93045-45-5Relevant academic research and scientific papers
O-Anisidine Dimer, 2-Methoxy- N4-(2-methoxyphenyl) Benzene-1,4-diamine, in Rat Urine Associated with Urinary bladder Carcinogenesis
Kobayashi, Takuma,Toyoda, Takeshi,Tajima, Yuya,Kishimoto, Shinji,Tsunematsu, Yuta,Sato, Michio,Matsushita, Kohei,Yamada, Takanori,Shimamura, Yuko,Masuda, Shuichi,Ochiai, Masako,Ogawa, Kumiko,Watanabe, Kenji,Takamura-Enya, Takeji,Totsuka, Yukari,Wakabayashi, Keiji,Miyoshi, Noriyuki
, p. 912 - 919 (2021/03/01)
Monocyclic aromatic amines, o-toluidine (o-Tol) and its structural analog o-anisidine (o-Ans), are IARC Group 1 and Group 2A urinary bladder carcinogens, respectively, and are involved in metabolic activation and DNA damage. Our recent study revealed that 2-methyl-N4-(2-methylphenyl) benzene-1,4-diamine (MMBD), a p-semidine-type homodimer of o-Tol, was detected and identified in an in vitro reaction of o-Tol with S9 mix and in vivo urinary samples of o-Tol-exposed rats. Potent mutagenic, genotoxic, and cytotoxic activities were reported with MMBD, suggesting its involvement in urinary bladder carcinogenesis. However, it remains unknown whether o-Ans is converted to active metabolites to induce DNA damage in a similar manner as o-Tol. In this study, we report that a novel o-Ans metabolite, 2-methoxy-N4-(2-methoxyphenyl) benzene-1,4-diamine (MxMxBD), a dimer by head-to-tail binding (p-semidine form), was for the first time identified in o-Ans-exposed rat urine. MxMxBD induced a stronger mutagenicity in N-acetyltransferase overexpressed Salmonella typhimurium strains and potent genotoxicity and cytotoxicity in human bladder carcinoma T24 cells compared with o-Ans. These results suggest that MxMxBD may to some extent contribute toward urinary bladder carcinogenesis. In addition to homodimerization, such as MxMxBD, heterodimerizations were observed when o-Ans was coincubated with o-Tol or aniline (Ani) in in vitro reactions with S9 mix. This study highlights the important consideration of homodimerizations and heterodimerizations of monocyclic aromatic amines, including o-Ans, o-Tol, and Ani, in the evaluation of the combined exposure risk of bladder carcinogenesis.
ELECTROCHEMICAL OXIDATIVE SUBSTITUTION AND DIMERISATION OF 1-ARYLAZO-2-NAPHTHOLS, LEADING TO A NEW SYNTHESIS OF SOME UNSYMMETRICAL DIARYLAMINES
Bentley, T. William,Richards, David J.,Hutchings, Michael G.
, p. 5261 - 5264 (2007/10/02)
Some electron-rich 1-arylazo-2-naphthols undergo novel electrochemical oxidations, leading either to substitution by a nucleophilic aniline or to oxidative dimerisation.In the former case subsequent reduction of the azo bond provides a new route to unsymmetrical diarylamines.
