Nitroarenes: Occurrence, Metabolism, and Biological Impact

323 Pages·1990·10.971 MB·English

by  Joe L. Mauderly, William C. Griffith, Rogene F. Henderson, Robert K. Jones (auth.), Paul C. Howard, Stephen S. Hecht, Frederick A. Beland (eds.)

NITROARENES
Occurrence, Metabolism, and
Biological Impact
ENVIRONMENTAL SCIENCE RESEARCH
Series Editor:
Herbert S. Rosenkranz
Department of Environmental and Occupational Hea/th
Graduate School of Public Health
University of Pittsburgh
130 DeSoto Street
Pittsburgh, Pennsylvania
Founding Editor:
Alexander Hollaender
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NITROARENES
Occurrence, Metabolism, and
Biological Impact
Edited by
c.
Paul Howard
Case Western Reserve University
Cleveland, Ohio
Stephen S. Hecht
American Health Foundation
Valhal/a, New York
and
Frederick A. 8eland
National Center for Toxicological Research
Jefferson, Arkansas
SPRINGER SCIENCE+BUSINESS MEDIA, LLC
Llbrary of Congress Cataloglng-ln-Publlcatlon Data
International Conference on N-Substituted Aryl Compounds, Occurrence,
Metabolism, and Biological Impact of Nitroarenes (4th 1989
Cleveland, Ohio)
Nitroarenes occurrence, metabolism, and biological impact I
edited by Paul C. Ho~ard, Stephen S. Hecht, and Frederlck A. Beland.
p. cm. -- (Environmental science research ; v. 40)
"Proceedings of the Fourth International Conference on N
-Substituted Aryl Compounds, Occurrence, Metabolism, and Biologlcal
I~pact of Nitroarenes, held July 15-19, 1989, in Cleveland, Ohio"
-T.p. verso.
Includes bibliographical references and index.
ISBN 978-1-4613-6694-2 ISBN 978-1-4615-3800-4 (eBook)
DOI 10.1007/978-1-4615-3800-4
1. Nitroaromatic compounds--Carcinogenlcity--Congresses.
2. Nitroaromatic compounds--Mutageniclty--Congresses.
3. Nitroaromatlc compounds--Metabollsm--Congresses. r. Howard,
Paul C. II. Hecht, Stephen S. III. Beland, F. A. (Frederlck A.)
IV. Title. V. Ser ies.
RC268.7.A74I59 1989
616.99'4071--dc20 90-22875
CIP
Proceedings of the Fourth International Conference on
N-Substituted Aryl Compounds: Occurrence, Metabolism,
and Biologicallmpact of Nitroarenes, held July 15-19, 1989,
in Cleveland, Ohio
ISBN 978-1-46l3-6694-2
© 1990 Springer Science+Business Media New York
Originally published by Plenum Press in 1990
Softcover reprint of the hardcover lst edition 1990
AII rights reserved
No part of this book may be reproduced, stored in a retrieval system, or transmitted
in any form or by any means, electronic, mechanical, photocopying, microfilming,
recording, or otherwise, without written permission from the Publisher
PREFACE
Prior to 1979, consideration of the problem of the carcinogenicity of
the aromatic amine class of chemicals took place primarily in poster sessions
and symposia of annual meetings of the American Association for Cancer
Research and analogous international associations.
In November 1979 the first meeting concerned with the aromatic amines
was held in Rockville, Haryland under primary sponsorship of the National
Cancer Institute. The proceedings from this meeting were published as
Monograph 58 of the Journal of the National Cancel' Institute in 1981.
The second meeting in this series, the Second International Conference
on N-Substituted Aryl Compounds, was held in March/April of 1982 in Hot
Springs, Arkansas. The National Cancer Institute and The National Center
for Toxicological Research were the primary sponsors of this meeting. The
proceedings were published as Volume 49 of the journal En-vil'onmental
Health Perspectives in 1983.
The third meeting in this series was held in April of 1987 at the
Dearborn Hyatt in Dearborn, Michigan. The principal sponsor of this
meeting was the Heyer L. Pre ntis Comprehensive Cancer Center of
Metropolitan Detroit. The proceedings, Carcinogenic and Mutagenic
Responses to Aromatic Amines and Nitroal'enes, were published in 1987 by
Elsevier Press.
The fourth meeting was held in Cleveland, Ohio, on July 15-19, 1989.
This meeting was also organized as a satellite of the Fifth International
Conference on Environmental Mutagens. This meeting differed from the
previous three meetings, in that the program was more focused on the
nitrated polycyclic aromatic hydrocarbons than the aromatic amines. This
was the first meeting devoting much of the program to the nitrated
polycyclic aromatic hydrocarbons since the Fifth Chemical Industry Institute
for Toxicology Conference on Toxicology in January of 1982 at Raleigh, North
Carolina.
The primary interest of the Organizing and Program Committee was to
bring together the leading researchers in the nitrated polycyclic aromatic
hydrocarbons and related areas of aromatic amine research. With this as
the goal, the conference was very effective. The program was indeed
representative of international researchers in these areas and was
highlighted by the keynote address by Takashi Sugimura, President of the
National Cancer Center, Tokyo, Japan.
The editors would like to thank the members of the Organizing and
Program Committee for their efforts in setting the speaking agenda:
Frederick A. Beland, Jefferson, Arkansas; Robert P.P. Fuchs, Strasbourg,
France; Stephen S. Hecht, Valhalla, New York; Paul C. Howard, Cleveland,
v
Ohio; Charles M. King, Detroit, Michigan; Dennis R. McCalla, Hamilton, Ontario,
Canada; Gerald M. Mulder, Leiden, The Netherlands; Miriam C. Poirier,
Bethesda, Ma17landj Herbert S. Rosenkranz, Cleveland, Ohio; Dennis
Schuetzle, Detroit, Michigan.
Our thanks is also offered to the financial sponsors of this
conference:
THE FORD MOTOR COMPANY
THE U.S. ENVIRONMENTAL PROTECTION AGENCY
CASE WESTERN RESERVE UNIVERSITY
lCN BIOCHEMICALS, INC.
Paul C. Howard
Stephen S. Hecht
Frederick A. Beland
vi
CONTENTS
EPIDEMIOLOGY AND CARCINOGENESIS
Evidence from Animal Studies for the Carcinogenicity of
Inhaled Diesel Exhaust • . • • . . • • . . . • . . . . . . . . • .. 1
Joe L. Mauderly, William C. Griffith, Rogene F. Henderson,
Robert K. Jones, and Roger O. McClellan
Interpretation of Carcinogenicity and Effective Dose in
Chronic Exposures of Rats to High Diesel Exhaust
Concentrations ...............•..... 15
Werner Stober
Carcinogenicity of Dinitroarenes in Rat Lung ...... . 29
Hiroshi Tokiwa, Kazumi Horikawa, Nobuyuki Sera,
Keisuke Izumi, Masanori Iwagawa, Hisashi Otsuka,
Yoshinari Ohnishi, Akio Nakashima, and
Khoichi Nakashima
In Vivo Metabolism and Genotoxic Effects of the Air Pollutant
and Marker for Nitro-PAH's, 2-Nitrofluorene •..•••. 39
L. Moller, J. Rafter, S. Tornquist, L. Eriksson,
B. Beije, R. Toftgard, T. Midvedt, M. Corrie,
and J-A. Gustafsson
CHEMISTRY, DETECTION, AND OCCURRENCE
Nitroarenes: Their Detection, Mutagenicity and Occurrence
in the Environment .......•............ 61
Joellen Lewtas and Marcia G. Nishioka
The Atmospheric Formation of Nitroarenes and Their
Occurrence in Ambient Air ....•••..•.• 73
Barbara Zielinska, Janet Arey, and Roger Atkinson
Metabolism of 1-Nitropyrene Oxides and Effect of Nitrogen
Dioxide on Arene Activation •.....•....•...• 85
Yoshinari Ohnishi, Takemi Kinouchi, Keiko Nishifuji,
Koichi Miyanishi, Takako Kanoh, and Masao Fukuda
vii
MOLECULAR MECHANISMS
Mutagenic and Biochemical Consequences of the Reaction of
Arylamines with DNA • • . • • . • . • . . • . . . . 95
Charles M. King, Thomas M. Reid, Nobuya Tamura,
and Pawan K. Gupta
Mutagenesis Induced by a Single Acetylaminofluorene Adduct
within the NarI Site is Position Dependent • • . . • . • • • . 105
Patrice Koehl, Dominique Burnouf, and Robert P.P. Fuchs
Unusual Hydrogen Bonding Patterns in 2-Aminofluorene (AF) and
2-Acetylaminofluorene (AAF) Modified DNA • . . . . . • . • . 113
Suse Broyde, Brian E. Hingerty, Robert Shapiro, and
D. Norman
DNA Adduct Formation during Chronic Administration of an
Aromatic Amine ..•.•.•...•••.•••.•••.. .••.• 125
Miriam C. Poirier, Nancy F. Fullerton, Henrik S. Huitfeldt,
Beverly A. Smith, Henry C. Pitot, John M. Hunt,
and Frederick A. Beland
Aerial Oxidation of Acetylaminofluorene-Derived DNA Adducts .••.. 135
Shinya Shibutani, Robert Gentles, and Francis Johnson
Mutations and Homologous Recombination Induced by N-Substituted
Aryl Compounds in Mammalian Cells . . . . . . • . • . . . . . . . • 149
Veronica M. Maher, M. Chia-Miao Mah, Jia-Ling Yang,
Nitai P. Bhattacharyya, and J. Justin McCormick
Comparison of the Mutagenic Potency of DNA Adducts Formed
by Reactive Derivatives of Aflatoxin, Benzidine and
1-Nitropyrene in a Plasmid System .....•..•..•.•.•• 157
Carl N. t>1artin and Gary S. Jennings
Mutations Induced in the la.cI Gene of E. coli by 1-Nitroso-8-
Nitropyrene and Furylfuramide: The Influence of Plasmid
pKM101 and Excision Repair on the Mutational Spectrum ... 167
LB. Lambert, A.J.E. Gordon, T.A. Chin, D.W. Brya.nt,
B.W. Glickman, and Dennis R. McCalla
DNA Adduct Formation by 1-Nitropyrene 4,5- and 9,10-0xide .•.•. 181
Beverly A. Smith, Robert H. Heflich, Yoshinari Ohnishi,
Akinobu Ohuchida, Takemi Kinouchi, Janice R.
Thornton-Manning, and Frederick A. Beland
Nitropolycyclic Aromatic Hydrocarbons and Diesel Exhaust:
Potential Role of DNA Binding in Carcinogenicity. ....... 189
James A. Bond, Charles E. Mitchell, Joe L. Mauderly,
and Ronald K. Wolff
Validation/ Application of 3ZP-Postlabeling Analysis for the
Detection of DNA Adducts Resulting from Complex Air
Pollution Sources Containing PAHs and Nitrated PAHs .•...• 201
J.E. Gallagher, M.J. Kohan, M.H. George, M.A. Jackson,
and J. Lewtas
Analysis of NOZ-PAH DNA Adducts by Mass Spectrometry ........ 211
Roger W. Giese, and Paul Vouros
viii
HETABOLISM
Generation of Reactive Intermediates from 2-Nitrofluorene
that Bind Covalently to DNA, RNA and Protein In Vitro
and In Vivo in the Rat ••••••...•.•.•••• .• • • . 219
Gerard J. Mulder, Frank C.J. Wierckx, Rinny Wedzinga,
and John H.N. Meerman
Activation of Carcinogenic N-Arylhydroxamic Acids by
Peroxidase/H~02/Halide Systems: Route to C-Nitroso
Aromatics • :. . . . . . . . . • . . . . • • . . . . . . . . • • . . . . . 231
Danuta Malejka-Giganti, Clare L. Ritter, and
Lauri J. Sammartano
Biochemical Studies on the Putative Nitroso Metabolite of
Chloramphenicol: A New Model for the Cause of
Aplastic Anemia . . • • . . . . . . . • • • . • . . • • • • • . . . . . . 245
Michael D. Corbett and Bernadette R. Corbett
Mechanisms of FANFT/ANFT Induced Bladder Cancer •....••••. 257
Terry V. Zenser, Michael B. Hattammal, Vijaya H. Lakshmi,
Ruthellen Dawley, Suhas V. Sohani, Leslie A. Spry,
and Bernard B. Davis
Mutagenic Arylazides, Arylnitrenes, Arylnitrenium Ions . . . . • • • • . 265
Dieter Wild
Products Obtained by In \"itro Reaction of 4,5-Epoxy-
4,5-Dihydro-1-Nitropyrene with DNA .....•• • •..••. 273
Karam EI-Bayoumy, Ajit K. Roy, and Stephen S. Hecht
Oxidative Metabolism of Nitrated Polycyclic Aromatic
Hydrocarbons in Mammalian Cell Fractions • . . . . . . • . . 285
Paul C. Howard and Scott F. Purvis
Metabolic Activation of 6-Nitrochrysene and 6-Aminochrysene
III Vitro and In Vivo . . . . . . . . . . . . . . . . . . . . . . . . . . 295
K. Barry Delclos, Glenn Talaska, Ralph P. Walker,
Christiane Brassinne, and Jean Paul Sculier
SUMMARY
The Possible Role of Nitroarenes in Human Cancer . . . . . . • • . . . . 309
Stephen S. Hecht and Karam El-Bayoumy
Abstracts Presented at the Meeting 317
Contributor Index 327
Subject Index ... 331
ix
EVIDENCE FROM ANIMAL STUDIES FOR THE
CARCINOGENICITY OF INHALED DIESEL EXHAUST
Joe L. Mauderly, William C. Griffith, Rogene F. Henderson,
Robert K. Jones, and Roger O. McClellan
Inhalation Toxicology Research Institute
Lovelace Biomedical and Environmental Research Institute
P. O. Box 5890
Albuquerque, NH 87185
INTRODUCTION
Concerns in the mid 1970s for petroleum shortages and the mandating of
fuel efficiency standards for automobiles led to speculation that the use
of diesel engines in the U. S. light-duty fleet would increase substantial
ly. It had been known for 20 years that diesel soot carried a solvent
extractable organic fraction containing numerous polycyclic aromatic
hydrocarbons, and that the extract was carcinogenic to mouse skin (Kotin et
al., 1955); thus, concern arose within the U. S. Environmental Protection
Agency (EPA) for the potential contribution of increased diesel emissions
to lung cancer in the U. S. The EPA issued a precautionary notice in 1977
(U. S. EPA, 1977) that the extracts were mutagenic in the Ames Salmonella
assay, and numerous studies have subsequently provided detailed information
on the nature of soot-associated mutagenic activity (reviewed in Ishinishi
et a1., 1986).
The EPA began studies of the toxicity of diesel exhaust in animals
exposed repeatedly by inhalation with a two-month exposure of cats and
rodents in 1977, followed by initiation of a two-year exposure of several
species in 1978 (Pepelko and Peirano, 1983). General Motors began a chronic
inhalation study in 1980 (Kaplan et al., 1983), and soon thereafter, other
long-term inhalation studies were begun in the U. S., Germany, Japan, and
Switzerland. The preliminary results of these studies were presented at a
symposium in 1986 (Ishinishi et al., 1986) and were reviewed by MCClellan
in 1987 (McClellan, 1987). The final results of most, but not all, of
these studies have now been published.
This paper reviews the results of the long-term inhalation studies and
the evidence they present for the pulmonary carcinogenicity of diesel
exhaust. It also reviews the current issue of the specificity of the
carcinogenic response of rats for diesel exhaust and the research that is
now being conducted to resolve this issue. The chemistry, dosimetry, and
genotoxicity of inhaled diesel exhaust are reviewed in other papers in this
volume, and are not discussed in detail in this paper.
Nilroarenes, Edited by P. C. Howard el al.
Plenum Press, New York, 1990