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 / Manini P.; Lino V.; Franchi P.; Gentile G.; Sibillano T.; Giannini C.; Picardi E.; Napolitano A.; Valgimigli L.; Chiappe C.; d'Ischia M.. - In: CHEMPLUSCHEM. - ISSN 2192-6506. - STAMPA. - 84:9(2019), pp. 1331-1337. [10.1002/cplu.201900195]

A Robust Fungal Allomelanin Mimic: An Antioxidant and Potent π-Electron Donor with Free-Radical Properties that can be Tuned by Ionic Liquids

Franchi P.;Valgimigli L.;
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.
2019
A Robust Fungal Allomelanin Mimic: An Antioxidant and Potent π-Electron Donor with Free-Radical Properties that can be Tuned by Ionic Liquids / Manini P.; Lino V.; Franchi P.; Gentile G.; Sibillano T.; Giannini C.; Picardi E.; Napolitano A.; Valgimigli L.; Chiappe C.; d'Ischia M.. - In: CHEMPLUSCHEM. - ISSN 2192-6506. - STAMPA. - 84:9(2019), pp. 1331-1337. [10.1002/cplu.201900195]
Manini P.; Lino V.; Franchi P.; Gentile G.; Sibillano T.; Giannini C.; Picardi E.; Napolitano A.; Valgimigli L.; Chiappe C.; d'Ischia M.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/710752
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