5,6-Dihydroxyindoles and Indole-5,6-diones (Q62661368)

1

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Alessandra Napolitano

2

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Edward J. Land

4

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Christopher A. Ramsden

5

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Patrick A. Riley

Advances in Heterocyclic Chemistry

6

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publication date

2005

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published in

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page(s)

1-63

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cites work

The Tyrosinase-tyrosine Reaction: Production from Tyrosine of 5: 6-Dihydroxyindole and 5: 6-Dihydroxyindole-2-carboxylic Acid-the Precursors of Melanin

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7 January 2021

Adrenaline and adrenochrome

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7 January 2021

The structure of adrenochrome and its reduction products

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7 January 2021

Melanin and its precursors; the synthesis of 5:6:5':6'-tetrahydroxyindigo.

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7 January 2021

The Melanin Problem : a Synthesis of 5 : 6-Dihydroxyindole

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7 January 2021

The Melanin Problem : a Synthesis of 5 : 6-Dihydroxy-Indole and Its Derivatives

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7 January 2021

Synthesis of 5:6-Dihydroxyindole Derivatives: an Oxido-reduction Rearrangement Catalysed by Zinc Ions

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7 January 2021

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7 January 2021

Reduction of Adrenochrome with Ascorbic Acid

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7 January 2021

On the origin of the free radical property of melanins

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7 January 2021

The band structure of melanins

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7 January 2021

ELECTRON SPIN RESONANCE STUDIES ON MELANIN.

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7 January 2021

879. The mechanism of the reduction of adrenochrome by ascorbic acid

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7 January 2021

Electrochemical Studies of the Oxidation Pathways of Catecholamines

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7 January 2021

Tumor localizing agents. I. Synthesis and tissue distribution of 14-C-labeled and radioiodinated 5,6-diacetoxyindole

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7 January 2021

Histochemical Demonstration of Melanocytes by the Use of 5,6-Diacetoxyindole as Substrate for Tyrosinase

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7 January 2021

Catechol amine oxidation and ionization properties indicated from the hydrogen ion release, tritium exchange, and spectral changes which occur during ferricyanide oxidation

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7 January 2021

The synthesis of cyclodopa (Leukodopachrom)

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7 January 2021

Chemistry of the aminochromes. Part X. Some further observations on the reactions of aminochromes with thiols

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7 January 2021

[Color reaction of adrenaline with nitrous acid]

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7 January 2021

Chemistry of the Aminochromes. Part XIV. Noradrenochrome

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7 January 2021

Chemistry of Aminochromes. Part XV. The Reaction of Epinochrome with Thiols

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7 January 2021

The Chemistry of the Aminochromes. Part XVI. Proton Magnetic Resonance Spectroscopy

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7 January 2021

Chemistry of the aminochromes. Part XVII. Formation of addition products with bisulphite and thiols

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7 January 2021

The pigments of reddish hair and feathers.

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https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Isolation of oligomers of 5,6-dihydroxyindole-2-carboxylic acid from the eye of the catfish

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https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Melanin. I. Kinetics of the oxidative cyclization of dopa to dopachrome

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https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Oxidative and cardiovascular studies on natural and synthetic catecholamines

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https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Recent advances in the chemistry of melanogenesis in mammals

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https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

New regulators of melanin biosynthesis and the autodestruction of melanoma cells

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https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Synthesis of hydrazone derivatives of 3a,4-dihydroadrenochrome-3a-sulfides and determination of their hemostatic activities

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Radioassay for oxidation of tyrosine by tyrosinase using L-[Ring-3H]tyrosine and L-[carboxyl-14C]tyrosine

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Catechol O-methyltransferase. 12. Affinity labeling the active site with the oxidation products of 5,6-dihydroxyindole

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https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Chemical intermediates in dopamine oxidation by tyrosinase, and kinetic studies of the process.

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Cyclodopa glucoside ( = (2S)-5-(?-D-glocopyranosyloxy)-6-hydroxyindoline-2-carboxylic acid) and its occurrence in red beet (beta vulgaris var.rubra L.)

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

A pulse radiolysis investigation of the oxidation of the melanin precursors 3,4-dihydroxyphenylalanine (dopa) and the cysteinyldopas

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Semiquinone anion radicals of catechol(amine)s, catechol estrogens, and their metal ion complexes

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Molecular mechanism of action of 5,6-dihydroxytryptamine. Synthesis and biological evaluation of 4-methyl-, 7-methyl-, and 4,7-dimethyl-5,6-dihydroxytryptamines

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Radicals and melanomas

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https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Effect of metal ions on the rearrangement of dopachrome

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https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Relationship between melanin content and superoxide dismutase (SOD) activity in the liver of various species of animals

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Photochemistry and photobiology of melanogenic metabolites: formation of free radicals

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https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Biomimetic Synthesis of 5,6-Dihydroxyindole-2-Carboxylic Acid and of its Benzyl Ester

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7 January 2021

Preparation of eumelanin-related metabolites 5,6-dihydroxyindole, 5,6-dihydroxyindole-2-carboxylic acid, and their O-methyl derivatives

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Adrenalin oxidation revisited. New products beyond the adrenochrome stage

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

A pulse radiolysis investigation of the oxidation of indolic melanin precursors: evidence for indolequinones and subsequent intermediates

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

A new look at the rearrangement of adrenochrome under biomimetic conditions

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Stereochemical studies on the formation of melanin by monophenol monooxygenase

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Selective uptake of 2-thiouracil into melanin-producing systems depends on chemical binding to enzymically generated dopaquinone

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

A pulse radiolysis investigation of the oxidation of methoxylated metabolites of indolic melanin precursors

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Dopachrome conversion factor functions as an isomerase

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Further insights into the oxidation chemistry and biochemistry of the serotonergic neurotoxin 5,6-dihydroxytryptamine

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Peroxidase as an alternative to tyrosinase in the oxidative polymerization of 5,6-dihydroxyindoles to melanin(s)

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Specificity of dopachrome tautomerase and inhibition by carboxylated indoles. Considerations on the enzyme active site.

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Evidence that dopachrome tautomerase is a ferrous iron-binding glycoprotein

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

(-)-Cryptaustoline: its synthesis, revision of absolute stereochemistry, and mechanism of inversion of stereochemistry

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Inhibitory effect of melanin precursors on arachidonic acid peroxidation

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Dopachrome tautomerase decreases the binding of indolic melanogenesis intermediates to proteins

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

A new dopachrome-rearranging enzyme from the ejected ink of the cuttlefish Sepia officinalis

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Effects of L-cysteine on the oxidation chemistry of dopamine: new reaction pathways of potential relevance to idiopathic Parkinson's disease

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

X-ray characterization of melanins--II.

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Generation of the Neurotoxin 6-Hydroxydopamine by Peroxidase/H2O2 Oxidation of Dopamine

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Dual role of melanins and melanin precursors as photoprotective and phototoxic agents: inhibition of ultraviolet radiation-induced lipid peroxidation

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Mechanism of selective incorporation of the melanoma seeker 2-thiouracil into growing melanin

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Oxidative polymerisation of 5,6-dihydroxyindole-2-carboxylic acid to melanin: A new insight

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

The first characterisation of a transient 5,6-indolequinone

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Diffusible melanin-related metabolites are potent inhibitors of lipid peroxidation

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Glutathione transferases catalyse the detoxication of oxidized metabolites (o-quinones) of catecholamines and may serve as an antioxidant system preventing degenerative cellular processes

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Human class Mu glutathione transferases, in particular isoenzyme M2-2, catalyze detoxication of the dopamine metabolite aminochrome

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Evidence of the indirect formation of the catecholic intermediate substrate responsible for the autoactivation kinetics of tyrosinase.

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

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

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Selective incorporation of the prototype melanoma seeker thiourea into nascent melanin: a chemical insight

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

The protein catalysing the conversion of D-dopachrome to 5,6-dihydroxyindole is a phenylpyruvate tautomerase (EC 5.3.2.1)

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

An integrated approach to the structure of Sepia melanin. Evidence for a high proportion of degraded 5,6-dihydroxyindole-2-carboxylic acid units in the pigment backbone

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Nitric oxide-induced oxidation of 5,6-dihydroxyindole and 5,6-dihydroxyindole-2-carboxylic acid under aerobic conditions: non-enzymatic route to melanin pigments of potential relevance to skin (photo)protection

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Acid-Promoted Competing Pathways in the Oxidative Polymerization of 5,6-Dihydroxyindoles and Related Compounds: Straightforward Cyclotrimerization Routes to Diindolocarbazole Derivatives

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Betanidin formation from dihydroxyphenylalanine in a model assay system

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

5,6-Dihydroxyindoles in the fenton reaction: a model study of the role of melanin precursors in oxidative stress and hyperpigmentary processes

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Catalytic turnover of benzylamine by a model for the lysine tyrosylquinone (LTQ) cofactor of lysyl oxidase

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Pulse radiolysis studies of ortho-quinone chemistry relevant to melanogenesis

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Electrospray tandem mass spectrometry of aminochromes

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

The possible role of one-electron reduction of aminochrome in the neurodegenerative process of the dopaminergic system.

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Enhanced study and control of analyte oxidation in electrospray using a thin-channel, planar electrode emitter

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Identification of Drosophila melanogaster yellow-f and yellow-f2 proteins as dopachrome-conversion enzymes

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Unusual sulfamate indoles and a novel indolo[3,2-a]carbazole from Ancorina sp.

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Atropoisomeric melanin intermediates by oxidation of the melanogenic precursor 5,6-dihydroxyindole-2-carboxylic acid under biomimetic conditions

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Tyrosinase autoactivation and the chemistry of ortho-quinone amines

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Effect of aluminum (III) on the conversion of dopachrome in the melanin synthesis pathway

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Aluminum ions accelerated the oxidative stress of copper-mediated melanin formation

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Formation of para-quinomethanes via 4-aminobutylcatechol oxidation and ortho-quinone tautomerism

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Mechanistic studies of catechol generation from secondary quinone amines relevant to indole formation and tyrosinase activation

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Rate constants for the first two chemical steps of eumelanogenesis

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Synthesis of optically active tetrameric melanin intermediates by oxidation of the melanogenic precursor 5,6-dihydroxyindole-2-carboxylic acid under biomimetic conditions

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

A first-principles density-functional calculation of the electronic and vibrational structure of the key melanin monomers

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Quinone chemistry and melanogenesis

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Design and synthesis of novel dihydroxyindole-2-carboxylic acids as HIV-1 integrase inhibitors

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

On the neurotoxicity mechanism of leukoaminochrome o-semiquinone radical derived from dopamine oxidation: mitochondria damage, necrosis, and hydroxyl radical formation

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

Melanin pigmentation in mammals

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021

5,5',6,6'-Tetrahydroxy-3,3'-biindolyl from beetroot (Beta vulgaris) peel extract

1 reference

https://api.crossref.org/works/10.1016%2FS0065-2725%2805%2989001-4

7 January 2021