Mechanism of DNA damage and apoptosis induced by tetrahydropapaveroline, a metabolite of dopamine

Neurochemical Research

Volumn 31, Issue 4, 2006, Pages 523-532

  Kobayashi, Hatasu ^a   Oikawa, Shinji ^a   Kawanishi, Shosuke ^a  

^a MIE UNIVERSITY   (Japan)

Author keywords

DNA damage; Hydrogen peroxide; L DOPA; Metal; Parkinson's disease; Tetrahydropapaveroline

Indexed keywords

BATHOCUPROINE; CATALASE; CUPRIC ION; DNA; DNA FRAGMENT; DOPAMINE; EDETIC ACID; FERRIC ION; HYDROGEN PEROXIDE; HYDROXYL RADICAL; LEVODOPA; METAL CHELATE; PHOSPHORUS 32; REACTIVE OXYGEN METABOLITE; SCAVENGER; TETRAHYDROPAPAVEROLINE; UNCLASSIFIED DRUG;

APOPTOSIS; ARTICLE; CELL CLONE; CELL STRAIN HL 60; CONTROLLED STUDY; CYTOTOXICITY; DISEASE ASSOCIATION; DNA DAMAGE; DOPAMINERGIC SYSTEM; DRUG EFFECT; HUMAN; HUMAN CELL; ISOTOPE LABELING; METABOLITE; MOLECULAR MECHANICS; NEUROTOXICITY; PRIORITY JOURNAL;

ANIMALS; APOPTOSIS; CALCIUM CHANNEL BLOCKERS; CATTLE; COPPER; DEOXYGUANOSINE; DNA DAMAGE; DNA FRAGMENTATION; DOPAMINE; EDETIC ACID; FERRIC COMPOUNDS; FREE RADICAL SCAVENGERS; HL-60 CELLS; HUMANS; IONS; IRON CHELATING AGENTS; METALS; MOLECULAR STRUCTURE; PHENANTHROLINES; PIPERIDINES; TETRAHYDROPAPAVEROLINE;

EID: 33745017422     PISSN: 03643190     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11064-006-9044-8     Document Type: Article

References (38)

1. Basma AN, Morris EJ, Nicklas WJ, Geller HM (1995) L-dopa cytotoxicity to PC12 cells in culture is via its auto-oxidation. J Neurochem 64:825-832
2. Walkinshaw G, Waters CM (1995) Induction of apoptosis in catecholaminergic PC12 cells by L-DOPA. Implications for the treatment of Parkinson's disease. J Clin Invest 95:2458-2464
3. Zou L, Jankovic J, Rowe DB, Xie W, Appel SH, Le W (1999) Neuroprotection by pramipexole against dopamine- and levodopa-induced cytotoxicity. Life Sci 64:1275-1285
4. Clement MV, Long LH, Ramalingam J, Halliwell B (2002) The cytotoxicity of dopamine may be an artefact of cell culture. J Neurochem 81:414-421
5. Liu WG, Chen Y, Li B, Lu GQ, Chen SD (2004) Neuroprotection by pergolide against levodopa-induced cytotoxicity of neural stem cells. Neurochem Res 29:2207-2214
6. Yin SY, Lee JJ, Kim YM, Jin CM, Yang YJ, Kang MH, Kai M, Lee MK (2004) Effects of (1R,9S)-beta-hydrastine on 1-DOPA-induced cytotoxicity in PC12 cells. Eur J Pharmacol 488:71-77
7. Sandler M, Carter SB, Hunter KR, Stern GM (1973) Tetrahydroisoquinoline alkaloids: in vivo metabolites of L-dopa in man. Nature 241:439-443
8. Matsubara K, Fukushima S, Akane A, Kobayashi S, Shiono H (1992) Increased urinary morphine, codeine and tetrahydropapaveroline in parkinsonian patient undergoing L-3,4-dihydroxyphenylalanine therapy: a possible biosynthetic pathway of morphine from L-3,4-dihydroxyphenylalanine in humans. J Pharmacol Exp Ther 260:974-978
9. Cashaw JL (1993) Determination of tetrahydropapaveroline in the urine of parkinsonian patients receiving L-dopa-carbidopa (Sinemet) therapy by high-performance liquid chromatography. J Chromatogr 613:267-273
10. Turner AJ, Baker KM, Algeri S, Erigerio A, Garattini S (1974) Tetrahydropapaveroline: formation in vivo and in vitro in rat brain. Life Sci 14:2247-2257
11. Maruyama W, Sango K, Iwasa K, Minami C, Dostert P, Kawai M, Moriyasu M, Naoi M (2000) Dopaminergic neurotoxins, 6,7- dihydroxy-1-(3′,4′- dihydroxybenzyl)-isoquinolines, cause different types of cell death in SH-SY5Y cells: apoptosis was induced by oxidized papaverolines and necrosis by reduced tetrahydropapaverolines. Neurosci Lett 291:89-92
12. Shin MH, Jang JH, Surh YJ (2004) Potential roles of NF-kappaB and ERK1/2 in cytoprotection against oxidative cell death induced by tetrahydropapaveroline. Free Radic Biol Med 36:1185-1194
13. Soh Y, Shin MH, Lee JS, Jang JH, Kim OH, Kang H, Surh YJ (2003) Oxidative DNA damage and glioma cell death induced by tetrahydropapaveroline. Mutat Res 544:129-142
14. Suzuki K, Mizuno Y, Yoshida M (1990) Inhibition of mitochondrial respiration by 1,2,3,4-tetrahydroisoquinoline-like endogenous alkaloids in mouse brain. Neurochem Res 15:705-710
15. Oikawa S, Nishino K, Inoue S, Mizutani T, Kawanishi S (1998) Oxidative DNA damage and apoptosis induced by metabolites of butylated hydroxytoluene. Biochem Pharmacol 56:361-370
16. Oikawa S, Murakami K, Kawanishi S (2003) Oxidative damage to cellular and isolated DNA by homocysteine: implications for carcinogenesis. Oncogene 22:3530-3538
17. Kobayashi H, Oikawa S, Hirakawa K, Kawanishi S (2004) Metal-mediated oxidative damage to cellular and isolated DNA by gallic acid, a metabolite of antioxidant propyl gallate. Mutat Res 558:111-120
18. Maxam AM, Gilbert W (1980) Sequencing end-labeled DNA with base-specific chemical cleavages. Methods Enzymol 65:499-560
19. Kasai H, Crain PF, Kuchino Y, Nishimura S, Ootsuyama A, Tanooka H (1986) Formation of 8-hydroxyguanine moiety in cellular DNA by agents producing oxygen radicals and evidence for its repair. Carcinogenesis 7:1849-1851
20. Ito K, Inoue S, Yamamoto K, Kawanishi S (1993) 8-Hydroxydeoxyguanosine formation at the 5′ site of 5′-GG-3′ sequences in double-stranded DNA by UV radiation with riboflavin. J Biol Chem 268:13221-13227
21. Rao PS, Luber JM, Jr. Milinowicz J, Lalezari P, Mueller HS (1988) Specificity of oxygen radical scavengers and assessment of free radical scavenger efficiency using luminol enhanced chemiluminescence. Biochem Biophys Res Commun 150:39-44
22. Spassky A, Angelov D (1997) Influence of the local helical conformation on the guanine modifications generated from one-electron DNA oxidation. Biochemistry 36:6571-6576
23. Kasugai I, Yamada M (1992) High production of catalase in hydrogen peroxide-resistant human leukemia HL-60 cell lines. Leuk Res 16:173-179
24. Hertzberg RP, Dervan PB (1984) Cleavage of DNA with methidiumpropyl-EDTA- iron(II): reaction conditions and product analyses Biochemistry. 23:3934-3945
25. Kawanishi S, Inoue S, Sano S (1986) Mechanism of DNA cleavage induced by sodium chromate(VI) in the presence of hydrogen peroxide. J Biol Chem 261:5952-5958
26. Inoue S, Kawanishi S (1987) Hydroxyl radical production and human DNA damage induced by ferric nitrilotriacetate and hydrogen peroxide. Cancer Res 47:6522-6527
27. Celander DW, Cech TR (1990) Iron(II)-ethylenediaminetetraacetic acid catalyzed cleavage of RNA and DNA oligonucleotides: similar reactivity toward single- and double-stranded forms. Biochemistry 29:1355-1361
28. Boiteux S, Gajewski E, Laval J, Dizdaroglu M (1992) Substrate specificity of the Escherichia coli Fpg protein (formamidopyrimidine-DNA glycosylase): excision of purine lesions in DNA produced by ionizing radiation or photosensitization. Biochemistry 31:106-110
29. Bruner SD, Norman DP, Verdine GL (2000) Structural basis for recognition and repair of the endogenous mutagen 8-oxoguanine in DNA. Nature 403:859-866
30. David-Cordonnier MH, Laval J, O'Neill P (2000) Clustered DNA damage, influence on damage excision by XRS5 nuclear extracts and Escherichia coli Nth and Fpg proteins. J Biol Chem 275:11865-11873
31. Box HC, Dawidzik JB, Budzinski EE (2001) Free radical-induced double lesions in DNA. Free Radic Biol Med 31:856-868
32. Ohnishi S, Kawanishi S (2002) Double base lesions of DNA by a metabolite of carcinogenic benzo[a]pyrene. Biochem Biophys Res Commun 290:778-782
33. Blaisdell JO, Wallace SS (2001) Abortive base-excision repair of radiation-induced clustered DNA lesions in Escherichia coli. Proc Natl Acad Sci USA 98:7426-7430
34. Olanow CW, Agid Y, Mizuno Y, Albanese A, Bonuccelli U, Damier P, De Yebenes J, Gershanik O, Guttman M, Grandas F, Hallett M, Hornykiewicz O, Jenner P, Katzenschlager R, Langston WJ, LeWitt P, Melamed E, Mena MA, Michel PP, Mytilineou C, Obeso JA, Poewe W, Quinn N, Raisman-Vozari R, Rajput AH, Rascol O, Sampaio C, Stocchi F (2004) Levodopa in the treatment of Parkinson's disease: current controversies. Mov Disord 19:997-1005
35. Fahn S, Oakes D, Shoulson I, Kieburtz K, Rudolph A, Lang A, Olanow CW, Tanner C, Marek K (2004) Levodopa and the progression of Parkinson's disease. N Engl J Med 351:2498-2508
36. Leveugle B, Faucheux BA, Bouras C, Nillesse N, Spik G, Hirsch EC, Agid Y, Hof PR (1996) Cellular distribution of the iron-binding protein lactotransferrin in the mesencephalon of Parkinson's disease cases. Acta Neuropathol (Berl) 91:566-572
37. Ke Y, Ming Qian Z (2003) Iron misregulation in the brain: a primary cause of neurodegenerative disorders. Lancet Neurol 2:246-253
38. Zecca L, Stroppolo A, Gatti A, Tampellini D, Toscani M, Gallorini M, Giaveri G, Arosio P, Santambrogio P, Fariello RG, Karatekin E, Kleinman MH, Turro N, Hornykiewicz O, Zucca FA (2004) The role of iron and copper molecules in the neuronal vulnerability of locus coeruleus and substantia nigra during aging. Proc Natl Acad Sci USA 101:9843-9848