dihydrodiol 13,14-Epoxides in Vitro Eleanor G. Rogan, and
Ercole L. Cavalieri*
Simultaneous Determination of Five Oxidative DNA Lesions in 802 Jean-Luc Ravanat, Pascale Guicherd,
Human Urine Zorana Tuce, and Jean Cadet*
Different Mechanisms for the Photoinduced Production of 809 Thomas E. Spratt,* Sherri S. Schultz,
Oxidative DNA Damage by Fluoroquinolones Differing in Douglas E. Levy, Di Chen,
Photostability Gerhardt Schluter, and
Gary M. Williams
Implications of Cytosine Methylation on 816 Padmanava Pradhan, Astrid Graslund,
(+)-anti-Benzo[a]pyrene 7,8-Dihydrodiol 9,10-Epoxide N2 dG Albrecht Seidel, and Bengt Jernstrom*
Adduct Formation in 5'-d(CGT), 5'-d(CGA), and 5'-d(CGC)
Sequence Contexts of Single- and Double-Stranded
Oligonucleotides
13C2-Labeled Methyl tert-Butyl Ether: Toxicokinetiesand 822 AnnsofiNihIen,* Susan C.J.Sumner,
Characterization of Urinary Metabolites in Humans Agneta L5f, and Gunnar Johanson
Glutathione Conjugation of ElectrophilicMetabolites of 831 KatherineC. Watt,* DexterM.Morin,
l-Nitronaphthalene in Rat Tracheobronchial Airways and Mark J. Kurth, Roger S. Mercer,
Liver: Identification by Mass Spectrometry and Proton Charles G. Plopper, and
Nuclear Magnetic Resonance Spectroscopy Alan R. Buckpitt
Treatment of Human Cells with 840 Jean-Francois Cloutier,
jV-Nitroso(acetoxymethyl)methylainine: Distribution Patterns Regen Drouin, and Andre Castonguay*
of Piperidine-Sensitive DNA Damage at the Nucleotide Level of
Resolution Are Related to the Sequence Context
Sonochemistry of Quinones in Argon-Saturated Aqueous 850 Raphael C. Lawson, Amaris Ferrer,
Solutions: Enhanced Cytochrome c Reduction Wilmarie Flores, and
Antonio E. Alegria*
Rapid Cross-Linking of Proteins by 4-Ketoaldehydes and 855 Guozhang Xu, Yahua Liu,
4-Hydroxy-2-alkenals Does Not Arise from the Lysine-Derived • Mayank M. Kansal, and
Monoalkylpyrroles Lawrence M. Sayre*
Structural Elucidation of a 2:2 4-Ketoaldehyde—Amine Adduct 862 Guozhang Xu and Lawrence M. Sayre*
as a Model for Lysine-Directed Cross-Linking of Proteins by •
4-Ketoaldehydes
_______________________________________
Chemical Research In Toxicology
VOLUME. 12, NUMBER. 11, NOVEMBER 1999
ARTICLES_______________________________________________________________________________________
An Enzyme-Linked Immunosorbent Assay for the Detection of 1033 Guornin Shan, Tngrid Wengatz,
Esfenvalerate Metabolites in Human Urine Donald W, Stoutamire,
Shiricy J, Gee, and
Bruce D. Hammock*
Hydroxyl Radical Production by Mouse Epidermal Cell Lines 1042 Beibei Li, Peter L. Guticrrez,
in the Presence ofQuinone Anti-Cancer Compounds Paul Amstad, and Neil V, Blough*
Quantitative Component Analysis of Mixtures for Risk 1050 Hitesh C, Patel, Jose S. Duca,
Assessment: Application to Eye Irritation A. J. Hopfiner,*
Cheryl D. Glendening, and
Edward D. Thompson
The Presence of Lead Decreases the Availability of 1057 Susan Z. Lever* and Teresa L, Parsons
meso-2,3-Dimercaptosuccinic Acid for Analysis in the
Monobromobimane Assay
Oxidation of Ochratoxin A by an Fe-Porphyrin System: Model 1066 Ivan G- Gillman, T. Nicole Glark, and
for Enzymatic Activation and DNA Cleavage Richard A, Manderville*
Nuclease PI Digestion Combined with Tandem Mass 1077 Yinsheng Wang,
Spectrometry for the Structure Determination of DNA John-Stephen Taylor,* and
Photoproducts Michael L, Gross*
Tamoxifen-DNA Adducts Formed by a-Acetoxytamoxifcn 1083 Atsushi Urnemoto* Yasumasa Monden,
N- Oxide Kansei Komaki, Masato Suwa,
Yoshikazu Kanno, Masanobu Suzuki,
Chun-Xing Lin, Yuji Ueyama,
Md. Abdul Momen,
Anisetti Ravindernath, and
Shinya Shibutani
New Reaction Pathways of Dopamine under Oxidative Stress 1090 Alessandra Napolitano,
Conditions: Nonenzymatic Iron-Assisted Conversion to Alessandro Pezzella, and
Norepinephrine and the Neurotoxins 6-Hydroxydopamine and Ginseppe Prota*
6,7-Dihydroxytetrahydroisoquinoline
Regulation of Expression of AT-Methylpurine DNA Glycosylase 1098 Sonia R. Cerda, Samuel S. Chu,
in Human Mammary Epithelial Cells: Role of Transcription Pablo Garcia, Jean Cluing,
Factor AP-2 Jordan D, Grumet,
Bayar Thimmapaya, and
Sigmund A, Weitzman*
Role otCytochrome P450 2EI in the Metabolism ofAcrylamidc 1110 Susan C, J, Sumner*
and Acrylonitrile in Mice Timothy R. Fennell, Timothy A- Moore,
Brian Chanas, Frank Gonzalez, and
Burhan I. Ghanayern
_______________________________________