Structural features of nitroaromatics that determine mutagenic activity in Salmonella typhimurium

Journal Article · Sat Dec 31 23:00:00 EST 1983 · Environ. Manage.; (United States)

DOI:https://doi.org/10.1002/em.2860060607· OSTI ID:5977029

Vance, W A; Levin, D E

Seventeen structurally homologous nitroaromatics were tested for direct-acting mutagenic potency in nine strains of Salmonella typhimurium. The following four structural features were determined to have a strong influence on mutagenic activity: physical dimensions of the aromatic rings, isomeric position of the nitro group, conformation of the nitro group with respect to the plane of the aromatic rings, and ability to resonance-stabilize the utimate electrophile. Progressive addition of five- and six-membered rings to a nitrobenzene nucleus demonstrated that mutagenic activity was a direct function of size. Nitroaromatics with a nitro group oriented along the long axis of symmetry of the molecule were more potent mutagens that those with the nitro group oriented along the short axis. These results are discussed in light of the insertion-denaturation model for intercalation of certain DNA adducts. Finally, structural features that contribute to resonance stabilization of the reactive nitrenium ion enhance mutagenic potency. The predictive value of these structure-activity relationships should permit a first approximation in the assessment of mutagenic potency of nitroaromatics.

• Research Organization: California State Department of Health Services, Berkeley
• OSTI ID: 5977029
• Journal Information: Environ. Manage.; (United States), Journal Name: Environ. Manage.; (United States) Vol. 6:6; ISSN EMNGD
• Country of Publication: United States
• Language: English

Related Subjects

560302* -- Chemicals Metabolism & Toxicology-- Microorganisms-- (-1987)
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
AROMATICS
BACTERIA
HYDROCARBONS
ISOMERS
MICROORGANISMS
MUTAGEN SCREENING
MUTATIONS
NITRO COMPOUNDS
NITROBENZENE
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
POLYCYCLIC AROMATIC HYDROCARBONS
SALMONELLA
SALMONELLA TYPHIMURIUM
SCREENING
STRUCTURAL CHEMICAL ANALYSIS