Chemical and structural diversity in eumelanins: unexplored bio-optoelectronic materials.

PubWeight™: 1.10‹?› | Rank: Top 10%

🔗 View Article (PMC 2799031)

Published in Angew Chem Int Ed Engl on January 01, 2009

Authors

Marco d'Ischia1, Alessandra Napolitano, Alessandro Pezzella, Paul Meredith, Tadeusz Sarna

Author Affiliations

1: Department of Organic Chemistry and Biochemistry, University of Naples Federico II, Complesso Universitario Monte S. Angelo, Via Cintia 4, I-80126, Naples, Italy. dischia@unina.it

Articles citing this

Fluorescence lifetime measurements and biological imaging. Chem Rev (2010) 3.99

Photovoltaic properties of PSi impregnated with eumelanin. Nanoscale Res Lett (2012) 1.01

Biologically derived melanin electrodes in aqueous sodium-ion energy storage devices. Proc Natl Acad Sci U S A (2013) 0.94

Polydopamine-enabled surface functionalization of gold nanorods for cancer cell-targeted imaging and photothermal therapy. Nanomedicine (Lond) (2012) 0.92

Ionization of dimethyluracil dimers leads to facile proton transfer in the absence of hydrogen bonds. Nat Chem (2012) 0.86

Using solid-state NMR to monitor the molecular consequences of Cryptococcus neoformans melanization with different catecholamine precursors. Biochemistry (2012) 0.84

Reverse Engineering Applied to Red Human Hair Pheomelanin Reveals Redox-Buffering as a Pro-Oxidant Mechanism. Sci Rep (2015) 0.81

The self-organizing fractal theory as a universal discovery method: the phenomenon of life. Theor Biol Med Model (2011) 0.81

Nonfouling poly(ethylene oxide) layers end-tethered to polydopamine. Langmuir (2012) 0.81

Dual-wavelength pump-probe microscopy analysis of melanin composition. Sci Rep (2016) 0.80

Demonstration of a common indole-based aromatic core in natural and synthetic eumelanins by solid-state NMR. Org Biomol Chem (2014) 0.80

High ionic strength formation of DOPA-melanin coating for loading and release of cationic antimicrobial compounds. Adv Mater Interfaces (2014) 0.76

Solid-state NMR Reveals the Carbon-based Molecular Architecture of Cryptococcus neoformans Fungal Eumelanins in the Cell Wall. J Biol Chem (2015) 0.76

Fabrication of DNA microarrays on polydopamine-modified gold thin films for SPR imaging measurements. Langmuir (2013) 0.76

Polydopamine-Assisted Surface Modification for Bone Biosubstitutes. Biomed Res Int (2016) 0.75

Melanin-based coatings as lead-binding agents. Bioinorg Chem Appl (2012) 0.75

Melanin and Melanin-Related Polymers as Materials with Biomedical and Biotechnological Applications-Cuttlefish Ink and Mussel Foot Proteins as Inspired Biomolecules. Int J Mol Sci (2017) 0.75

Deciphering Molecular Mechanisms of Interface Buildup and Stability in Porous Si/Eumelanin Hybrids. Int J Mol Sci (2017) 0.75

Articles cited by this

Mussel-inspired surface chemistry for multifunctional coatings. Science (2007) 6.68

The physical and chemical properties of eumelanin. Pigment Cell Res (2006) 2.53

Base stacking controls excited-state dynamics in A.T DNA. Nature (2005) 2.29

The IFPCS presidential lecture: a chemist's view of melanogenesis. Pigment Cell Res (2003) 1.83

Isolation and biophysical studies of natural eumelanins: applications of imaging technologies and ultrafast spectroscopy. Pigment Cell Res (2003) 1.60

Metal-ion interactions and the structural organization of Sepia eumelanin. Pigment Cell Res (2005) 1.35

Ion-exchange and adsorption of Fe(III) by Sepia melanin. Pigment Cell Res (2004) 1.32

Amorphous semiconductor switching in melanins. Science (1974) 1.31

Loss of melanin from human RPE with aging: possible role of melanin photooxidation. Exp Eye Res (2003) 1.28

Chemical and structural disorder in eumelanins: a possible explanation for broadband absorbance. Biophys J (2005) 1.27

Quantitative analysis of eumelanin and pheomelanin in humans, mice, and other animals: a comparative review. Pigment Cell Res (2003) 1.26

Free radical scavenging properties of melanin interaction of eu- and pheo-melanin models with reducing and oxidising radicals. Free Radic Biol Med (1999) 1.22

The fundamental unit of synthetic melanin: a verification by tunneling microscopy of X-ray scattering results. Biochim Biophys Acta (1994) 1.14

Structure, chemistry, and biosynthesis of the melanins. Fortschr Chem Org Naturst (1974) 1.13

X-ray characterization of melanins--II. Pigment Cell Res (1994) 1.09

X-ray characterization of melanins--I. Pigment Cell Res (1994) 1.08

Photoreactivity of aged human RPE melanosomes: a comparison with lipofuscin. Invest Ophthalmol Vis Sci (2002) 1.06

Structural model of eumelanin. Phys Rev Lett (2006) 1.06

Metal binding by melanins: studies of colloidal dihydroxyindole-melanin, and its complexation by Cu(II) and Zn(II) ions. J Inorg Biochem (2002) 1.04

Photoprotection of human retinal pigment epithelium cells against blue light-induced apoptosis by melanin free radicals from Sepia officinalis. Proc Natl Acad Sci U S A (2006) 1.04

Role of ocular melanin in ophthalmic physiology and pathology. Photochem Photobiol (2008) 1.02

Melanin photoprotection in the human retinal pigment epithelium and its correlation with light-induced cell apoptosis. Proc Natl Acad Sci U S A (2005) 1.00

Theoretical models of eumelanin protomolecules and their optical properties. Biophys J (2007) 0.99

Melanins, melanogenesis and melanocytes: looking at their functional significance from the chemist's viewpoint. Pigment Cell Res (2000) 0.99

A first-principles density-functional calculation of the electronic and vibrational structure of the key melanin monomers. J Chem Phys (2004) 0.98

Ultrastructural organization of eumelanin from Sepia officinalis measured by atomic force microscopy. Biochemistry (2001) 0.98

Radiative relaxation quantum yields for synthetic eumelanin. Photochem Photobiol (2004) 0.97

Effects of photodegradation on the physical and antioxidant properties of melanosomes isolated from retinal pigment epithelium. Photochem Photobiol (2007) 0.96

Quantitative fluorescence excitation spectra of synthetic eumelanin. J Phys Chem B (2005) 0.95

Structural studies of bleached melanin by synchrotron small-angle X-ray scattering. Photochem Photobiol (2003) 0.95

Tyrosinase autoactivation and the chemistry of ortho-quinone amines. Acc Chem Res (2003) 0.93

Probing the building blocks of eumelanins using scanning electron microscopy. Pigment Cell Res (2000) 0.91

Analysis of the ESR spectrum of synthetic dopa melanin. Biochim Biophys Acta (1986) 0.91

Time-resolved detection of melanin free radicals quenching reactive oxygen species. J Am Chem Soc (2005) 0.91

Radiative relaxation of Sepia eumelanin is affected by aggregation. Photochem Photobiol (2001) 0.89

The chemistry of melanins and melanogenesis. Fortschr Chem Org Naturst (1995) 0.89

Melanin affinity of manganese. Acta Pharmacol Toxicol (Copenh) (1984) 0.89

Effect of stacking and redox state on optical absorption spectra of melanins -- comparison of theoretical and experimental results. J Phys Chem B (2005) 0.89

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. Photochem Photobiol (2008) 0.88

The phototoxicity of aged human retinal melanosomes. Photochem Photobiol (2007) 0.88

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. Org Lett (2007) 0.87

Short-lived quinonoid species from 5,6-dihydroxyindole dimers en route to eumelanin polymers: integrated chemical, pulse radiolytic, and quantum mechanical investigation. J Am Chem Soc (2006) 0.87

Convergent proton-transfer photocycles violate mirror-image symmetry in a key melanin monomer. J Am Chem Soc (2007) 0.86

Electrochemical self-assembly of melanin films on gold. Langmuir (2005) 0.86

Photobleaching of retinal pigment epithelium melanosomes reduces their ability to inhibit iron-induced peroxidation of lipids. Pigment Cell Res (2007) 0.86

Mobility gaps: a mechanism for band gaps in melanins. Science (1972) 0.85

Wavelength-dependent photoacoustic calorimetry study of melanin. Photochem Photobiol (1998) 0.85

Study of optical properties of electropolymerized melanin films by photopyroelectric spectroscopy. Eur Biophys J (2005) 0.84

Photophysics of eumelanin: ab initio studies on the electronic spectroscopy and photochemistry of 5,6-dihydroxyindole. Chemphyschem (2007) 0.83

Characterization of human hair melanin and its degradation products by means of magnetic resonance techniques. Magn Reson Chem (2008) 0.83

Electrical conductivity of synthetic DOPA-melanin polymer for different hydration states and temperatures. J Biomater Sci Polym Ed (1995) 0.82

A quantum yield map for synthetic eumelanin. J Chem Phys (2005) 0.80

Physical and chemical characterization of iris and choroid melanosomes isolated from newborn and mature cows. Photochem Photobiol (2005) 0.79

Transition dipole strength of eumelanin. Phys Rev E Stat Nonlin Soft Matter Phys (2007) 0.79

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. J Org Chem (2007) 0.79

The chemical structure of melanin. Pigment Cell Res (2004) 0.79

Time-resolved and steady-state fluorescence spectroscopy of eumelanin and indolic polymers. Photochem Photobiol (2007) 0.78

Ultra-low temperature oxidation of 5,6-dihydroxyindole: a novel approach to study synthetic melanogenesis. Photochem Photobiol (2008) 0.77

Microanalysis of melanins in mammalian hair by alkaline hydrogen peroxide degradation: identification of a new structural marker of pheomelanins. J Invest Dermatol (2000) 0.77

Chemical, pulse radiolysis and density functional studies of a new, labile 5,6-indolequinone and its semiquinone. J Org Chem (2007) 0.76

Synthesis and polymerization studies of organic-soluble eumelanins. Photochem Photobiol (2008) 0.76

Effect of dimerization on vibrational spectra of eumelanin precursors. Photochem Photobiol (2008) 0.76

Magnetic properties of synthetic eumelanin--preliminary results. Photochem Photobiol (2008) 0.76

Articles by these authors

The ability of the National Early Warning Score (NEWS) to discriminate patients at risk of early cardiac arrest, unanticipated intensive care unit admission, and death. Resuscitation (2013) 4.89

S(p)O(2) values in acute medical admissions breathing air--implications for the British Thoracic Society guideline for emergency oxygen use in adult patients? Resuscitation (2012) 2.68

The physical and chemical properties of eumelanin. Pigment Cell Res (2006) 2.53

Nitro-fatty acid formation and signaling. J Biol Chem (2008) 1.95

Melanin in human irides of different color and age of donors. Pigment Cell Res (2005) 1.65

Patterns in the recording of vital signs and early warning scores: compliance with a clinical escalation protocol. BMJ Qual Saf (2013) 1.60

The microenvironment effect on the generation of reactive oxygen species by Pd-bacteriopheophorbide. J Am Chem Soc (2005) 1.47

Pain: a quality of care issue during patients' admission to hospital. J Adv Nurs (2013) 1.43

Functionalized fullerenes mediate photodynamic killing of cancer cells: Type I versus Type II photochemical mechanism. Free Radic Biol Med (2007) 1.37

Photodynamic therapy with fullerenes. Photochem Photobiol Sci (2007) 1.32

Light-induced damage to the retina: role of rhodopsin chromophore revisited. Photochem Photobiol (2005) 1.28

Chemical and structural disorder in eumelanins: a possible explanation for broadband absorbance. Biophys J (2005) 1.27

Photocatalytic generation of oxygen radicals by the water-soluble bacteriochlorophyll derivative WST11, noncovalently bound to serum albumin. J Phys Chem A (2009) 1.26

Spectroscopic and morphological studies of human retinal lipofuscin granules. Proc Natl Acad Sci U S A (2003) 1.23

Melanins and melanogenesis: methods, standards, protocols. Pigment Cell Melanoma Res (2013) 1.23

Efficient, large area ITO-and-PEDOT-free organic solar cell sub-modules. Adv Mater (2012) 1.21

Neuromelanin can protect against iron-mediated oxidative damage in system modeling iron overload of brain aging and Parkinson's disease. J Neurochem (2008) 1.15

Pulse radiolysis and steady-state analyses of the reaction between hydroethidine and superoxide and other oxidants. Arch Biochem Biophys (2006) 1.09

Photoreactivity of aged human RPE melanosomes: a comparison with lipofuscin. Invest Ophthalmol Vis Sci (2002) 1.06

Comparison of the aerobic photoreactivity of A2E with its precursor retinal. Photochem Photobiol (2003) 1.06

Role of semiconductivity and ion transport in the electrical conduction of melanin. Proc Natl Acad Sci U S A (2012) 1.03

Role of ocular melanin in ophthalmic physiology and pathology. Photochem Photobiol (2008) 1.02

Photovoltaic properties of PSi impregnated with eumelanin. Nanoscale Res Lett (2012) 1.01

Paradoxical potentiation of methylene blue-mediated antimicrobial photodynamic inactivation by sodium azide: role of ambient oxygen and azide radicals. Free Radic Biol Med (2012) 1.00

Oxidative stress in ARPE-19 cultures: do melanosomes confer cytoprotection? Free Radic Biol Med (2005) 0.98

Photoionization thresholds of melanins obtained from free electron laser-photoelectron emission microscopy, femtosecond transient absorption spectroscopy and electron paramagnetic resonance measurements of oxygen photoconsumption. Photochem Photobiol (2006) 0.98

Dynamics of H2O2 availability to ARPE-19 cultures in models of oxidative stress. Free Radic Biol Med (2010) 0.97

Effects of photodegradation on the physical and antioxidant properties of melanosomes isolated from retinal pigment epithelium. Photochem Photobiol (2007) 0.96

Age-related changes in the photoreactivity of retinal lipofuscin granules: role of chloroform-insoluble components. Invest Ophthalmol Vis Sci (2004) 0.95

Quantitative fluorescence excitation spectra of synthetic eumelanin. J Phys Chem B (2005) 0.95

Measuring internal quantum efficiency to demonstrate hot exciton dissociation. Nat Mater (2013) 0.95

Zeaxanthin in combination with ascorbic acid or alpha-tocopherol protects ARPE-19 cells against photosensitized peroxidation of lipids. Free Radic Biol Med (2004) 0.93

Human RPE melanosomes protect from photosensitized and iron-mediated oxidation but become pro-oxidant in the presence of iron upon photodegradation. Invest Ophthalmol Vis Sci (2008) 0.93

Cooperation of antioxidants in protection against photosensitized oxidation. Free Radic Biol Med (2003) 0.92

Polydopamine and eumelanin: from structure-property relationships to a unified tailoring strategy. Acc Chem Res (2014) 0.92

Morphology of all-solution-processed "bilayer" organic solar cells. Adv Mater (2010) 0.91

Zinc-induced structural effects enhance oxygen consumption and superoxide generation in synthetic pheomelanins on UVA/visible light irradiation. Photochem Photobiol (2010) 0.90

Red human hair pheomelanin is a potent pro-oxidant mediating UV-independent contributory mechanisms of melanomagenesis. Pigment Cell Melanoma Res (2014) 0.90

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. J Am Chem Soc (2009) 0.89

9-cis Retinal increased in retina of RPE65 knockout mice with decrease in coat pigmentation. Photochem Photobiol (2007) 0.89

Nanostructured, active organic-metal junctions for highly efficient charge generation and extraction in polymer-fullerene solar cells. Adv Mater (2012) 0.89

Early warning scores: unravelling detection and escalation. Int J Health Care Qual Assur (2015) 0.89

Antimicrobial photodynamic therapy with fulleropyrrolidine: photoinactivation mechanism of Staphylococcus aureus, in vitro and in vivo studies. Appl Microbiol Biotechnol (2015) 0.88

Kinetic and chemical assessment of the UV/H2O2 treatment of antiepileptic drug carbamazepine. Chemosphere (2004) 0.88

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. Photochem Photobiol (2008) 0.88

The eumelanin intermediate 5,6-dihydroxyindole-2-carboxylic acid is a messenger in the cross-talk among epidermal cells. J Invest Dermatol (2012) 0.88

The phototoxicity of aged human retinal melanosomes. Photochem Photobiol (2007) 0.88

Cell elasticity is an important indicator of the metastatic phenotype of melanoma cells. Exp Dermatol (2014) 0.88

Dynamic analyses reveal cytoprotection by RPE melanosomes against non-photic stress. Mol Vis (2011) 0.87

Energy transfer dynamics of nanocrystal-polymer composites. J Phys Chem B (2005) 0.87

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. Org Lett (2007) 0.87

Short-lived quinonoid species from 5,6-dihydroxyindole dimers en route to eumelanin polymers: integrated chemical, pulse radiolytic, and quantum mechanical investigation. J Am Chem Soc (2006) 0.87

Atypical structural and π-electron features of a melanin polymer that lead to superior free-radical-scavenging properties. Angew Chem Int Ed Engl (2013) 0.87

Low noise, IR-blind organohalide perovskite photodiodes for visible light detection and imaging. Adv Mater (2015) 0.86

Convergent proton-transfer photocycles violate mirror-image symmetry in a key melanin monomer. J Am Chem Soc (2007) 0.86

Action spectra for the photoconsumption of oxygen by human ocular lipofuscin and lipofuscin extracts. Arch Biochem Biophys (2002) 0.86

A reactive ortho-quinone generated by tyrosinase-catalyzed oxidation of the skin depigmenting agent monobenzone: self-coupling and thiol-conjugation reactions and possible implications for melanocyte toxicity. Chem Res Toxicol (2009) 0.86

Thiocyanate potentiates antimicrobial photodynamic therapy: in situ generation of the sulfur trioxide radical anion by singlet oxygen. Free Radic Biol Med (2013) 0.86

Uncovering the structure of human red hair pheomelanin: benzothiazolylthiazinodihydroisoquinolines as key building blocks. J Nat Prod (2011) 0.86

Quantitative scattering of melanin solutions. Biophys J (2006) 0.86

Interactions of plasmalogens and their diacyl analogs with singlet oxygen in selected model systems. Free Radic Biol Med (2011) 0.85

Simultaneous enhancement of brightness, efficiency, and switching in RGB organic light emitting transistors. Adv Mater (2013) 0.85

The haptenation theory of vitiligo and melanoma rejection: a close-up. Exp Dermatol (2011) 0.85

Melanosome-iron interactions within retinal pigment epithelium-derived cells. Pigment Cell Melanoma Res (2012) 0.85

Oxidation chemistry of norepinephrine: partitioning of the O-quinone between competing cyclization and chain breakdown pathways and their roles in melanin formation. Chem Res Toxicol (2007) 0.85

Study of optical properties of electropolymerized melanin films by photopyroelectric spectroscopy. Eur Biophys J (2005) 0.84

Sub-lethal photodynamic damage to ARPE-19 cells transiently inhibits their phagocytic activity. Photochem Photobiol (2010) 0.84

Glyoxal formation by Fenton-induced degradation of carbohydrates and related compounds. Carbohydr Res (2006) 0.84

Photobleaching of melanosomes from retinal pigment epithelium: II. Effects on the response of living cells to photic stress. Photochem Photobiol (2007) 0.84

Superior photoprotective motifs and mechanisms in eumelanins uncovered. J Am Chem Soc (2014) 0.84

Eumelanin buildup on the nanoscale: aggregate growth/assembly and visible absorption development in biomimetic 5,6-dihydroxyindole polymerization. Biomacromolecules (2012) 0.84

Quantitative photoluminescence of broad band absorbing melanins: a procedure to correct for inner filter and re-absorption effects. Spectrochim Acta A Mol Biomol Spectrosc (2005) 0.83

Tris buffer modulates polydopamine growth, aggregation, and paramagnetic properties. Langmuir (2014) 0.83

Functionality of epidermal melanin pigments: current knowledge on UV-dissipative mechanisms and research perspectives. Phys Chem Chem Phys (2011) 0.83

Solid-state dendrimer sensors: probing the diffusion of an explosive analogue using neutron reflectometry. Langmuir (2009) 0.83

Different molecular constituents in pheomelanin are responsible for emission, transient absorption and oxygen photoconsumption. Photochem Photobiol (2008) 0.83

Photobleaching of melanosomes from retinal pigment epithelium: I. Effects on protein oxidation. Photochem Photobiol (2007) 0.82

Is DHICA the key to dopachrome tautomerase and melanocyte functions? Pigment Cell Melanoma Res (2010) 0.82

A new approach to the synthesis of conjugated polymer-nanocrystal composites for heterojunction optoelectronics. Chem Commun (Camb) (2004) 0.82

5,6-Dihydroxyindole oxidation in phosphate buffer/polyvinyl alcohol: a new model system for studies of visible chromophore development in synthetic eumelanin polymers. Photochem Photobiol (2010) 0.82

A melanin-inspired pro-oxidant system for dopa(mine) polymerization: mimicking the natural casing process. Chem Commun (Camb) (2011) 0.81

Secondary targets of nitrite-derived reactive nitrogen species: nitrosation/nitration pathways, antioxidant defense mechanisms and toxicological implications. Chem Res Toxicol (2011) 0.81

Melanin structure and the potential functions of uveal melanosomes. Pigment Cell Res (2006) 0.81

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. J Org Chem (2009) 0.81

New insight into singlet oxygen generation at surface modified nanocrystalline TiO2--the effect of near-infrared irradiation. Dalton Trans (2013) 0.80

Spectral dependence of the internal quantum efficiency of organic solar cells: effect of charge generation pathways. J Am Chem Soc (2014) 0.80

A quantum yield map for synthetic eumelanin. J Chem Phys (2005) 0.80

Nanomechanical analysis of pigmented human melanoma cells. Pigment Cell Melanoma Res (2013) 0.80

A reappraisal of traditional apple cultivars from Southern Italy as a rich source of phenols with superior antioxidant activity. Food Chem (2013) 0.80

Time-resolved neutron reflectometry and photovoltaic device studies on sequentially deposited PCDTBT-fullerene layers. Langmuir (2014) 0.80

Development and validation of a decision tree early warning score based on routine laboratory test results for the discrimination of hospital mortality in emergency medical admissions. Resuscitation (2013) 0.80

Long-lasting pigmentation more than its intensity is a reliable indicator of skin sun resistance. Dermatology (2007) 0.80

A Comparison of the Ability of the Physiologic Components of Medical Emergency Team Criteria and the U.K. National Early Warning Score to Discriminate Patients at Risk of a Range of Adverse Clinical Outcomes. Crit Care Med (2016) 0.80