Review of mutagenicity of monocyclic aromatic amines: quantitative structure-activity relationships. 1997

K T Chung, and L Kirkovsky, and A Kirkovsky, and W P Purcell
Department of Microbiology and Molecular Sciences, University of Memphis, TN, USA.

Monocyclic aromatic amines (MAAs) are environmental pollutants. Many of them are genotoxic and impose hazards to human health. The mutagenicity of more than 80 of these amines was reviewed with primary emphasis on evaluation by the Ames Salmonella/microsome testing system. Many amines are mutagenic in Salmonella tester strains TA98 and TA100, but S9 mix is required for activity for most of the active ones. 2,4-Diaminotoluene, 2,4-diaminoethylbenzene, and a few amines containing a nitro-group are direct mutagens. There are several quantitative structure-activity relationship (QSAR) models which rationalize mutagenicity of many aromatic amines and several parameters, such as the lowest unoccupied molecular orbital energy (ELUMO), highest occupied molecular orbital energy (EHOMO), and hydrophobicity that are important. What factors determine the minimum requirement for the compound to be mutagenic and what factors determine the extent of mutagenicity suggest questions for further study.

UI MeSH Term Description Entries
D009152 Mutagenicity Tests Tests of chemical substances and physical agents for mutagenic potential. They include microbial, insect, mammalian cell, and whole animal tests. Genetic Toxicity Tests,Genotoxicity Tests,Mutagen Screening,Tests, Genetic Toxicity,Toxicity Tests, Genetic,Genetic Toxicity Test,Genotoxicity Test,Mutagen Screenings,Mutagenicity Test,Screening, Mutagen,Screenings, Mutagen,Test, Genotoxicity,Tests, Genotoxicity,Toxicity Test, Genetic
D009153 Mutagens Chemical agents that increase the rate of genetic mutation by interfering with the function of nucleic acids. A clastogen is a specific mutagen that causes breaks in chromosomes. Clastogen,Clastogens,Genotoxin,Genotoxins,Mutagen
D006571 Heterocyclic Compounds Cyclic compounds that include atoms other than carbon in their ring structure. Heterocyclic Compound,Compound, Heterocyclic,Compounds, Heterocyclic
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D000588 Amines A group of compounds derived from ammonia by substituting organic radicals for the hydrogens. (From Grant & Hackh's Chemical Dictionary, 5th ed) Amine
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships

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