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 13C 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 Å 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.
A Robust Fungal Allomelanin Mimic: An Antioxidant and Potent π-Electron Donor with Free-Radical Properties that can be Tuned by Ionic Liquids
LINO, VALERIA;d'Ischia M.
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 13C 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 Å 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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
