Evidence of direct generation of oxygen free radicals from heterocyclic amines by NADPH/cytochrome P-450 reductase in vitro - PubMed (original) (raw)
Evidence of direct generation of oxygen free radicals from heterocyclic amines by NADPH/cytochrome P-450 reductase in vitro
K Sato et al. Jpn J Cancer Res. 1992 Nov.
Abstract
Highly purified cytochrome P-450 reductase (also called cytochrome c reductase; EC 1.6.2.4.) and NADPH were used to generate superoxide radical (O2.-) from 11 different heterocyclic amines (HCAs) as identified by electron spin resonance spectroscopy using the spin trapping method with 5,5-dimethyl-1-pyrroline N-oxide (DMPO). The signal intensity of DMPO-OOH(-O2-) (i.e., the DMPO spin adduct of O2.-) was strongest for 2-amino-3,4-dimethylimidazo[4,5-f]quinoline (MeIQ). The O2.- generation with HCAs decreased in the following order: 2-amino-3,8-dimethyl-imidazo[4,5-f]quinoxaline (MeIQx) = 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) > 2-amino-3,4,8-trimethylimidazo[4,5-f]quinoxaline (diMeIQx) > or = other HCAs; O2.- generation was lowest with 2-amino-3-methyl-9H-pyrido[2,3-b]indole .CH3COOH (MeA alpha C). By using Lineweaver-Burk plots, Km values of cytochrome P-450 reductase for mitomycin C, IQ, and MeIQ were determined to be 1.60 x 10(-6) M, 1.97 x 10(-5) M, and 2.83 x 10(-6) M, respectively. The present findings have important implications for carcinogenesis because of the known effect of oxygen radicals on cell proliferation.
Similar articles
- Superoxide radical generation from heterocyclic amines.
Maeda H, Sato K, Akaike T. Maeda H, et al. Princess Takamatsu Symp. 1995;23:103-12. Princess Takamatsu Symp. 1995. PMID: 8844801 Review. - Activation and effects of the food-derived heterocyclic amines in extrahepatic tissues.
Overvik E, Hellmold H, Branting C, Gustafsson JA. Overvik E, et al. Princess Takamatsu Symp. 1995;23:123-33. Princess Takamatsu Symp. 1995. PMID: 8844803 Review. - Use of genetically engineered Salmonella typhimurium OY1002/1A2 strain coexpressing human cytochrome P450 1A2 and NADPH-cytochrome P450 reductase and bacterial O-acetyltransferase in SOS/umu assay.
Aryal P, Terashita T, Guengerich FP, Shimada T, Oda Y. Aryal P, et al. Environ Mol Mutagen. 2000;36(2):121-6. doi: 10.1002/1098-2280(2000)36:2<121::aid-em6>3.0.co;2-p. Environ Mol Mutagen. 2000. PMID: 11013410 - Inhibitory Effect of Rosa rugosa Tea Extract on the Formation of Heterocyclic Amines in Meat Patties at Different Temperatures.
Jamali MA, Zhang Y, Teng H, Li S, Wang F, Peng Z. Jamali MA, et al. Molecules. 2016 Jan 30;21(2):173. doi: 10.3390/molecules21020173. Molecules. 2016. PMID: 26840288 Free PMC article.
Cited by
- Analyses of repeated failures in cancer therapy for solid tumors: poor tumor-selective drug delivery, low therapeutic efficacy and unsustainable costs.
Maeda H, Khatami M. Maeda H, et al. Clin Transl Med. 2018 Mar 1;7(1):11. doi: 10.1186/s40169-018-0185-6. Clin Transl Med. 2018. PMID: 29541939 Free PMC article. - Curcumin inhibits PhIP induced cytotoxicity in breast epithelial cells through multiple molecular targets.
Jain A, Samykutty A, Jackson C, Browning D, Bollag WB, Thangaraju M, Takahashi S, Singh SR. Jain A, et al. Cancer Lett. 2015 Aug 28;365(1):122-31. doi: 10.1016/j.canlet.2015.05.017. Epub 2015 May 21. Cancer Lett. 2015. PMID: 26004342 Free PMC article. - The link between infection and cancer: tumor vasculature, free radicals, and drug delivery to tumors via the EPR effect.
Maeda H. Maeda H. Cancer Sci. 2013 Jul;104(7):779-89. doi: 10.1111/cas.12152. Epub 2013 Apr 22. Cancer Sci. 2013. PMID: 23495730 Free PMC article. Review. - Protective effect of melatonin against mitomycin C-induced genotoxic damage in peripheral blood of rats.
Ortega-Gutiérrez S, López-Vicente M, Lostalé F, Fuentes-Broto L, Martínez-Ballarín E, García JJ. Ortega-Gutiérrez S, et al. J Biomed Biotechnol. 2009;2009:791432. doi: 10.1155/2009/791432. Epub 2009 Oct 20. J Biomed Biotechnol. 2009. PMID: 19859567 Free PMC article. - 8-nitroguanosine formation in viral pneumonia and its implication for pathogenesis.
Akaike T, Okamoto S, Sawa T, Yoshitake J, Tamura F, Ichimori K, Miyazaki K, Sasamoto K, Maeda H. Akaike T, et al. Proc Natl Acad Sci U S A. 2003 Jan 21;100(2):685-90. doi: 10.1073/pnas.0235623100. Epub 2003 Jan 8. Proc Natl Acad Sci U S A. 2003. PMID: 12522148 Free PMC article.
References
- ) Guengerich , F. P.Roles of cytochrome P‐450 enzymes in chemical carcinogenesis and cancer chemotherapy . Cancer Res. , 48 , 2946 – 2954 ( 1989. ). - PubMed
- ) Guengerich , F. P.Reactions and significance of cytochrome P‐450 enzymes . Biol. Chem. , 266 , 10019 – 10022 ( 1991. ). - PubMed
- ) Witz , G.Active oxygen species as factors in multistage carcinogenesis . Proc. Soc. Exp. Biol. Med. , 198 , 675 – 682 ( 1991. ). - PubMed
- ) Harris , C. C.Chemical and physical carcinogenesis: advances and perspectives for the 1990s . Cancer Res. ( Suppl ), 51 , 5023s – 5044s ( 1991. ). - PubMed
- ) Kasai , H. , Okada , Y. , Nishimura , S. , Rao , M. S. and Reddy , J. K.Formation of 8‐hydroxydeoxyguanosine in liver DNA of rats following long‐term exposure to a peroxisome proliferator . Cancer Res. , 49 , 2603 – 2605 ( 1989. ). - PubMed
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources