110299-23-5Relevant academic research and scientific papers
Toward electron-deficient pyrene derivatives: Construction of pyrene tetracarboxylic diimide containing five-membered imide rings
Zou, Lin,Wang, Xiao-Ye,Zhang, Xiao-Xiao,Dai, Ya-Zhong,Wu, Yun-Dong,Wang, Jie-Yu,Pei, Jian
, p. 12585 - 12588 (2015)
Electron-deficient pyrene-1,2,6,7-tetracarboxylic diimide (PyrDI) and its cyano derivative (PyrDI-CN) have been designed and synthesized as a new family of aromatic diimides. PyrDI has two unexpected five-membered imide rings and can form excimers facilely in the solid state. These new pyrene derivatives are promising n-type semiconductors for organic electronics.
Oxidation of alcohols and reduction of aldehydes derived from methyl- and dimethylpyrenes by cDNA-expressed human alcohol dehydrogenases
Kollock, Ronny,Frank, Heinz,Seidel, Albrecht,Meinl, Walter,Glatt, Hansruedi
, p. 65 - 75 (2008)
Some methylated pyrenes can form DNA adducts in rat tissues after benzylic hydroxylation and sulpho conjugation. However, oxidation of the intermediate alcohols to carboxylic acids is an important competing pathway leading to detoxification. We previously showed that co-administration of ethanol or 4-methylpyrazole strongly enhances DNA adduct formation by 1-hydroxymethylpyrene, indicating an involvement of alcohol dehydrogenases (ADHs) in the detoxification. This mechanism may be involved in the observed synergism of smoking and alcohol consumption in certain human cancers. In a preceding study, cDNA-expressed human ADH2 efficiently oxidised 1-, 2- and 4-hydroxymethylpyrene; these reactions were inhibited in the presence of ethanol or 4-methylpyrazole. Here we report that ADH1C, ADH3 and ADH4 also show substantial activity towards these substrates and two further congeners, 1-hydroxymethyl-6-methylpyrene and 1-hydroxymethyl-8-methylpyrene. All four ADH forms also catalysed the reverse reaction, implying that the aldehydes have to be sequestered by other enzymes, such as aldehyde dehydrogenases, for final detoxification. ADH1C and ADH4 activities towards hydroxymethylpyrenes were more strongly inhibited in the presence of ethanol and 4-methylpyrazole than those of ADH2. ADH3 was only inhibited at very high concentrations of the modulators. In conclusions, several human ADHs are capable of detoxifying benzylic alcohols of alkylated polycyclic aromatic hydrocarbons. However, some competing substrates and inhibitors may affect all these redundant detoxification systems, although to various extents.
