Cargando…

Nonenzymatic Spontaneous Oxidative Transformation of 5,6-Dihydroxyindole

Melanin is an important phenolic skin pigment found throughout the animal kingdom. Tyrosine and its hydroxylated product dopa provide the starting material for melanin biosynthesis in all animals. Through a set of well-established reactions, they are converted to 5,6-dihydroxyindole (DHI) and DHI-2-...

Descripción completa

Detalles Bibliográficos
Autores principales:	Sugumaran, Manickam, Evans, Jason, Ito, Shosuke, Wakamatsu, Kazumasa
Formato:	Online Artículo Texto
Lenguaje:	English
Publicado:	MDPI 2020
Materias:	Article
Acceso en línea:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7583787/ https://www.ncbi.nlm.nih.gov/pubmed/33023030 http://dx.doi.org/10.3390/ijms21197321

Ejemplares similares

5,6‐Dihydroxyindole eumelanin content in human skin with varying degrees of constitutive pigmentation
por: Del Bino, Sandra, et al.
Publicado: (2022)

Oxidative Transformations of 3,4-Dihydroxyphenylacetaldehyde Generate Potential Reactive Intermediates as Causative Agents for Its Neurotoxicity
por: Ito, Shosuke, et al.
Publicado: (2021)

Oxidative Oligomerization of DBL Catechol, a Potential Cytotoxic Compound for Melanocytes, Reveals the Occurrence of Novel Ionic Diels-Alder Type Additions
por: Sugumaran, Manickam, et al.
Publicado: (2020)

Chemical Reactivities of ortho-Quinones Produced in Living Organisms: Fate of Quinonoid Products Formed by Tyrosinase and Phenoloxidase Action on Phenols and Catechols
por: Ito, Shosuke, et al.
Publicado: (2020)

Expedient synthesis of eumelanin-inspired 5,6-dihydroxyindole-2-carboxylate ethyl ester derivatives
por: Aebly, Andrew H., et al.
Publicado: (2018)

Correction: Expedient synthesis of eumelanin-inspired 5,6-dihydroxyindole-2-carboxylate ethyl ester derivatives
por: Aebly, Andrew H., et al.
Publicado: (2019)

Eumelanin Coating of Silica Aerogel by Supercritical Carbon Dioxide Deposition of a 5,6-Dihydroxyindole Thin Film
por: Caputo, Giuseppe, et al.
Publicado: (2018)

In situ insights into the nanoscale deposition of 5,6-dihydroxyindole-based coatings and the implications on the underwater adhesion mechanism of polydopamine coatings
por: Lyu, Qinghua, et al.
Publicado: (2018)

[Image: see text] Biological activity and synthesis of 5,6-dihydroxyindole-2-carboxylic acid – biosynthetic precursor of melanins (microreview)
por: Barabanov, Mikhail А., et al.
Publicado: (2021)

A Straightforward Access to New Amides of the Melanin Precursor 5,6-Dihydroxyindole-2-carboxylic Acid and Characterization of the Properties of the Pigments Thereof
por: Argenziano, Rita, et al.
Publicado: (2022)

Gelatin-Based Hydrogels for the Controlled Release of 5,6-Dihydroxyindole-2-Carboxylic Acid, a Melanin-Related Metabolite with Potent Antioxidant Activity
por: Alfieri, Maria Laura, et al.
Publicado: (2020)

Eumelanin Precursor 2-Carboxy-5,6-Dihydroxyindole (DHICA) as Doping Factor in Ternary (PEDOT:PSS/Eumelanin) Thin Films for Conductivity Enhancement
por: Migliaccio, Ludovico, et al.
Publicado: (2020)

A Model Eumelanin from 5,6-Dihydroxyindole-2-Carboxybutanamide Combining Remarkable Antioxidant and Photoprotective Properties with a Favourable Solubility Profile for Dermo-Cosmetic Applications
por: Argenziano, Rita, et al.
Publicado: (2023)

Eumelanin pigment precursor 2-carboxy-5,6-dihydroxyindole and 2-amino-6-methylbenzothiazole chromophore integration towards melanin inspired chemoresponsive materials: the case of the Zn(2+) ion
por: Mocerino, Fabio, et al.
Publicado: (2022)

Biochemical Mechanism of Rhododendrol-Induced Leukoderma
por: Ito, Shosuke, et al.
Publicado: (2018)

Recent Advances in Characterization of Melanin Pigments in Biological Samples
por: Wakamatsu, Kazumasa, et al.
Publicado: (2023)

Chemical Evaluation of Eumelanin Maturation by ToF-SIMS and Alkaline Peroxide Oxidation HPLC Analysis
por: Jarenmark, Martin, et al.
Publicado: (2020)

Effects of Aging on Hair Color, Melanosome Morphology, and Melanin Composition in Japanese Females
por: Itou, Takashi, et al.
Publicado: (2019)

Effects of Aging on Hair Color, Melanosomes, and Melanin Composition in Japanese Males and Their Sex Differences
por: Itou, Takashi, et al.
Publicado: (2022)

The Oxidative Pathway to Dopamine–Protein Conjugates and Their Pro-Oxidant Activities: Implications for the Neurodegeneration of Parkinson’s Disease
por: Wakamatsu, Kazumasa, et al.
Publicado: (2019)

The Pro-Oxidant Activity of Pheomelanin is Significantly Enhanced by UVA Irradiation: Benzothiazole Moieties Are More Reactive than Benzothiazine Moieties
por: Tanaka, Hitomi, et al.
Publicado: (2018)

Unique Nonenzymatic Glucose Sensor Using a Hollow-Shelled Triple Oxide Mn–Cu–Al Nanocomposite
por: Chandrasekaran, Nivedhini Iswarya, et al.
Publicado: (2020)

The Oxidation of Equol by Tyrosinase Produces a Unique Di-ortho-Quinone: Possible Implications for Melanocyte Toxicity
por: Tanaka, Hitomi, et al.
Publicado: (2021)

The Metabolic Fate of ortho-Quinones Derived from Catecholamine Metabolites
por: Ito, Shosuke, et al.
Publicado: (2016)

Density Functional Theory-Based Calculation Shed New Light on the Bizarre Addition of Cysteine Thiol to Dopaquinone
por: Kishida, Ryo, et al.
Publicado: (2021)

Improved HPLC Conditions to Determine Eumelanin and Pheomelanin Contents in Biological Samples Using an Ion Pair Reagent
por: Ito, Shosuke, et al.
Publicado: (2020)

Catecholamine Derivatives as Novel Crosslinkers for the Synthesis of Versatile Biopolymers
por: Sugumaran, Manickam, et al.
Publicado: (2023)

Structure-Guided Design of Nurr1 Agonists Derived from the Natural Ligand Dihydroxyindole
por: Sai, Minh, et al.
Publicado: (2023)

The influence of iron on selected properties of synthetic pheomelanin
por: Zadlo, Andrzej, et al.
Publicado: (2020)

Neuromelanin in Parkinson’s Disease: Tyrosine Hydroxylase and Tyrosinase
por: Nagatsu, Toshiharu, et al.
Publicado: (2022)

Adaptive Melanin Response of the Soil Fungus Aspergillus niger to UV Radiation Stress at “Evolution Canyon”, Mount Carmel, Israel
por: Singaravelan, Natarajan, et al.
Publicado: (2008)

Spiny Mice Modulate Eumelanin to Pheomelanin Ratio to Achieve Cryptic Coloration in “Evolution Canyon,” Israel
por: Singaravelan, Natarajan, et al.
Publicado: (2010)

Eumelanin levels in rufous feathers explain plasma testosterone levels and survival in swallows
por: Arai, Emi, et al.
Publicado: (2019)

Utility of Melanin Degradation Products in the Nail for Diagnosing Nail Apparatus Melanoma
por: MIYAKE, Tomomi, et al.
Publicado: (2021)

A Sulfur Containing Melanogenesis Substrate, N-Pr-4-S-CAP as a Potential Source for Selective Chemoimmunotherapy of Malignant Melanoma
por: Tamura, Yasuaki, et al.
Publicado: (2023)

A nonenzymatic reduced graphene oxide-based nanosensor for parathion
por: Sen, Sarani, et al.
Publicado: (2022)

Norepinephrine and its metabolites are involved in the synthesis of neuromelanin derived from the locus coeruleus
por: Wakamatsu, Kazumasa, et al.
Publicado: (2015)

Tissue-specific geometry and chemistry of modern and fossilized melanosomes reveal internal anatomy of extinct vertebrates
por: Rossi, Valentina, et al.
Publicado: (2019)

Photoreactivity of Hair Melanin from Different Skin Phototypes—Contribution of Melanin Subunits to the Pigments Photoreactive Properties
por: Mokrzynski, Krystian, et al.
Publicado: (2021)

Multiphoton FLIM Analyses of Native and UVA-Modified Synthetic Melanins
por: Pena, Ana-Maria, et al.
Publicado: (2023)

Cannot write session to /tmp/vufind_sessions/sess_k94trhhct6vp4vbgri6f69agem