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A Robust Fungal Allomelanin Mimic: An Antioxidant and Potent π-Electron Donor with Free-Radical Properties that can be Tuned by Ionic Liquids
- Source :
- ChemPlusChem. 84(9)
- Publication Year :
- 2019
-
Abstract
- Developing effective strategies to increase the chemical stability and to fine-tune the physico-chemical properties of melanin biopolymers by rational control of π-electron conjugation is an important goal in materials science for biomedical and technological applications. Herein we report that poly-1,8-dihydroxynaphthalene (pDHN), a non-nitrogenous, catechol-free fungal melanin mimic, displays a high degree of structural integrity (from MALDI-MS and CP/MAS 13 C NMR analysis), a strong radical scavenging capacity (DPPH and FRAP assays), and an unusually intense EPR signal (g=2.0030). Morphological and spectral characterization of pDHN, along with deassembly experiments in ionic liquids, indicated amorphous aggregates of small globular structures with an estimated stacking distance of 3.9 A and broadband absorption throughout the visible range. These results indicate that DHN-based melanins exhibit a high structural integrity and enhanced antioxidant and free-radical properties of potentially greater biomedical and technological relevance than for typical indole-based eumelanins.
- Subjects :
- Indole test
free radical
antioxidant
010405 organic chemistry
DPPH
Stacking
electron paramagnetic resonance spectroscopy
Electron donor
General Chemistry
Carbon-13 NMR
010402 general chemistry
Photochemistry
01 natural sciences
0104 chemical sciences
law.invention
ionic liquids
chemistry.chemical_compound
chemistry
law
allomelanin
Ionic liquid
Chemical stability
Electron paramagnetic resonance
Subjects
Details
- ISSN :
- 21926506
- Volume :
- 84
- Issue :
- 9
- Database :
- OpenAIRE
- Journal :
- ChemPlusChem
- Accession number :
- edsair.doi.dedup.....451359e1c7042302f64c159a556c0b8c