The enhancement of oxidative DNA damage by anti-diabetic metformin, buformin, and phenformin, via nitrogen-centered radicals

Free Radical Research

Volumn 50, Issue 8, 2016, Pages 929-937

  Ohnishi, Shiho ^a   Mizutani, Hideki ^b   Kawanishi, Shosuke ^a  

^a SUZUKA UNIVERSITY OF MEDICAL SCIENCE   (Japan)

^b KINJO GAKUIN UNIVERSITY   (Japan)

Author keywords

8 OHdG; biguanide; cancer; EPR; oxidative stress

Indexed keywords

3,3,5,5 TETRAMETHYL 1 PYRROLINE N OXIDE; 8 HYDROXYDEOXYGUANOSINE; BUFORMIN; COPPER; HYDROGEN PEROXIDE; METFORMIN; N TERT BUTYL ALPHA (4 PYRIDYL 1 OXIDE) NITRONE; NITROGEN; PHENFORMIN; PYRROLINE DERIVATIVE; RADICAL; UNCLASSIFIED DRUG; ANTIDIABETIC AGENT; REACTIVE OXYGEN METABOLITE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CONTROLLED STUDY; DNA DAMAGE; DNA STRAND BREAKAGE; ELECTRON SPIN RESONANCE; OXIDATIVE STRESS; SPIN TRAPPING; ANIMAL; BOVINE; DRUG EFFECTS; GENETICS; HUMAN; OXIDATION REDUCTION REACTION;

ANIMALS; BUFORMIN; CATTLE; DNA DAMAGE; HUMANS; HYPOGLYCEMIC AGENTS; METFORMIN; OXIDATION-REDUCTION; PHENFORMIN; REACTIVE OXYGEN SPECIES;

EID: 84978737375     PISSN: 10715762     EISSN: 10292470     Source Type: Journal    
DOI: 10.1080/10715762.2016.1204651     Document Type: Article

References (42)

1. E.Ferrannini The target of metformin in type 2 diabetes. N Engl J Med 2014;371:1547–1548.
2. C.J.Bailey, R.C.Turner Metformin. N Engl J Med 1996;334:574–579.
3. M.Kasuga, K.Ueki, N.Tajima, M.Noda, K.Ohashi, H.Noto,. Report of the Japan diabetes society/Japanese cancer association joint committee on diabetes and cancer. Cancer Sci 2013;104:965–976.
4. V.N.Anisimov Do metformin a real anticarcinogen? A critical reappraisal of experimental data. Ann Transl Med 2014;2:60.
5. W.K.Miskimins, H.J.Ahn, J.Y.Kim, S.Ryu, Y.S.Jung, J.Y.Choi Synergistic anti-cancer effect of phenformin and oxamate. PLoS One 2014;9:e85576.
6. B.Bao, Z.Wang, Y.Li, D.Kong, S.Ali, S.Banerjee,. The complexities of obesity and diabetes with the development and progression of pancreatic cancer. Biochim Biophys Acta 2011;1815:135–146.
7. A.M.Gonzalez-Angulo, F.Meric-Bernstam Metformin: a therapeutic opportunity in breast cancer. Clin Cancer Res 2010;16:1695–1700.
8. I.Pernicova, M.Korbonits. Metformin-mode of action and clinical implications for diabetes and cancer. Nat Rev Endocrinol 2014;10:143–156.
9. Y.K.Choi, K.G.Park Metabolic roles of AMPK and metformin in cancer cells. Mol Cells 2013;36:279–287.
10. K.Y.Hur, M.S.Lee New mechanisms of metformin action: focusing on mitochondria and the gut. J Diabetes Investig 2015;6:600–609.
11. S.Ohnishi, N.Ma, R.Thanan, S.Pinlaor, O.Hammam, M.Murata, S.Kawanishi DNA damage in inflammation-related carcinogenesis and cancer stem cells. Oxid Med Cell Longev 2013;2013:387014.
12. S.Kawanishi, Y.Hiraku, S.Oikawa Mechanism of guanine-specific DNA damage by oxidative stress and its role in carcinogenesis and aging. Mutat Res 2001;488:65–76.
13. S.Shibutani, M.Takeshita, A.P.Grollman Insertion of specific bases during DNA synthesis past the oxidation-damaged base 8-oxodG. Nature 1991;349:431–434.
14. L.A.Loeb, B.D.Preston Mutagenesis by apurinic/apyrimidinic sites. Annu Rev Genet 1986;20:201–230.
15. P.Dandona, K.Thusu, S.Cook, B.Snyder, J.Makowski, D.Armstrong, T.Nicotera Oxidative damage to DNA in diabetes mellitus. Lancet 1996;347:444–445.
16. L.L.Wu, C.C.Chiou, P.Y.Chang, J.T.Wu Urinary 8-OHdG: a marker of oxidative stress to DNA and a risk factor for cancer, atherosclerosis and diabetics. Clin Chim Acta 2004;339:1–9.
17. M.Kakimoto, T.Inoguchi, T.Sonta, H.Y.Yu, M.Imamura, T.Etoh,. Accumulation of 8-hydroxy-2'-deoxyguanosine and mitochondrial DNA deletion in kidney of diabetic rats. Diabetes 2002;51:1588–1595.
18. M.Murata, M.Mizutani, S.Oikawa, Y.Hiraku, S.Kawanishi Oxidative DNA damage by hyperglycemia-related aldehydes and its marked enhancement by hydrogen peroxide. FEBS Lett 2003;554:138–142.
19. H.Sova, U.Puistola, L.Morin-Papunen, P.Karihtala Metformin decreases serum 8-hydroxy-2'-deoxyguanosine levels in polycystic ovary syndrome. Fertil Steril 2013;99:593–598.
20. J.Kim, E.Shon, C.S.Kim, J.S.Kim Renal podocyte injury in a rat model of type 2 diabetes is prevented by metformin. Exp Diabetes Res 2012;2012:210821.
21. Z.H.Maayah, H.Ghebeh, A.A.Alhaider, A.O.El-Kadi, A.A.Soshilov, M.S.Denison,. Metformin inhibits 7,12-dimethylbenz[a]anthracene-induced breast carcinogenesis and adduct formation in human breast cells by inhibiting the cytochrome P4501A1/aryl hydrocarbon receptor signaling pathway. Toxicol Appl Pharmacol 2015;284:217–226.
22. H.Ece, E.Cigdem, K.Yuksel, D.Ahmet, E.Hakan, T.M.Oktay Use of oral antidiabetic drugs (metformin and pioglitazone) in diabetic patients with breast cancer: how does it effect serum Hif-1 alpha and 8Ohdg levels? Asian Pac J Cancer Prev 2012;13:5143–5148.
23. M.Murata, K.Moriya, S.Inoue, S.Kawanishi Oxidative damage to cellular and isolated DNA by metabolites of a fungicide ortho-phenylphenol. Carcinogenesis 1999;20:851–857.
24. G.R.Buettner Spin trapping: ESR parameters of spin adducts. Free Radic Biol Med 1987;3:259–303.
25. K.Yamamoto, S.Kawanishi Hydroxyl free radical is not the main active species in site-specific DNA damage induced by copper (II) ion and hydrogen peroxide. J Biol Chem 1989;264:15435–15440.
26. K.Yamamoto, S.Kawanishi Site-specific DNA damage induced by hydrazine in the presence of manganese and copper ions. The role of hydroxyl radical and hydrogen atom. J Biol Chem 1991;266:1509–1515.
27. W.A.Pryor, R.H.Tang Ethylene formation from methional. Biochem Biophys Res Commun 1978;81:498–503.
28. J.M.Gutteridge, S.Wilkins Copper salt-dependent hydroxyl radical formation. Damage to proteins acting as antioxidants. Biochim Biophys Acta 1983;759:38–41.
29. D.A.Rowley, B.Halliwell Superoxide-dependent and ascorbate-dependent formation of hydroxyl radicals in the presence of copper salts: a physiologically significant reaction? Arch Biochem Biophys 1983;225:279–284.
30. J.A.Simpson, K.H.Cheeseman, S.E.Smith, R.T.Dean Free-radical generation by copper ions and hydrogen peroxide. Stimulation by Hepes buffer. Biochem J 1988;254:519–523.
31. L.Logie, J.Harthill, K.Patel, S.Bacon, D.L.Hamilton, K.Macrae,. Cellular responses to the metal-binding properties of metformin. Diabetes 2012;61:1423–1433.
32. W.Jeng, A.Ramkissoon, T.Parman, P.G.Wells Prostaglandin H synthase-catalyzed bioactivation of amphetamines to free radical intermediates that cause CNS regional DNA oxidation and nerve terminal degeneration. FASEB J 2006;20:638–650.
33. K.Hirakawa, K.Midorikawa, S.Oikawa, S.Kawanishi Carcinogenic semicarbazide induces sequence-specific DNA damage through the generation of reactive oxygen species and the derived organic radicals. Mutat Res 2003;536:91–101.
34. M.Murata, S.Ohnishi, S.Kawanishi Acrylonitrile enhances H2O2-mediated DNA damage via nitrogen-centered radical formation. Chem Res Toxicol 2001;14:1421–1427.
35. K.Midorikawa, M.Murata, S.Oikawa, S.Tada-Oikawa, S.Kawanishi DNA damage by dimethylformamide: role of hydrogen peroxide generated during degradation. Chem Res Toxicol 2000;13:309–315.
36. K.Yamamoto, S.Kawanishi Free radical production and site-specific DNA damage induced by hydralazine in the presence of metal ions or peroxidase/hydrogen peroxide. Biochem Pharmacol 1991;41:905–914.
37. W.A.Pryor Oxy-radicals and related species: their formation, lifetimes, and reactions. Annu Rev Physiol 1986;48:657–667.
38. P.S.Rao, E.Hayon Oxidation of aromatic amines and diamines by OH radicals. Formation and ionization constants of amine cation radicals in water. J Phys Chem 1975;79:1063–1066.
39. T.Theophanides, J.Anastassopoulou Copper and carcinogenesis. Crit Rev Oncol Hematol 2002;42:57–64.
40. R.E.Shackelford, W.K.Kaufmann, R.S.Paules Oxidative stress and cell cycle checkpoint function. Free Radic Biol Med 2000;28:1387–1404.
41. H.Sies Oxidative stress: oxidants and antioxidants. Exp Physiol 1997;82:291–295.
42. Y.Yoshie, H.Ohshima Synergistic induction of DNA strand breakage by cigarette tar and nitric oxide. Carcinogenesis 1997;18:1359–1363.