Iron and copper ions accelerate and modify dopamine oxidation to eumelanin: implications for neuromelanin genesis

[1]  K. Double,et al.  A brief history of brain iron accumulation in Parkinson disease and related disorders , 2022, Journal of Neural Transmission.

[2]  K. Wakamatsu,et al.  Neuromelanin in Parkinson’s Disease: Tyrosine Hydroxylase and Tyrosinase , 2022, International journal of molecular sciences.

[3]  Hong Zhang,et al.  Mass spectrometric observation on free radicals during electrooxidation of dopamine. , 2021, Analytica chimica acta.

[4]  P. Riederer,et al.  Iron as the concert master in the pathogenic orchestra playing in sporadic Parkinson’s disease , 2021, Journal of Neural Transmission.

[5]  K. Wakamatsu,et al.  Photobleached Oxidative Degradation of Melanins: Chemical Characterization of Melanins Present in Alpaca Fiber , 2021, Photochemistry and photobiology.

[6]  S. Bardien,et al.  Toxic Feedback Loop Involving Iron, Reactive Oxygen Species, α-Synuclein and Neuromelanin in Parkinson’s Disease and Intervention with Turmeric , 2021, Molecular Neurobiology.

[7]  A. Veraksa,et al.  Drosophila yellow‐h encodes dopaminechrome tautomerase: A new enzyme in the eumelanin biosynthetic pathway , 2021, Pigment cell & melanoma research.

[8]  L. Blancafort,et al.  Stability and Optical Absorption of a Comprehensive Virtual Library of Minimal Eumelanin Oligomer Models , 2021, Angewandte Chemie.

[9]  K. Wakamatsu,et al.  Chemical and biochemical control of skin pigmentation with special emphasis on mixed melanogenesis , 2021, Pigment cell & melanoma research.

[10]  Nathan D. Schilaty,et al.  Spontaneous Formation of Melanin from Dopamine in the Presence of Iron , 2020, Antioxidants.

[11]  K. Wakamatsu,et al.  Nonenzymatic Spontaneous Oxidative Transformation of 5,6-Dihydroxyindole , 2020, International journal of molecular sciences.

[12]  K. Wakamatsu,et al.  Chemical Reactivities of ortho-Quinones Produced in Living Organisms: Fate of Quinonoid Products Formed by Tyrosinase and Phenoloxidase Action on Phenols and Catechols , 2020, International journal of molecular sciences.

[13]  K. Wakamatsu,et al.  Improved HPLC Conditions to Determine Eumelanin and Pheomelanin Contents in Biological Samples Using an Ion Pair Reagent , 2020, International journal of molecular sciences.

[14]  L. Bubacco,et al.  Copper Ions and Parkinson’s Disease: Why Is Homeostasis So Relevant? , 2020, Biomolecules.

[15]  K. Wakamatsu,et al.  Effects of Aging on Hair Color, Melanosome Morphology, and Melanin Composition in Japanese Females , 2019, International journal of molecular sciences.

[16]  D. Sulzer,et al.  Dopamine, Oxidative Stress and Protein-Quinone Modifications in Parkinson's and Other Neurodegenerative Diseases. , 2019, Angewandte Chemie.

[17]  K. Wakamatsu,et al.  The Oxidative Pathway to Dopamine–Protein Conjugates and Their Pro-Oxidant Activities: Implications for the Neurodegeneration of Parkinson’s Disease , 2019, International journal of molecular sciences.

[18]  T. Waite,et al.  Kinetic Modeling of pH-Dependent Oxidation of Dopamine by Iron and Its Relevance to Parkinson's Disease , 2018, Front. Neurosci..

[19]  B. Mannervik,et al.  Novel Alpha-Synuclein Oligomers Formed with the Aminochrome-Glutathione Conjugate Are Not Neurotoxic , 2018, Neurotoxicity Research.

[20]  P. Maddalena,et al.  The Chemistry of Polydopamine Film Formation: The Amine-Quinone Interplay , 2018, Biomimetics.

[21]  K. Wakamatsu,et al.  Insect cuticular melanins are distinctly different from those of mammalian epidermal melanins , 2018, Pigment cell & melanoma research.

[22]  K. Wakamatsu,et al.  Photodegradation of Eumelanin and Pheomelanin and Its Pathophysiological Implications , 2018, Photochemistry and photobiology.

[23]  P. Maddalena,et al.  Structural Basis of Polydopamine Film Formation: Probing 5,6-Dihydroxyindole-Based Eumelanin Type Units and the Porphyrin Issue. , 2017, ACS applied materials & interfaces.

[24]  Tadeusz Sarna,et al.  Interactions of iron, dopamine and neuromelanin pathways in brain aging and Parkinson's disease , 2017, Progress in Neurobiology.

[25]  A. Pawlak,et al.  Redox Active Transition Metal ions Make Melanin Susceptible to Chemical Degradation Induced by Organic Peroxide , 2017, Cell Biochemistry and Biophysics.

[26]  M. G. Bridelli,et al.  Synthesis, Structure Characterization, and Evaluation in Microglia Cultures of Neuromelanin Analogues Suitable for Modeling Parkinson's Disease. , 2017, ACS chemical neuroscience.

[27]  J. Segura-Aguilar,et al.  Are Dopamine Oxidation Metabolites Involved in the Loss of Dopaminergic Neurons in the Nigrostriatal System in Parkinson's Disease? , 2017, ACS chemical neuroscience.

[28]  I. Cacelli,et al.  Eumelanin broadband absorption develops from aggregation-modulated chromophore interactions under structural and redox control , 2017, Scientific Reports.

[29]  M. Sugumaran,et al.  Critical Analysis of the Melanogenic Pathway in Insects and Higher Animals , 2016, International journal of molecular sciences.

[30]  G. Monfrecola,et al.  “Fifty Shades” of Black and Red or How Carboxyl Groups Fine Tune Eumelanin and Pheomelanin Properties , 2016, International journal of molecular sciences.

[31]  Shosuke Ito,et al.  Norepinephrine and its metabolites are involved in the synthesis of neuromelanin derived from the locus coeruleus , 2015, Journal of neurochemistry.

[32]  K. Wakamatsu,et al.  Melanins and melanogenesis: from pigment cells to human health and technological applications , 2015, Pigment cell & melanoma research.

[33]  R. Kishida,et al.  Mechanism of dopachrome tautomerization into 5,6-dihydroxyindole-2-carboxylic acid catalyzed by Cu(II) based on quantum chemical calculations. , 2015, Biochimica et biophysica acta.

[34]  T. Waite,et al.  Cu(II)-catalyzed oxidation of dopamine in aqueous solutions: mechanism and kinetics. , 2014, Journal of inorganic biochemistry.

[35]  J. Segura-Aguilar,et al.  Protective and toxic roles of dopamine in Parkinson's disease , 2014, Journal of neurochemistry.

[36]  K. Wakamatsu,et al.  Neutral pH and copper ions promote eumelanogenesis after the dopachrome stage , 2013, Pigment cell & melanoma research.

[37]  M. Buehler,et al.  Comparison of synthetic dopamine-eumelanin formed in the presence of oxygen and Cu2+ cations as oxidants. , 2013, Langmuir : the ACS journal of surfaces and colloids.

[38]  K. Wakamatsu,et al.  Melanins and melanogenesis: methods, standards, protocols , 2013, Pigment cell & melanoma research.

[39]  K. Wakamatsu,et al.  High-performance liquid chromatography estimation of cross-linking of dihydroxyindole moiety in eumelanin. , 2013, Analytical biochemistry.

[40]  D. Sulzer,et al.  Neuromelanin of the Human Substantia Nigra: An Update , 2013, Neurotoxicity Research.

[41]  K. Wakamatsu,et al.  Biosynthetic pathway to neuromelanin and its aging process , 2012, Pigment cell & melanoma research.

[42]  R. Heenan,et al.  Eumelanin buildup on the nanoscale: aggregate growth/assembly and visible absorption development in biomimetic 5,6-dihydroxyindole polymerization. , 2012, Biomacromolecules.

[43]  L. Bubacco,et al.  Synthesis and structural characterization of soluble neuromelanin analogs provides important clues to its biosynthesis , 2012, JBIC Journal of Biological Inorganic Chemistry.

[44]  A. Napolitano,et al.  5,6‐Dihydroxyindole Chemistry: Unexplored Opportunities Beyond Eumelanin , 2011 .

[45]  G. Greco,et al.  A melanin-inspired pro-oxidant system for dopa(mine) polymerization: mimicking the natural casing process. , 2011, Chemical communications.

[46]  M. Brilliant,et al.  Usefulness of alkaline hydrogen peroxide oxidation to analyze eumelanin and pheomelanin in various tissue samples: application to chemical analysis of human hair melanins , 2011, Pigment cell & melanoma research.

[47]  D. Dickson,et al.  Iron and reactive oxygen species activity in parkinsonian substantia nigra. , 2010, Parkinsonism & related disorders.

[48]  D. Sulzer,et al.  Interplay between Cytosolic Dopamine, Calcium, and α-Synuclein Causes Selective Death of Substantia Nigra Neurons , 2009, Neuron.

[49]  P. Riederer,et al.  Neuromelanin and its interaction with iron as a potential risk factor for dopaminergic neurodegeneration underlying Parkinson's disease , 2009, Neurotoxicity Research.

[50]  P. Cloetens,et al.  Intracellular chemical imaging of the developmental phases of human neuromelanin using synchrotron X-ray microspectroscopy. , 2008, Analytical chemistry.

[51]  N. Turro,et al.  New melanic pigments in the human brain that accumulate in aging and block environmental toxic metals , 2008, Proceedings of the National Academy of Sciences.

[52]  Alberto Albertini,et al.  Neuromelanin can protect against iron‐mediated oxidative damage in system modeling iron overload of brain aging and Parkinson’s disease , 2008, Journal of neurochemistry.

[53]  M. Asanuma,et al.  Dopaminergic neuron-specific oxidative stress caused by dopamine itself. , 2008, Acta medica Okayama.

[54]  P. Riederer,et al.  Tyrosinase is not detected in human catecholaminergic neurons by immunohistochemistry and Western blot analysis. , 2007, Journal of neural transmission. Supplementum.

[55]  L. Bubacco,et al.  ANALYSIS OF THE INTERACTIONS WITH α-SYNUCLEIN * , 2007 .

[56]  V. Barone,et al.  Short-lived quinonoid species from 5,6-dihydroxyindole dimers en route to eumelanin polymers: integrated chemical, pulse radiolytic, and quantum mechanical investigation. , 2006, Journal of the American Chemical Society.

[57]  S. Ito.  Encapsulation of a reactive core in neuromelanin , 2006, Proceedings of the National Academy of Sciences.

[58]  G. Edwards,et al.  The surface oxidation potential of human neuromelanin reveals a spherical architecture with a pheomelanin core and a eumelanin surface , 2006, Proceedings of the National Academy of Sciences.

[59]  B. Powell,et al.  Chemical and structural disorder in eumelanins: a possible explanation for broadband absorbance. , 2005, Biophysical journal.

[60]  S. Shimohama,et al.  Iron accelerates the conversion of dopamine‐oxidized intermediates into melanin and provides protection in SH‐SY5Y cells , 2005, Journal of neuroscience research.

[61]  G. Reynolds,et al.  Increased iron (III) and total iron content in post mortem substantia nigra of parkinsonian brain , 2005, Journal of Neural Transmission.

[62]  Masayoshi Yamamoto,et al.  Regional distribution of manganese, iron, copper, and zinc in the rat brain during development , 2004, Analytical and bioanalytical chemistry.

[63]  Alberto Gatti,et al.  The role of iron and copper molecules in the neuronal vulnerability of locus coeruleus and substantia nigra during aging. , 2004, Proceedings of the National Academy of Sciences of the United States of America.

[64]  P. Riederer,et al.  Iron-binding characteristics of neuromelanin of the human substantia nigra. , 2003, Biochemical pharmacology.

[65]  K. Wakamatsu,et al.  The structure of neuromelanin as studied by chemical degradative methods , 2003, Journal of neurochemistry.

[66]  P. Farmer,et al.  Metal binding by melanins: studies of colloidal dihydroxyindole-melanin, and its complexation by Cu(II) and Zn(II) ions. , 2002, Journal of inorganic biochemistry.

[67]  Alberto Gatti,et al.  The absolute concentration of nigral neuromelanin, assayed by a new sensitive method, increases throughout the life and is dramatically decreased in Parkinson's disease , 2002, FEBS letters.

[68]  L. Greene,et al.  Neuromelanin biosynthesis is driven by excess cytosolic catecholamines not accumulated by synaptic vesicles. , 2000, Proceedings of the National Academy of Sciences of the United States of America.

[69]  A. Napolitano,et al.  New reaction pathways of dopamine under oxidative stress conditions: nonenzymatic iron-assisted conversion to norepinephrine and the neurotoxins 6-hydroxydopamine and 6, 7-dihydroxytetrahydroisoquinoline. , 1999, Chemical research in toxicology.

[70]  K. Wakamatsu,et al.  Chemical degradation of melanins: application to identification of dopamine-melanin. , 1998, Pigment cell research.

[71]  J. Cadet,et al.  Invited Review Free radicals and the pathobiology of brain dopamine systems , 1998, Neurochemistry International.

[72]  F Beermann,et al.  New evidence for presence of tyrosinase in substantia nigra, forebrain and midbrain. , 1998, Brain research. Molecular brain research.

[73]  K. Wakamatsu,et al.  Spectrophotometric characterization of eumelanin and pheomelanin in hair. , 1996, Pigment cell research.

[74]  P. Riederer,et al.  Injection of a minuscule dose of FeCl3 within the ventrolateral striatum causes a chronic disturbance of the integrative function within the limbic part of the ventral striatum , 1995, Journal of neural transmission. Parkinson's disease and dementia section.

[75]  K. Jellinger,et al.  Iron‐Melanin Complex in Substantia Nigra of Parkinsonian Brains: An X‐Ray Microanalysis , 1992, Journal of neurochemistry.

[76]  G. Prota,et al.  Melanins and melanogenesis , 1992 .

[77]  T. Sarna,et al.  Modulation by neuromelanin of the availability and reactivity of metal ions , 1992, Annals of neurology.

[78]  P. Riederer,et al.  Iron‐Melanin Interaction and Lipid Peroxidation: Implications for Parkinson's Disease , 1991, Journal of neurochemistry.

[79]  E. Rosengren,et al.  The neuromelanin of the human substantia nigra. , 1991, Biochimica et biophysica acta.

[80]  A. Carlsson,et al.  In Vivo Autoxidation of Dopamine in Guinea Pig Striatum Increases with Age , 1990, Journal of neurochemistry.

[81]  T. Sarna,et al.  Bleaching of melanin pigments. Role of copper ions and hydrogen peroxide in autooxidation and photooxidation of synthetic dopa-melanin. , 1990, The Journal of biological chemistry.

[82]  W. Korytowski.  Bleaching of melanin pigments , 1990 .

[83]  E. Land,et al.  A pulse radiolysis investigation of the oxidation of indolic melanin precursors: evidence for indolequinones and subsequent intermediates. , 1989, Biochimica et biophysica acta.

[84]  A. Graybiel,et al.  Melanized dopaminergic neurons are differentially susceptible to degeneration in Parkinson's disease , 1988, Nature.

[85]  M. d’Ischia,et al.  Effect of metal ions on the rearrangement of dopachrome. , 1987, Biochimica et biophysica acta.

[86]  R. Fariello,et al.  Neuromelanic pigment in substantia nigra neurons of rats and dogs , 1986, Neuroscience Letters.

[87]  A. Napolitano,et al.  A reinvestigation of the structure of melanochrome , 1985 .

[88]  J. Donaldson,et al.  Enhanced autoxidation of dopamine as a possible basis of manganese neurotoxicity. , 1981, Neurotoxicology.

[89]  D. Tse,et al.  Potential oxidative pathways of brain catecholamines. , 1976, Journal of medicinal chemistry.

[90]  A. Percival,et al.  Studies related to the chemistry of melanins. Part XIII. Studies on the structure of dopamine-melanin , 1970 .

[91]  Mishra Sn,et al.  Studies related to the chemistry of melanins. V. Investigations on the specific deuteriation of 5,6-dihydroxyindoline and 5,6-dihydroxy-indole. , 1967 .