85964-28-9

Usage

InChI:InChI=1/C16H11NO/c18-17-14-9-7-12-5-4-10-2-1-3-11-6-8-13(14)16(12)15(10)11/h1-9,17-18H

Upstream product

• 5522-43-0 1-nitropyrene 

Downstream Products

• 1606-67-3 1-aminopyrene 
• 86674-51-3 1-nitrosopyrene 
• 58447-78-2 [1.1']Azoxypyren 

Relevant academic research and scientific papers

Identification of Two N2-Deoxyguanosinyl DNA Adducts upon Nitroreduction of the Environmental Mutagen 1-Nitropyrene

1-Nitropyrene, the most abundant nitro-polycyclic aromatic hydrocarbon in the environment, is a known mammalian and bacterial mutagen and a tumorigen in animals. Early studies on DNA adduct characterization for 1-nitropyrene identified N-(deoxyguanosin-8-yl)-1-aminopyrene as the major product from the modification of calf thymus DNA with N-hydroxy-1-aminopyrene, the activated metabolite from nitroreduction of 1-nitropyrene. In this paper, we report the identification of two N2-deoxyguanosinyl adducts, in addition to N-(deoxyguanosin-8-yl)-1-aminopyrene, formed from the reaction of N-hydroxy-1-aminopyrene, prepared in situ, with calf thymus DNA. These DNA adducts were identified as 6-(deoxyguanosin-N2-yl)-1-aminopyrene and 8-(deoxyguanosin-N2-yl)-1-aminopyrene. The two N2-deoxyguanosinyl adducts were also identified in an ascorbic acid-catalyzed activation of 1-nitrosopyrene and in the mammary gland of female Sprague-Dawley rats administered 1-nitropyrene. The DNA adducts were also formed when 1-nitropyrene was metabolized by xanthine oxidase in the presence of calf thymus DNA, and when 1-nitropyrene was activated by rat liver microsomes and cytosols, as well as from DNA isolated from Salmonella typhimurium suspension cultures incubated with 1-nitropyrene.

Synthesis and characterization of nitro-, nitroso-, and aminofluoranthenes

The synthesis is reported of the five mononitrofluoranthenes. 1-Nitrofluoranthene was synthesized in 20percent from fluoranthene, 2-nitrofluoranthene in 24percent from 1,2,3,10b-tetrahydrofluoranthene, 3-nitrofluoranthene in 13percent from fluoranthene and 7- and 8-nitrofluoranthene in 34percent from 1,2,3,10b-tetrahydrofluoranthene.The pure nitrofluoranthenes were converted into their nitroso and amino analogues.The nitrosopyrenes were also synthesized.Characterisation of each compound is described.