Synthesis, chemical properties and mutagenicity of 1,6- and 3,6-dinitrobenzo[a]pyrenes.
Nitration of benzo[a]pyrene (BaP) with HNO3 (d = 1.38) produced a mixture of dinitroBaPs (1,6- and 3,6-isomers) and mononitroBaPs (1-, 3- and 6-isomers). Pure 1,6-dinitroBaP and 3,6-dinitroBaP were obtained by the reduction of the dinitroBaPs mixture with NaSH to yield the separable products 1-amino-6-nitroBaP and 3-amino-6-nitroBaP, followed by conversion to dinitroBaPs via the the diazonium salts. The half-wave potentials (E1/2) corresponding to the one-electron reduction of dinitroBaPs were measured and the relationship of these values to the mutagenicity is discussed.
Fukuhara
K
K
National Institute of Hygienic Sciences, Tokyo, Japan.
Miyata
N
N
Matsui
M
M
Matsui
K
K
Ishidate
M
M
Kamiya
S
S
D001580:Benzopyrenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D009153:Mutagens / Q000138:chemical synthesis* / Q000737:chemistry; D009574:Nitro Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity
D001580:Benzopyrenes; D009153:Mutagens; D009574:Nitro Compounds