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dopamine lutine

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CAS Number: 3131-52-0Picture of molecule3D/inchi
Nikkaji Web:J434.158I
XlogP3-AA:1.30 (est)
Molecular Weight:149.14919000
Formula:C8 H7 N O2
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:hair dyeing agents
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 411.20 °C. @ 760.00 mm Hg (est)
Flash Point: 397.00 °F. TCC ( 202.50 °C. ) (est)
logP (o/w): 0.370 (est)
Soluble in:
 water, 3.382e+004 mg/L @ 25 °C (est)
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: hair dyeing agents
BOC Sciences
For experimental / research use only.
5,6-Dihydroxyindole ≥97%
Santa Cruz Biotechnology
For experimental / research use only.
5,6-Dihydroxyindole ≥97%
Sigma-Aldrich: Aldrich
For experimental / research use only.
Safety Information:
Preferred SDS: View
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
Safety in Use Information:
hair dyeing agents
Recommendation for 5,6-dihydroxyindole usage levels up to:
 not for fragrance use.
Recommendation for 5,6-dihydroxyindole flavor usage levels up to:
 not for flavor use.
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :114683
National Institute of Allergy and Infectious Diseases:Data
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):114683
Pubchem (sid):135069683
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
KEGG (GenomeNet):C05578
HMDB (The Human Metabolome Database):HMDB04058
Potential Blenders and core components note
None Found
Potential Uses:
None Found
Occurrence (nature, food, other):note
 not found in nature
 dopamine lutine


PubMed:Preparation of melanin from Catharsius molossus L. and preliminary study on its chemical structure.
PubMed:Insights into the aggregation/deposition and structure of a polydopamine film.
PubMed:Artificial biomelanin: highly light-absorbing nano-sized eumelanin by biomimetic synthesis in chicken egg white.
PubMed:Superior photoprotective motifs and mechanisms in eumelanins uncovered.
PubMed:Melanization reaction products of shrimp display antimicrobial properties against their major bacterial and fungal pathogens.
PubMed:Effects of the melanin precursor 5,6-dihydroxy-indole-2-carboxylic acid (DHICA) on DNA damage and repair in the presence of reactive oxygen species.
PubMed:Effect of pH on elementary steps of dopachrome conversion from first-principles calculation.
PubMed:Characterization of carbonized polydopamine nanoparticles suggests ordered supramolecular structure of polydopamine.
PubMed:Degree of polymerization of 5,6-dihydroxyindole-derived eumelanin from chemical degradation study.
PubMed:Tuning heterogeneous poly(dopamine) structures and mechanics: in silico covalent cross-linking and thin film nanoindentation.
PubMed:Towards eumelanin@zeolite hybrids: pore-size-controlled 5,6-dihydroxyindole polymerization.
PubMed:Comparison of synthetic dopamine-eumelanin formed in the presence of oxygen and Cu2+ cations as oxidants.
PubMed:Free radical coupling of o-semiquinones uncovered.
PubMed:Neutral pH and copper ions promote eumelanogenesis after the dopachrome stage.
PubMed:Self-assembly of tetramers of 5,6-dihydroxyindole explains the primary physical properties of eumelanin: experiment, simulation, and design.
PubMed:High-performance liquid chromatography estimation of cross-linking of dihydroxyindole moiety in eumelanin.
PubMed:Bottom-up approach to eumelanin photoprotection: emission dynamics in parallel sets of water-soluble 5,6-dihydroxyindole-based model systems.
PubMed:Intermolecular π-electron perturbations generate extrinsic visible contributions to eumelanin black chromophore in model polymers with interrupted interring conjugation.
PubMed:Synthesis and Agonistic Activity at the GPR35 of 5,6-Dihydroxyindole-2-carboxylic Acid Analogues.
PubMed:Eumelanin buildup on the nanoscale: aggregate growth/assembly and visible absorption development in biomimetic 5,6-dihydroxyindole polymerization.
PubMed:Multiple tyrosine metabolites are GPR35 agonists.
PubMed:The eumelanin intermediate 5,6-dihydroxyindole-2-carboxylic acid is a messenger in the cross-talk among epidermal cells.
PubMed:Exploring the frontiers of synthetic eumelanin polymers by high-resolution matrix-assisted laser/desorption ionization mass spectrometry.
PubMed:Metabolomic profiling reveals that Drosophila melanogaster larvae with the y mutation have altered lysine metabolism.
PubMed:Age-dependent changes in eumelanin composition in hairs of various ethnic origins.
PubMed:UV-absorption spectra of melanosomes containing varying 5,6-dihydroxyindole and 5,6-dihydroxyindole-2-carboxylic acid content.
PubMed:New pathways of betanidin and betanin enzymatic oxidation.
PubMed:Inactivation of tautomerase activity of macrophage migration inhibitory factor by sulforaphane: a potential biomarker for anti-inflammatory intervention.
PubMed:Antiviral, anti-parasitic, and cytotoxic effects of 5,6-dihydroxyindole (DHI), a reactive compound generated by phenoloxidase during insect immune response.
PubMed:π-Electron manipulation of the 5,6-dihydroxyindole/quinone system by 3-alkynylation: mild acid-mediated entry to (cross)-conjugated scaffolds and paradigms for medium-tunable chromophores.
PubMed:Usefulness of alkaline hydrogen peroxide oxidation to analyze eumelanin and pheomelanin in various tissue samples: application to chemical analysis of human hair melanins.
PubMed:Maintenance of immune hyporesponsiveness to melanosomal proteins by DHICA-mediated antioxidation: Possible implications for autoimmune vitiligo.
PubMed:First synthetic entry to the trimer stage of 5,6-dihydroxyindole polymerization: ortho-alkynylaniline-based access to the missing 2,7':2',7''-triindole.
PubMed:Cyclic structural motifs in 5,6-dihydroxyindole polymerization uncovered: biomimetic modular buildup of a unique five-membered macrocycle.
PubMed:UV-dissipation mechanisms in the eumelanin building block DHICA.
PubMed:5,6-Dihydroxyindole oxidation in phosphate buffer/polyvinyl alcohol: a new model system for studies of visible chromophore development in synthetic eumelanin polymers.
PubMed:Regulation of DHICA-mediated antioxidation by dopachrome tautomerase: implication for skin photoprotection against UVA radiation.
PubMed:Direct measurement of the ultraviolet absorption coefficient of single retinal melanosomes.
PubMed:Disentangling eumelanin "black chromophore": visible absorption changes as signatures of oxidation state- and aggregation-dependent dynamic interactions in a model water-soluble 5,6-dihydroxyindole polymer.
PubMed:Ultrafast excited state dynamics of 5,6-dihydroxyindole, a key eumelanin building block: nonradiative decay mechanism.
PubMed:Efficient synthesis of 5,6-dihydroxyindole dimers, key eumelanin building blocks, by a unified o-ethynylaniline-based strategy for the construction of 2-linked biindolyl scaffolds.
PubMed:Lack of visible chromophore development in the pulse radiolysis oxidation of 5,6-dihydroxyindole-2-carboxylic acid oligomers: DFT investigation and implications for eumelanin absorption properties.
PubMed:Dopamine and the dopamine oxidation product 5,6-dihydroxylindole promote distinct on-pathway and off-pathway aggregation of alpha-synuclein in a pH-dependent manner.
PubMed:Structural, electrical, electronic and optical properties of melanin films.
PubMed:Role of solvent, pH, and molecular size in excited-state deactivation of key eumelanin building blocks: implications for melanin pigment photostability.
PubMed:Possible oxidative polymerization mechanism of 5,6-dihydroxyindole from ab initio calculations.
PubMed:Skin-lightening products revisited.
PubMed:Structural effects on the electronic absorption properties of 5,6-dihydroxyindole oligomers: the potential of an integrated experimental and DFT approach to model eumelanin optical properties.
PubMed:Chemistry of mixed melanogenesis--pivotal roles of dopaquinone.
PubMed:Ultra-low temperature oxidation of 5,6-dihydroxyindole: a novel approach to study synthetic melanogenesis.
PubMed:Synthesis and polymerization studies of organic-soluble eumelanins.
PubMed:Solvochromic effects in model eumelanin compounds.
PubMed:Effect of dimerization on vibrational spectra of eumelanin precursors.
PubMed:Melanin precursor 5,6-dihydroxyindol: protective effects and cytotoxicity on retinal cells in vitro and in vivo.
PubMed:Hyperbranched molecular structures with potential antiviral activity: derivatives of 5,6-dihydroxyindole-2-carboxylic Acid.
PubMed:5,6-dihydroxyindole tetramers with "anomalous" interunit bonding patterns by oxidative coupling of 5,5',6,6'-tetrahydroxy-2,7'-biindolyl: emerging complexities on the way toward an improved model of eumelanin buildup.
PubMed:Transition dipole strength of eumelanin.
PubMed:Oxidation chemistry of norepinephrine: partitioning of the O-quinone between competing cyclization and chain breakdown pathways and their roles in melanin formation.
PubMed:Parasite suppression of the oxidations of eumelanin precursors in Drosophila melanogaster.
PubMed:Broad-spectrum antimicrobial activity of the reactive compounds generated in vitro by Manduca sexta phenoloxidase.
PubMed:The melanogenic system of the liver pigmented macrophages of Rana esculenta L.--tyrosinase activity.
PubMed:Changes of melanosome morphology associated with the differentiation of epidermal melanocytes in slaty mice.
PubMed:Kinetic and structural analysis of the early oxidation products of dopamine: analysis of the interactions with alpha-synuclein.
PubMed:Evaluation of efficacy and safety of rucinol serum in patients with melasma: a randomized controlled trial.
PubMed:The first 5,6-dihydroxyindole tetramer by oxidation of 5,5',6,6'-tetrahydroxy- 2,4'-biindolyl and an unexpected issue of positional reactivity en route to eumelanin-related polymers.
PubMed:Photophysics of eumelanin: ab initio studies on the electronic spectroscopy and photochemistry of 5,6-dihydroxyindole.
PubMed:Short-lived quinonoid species from 5,6-dihydroxyindole dimers en route to eumelanin polymers: integrated chemical, pulse radiolytic, and quantum mechanical investigation.
PubMed:Dopaquinone redox exchange with dihydroxyindole and dihydroxyindole carboxylic acid.
PubMed:Synthesis, discovery and mechanism of 2,6-dimethoxy-N-(4-methoxyphenyl)benzamide as potent depigmenting agent in the skin.
PubMed:Quantitative fluorescence excitation spectra of synthetic eumelanin.
PubMed:Fe(III)-coordination properties of neuromelanin components: 5,6-dihydroxyindole and 5,6-dihydroxyindole-2-carboxylic acid.
PubMed:Role of dopachrome conversion enzyme in the melanization of filarial worms in mosquitoes.
PubMed:An oxygen transporter hemocyanin can act on the late pathway of melanin synthesis.
PubMed:[UV-Vis spectroscopic study of aluminum-manganese cooperative effect on the melanin formation from DOPA oxidation].
PubMed:[UV-vis spectroscopic study of the effect of Cu(II) ions on dopachrome].
PubMed:Comparisons of the structural and chemical properties of melanosomes isolated from retinal pigment epithelium, iris and choroid of newborn and mature bovine eyes.
PubMed:Metal-ion interactions and the structural organization of Sepia eumelanin.
PubMed:Comparison of structural and chemical properties of black and red human hair melanosomes.
PubMed:Design and synthesis of novel dihydroxyindole-2-carboxylic acids as HIV-1 integrase inhibitors.
PubMed:Aluminum facilitation of the iron-mediated oxidation of DOPA to melanin.
PubMed:Involvement of photooxidation of melanogenic precursors in prolonged pigmentation induced by ultraviolet A.
PubMed:Benzylamide derivative compound attenuates the ultraviolet B-induced hyperpigmentation in the brownish guinea pig skin.
PubMed:Changes in the proliferation and differentiation of neonatal mouse pink-eyed dilution melanocytes in the presence of excess tyrosine.
PubMed:Aluminum ions accelerated the oxidative stress of copper-mediated melanin formation.
PubMed:Melanogenesis in the ink gland of Sepia officinalis.
PubMed:Neurotoxicity due to o-quinones: neuromelanin formation and possible mechanisms for o-quinone detoxification.
PubMed:Melanin as a target for melanoma chemotherapy: pro-oxidant effect of oxygen and metals on melanoma viability.
PubMed:The IFPCS presidential lecture: a chemist's view of melanogenesis.
PubMed:Effect of aluminum (III) on the conversion of dopachrome in the melanin synthesis pathway.
PubMed:Cocaine, benzoylecgonine, amphetamine, and N-acetylamphetamine binding to melanin subtypes.
PubMed:Identification of Drosophila melanogaster yellow-f and yellow-f2 proteins as dopachrome-conversion enzymes.
PubMed:Stimulation of the proliferation and differentiation of mouse pink-eyed dilution epidermal melanocytes by excess tyrosine in serum-free primary culture.
PubMed:Redox behavior of melanins: direct electrochemistry of dihydroxyindole-melanin and its Cu and Zn adducts.
PubMed:Comparative biochemistry of eumelanogenesis and the protective roles of phenoloxidase and melanin in insects.
PubMed:Acid-Promoted Competing Pathways in the Oxidative Polymerization of 5,6-Dihydroxyindoles and Related Compounds: Straightforward Cyclotrimerization Routes to Diindolocarbazole Derivatives.
PubMed:Variation in melanin content and composition in type V and VI photoexposed and photoprotected human skin: the dominant role of DHI.
PubMed:Cloning and characterization of a dopachrome conversion enzyme from the yellow fever mosquito, Aedes aegypti.
PubMed:Melanogenesis by tyrosinase action on 3,4-dihydroxyphenylalanine (DOPA) in the presence of polyethylene glycol: a matrix-assisted laser desorption/ionization mass spectrometric investigation.
PubMed:Interaction of major coat color gene functions in mice as studied by chemical analysis of eumelanin and pheomelanin.
PubMed:Relationship of melanin degradation products to actual melanin content: application to human hair.
PubMed:The 5,6-dihydroxyindole-2-carboxylic acid (DHICA) oxidase activity of human tyrosinase.
PubMed:TYRP2-mediated resistance to cis-diamminedichloroplatinum (II) in human melanoma cells is independent of tyrosinase and TYRP1 expression and melanin content.
PubMed:Macrophage migration inhibitory factor (MIF): its essential role in the immune system and cell growth.
PubMed:Effects of ultraviolet irradiation on melanogenesis from tyrosine, Dopa and dopamine: a matrix-assisted laser desorption/ionization mass spectrometric study.
PubMed:Tyrosinase-induced cross-linking of tyrosine-containing peptides investigated by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry.
PubMed:Isolation and characterization of mammalian eumelanins from hair and irides.
PubMed:Absolute rate constants for the quenching of reactive excited states by melanin and related 5,6-dihydroxyindole metabolites: implications for their antioxidant activity.
PubMed:Macrophage migration inhibitory factor (MIF)--its role in catecholamine metabolism.
PubMed:Cross-polarization/magic-angle-spinning nuclear magnetic resonance in selectively 13C-labeled synthetic eumelanins.
PubMed:A method for detecting dopaminechrome isomerase activity on gels.
PubMed:5,6-Dihydroxyindoles in the fenton reaction: a model study of the role of melanin precursors in oxidative stress and hyperpigmentary processes.
PubMed:Enzymatically inactive macrophage migration inhibitory factor inhibits monocyte chemotaxis and random migration.
PubMed:Application of matrix-assisted laser desorption/ionization mass spectrometry to the detection of melanins formed from Dopa and dopamine.
PubMed:The soluble eumelanin precursor 5,6-dihydroxyindole-2-carboxylic acid enhances oxidative damage in human keratinocyte DNA after UVA irradiation.
PubMed:The depigmenting effect of alpha-tocopheryl ferulate on human melanoma cells.
PubMed:Insect melanogenesis. II. Inability of Manduca phenoloxidase to act on 5,6-dihydroxyindole-2-carboxylic acid.
PubMed:Lipoxygenase/H2O2-catalyzed oxidation of dihdroxyindoles: synthesis of melanin pigments and study of their antioxidant properties.
PubMed:Cloning of the mouse gene for D-dopachrome tautomerase.
PubMed:Tyrosinase stabilization by Tyrp1 (the brown locus protein).
PubMed:Cooperation of dopachrome conversion factor with phenoloxidase in the eumelanin pathway in haemolymph of Locusta migratoria (Insecta).
PubMed: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.
PubMed:Role of neurofibromin in modulation of expression of the tyrosinase-related protein 2 gene.
PubMed:Human tyrosinase related protein-1 (TRP-1) does not function as a DHICA oxidase activity in contrast to murine TRP-1.
PubMed:Lactoperoxidase-catalyzed oxidation of melanin by reactive nitrogen species derived from nitrite (NO2-): an EPR study.
PubMed:Chemical degradation of melanins: application to identification of dopamine-melanin.
PubMed:Production of melanins by ceruloplasmin.
PubMed:Molecular cloning of human D-dopachrome tautomerase cDNA: N-terminal proline is essential for enzyme activation.
PubMed:The protein catalysing the conversion of D-dopachrome to 5,6-dihydroxyindole is a phenylpyruvate tautomerase (EC
PubMed:Selective incorporation of the prototype melanoma seeker thiourea into nascent melanin: a chemical insight.
PubMed:Substrate specificity for isomerase activity of macrophage migration inhibitory factor and its inhibition by indole derivatives.
PubMed:Crystallization and preliminary X-ray analysis of human D-dopachrome tautomerase.
PubMed:NMR characterization of physicochemical properties of rat D-dopachrome tautomerase.
PubMed:Diffusible melanin-related metabolites are potent inhibitors of lipid peroxidation.
PubMed:Chemical characterization of eumelanins with special emphasis on 5,6-dihydroxyindole-2-carboxylic acid content and molecular size.
PubMed:Molecular approach to the nucleo-melanosomal interaction in human melanoma cells.
PubMed:Mechanism of selective incorporation of the melanoma seeker 2-thiouracil into growing melanin.
PubMed:Mouse fibroblast expressing human tyrosinase with DHICA-oxidase activity produces predominantly pheomelanin deposit in lysosome.
PubMed:Negative ion electrospray mass spectrometry of polyphenols, catecholamines and their oxidation products.
PubMed:Hydrogen peroxide generation associated with the oxidations of the eumelanin precursors 5,6-dihydroxyindole and 5,6-dihydroxyindole-2-carboxylic acid.
PubMed:Composition of mammalian eumelanins: analyses of DHICA-derived units in pigments from hair and melanoma cells.
PubMed:Chemical characterization of melanins in sheep wool and human hair.
PubMed:Polymerization of 5,6-dihydroxyindole-2-carboxylic acid to melanin by the pmel 17/silver locus protein.
PubMed:Molecular mechanism for catalysis by a new zinc-enzyme, dopachrome tautomerase.
PubMed:The immunoregulatory mediator macrophage migration inhibitory factor (MIF) catalyzes a tautomerization reaction.
PubMed:5,6-Dihydroxyindole-2-carboxylic acid, a diffusible melanin precursor, is a potent stimulator of lipopolysaccharide-induced production of nitric oxide by J774 macrophages.
PubMed:Cloning and sequencing of a cDNA encoding rat D-dopachrome tautomerase.
PubMed:Chemical characterization of hair melanins in various coat-color mutants of mice.
PubMed:Modulation of melanogenic protein expression during the switch from eu- to pheomelanogenesis.
PubMed:Dual role of melanins and melanin precursors as photoprotective and phototoxic agents: inhibition of ultraviolet radiation-induced lipid peroxidation.
PubMed:The expression of tyrosinase, tyrosinase-related proteins 1 and 2 (TRP1 and TRP2), the silver protein, and a melanogenic inhibitor in human melanoma cells of differing melanogenic activities.
PubMed:Some aspects of melanin formation of melanocytes cultured on collagen-coated microcarrier beads.
PubMed:Generation of the neurotoxin 6-hydroxydopamine by peroxidase/H2O2 oxidation of dopamine.
PubMed:Tyrosinase related protein 1 (TRP1) functions as a DHICA oxidase in melanin biosynthesis.
PubMed:Egg chorion tanning in Aedes aegypti mosquito.
PubMed:Dopachrome conversion activity in Aedes aegypti: significance during melanotic encapsulation of parasites and cuticular tanning.
PubMed:One-electron oxidation of C(2) and C(3) methyl substituted 5,6-dihydroxyindoles: model pathways of melanogenesis.
PubMed:Dopachrome tautomerase is a zinc-containing enzyme.
PubMed:The mouse brown (b) locus protein functions as a dopachrome tautomerase.
PubMed:Specific incorporation of 2-thiouracil into biological melanins.
PubMed:Characterization of peroxidative oxidation products of dopamine by mass spectrometry.
PubMed:DHICA oxidase activity of TRP1 and interactions with other melanogenic enzymes.
PubMed:A new enzymatic function in the melanogenic pathway. The 5,6-dihydroxyindole-2-carboxylic acid oxidase activity of tyrosinase-related protein-1 (TRP1).
PubMed:Detection of dopachrome isomerase activity on gels.
PubMed:A new dopachrome-rearranging enzyme from the ejected ink of the cuttlefish Sepia officinalis.
PubMed:The inherent cytotoxicity of melanin precursors: a revision.
PubMed:Evaluation of melanin-related metabolites as markers of melanoma progression.
PubMed:Dopachrome tautomerase decreases the binding of indolic melanogenesis intermediates to proteins.
PubMed:A 13C solid-state NMR study of the structure and auto-oxidation process of natural and synthetic melanins.
PubMed:Isolation of a new tautomerase monitored by the conversion of D-dopachrome to 5,6-dihydroxyindole.
PubMed:Spectrophotometric assay of eumelanin in tissue samples.
PubMed:The mouse brown (b) locus protein has dopachrome tautomerase activity and is located in lysosomes in transfected fibroblasts.
PubMed:Regulatory factors for polymerization of melanin monomers within coated vesicles and premelanosomes in melanoma cells.
PubMed:Inhibitory effect of melanin precursors on arachidonic acid peroxidation.
PubMed:Metabolism of 3-indolylacetic acid during percutaneous absorption in human skin.
PubMed:Exploitation of pigment biosynthesis pathway as a selective chemotherapeutic approach for malignant melanoma.
PubMed:Differences in subcellular distribution of catechol-O-methyltransferase and tyrosinase in malignant melanoma.
PubMed:Dynamics of melanogenesis intermediates.
PubMed:Preparation of monoclonal mouse antibodies against two specific eu-melanin related compounds.
PubMed:Mutational mapping of the catalytic activities of human tyrosinase.
PubMed:Functional properties of cloned melanogenic proteins.
PubMed:5,6-Dihydroxyindole-2-carboxylic acid is incorporated in mammalian melanin.
PubMed:Synthesis and characterization of melanins from dihydroxyindole-2-carboxylic acid and dihydroxyindole.
PubMed:Regulation of the final phase of mammalian melanogenesis. The role of dopachrome tautomerase and the ratio between 5,6-dihydroxyindole-2-carboxylic acid and 5,6-dihydroxyindole.
PubMed:Evidence that dopachrome tautomerase is a ferrous iron-binding glycoprotein.
PubMed:Measurement of eumelanin precursor metabolites in the urine as a new marker for melanoma metastases.
PubMed:Reduced cellular immune competence of a temperature-sensitive dopa decarboxylase mutant strain of Drosophila melanogaster against the parasite Leptopilina boulardi.
PubMed:A second tyrosinase-related protein, TRP-2, is a melanogenic enzyme termed DOPAchrome tautomerase.
PubMed:Identification of 3,4-dihydroxyphenylalanine, 5,6-dihydroxyindole, and N-acetylarterenone during eumelanin formation in immune reactive larvae of Drosophila melanogaster.
PubMed:The role of peroxidase in melanogenesis revisited.
PubMed:Comparative action of dopachrome tautomerase and metal ions on the rearrangement of dopachrome.
PubMed:Electrochemical identification of dopachrome isomerase in Drosophila melanogaster.
PubMed:Specificity of dopachrome tautomerase and inhibition by carboxylated indoles. Considerations on the enzyme active site.
PubMed:Quinone methide as a new intermediate in eumelanin biosynthesis.
PubMed:Peroxidase as an alternative to tyrosinase in the oxidative polymerization of 5,6-dihydroxyindoles to melanin(s).
PubMed:After dopachrome?
PubMed:Determination of catechol O-methyltransferase activity in relation to melanin metabolism using high-performance liquid chromatography with fluorimetric detection.
PubMed:A pulse radiolysis investigation of the oxidation of methoxylated metabolites of indolic melanin precursors.
PubMed:Regulation of mammalian melanogenesis. I: Partial purification and characterization of a dopachrome converting factor: dopachrome tautomerase.
PubMed:A new spectrophotometric assay for dopachrome tautomerase.
PubMed:Mutagenicity test for unstable compounds, such as 5,6-dihydroxyindole, using an Escherichia coli HB101/pBR322 transfection system.
PubMed:A pulse radiolysis investigation of the oxidation of indolic melanin precursors: evidence for indolequinones and subsequent intermediates.
PubMed:Correlation between urinary melanin-related metabolites and tumour weight in melanoma-bearing mice.
PubMed:Liposome-entrapped tyrosinase: a tool to investigate the regulation of the Raper-Mason pathway.
PubMed:Function of dopachrome oxidoreductase and metal ions in dopachrome conversion in the eumelanin pathway.
PubMed:Melanin monomers within coated vesicles and premelanosomes in melanin synthesizing cells.
PubMed:Preparation of eumelanin-related metabolites 5,6-dihydroxyindole, 5,6-dihydroxyindole-2-carboxylic acid, and their O-methyl derivatives.
PubMed:Melanogenesis in Cryptococcus neoformans.
PubMed:Structural modifications in biosynthetic melanins induced by metal ions.
PubMed:Some indolic compounds as markers of the melanocyte activity.
PubMed:Activation of tyrosinase in mouse melanoma cell cultures.
PubMed:Effect of metal ions on the rearrangement of dopachrome.
PubMed:Photogeneration of free radicals from eumelanogenic intermediates and metabolites.
PubMed:Restriction patterns of model DNA treated with 5,6-dihydroxyindole, a potent cytotoxic intermediate of melanin synthesis: effect of u.v. irradiation.
PubMed:Reexamination of the structure of eumelanin.
PubMed:Eumelanin-related indolic compounds in the urine of treated melanoma patients.
PubMed:Synthesis in vitro of 5,6-dihydroxyindole-2-carboxylic acid by dopachrome conversion factor from Cloudman S91 melanoma cells.
PubMed:5,6-Dihydroxyindole oxidation by mammalian, mushroom and amphibian tyrosinase preparations.
PubMed:A spectrophotometric assay for mammalian tyrosinase utilizing the formation of melanochrome from L-dopa.
PubMed:Decreased dopachrome oxidoreductase activity in yellow mice.
PubMed:Dopachrome oxidoreductase: a new enzyme in the pigment pathway.
PubMed:A new possible pathogenesis of some gallstones.
PubMed:Identification of 5-hydroxy-6-indolyl-O-sulfate in urine of patients with malignant melanoma.
PubMed:Tyrosinase-like activity in normal human substantia nigra.
PubMed:New regulatory factors for melanogenesis: developmental changes in neonatal mice of various genotypes.
PubMed:A quantitative method for determination of 5,6-dihydroxyindole-2-carboxylic acid using high-pressure liquid chromatography with fluorometric detection.
PubMed:Eumelanin (precursor) metabolites as markers for pigmented malignant melanoma: a preliminary report.
PubMed:Dopa oxidation and tyrosine oxygenation by human melanoma tyrosinase.
PubMed:Demonstration of 5,6-dihydroxyindole-2-carboxylic acid, a melanin precursor, in normal urine.
PubMed:Mammalian tyrosinase catalyzes three reactions in the biosynthesis of melanin.
PubMed:DNA damage and selective toxicity of dopa and ascorbate:copper in human melanoma cells.
PubMed:The role of pH in the melanin biosynthesis pathway.
PubMed:New regulators of melanogenesis are associated with purified tyrosinase isozymes.
PubMed:Catechol O-methyltransferase. 12. Affinity labeling the active site with the oxidation products of 5,6-dihydroxyindole.
PubMed:A qualitative gas chromatographic analysis of substituted 5,6-dihydroxyindoles from the urine of patients with melanoma.
PubMed:The identification of Thormählen positive melanogen "A" from the urine of melanoma patients as 6-methoxy-5-indolylglucosiduronate.
PubMed:5,6-Dihydroxyindole is a melanin precursor showing potent cytotoxicity.
PubMed:Isolation of oligomers of 5,6-dihydroxyindole-2-carboxylic acid from the eye of the catfish.
PubMed:5,6-Dihydroxyindole formation from oxidized 6-hydroxydopamine.
5,6-Dihydroxyindole is a substrate for Tyrosinase. [HMDB]
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