Copper-mediated DNA damage by metabolites of p-dichlorobenzene

Carcinogenesis
S Oikawa, S Kawanishi

Abstract

p-Dichlorobenzene (p-DCB) has been reported to be carcinogenic for rodents, although it does not seem to be mutagenic in bacterial test systems. In this study, the mechanism of DNA damage by metabolites of p-DCB in the presence of metals was investigated by a DNA sequencing technique using 32P-labeled DNA fragments and by an electrochemical detector coupled to an HPLC. 2,5-Dichlorohydroquinone (DCHQ), one of the major metabolites, caused DNA damage in the presence of Cu(II). 2,5-Dichloro-p-benzoquinone (DCBQ) slightly induced DNA damage in the presence of Cu(II), but addition of NADH induced DNA damage very efficiently. DCHQ plus Cu(II) induced piperidine-labile sites at thymine residues at high frequency. A similar DNA cleavage pattern was observed with DCBQ plus Cu(II) in the presence of NADH. Both DCHQ and DCBQ plus NADH increased 8-oxo-7,8-dihydro-2'-deoxyguanosine in calf thymus DNA in the presence of Cu(II). Typical hydroxyl radical scavengers showed no inhibitory effects on this Cu(II)-mediated DNA damage. Bathocuproine and catalase inhibited the DNA damage, indicating the participation of Cu(I) and hydrogen peroxide (H2O2) in the DNA damage. UV-visible and ESR spectroscopy has demonstrated that DCHQ is rapidly autoxidiz...Continue Reading

Citations

Jun 27, 2007·Archives of Toxicology·Osamu TakahashiHisashi Kamimura
Nov 6, 2009·Biological Trace Element Research·Wang SuhuaMichael Aschner
Jan 3, 2001·Free Radical Biology & Medicine·P A ThibodeauB Paquette
Apr 30, 2002·Free Radical Biology & Medicine·Shosuke KawanishiShinji Oikawa
Sep 5, 2002·Free Radical Biology & Medicine·Katsuhisa SakanoShosuke Kawanishi
Jun 15, 2006·Antioxidants & Redox Signaling·Shosuke Kawanishi, Yusuke Hiraku
Feb 8, 2014·Chemical Research in Toxicology·Birandra K SinhaRonald P Mason
Apr 13, 1999·Biochemical and Biophysical Research Communications·Y Ohkuma, S Kawanishi
Oct 12, 2010·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·Osamu TakahashiAkio Ogata
Nov 21, 2001·Japanese Journal of Cancer Research : Gann·K SakanoS Kawanishi
May 3, 2014·Therapeutic Advances in Neurological Disorders·Divyanshu DubeyOlaf Stüve

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