Characterization of rat hepatic acetyltransferase.

Land, Susan; King, Charles M.

doi:10.1289/ehp.94102s691

Cited by 8 publications

(1 citation statement)

References 10 publications

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“…Many of the enzymes (e.g. acetyltransferase, sulfotransferase) involved in these reactions have been identified and recendy been characterized at the molecular level (15,16). The multiple metabolic activation pathways of aromatic amines are summarized in Figure 2.…”

Section: Bioactivation Mechanisms In Relation To Structural Criteria mentioning

confidence: 99%

Cancer Risk Reduction Through Mechanism-Based Molecular Design of Chemicals

Lai¹,

Woo²,

Argus³

et al. 1996

ACS Symposium Series

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Increased understanding of the mechanistic basis of chemical carcinogenesis and the relationship between molecular structure and carcinogenic activity provides opportunities not only for identifying suspect carcinogens but also for designing chemicals with lower carcinogenic potential. One of the chemical classes in which the structural and molecular basis of carcinogenicity is the most clearly understood is the aromatic amines. This paper summarizes the bioactivation mechanisms and structural criteria for aromatic amine carcinogenesis; a strategic approach of risk reduction through mechanism-based molecular design of aromatic amine dyes with lower carcinogenic potential is discussed. With our increasing knowledge of the mechanisms and structure-activity relationships, it should be possible to develop safer products for other chemical classes using similar molecular design approaches. Mechanisms of Chemical Carcinogenesis and Structure-Activity RelationshipsConsiderable knowledge of the mechanisms of chemical carcinogenesis has accrued since the pioneer work by James A. and Elizabeth C. Miller at the University of Wisconsin beginning in the 1940's, particularly concepts on the metabolic activation of chemicals to reactive electrophilic intermediates that interact with cellular nucleophiles to initiate carcinogenesis (7,2). For many carcinogen classes, the molecular basis of carcinogenic activity is now known in considerable detail and the concept of electrophiles provides the most probable rationale for their carcinogenic action. Some of the electrophilic, reactive intermediates believed to be responsible for the carcinogenicity of genotoxic chemicals include: carbonium, aziridium, episulfonium, oxonium, nitrenium or arylamidonium ions, free radicals, epoxides, lactones, aldehydes, semiquinones/quinoneimines, and acylating moieties. The metabolic activation of various genotoxic chemicals to their ultimate carcinogenic metabolites has been reviewed (3).

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Section: Bioactivation Mechanisms In Relation To Structural Criteria mentioning

confidence: 99%

Cancer Risk Reduction Through Mechanism-Based Molecular Design of Chemicals

Lai¹,

Woo²,

Argus³

et al. 1996

ACS Symposium Series

View full text Add to dashboard Cite

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Aromatic Amino and Nitro–Amino Compounds and Their Halogenated Derivatives

Darby

2023

Patty's Toxicology

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The fundamental aromatic hydrocarbon benzene, when substituted by one or more functional groups of the amine, nitro, or halogen classes, alone or in various combinations, provides an enormous number of compounds of immense practical value, ubiquitous presence in the industrial world, and often heightened toxicity relative to benzene itself, a notorious cause of blood cancer. This chapter begins by providing a general overview of aromatic compounds possessing amino and/or nitro substituents, with or without halogen substituents. The production and uses, exposure and biomonitoring, toxicity, and toxic mechanism of action are introduced. The remainder of the chapter focuses on specific compounds in a roughly systematic order based upon chemical structure, expanding on the same subheadings as covered in the general overview. The nomenclature of these compounds can be very confusing since many have traditional names that sometimes markedly differ from their systematized formal names. In this chapter, the same traditional names are used as were used in the previous edition of this publication, but if there is ambiguity of nomenclature, the Chemical Abstracts Service (CAS) numbers provided herein correspond to unique structures, each of which may have several names depending upon the naming convention. In general, when an aromatic compound has an amino or a nitro substituent, it is referred to as an “aniline” or a “nitrobenzene,” respectively, based upon the names of the parent compounds, even though other substituents may be present. When amino and nitro groups are present on the same benzene ring, “aniline” takes precedence, and both “aniline” and “nitrobenzene” take precedence over halogens. There are many exceptions to these general rules, however.

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Aromatic Amino and Nitro–Amino Compounds and their Halogenated Derivatives

Woo¹,

Lai²

2004

Patty's Toxicology

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Aromatic amines are organic compounds that contain at least one amino group attached directly to an aryl moiety. Aromatic amines represent one of the most important classes of industrial and environmental chemicals. Many aromatic amines have been shown to be potent carcinogens and mutagens and/or hemotoxicants capable of inducing methemoglobinemia. Since the introduction of substituted anilines and naphthylamines as intermediates for the manufacture of azo dyes in the mid‐1800s, aromatic amines have found numerous uses in various industries. Substantial worker exposure to aromatic amines with subsequent induction of bladder cancer occurred before preventive measures were instituted. Beyond occupational exposure, humans may also be exposed to aromatic amines through environmental sources. At least three carcinogenic aromatic amines (4‐aminobiphenyl, 2‐naphthylamine, and o ‐toludine) have been detected in cigarette smoke. Many commonly used pharmaceuticals contain or are aromatic amines. Owing to their hazard potential, aromatic amines have been the subject of many biomonitoring studies, making them model compounds in molecular dosimetry and epidemiology studies. Since extensive information is available on the metabolic pathways and, to a lesser extent, the mechanism(s) of action, aromatic amines have also become targets for genetic polymorphism studies with ultimate goals of identifying susceptible subpopulations, and designing of strategies for cancer prevention and intervention. The multifaceted interest in aromatic amines has continued to attract a tremendous amount of scientific studies and attention. Since the publication of the previous edition of Patty's on aromatic amines, many reviews and important research articles on aromatic amines have been published. In this chapter, we present an overview of the aromatic amine class as a whole with emphasis on recent studies, followed by an updated description on individual chemicals grouped into seven subgroups of structurally related compounds.

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Characterization of rat hepatic acetyltransferase.

Cited by 8 publications

References 10 publications

Cancer Risk Reduction Through Mechanism-Based Molecular Design of Chemicals

Cancer Risk Reduction Through Mechanism-Based Molecular Design of Chemicals

Aromatic Amino and Nitro–Amino Compounds and Their Halogenated Derivatives

Aromatic Amino and Nitro–Amino Compounds and their Halogenated Derivatives

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