Disubstituted amino-, nitroso-, and nitrofluorenes: a physicochemical basis for structure-activity relationships in Salmonella typhimurium

Journal Article · Thu Jan 01 00:00:00 EST 1987 · Environ. Mutagen.; (United States)

DOI:https://doi.org/10.1002/em.2860090204· OSTI ID:5764555

Vance, W A; Wang, Y Y; Okamoto, H S

Twenty-nine derivatives of fluorene were tested for mutagenic potency in four strains of Salmonella typhimurium with and/or without S9 microsomal activation. The effects of a second functional group on the mutagenic activity of an amino-nitroso-, and nitrofluorene were correlated with its physical and chemical properties. When the functional group is conjugated by resonance, both inductive and resonance effects are determinants of mutagenic potency. Electron-withdrawing groups such as the halogens (F, Cl, Br, and I), nitro, nitroso, and cyano at C-7 increased the mutagenic potency of 2-nitrofluorene. Acetylation of a hydroxy or an amino group at C-7 increased the mutagenic potency of 2-nitrofluorene. The physical properties of a second functional group are expected to exert their effect(s) at three points in the metabolic activation of 2,7-disubstituted fluorene derivatives: 1) initial reduction of the nitro group (redox effect), 2) stabilization of the hydroxylamine (inductive effect), and 3) stabilization/destabilization of the nitrenium ion (resonance and inductive effects). The relationships between the physical properties of a second functional group and their effects on biological activities of nitro- and aminofluorenes in the Ames Salmonella assay may be of predictive value in a first approximation of both the mutagenic and carcinogenic potency of chemicals with comparable structures such as fluoranthene and biphenyl.

• Research Organization: California State Dept. of Health Services, Berkeley
• OSTI ID: 5764555
• Journal Information: Environ. Mutagen.; (United States), Vol. 9:2
• Country of Publication: United States
• Language: English

Related Subjects

63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
ORGANIC NITROGEN COMPOUNDS
MUTAGEN SCREENING
STRUCTURE-ACTIVITY RELATIONSHIPS
FLUORENE
MICROSOMES
NITRO COMPOUNDS
SALMONELLA TYPHIMURIUM
AROMATICS
BACTERIA
CELL CONSTITUENTS
CONDENSED AROMATICS
HYDROCARBONS
MICROORGANISMS
ORGANIC COMPOUNDS
ORGANOIDS
SALMONELLA
SCREENING
560300* - Chemicals Metabolism & Toxicology