Skip to main content
SpringerLink
Log in

Amide-Type Adduct of Dopamine – Plausible Cause of Parkinson Diseases

  • Chapter
  • First Online:
Lipid Hydroperoxide-Derived Modification of Biomolecules

Part of the book series: Subcellular Biochemistry ((SCBI,volume 77))

Abstract

Dopamine is the endogenous neurotransmitter produced by nigral neurons. Dopamine loss can trigger not only prominent secondary morphological changes, but also changes in the density and sensitivity of dopamine receptors; therefore, it is a sign of PD development. The reasons for dopamine loss are attributed to dopamine’s molecular instability due to it is a member of catecholamine family, whose catechol structure contributes to high oxidative stress through enzymatic and non-enzymatic oxidation. Oxidative stress in the brain easily leads to the lipid peroxidation reaction due to a high concentration of polyunsaturated fatty acids (PUFA), such as docosahexaenoic acid (DHA, C22:6/ω-3) and arachidonic acid (AA, C18:4/ω-6). Recent studies have shown that lipid hydroperoxides, the primary peroxidative products, could non-specifically react with primary amino groups to form N-acyl-type (amide-linkage) adducts. Therefore, based on the NH2-teminals in dopamine’s structure, the aims of this chapter are to describes the possibility that reactive LOOH species derived from DHA/AA lipid peroxidation may modify dopamine to form amide-linkage dopamine adducts, which might be related to etiology of Parkinson’s diseases.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 84.99
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Hardcover Book
USD 109.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  • Ang SL (2006) Transcriptional control of midbrain dopaminergic neuron development. Development 133:3499–3506

    Article  CAS  PubMed  Google Scholar 

  • Asanuma M, Miyazaki I, Ogawa N (2003) Dopamine- or L-DOPA-induced Neurotoxicity: the role of dopamine quinone formation and tyrosinase in a model of Parkinson’s disease. Neurotox Res 5:165–176

    Article  PubMed  Google Scholar 

  • Balaban RS, Nemoto S, Finkel T (2005) Mitochondria, oxidants, and aging. Cell 120:483–495

    Article  CAS  PubMed  Google Scholar 

  • Bazan NG, Palacios-Pelaez R, Lukiw WJ (2002) Hypoxia signaling to genes: significance in Alzheimer’s disease. Mol Neurobiol 26:283–298

    Article  CAS  PubMed  Google Scholar 

  • Beermann C, Möbius M, Winterling N, Schmitt JJ, Boehm G (2005) sn-position determination of phospholipid-linked fatty acids derived from erythrocytes by liquid chromatography electrospray ionization ion-trap mass spectrometry. Lipids 40:211–218

    Article  CAS  PubMed  Google Scholar 

  • Berman SB, Hastings TG (1999) Dopamine oxidation alters mitochondrial respiration and induces permeability transition in brain mitochondria: implications for Parkinson’s disease. J Neurochem 73:1127–1137

    Article  CAS  PubMed  Google Scholar 

  • Bove J, Prou D, Perier C, Przedborski S (2005) Toxin-induced models of Parkinson’s disease. NeuroRx 2:484–494

    Article  PubMed Central  PubMed  Google Scholar 

  • Boveris A, Navarro A (2008) Brain mitochondrial dysfunction in aging. IMUBM Life 60:308–314

    Article  CAS  Google Scholar 

  • Buhmann C, Arlt S, Kontush A, Moeller-Bertram T, Sperber S, Oechsner M, Stuerenburg HJ, Beisiegel U (2004) Plasma and CSF markers of oxidative stress are increased in Parkinson’s disease and influenced by antiparkinsonian medication. Neurobiol Dis 15:160–170

    Article  CAS  PubMed  Google Scholar 

  • Chalovich EM, Zhu JH, Caltagarone J, Bowser R, Chu CT (2006) Functional repression of cAMP response element in 6-hydroxydopamine-treated neuronal cells. J Biol Chem 281:17870–17881

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  • Chinopoulos C, Adam-Vizi V (2006) Calcium, mitochondria and oxidative stress in neuronal pathology. Novel aspects of an enduring theme. FEBS J 273:433–450

    Article  CAS  PubMed  Google Scholar 

  • Dexter DT, Carter CJ, Wells FR, Javoy-Agid F, Agid Y, Lees A, Jenner P, Marsden CD (1989) Basal lipid peroxidation in substantia nigra is increased in Parkinson’s disease. J Neurochem 52:381–389

    Article  CAS  PubMed  Google Scholar 

  • Dexter DT, Holley AE, Filtter WD, Slater TF, Wells FR, Daniel SE, Lees A, Jenner P, Marsden CD (1994) Increased levels of lipid hydroperoxides in the parkinsonian substantia nigra: an HPLC and ESR study. Mov Disord 9:92–97

    Article  CAS  PubMed  Google Scholar 

  • Diez E, Chilton FH, Stroup G, Mayer RJ, Winkler JD, Fonteh AN (1994) Fatty acid and phospholipid selectivity of different phospholipase A2 enzymes studied by using a mammalian membrane as substrate. Biochem J 301:721–726

    CAS  PubMed  Google Scholar 

  • Fahn S, Cohen G (1992) The oxidant stress hypothesis in Parkinson’s disease: evidence supporting it. Ann Neurol 32:804–812

    Article  CAS  PubMed  Google Scholar 

  • Forster MJ, Dubey A, Dawson KM, Stutts WA, Lal H, Sohal RS (1996) Age-related losses of cognitive function and motor skills in mice are associated with oxidative protein damage in the brain. Proc Natl Acad Sci USA 93:4765–4769

    Article  CAS  PubMed  Google Scholar 

  • Galvan A, Wichmann T (2008) Pathophysiology of parkinsonism. Clin Neurophysiol 119:1459–1474

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  • Gethe U, Andersen PH, Larsson OM, Schousboe A (2006) Neurotransmitter transporters: molecular function of important drug targets. Trends Pharmacol Sci 27:375–383

    Article  Google Scholar 

  • Gorman AM, Ceccatelli S, Orrenius S (2000) Role of mitochondria in neuronal apoptosis. Dev Neurosci 22:348–358

    Article  CAS  PubMed  Google Scholar 

  • Gotz ME, Kunig G, Riederer P, Youdim MB (1994) Oxidative stress: free radical production in neural degeneration. Pharmacol Ther 63:37–122

    Article  CAS  PubMed  Google Scholar 

  • Graumann R, Paris I, Martinez-Alvarado P, Rumanque P, Perez-Pastene C, Cardenas SP, Marin P, Diaz-Grez F, Caviedes R, Caviedes P, Segura-Aguilar J (2002) Oxidation of dopamine to aminochrome as a mechanism for neurodegeneration of dopaminergic systems in Parkinson’s disease. Possible neuroprotective role of DT-diaphorase. Pol J Pharmacol 54:573–579

    CAS  PubMed  Google Scholar 

  • Hadders-Algra M (2008) Prenatal long-chain polyunsaturated fatty acid status: the importance of a balanced intake of docosahexaenoic acid and arachidonic acid. J Perinat Med 36:101–109

    CAS  PubMed  Google Scholar 

  • Hald A, Lotharius J (2005) Oxidative stress and inflammation in Parkinson’s disease: is there a causal link? Exp Neurol 176:154–162

    Google Scholar 

  • Hanrott K, Gudmunsen L, O'Neill MJ, Wonnacott S (2006) 6-hydroxydopamine-induced apoptosis is mediated via extracellular auto-oxidation and caspase 3-dependent activation of protein kinase Cdelta. J Biol Chem 281:5373–5382

    Article  CAS  PubMed  Google Scholar 

  • Izumi Y, Sawada H, Sakka N, Yamamoto N, Kume T, Katsuki H, Shimohama S, Akaike A (2005) p-Quinone mediates 6-hydroxydopamine-induced dopaminergic neuronal death and ferrous iron accelerates the conversion of p-quinone into melanin extracellularly. J Neurosci Res 79:849–860

    Article  CAS  PubMed  Google Scholar 

  • Jenner P (2003) Oxidative stress in Parkinson’s disease. Ann Neurol 53:S26–S38

    Article  CAS  PubMed  Google Scholar 

  • Jia Z, Zhu H, Misra HP, Li Y (2008) Potent induction of total cellular GSH and NQO1 as well as mitochondrial GSH by 3H-1,2-dithiole-3-thione in SH-SY5Y neuroblastoma cells and primary human neurons: protection against neurocytotoxicity elicited by dopamine, 6-hydroxydopamine, 4-hydroxy-2-nonenal, or hydrogen peroxide. Brain Res 1197:159–169

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  • Kato Y, Makino Y, Osawa T (1997) Formation of N ε-(hexanonyl) lysine in protein exposed to lipid hydroperoxide A plausible marker for lipid hydroperoxide-derived protein modification. J Lipid Res 38:1334–1346

    CAS  PubMed  Google Scholar 

  • Kato Y, Mori Y, Makino Y, Morimitsu Y, Hiroi S, Ishikawa T, Osawa T (1999) Formation of N ε-(hexanonyl) lysine in protein exposed to lipid hydroperoxide A plausible marker for lipid hydroperoxide-derived protein modification. J Biol Chem 274:20406–20414

    Article  CAS  PubMed  Google Scholar 

  • Kato Y, Osawa T (1998) Detection of oxidized phospholipid-protein adducts using anti-15-hydroperoxyeicosatetraenoic acid-modified protein antibody: contribution of esterified fatty acid-protein adduct to oxidative modification of LDL. Arch Biochem Biophys 351:106–114

    Article  CAS  PubMed  Google Scholar 

  • Kawai Y, Fujii H, Kato Y, Kodama M, Naito N, Uchida K, Osawa T (2004) Esterified lipid hydroperoxide-derived modification of protein: formation of a carboxyalkylamide-type lysine adduct in human atherosclerotic lesions. Biochem Biophys Res Commun 313:271–276

    Article  CAS  PubMed  Google Scholar 

  • Kawai Y, Fujii H, Okada M, Tsuchie Y, Uchida K, Osawa T (2006) Formation of Nepsilon-(succinyl)lysine in vivo: a novel marker for docosahexaenoic acid-derived protein modification. J Lipid Res 47:1386–1398

    Article  CAS  PubMed  Google Scholar 

  • Kawai Y, Kato Y, Fujii H, Mkino Y, Mori Y, Naito N, Osawa T (2003) Immunochemical detection of a novel lysine adduct using an antibody to linoleic acid hydroperoxide-modified protein. J Lipid Res 44:1124–1131

    Article  CAS  PubMed  Google Scholar 

  • Kita T, Wagner GC, Nakashima T (2003) Current research on methamphetamine-induced neurotoxicity: animal models of monoamine disruption. J Pharmacol Sci 92:178–195

    Article  CAS  PubMed  Google Scholar 

  • Kluck RM, Bossy-Wetzel E, Green DR, Newmeyer DD (1997) The release of cytochrome c from mitochondria: a primary site for Bcl-2 regulation of apoptosis. Science 275:1132–1136

    Article  CAS  PubMed  Google Scholar 

  • LaVoie MJ, Hastings TG (1999) Peroxynitrite‐and nitrite‐induced oxidation of dopamine: implications for nitric oxide in dopaminergic cell loss. J Neurochem 73:2546–2554

    Article  CAS  PubMed  Google Scholar 

  • Lee YM, Park SH, Shin DI, Hwang JY, Park B, Park YJ, Lee TH, Chae HZ, Jin BK, Oh TH, Oh YJ (2008) Oxidative modification of peroxiredoxin is associated with drug-induced apoptotic signaling in experimental models of Parkinson disease. J Biol Chem 283:9986–9998

    Article  CAS  PubMed  Google Scholar 

  • Leroy E, Boyer R, Auburger G, Leube B, Ulm G, Mezey E, Harta G, Brownstein MJ, Jonnalagada S, Chernova T, Dehejia A, Lavedan C, Gasser T, Steinbach PJ, Wilkinson KD, Polymeropoulos MH (1998) The ubiquitin pathway in Parkinson’s disease. Nature 395:451–452

    Article  CAS  PubMed  Google Scholar 

  • Lin MT, Flint BM (2006) Mitochondrial dysfunction and oxidative stress in neurodegenerative diseases. Nature 433:787–795

    Article  Google Scholar 

  • Liu XB, Shibata T, Hisaka S, Osawa T (2008) DHA hydroperoxides as a potential inducer of neuronal cell death: a mitochondrial dysfunction-mediated pathway. J Clin Biochem Nutr 43:26–33

    Article  PubMed Central  PubMed  Google Scholar 

  • Long EK, Murphy TC, Leiphon LJ, Watt J, Morrow JD, Milne GL, Howard JR, Picklo MJ Sr (2008) Trans-4-hydroxy-2-hexenal is a neurotoxic product of docosahexaenoic (22:6; n-3) acid oxidation. J Neurochem 105:714–724

    Article  CAS  PubMed  Google Scholar 

  • Ma QL, Teter B, Ubeda OJ, Morihara T, Dhoot D, Nyby MD, Tuck ML, Frautschy SA, Cole GM (2007) Omega-3 fatty acid docosahexaenoic acid increases SorLA/LR11, a sorting protein with reduced expression in sporadic Alzheimer's disease (AD): relevance to AD prevention. J Neurosci 27:14299–14307

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  • Maharaj H, Mahara DS, Scheepers M, Mokokong R, Daya S (2005) l-DOPA administration enhances 6-hydroxydopamine generation. Brain Res 1063:180–186

    Article  CAS  PubMed  Google Scholar 

  • Mariani E, Polidori MC, Cherubini A, Mecocci P (2005) Oxidative stress in brain aging, neurodegenerative and vascular diseases: an overview. J Chromatogr B 827:65–75

    Article  CAS  Google Scholar 

  • Maruyama W, Naoi M (2002) Cell death in Parkinson’s disease. J Neurol 249(Suppl 2):6–10

    CAS  Google Scholar 

  • Montine KS, Quinn JF, Zhang J, Fessel JP, Roberts LJ 2nd, Morrow JD, Montine TJ (2004) Isoprostanes and related products of lipid peroxidation in neurodegenerative diseases. Chem Phys Lipids 128:117–124

    Article  CAS  PubMed  Google Scholar 

  • Navarro A, Boveris A (2007) The mitochondrial energy transduction system and the aging process. Am J Physiol Cell Physiol 292:C670–C686

    Article  CAS  PubMed  Google Scholar 

  • Pezzella A, d’Ischia M, Napolitano A, Misuraca G, Prota G (1997) Iron-mediated generation of the neurotoxin 6-hydroxydopamine quinone by reaction of fatty acid hydroperoxides with dopamine: a possible contributory mechanism for neuronal degeneration in Parkinson’s disease. J Med Chem 40:2211–2216

    Article  CAS  PubMed  Google Scholar 

  • Porter NA, Caldwell SE, Mills KA (1995) Mechanisms of free radical oxidation of unsaturated lipids. Lipids 30:277–290

    Article  CAS  PubMed  Google Scholar 

  • Qu Y, Chang L, Klaff J, Seeman R, Balbo A, Rapoport SI (2003) Imaging of brain serotonergic neurotransmission involving phospholipase A2 activation and arachidonic acid release in unanesthetized rats. Brain Res Brain Res Protoc 12:16–25

    Article  CAS  PubMed  Google Scholar 

  • Rapoport SI (1999) In vivo fatty acid incorporation into brain phospholipids in relation to signal transduction and membrane remodeling. Neurochem Res 24:1403–1415

    Article  CAS  PubMed  Google Scholar 

  • Rosenberger TA, Villacreses NE, Hovda JT, Bosetti F, Weerasinghe G, Wine RN, Harry GJ, Rapoport SI (2004) Rat brain arachidonic acid metabolism is increased by a 6-day intracerebral ventricular infusion of bacterial lipopolysaccharide. J Neurochem 88:1168–1178

    Article  CAS  PubMed  Google Scholar 

  • Saner A, Thoenen H (1970) Model experiments on the molecular mechanism of action of 6-hydroxydopamine. Mol Pharmacol 7:147–154

    Google Scholar 

  • Schapira AH (2001) Causes of neuronal death in Parkinson’s disease. Adv Neurol 86:155–162

    CAS  PubMed  Google Scholar 

  • Shamoto-Nagai M, Maruyama W, Kato Y, Isobe K, Tanaka M, Naoi M, Osawa T (2003) An inhibitor of mitochondrial complex I, rotenone, inactivates proteasome by oxidative modification and induces aggregation of oxidized proteins in SH-SY5Y cells. J Neurosci Res 74:589–597

    Article  CAS  PubMed  Google Scholar 

  • Shibata T, Iio K, Kawai Y, Shibata Y, Kawaguchi M, Toi S, Kobayashi M, Kobayashi M, Yamamoto K, Uchida K (2006) Identification of a lipid peroxidation product as a potential trigger of the p53 pathway. J Biol Chem 281:1196–1204

    Article  CAS  PubMed  Google Scholar 

  • Siegel SJ, Bieschke J, Powers ET, Kelly JW (2007) The oxidative stress metabolite 4-hydroxynonenal promotes Alzheimer protofibril formation. Biochemistry 46:1503–1510

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  • Simopoulos AP (1999) Essential fatty acids in health and chronic disease. Am J Clin Nutr 70(Suppl):560–569

    Google Scholar 

  • Tapiero H, Ba GN, Couvreur P, Tew KD (2002) Polyunsaturated fatty acids (PUFA) and eicosanoids in human health and pathologies. Biomed Pharmacother 56:215–222

    Article  CAS  PubMed  Google Scholar 

  • Wakamatsu K, Fujikawa K, Zucca FA, Zecca L, Ito S (2003) The structure of neuromelanin as studied by chemical degradative methods. J Neurochem 86:1015–1023

    Article  CAS  PubMed  Google Scholar 

  • Yoritaka A, Hattori N, Uchida K, Tanaka M, Stadtman ER, Mizuno Y (1996) Immunohistochemical detection of 4-hydroxynonenal protein adducts in Parkinson disease. Proc Natl Acad Sci USA 93:2696–2701

    Article  CAS  PubMed  Google Scholar 

  • Zecca L, Youdim MBH, Riederer P, Connor JR, Crichton RR (2004) Iron, brain ageing and neurodegenerative disorders. Nat Rev Neurosci 5:863–873

    Article  CAS  PubMed  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. The Laboratory of Food and Biodynamics, Graduate School of Bioagricultural Science, Nagoya University, Nagoya, 464-8601, Japan

    Xuebo Liu, Naruomi Yamada & Toshihiko Osawa

  2. College of Food Science and Engineering, Northwest A&F University, Yangling, China

    Xuebo Liu

Authors
  1. Xuebo Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Naruomi Yamada
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Toshihiko Osawa
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Xuebo Liu .

Editor information

Editors and Affiliations

  1. School of Human Science & Environment, University of Hyogo, Himeji, Hyogo, Japan

    Yoji Kato

Rights and permissions

Reprints and permissions

Copyright information

© 2014 Springer Science+Business Media Dordrecht

About this chapter

Cite this chapter

Liu, X., Yamada, N., Osawa, T. (2014). Amide-Type Adduct of Dopamine – Plausible Cause of Parkinson Diseases. In: Kato, Y. (eds) Lipid Hydroperoxide-Derived Modification of Biomolecules. Subcellular Biochemistry, vol 77. Springer, Dordrecht. https://doi.org/10.1007/978-94-007-7920-4_4

Download citation

Publish with us

Policies and ethics

Search

Navigation