Preparation, Characterization, Cytotoxicity and Antioxidant Activity of DOPA Melanin Modified by Amino Acids: Melanin-Like Oligomeric Aggregates

Costa, Thiago A.; Feldhaus, Mateus J.; Vilhena, Felipe S.; Heller, Melina; Micke, Gustavo Amadeu; Oliveira, Aldo Sena de; Brighente, Inês Maria Costa; Filippin-Monteiro, Fabíola Branco; Creczynski-Pasa, Tânia B.; Szpoganicz, Bruno

doi:10.5935/0103-5053.20140277

Cited by 7 publications

(11 citation statements)

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“…The outcome of this set of experiments suggested that pyomelanin is not toxic for the two mammalian cell lines tested at least in those experimental conditions. These results are in accordance with those obtained with synthetic pheomelanin on mouse fibroblasts, where three different synthetic forms of the compound showed no cytotoxicity even at high concentration …”

Section: Resultssupporting

confidence: 91%

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Characterization of a nontoxic pyomelanin pigment produced by the yeast Yarrowia lipolytica

Tahar

Kus‐Liśkiewicz

Lara

et al. 2019

Biotechnology Progress

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In this study, we report on the ability of the yeast Yarrowia lipolytica W29 to produce an extracellular melanin‐like brown pigment at high yield (0.5 mg/ml) in culture medium supplemented with L‐tyrosine. This pigment has been characterized as pyomelanin and its synthesis was found to occur by the so‐called HGA‐melanin pathway. The purified pyomelanin was found embedded with antioxidant properties as it exhibited a radical scavenging activity toward 1,1‐diphenyl‐2‐picrylhydrazyl (DPPH) with IC50 of 230 μg/ml. It was also characterized as noncytotoxic toward two mammalian cell lines, namely the mouse fibroblast NIH3T3 and human keratinocytes HaCaT. When blended with different commercial sunscreens, the purified pyomelanin increased significantly the sun protection factor (SPF) value, highlighting its potential utilization as UV‐filter in cosmetic preparations.

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Section: Resultssupporting

confidence: 91%

“…These results are in accordance with those obtained with synthetic pheomelanin on mouse fibroblasts, where three different synthetic forms of the compound showed no cytotoxicity even at high concentration. 51…”

Section: Evaluation Of the Pyomelanin Cytotoxicitymentioning

confidence: 99%

Characterization of a nontoxic pyomelanin pigment produced by the yeast Yarrowia lipolytica

Tahar

Kus‐Liśkiewicz

Lara

et al. 2019

Biotechnology Progress

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“…9–16% sulphur content. These findings are in accordance with those reported by Harki et al (1997; Costa et al 2015; Sun et al 2016b). According to Ye et al (2014), about 14.83% sulphur content was determined by elemental analysis from Lachnum YM404 strain.…”

Section: Discussionsupporting

confidence: 93%

Purification and characterisation of a sulphur rich melanin from edible mushroom Termitomyces albuminosus Heim

2018

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Production, purification and characterisation of a black pigment from Termitomyces albuminosus as melanin is reported, for the first time, from shaken submerged culture condition using scanning electron microscopy (SEM), elemental analysis, ultraviolet–visible (UV-VIS), and Fourier transformed infrared spectroscopy (FTIR), electron paramagnetic resonance (EPR) and 13C (CP/MAS) NMR spectra. SEM results on T. albuminosus revealed nanogranular nature of melanin nanoparticles within size range of 400–100 nm with fractal dimension D = 1.195–1.73. Elemental analysis of melanin indicated 54.6% C, 3.5% H, 2.4% N, 26.9% O, and 12% S. UV-VIS and FTIR spectra confirmed to the characteristic of melanin and were identical to the reference commercial sepia melanin. Further validation of the identity of pigment as melanin was achieved by EPR analysis. Termitomyces albuminosus melanin is postulated to be DOPA-type melanin confirmed by 13C (CP/MAS) NMR spectral analysis showing chemical shift at 200–170 ppm carbonyl, 160–110 ppm aromatic region, and with high 40–30 ppm open chain aliphatic region. Chemical modification through oxidation and cysteinylation (Pheomelanin) is implied as indicated by relatively high sulphur content (12%).

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“…Some common models for melanin structure: (a) eumelanin fragment; (b) cyclic tetramer; (c) compact cyclic eumelanin; (d) non‐covalent stacked l ‐dopa; (e) pheomelanin fragment.…”

Section: Melanin Types and Structurementioning

confidence: 99%

“…These tetramers can arrange into eumelanin macromolecules through interlayer stacking, but also through formation of helical superstructures. Recently Costa et al proposed the cyclic compacted model depicted in Fig. (c) that might be considered a possible but unlikely structure.…”

Section: Melanin Types and Structurementioning

confidence: 99%

Photoprotection versus photodamage: updating an old but still unsolved controversy about melanin

Solano

2016

Polymer International

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Melanin is the main pigment in animal skin. It is a heterogeneous polyphenolic molecule with a generalized absorption in the UV−visible range synthesized in melanocytes, a kind of specialized epidermal cells. There are two types of melanin, eumelanin and pheomelanin, more abundant in dark or fair skin respectively. Melanin plays several roles, but in mammalian skin the main one is related to photoprotection against sunlight. The absorption energy from UV light implies that elements of the melanin structure are photoexcited, and the subsequent transference of energy can provoke several effects on surrounding molecules. These processes raise the possibility that melanin becomes a photosensitizer instead of a photoprotector. Thus, melanins should be considered double-faced molecules. This was first evident for pheomelanin, but very recent new data on eumelanin indicate that the balance is subtler than thought so far, and photodamage can overcome photoprotection for both types. In this updated review, the consequences of the eumelanin versus pheomelanin photochemical properties are discussed in relation to DNA lesions. Melanin is considered photoprotective, but it can also produce DNA photodamage and this would be related to the high incidence of skin cancer, mostly in Caucasian people.

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Preparation, Characterization, Cytotoxicity and Antioxidant Activity of DOPA Melanin Modified by Amino Acids: Melanin-Like Oligomeric Aggregates

Cited by 7 publications

References 0 publications

Characterization of a nontoxic pyomelanin pigment produced by the yeast Yarrowia lipolytica

Characterization of a nontoxic pyomelanin pigment produced by the yeast Yarrowia lipolytica

Purification and characterisation of a sulphur rich melanin from edible mushroom Termitomyces albuminosus Heim

Photoprotection versus photodamage: updating an old but still unsolved controversy about melanin

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