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Can I read 7-Azabicyclo[2.2.1]heptane as a structural motif to block mutagenicity of nitrosamines on EtoBox?
7-Azabicyclo[2.2.1]heptane as a structural motif to block mutagenicity of nitrosamines by Tomohiko Ohwada; Satoko Ishikawa; Yusuke Mine; Keiko Inami; Takahiro Yanagimoto; Fumika Karaki; Yoji Kabasawa; Yuko Otani; Masataka Mochizuki is a Biochemistry, Genetics and Molecular Biology article available to read on EtoBox.
What is 7-Azabicyclo[2.2.1]heptane as a structural motif to block mutagenicity of nitrosamines about?
Nitrosamines are potent carcinogens and toxicants in the rat and potential genotoxins in humans. They are metabolically activated by hydroxylation at an α-carbon atom with respect to the nitrosoamino group, catalyzed by cytochrome P450. However, there has been little systematic investigation of the structure-mutagenic activity relationship of N-nitrosamines. Herein, we evaluated the mutagenicity of a series of 7-azabicyclo[2.2.1]heptane N-nitrosamines and related monocyclic nitrosamines by using the Ames assay. Our results show that the N-nitrosamine functionality embedded in the bicyclic 7-azabicylo[2.2.1]heptane structure lacks mutagenicity, that is, it is inert to α-hydroxylation, which is the trigger of mutagenic events. Further, the calculated α-C-H bond dissociation energies of the bicyclic nitrosamines are larger in magnitude than those of the corresponding monocyclic nitrosamines and N-nitrosodimethylamine by as much as 20-30 kcal/mol. These results are consistent with lower α-C-H bond reactivity of the bicyclic nitrosamines. Thus, the 7-azabicyclo[2.2.1]heptane structural motif may be useful for the design of nongenotoxic nitrosamine compounds with potential biological/med
Who reads 7-Azabicyclo[2.2.1]heptane as a structural motif to block mutagenicity of nitrosamines?
It is typically read by researchers, students, and practitioners in Biochemistry, Genetics and Molecular Biology.
- Author
- Tomohiko Ohwada; Satoko Ishikawa; Yusuke Mine; Keiko Inami; Takahiro Yanagimoto; Fumika Karaki; Yoji Kabasawa; Yuko Otani; Masataka Mochizuki
- Publisher
- Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0968-0896)
- Published
- 2011
- Language
- EN
- Field
- Biochemistry, Genetics and Molecular Biology (Life Sciences)