Mutagenicity of halogenated propanes and their methylated derivatives. 1988

F Ratpan, and H Plaumann
Corporate Research and Development, Polysar Limited, Sarnia, Ontario, Canada.

1,2,3-Tribromopropane, 1,2,3-trichloropropane, and 1,2-dibromo-3-chloropropane are mutagenic in strains TA1535 and TA100 of Salmonella typhimurium, but only in the presence of rat liver S9 mix. This requirement for metabolic activation was unexpected for an alkyl halide and thus suggested the metabolic formation of the 2-keto derivatives (di-haloacetone). The 2-methyl derivatives of the halopropane compounds did not induce a doubling of revertants compared to controls. It was demonstrated that none of these compounds is converted into a secondary material that could be determined as structurally different by gas chromatography. These observations suggest that lack of mutagenicity of the methylated compounds is a manifestation of a steric effect.

UI MeSH Term Description Entries
D008745 Methylation Addition of methyl groups. In histo-chemistry methylation is used to esterify carboxyl groups and remove sulfate groups by treating tissue sections with hot methanol in the presence of hydrochloric acid. (From Stedman, 25th ed) Methylations
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
D011407 Propane A three carbon alkane with the formula H3CCH2CH3.
D006846 Hydrocarbons, Halogenated Hydrocarbon compounds with one or more HYDROGEN atoms substituted with HALOGENS. Halogenated Hydrocarbons
D001711 Biotransformation The chemical alteration of an exogenous substance by or in a biological system. The alteration may inactivate the compound or it may result in the production of an active metabolite of an inactive parent compound. The alterations may be divided into METABOLIC DETOXICATION, PHASE I and METABOLIC DETOXICATION, PHASE II.
D012486 Salmonella typhimurium A serotype of Salmonella enterica that is a frequent agent of Salmonella gastroenteritis in humans. It also causes PARATYPHOID FEVER. Salmonella typhimurium LT2
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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