Comparison of synthetic dopamine-eumelanin formed in the presence of oxygen and Cu2+ cations as oxidants

Langmuir

Volumn 29, Issue 41, 2013, Pages 12754-12761

  Ball, Vincent ^a,b,c   Gracio, José ^d,e   Vila, Mercedes ^f,g   Singh, Manoj Kumar ^e   Metz Boutigue, Marie Hélène ^b   Michel, Marc ^h   Bour, Jéroîme ^h   Toniazzo, Valérie ^h   Ruch, David ^h   Buehler, Markus J ⁱ  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b INSERM   (France)

^c Fédération de Médecine Translationelle de Strasbourg ^*  (France)

^d UNIVERSITY OF AVEIRO   (Portugal)

^e UNIVERSITY OF AVEIRO   (Portugal)

^f UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^g BIOMATERIALES Y NANOMEDICINA CIBER BBN   (Spain)

^h LUXEMBOURG INSTITUTE OF SCIENCE AND TECHNOLOGY   (Luxembourg)

ⁱ Massachusetts Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AGGREGATE STRUCTURES; COATING PLATFORM; COLLOIDAL PROPERTIES; DIHYDROXYINDOLE; LIVING ORGANISMS; OXIDATION PRODUCTS; RELATED COMPOUNDS; SUPRAMOLECULAR ASSEMBLIES;

AMINES; BIOLOGY; NEUROPHYSIOLOGY; OXIDANTS; POSITIVE IONS;

MELANIN;

CATION; COPPER; DOPAMINE; EUMELANIN; MELANIN; OXIDIZING AGENT; OXYGEN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMPARATIVE STUDY; PARTICLE SIZE; SURFACE PROPERTY;

CATIONS; COPPER; DOPAMINE; MELANINS; MOLECULAR STRUCTURE; OXIDANTS; OXYGEN; PARTICLE SIZE; SURFACE PROPERTIES;

EID: 84886931961     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la4029782     Document Type: Article

References (31)

1. Ward, W. C.; Zucca, F.; Belei, C.; Zecca, L.; Simon, J. D. Neuromelanins in various regions of human brain are associated with native and oxidized isoprenoid lipids Arch. Biochem. Biophys. 2009, 484, 94-99
2. Jastrzebska, M.; Kocot, A.; Tajber, L. Photoconductivity of synthetic dopa-melanin polymer J. Photochem. Photobiol., B 2002, 66, 201-206
3. Bothma, J. P.; de Boor, J.; Divakar, U.; Schwenn, P. E.; Meredith, P. Device-quality electrically conducting melanin thin films Adv. Mater. 2008, 20, 3539-3542
4. Meredith, P.; Riesz, J. Radiative relaxation quantum yields for synthetic eumelanin Photochem. Photobiol. 2004, 79, 211-216
5. de Albuquerque, J. E.; Giacomantonio, C.; White, A. G.; Meredith, P. Study of optical properties of electropolymerized melanin films by photopyroelectric spectroscopy Eur. Biophys. J. 2006, 35, 190-195
6. Kaxiras, E.; Tsolakidis, A.; Zonios, G.; Meng, S. Structural model of eumelanin Phys. Rev. Lett. 2006, 97, art218102
7. D'Ischia, M.; Napolitano, A.; Pezzella, A.; Meredith, P.; Sarna, T. Chemical and structural diversity in eumelanins: Unexplored bio-optoelectronic materials Angew. Chem., Int. Ed. 2009, 48, 3914-3921
8. Della Vecchia, N. F.; Avolio, R.; Alfè, M.; Errico, M. E.; Napolitano, A.; d'Ischia, M. Building-block diversity in polydopamine underpins a multifunctional eumelanin-type platform tunable through a quinone control point Adv. Funct. Mater. 2012, 23, 1331-1340
9. Dreyer, D. R.; Miller, D. J.; Freeman, B. D.; Paul, D. R.; Bielawski, C. W. Elucidating the structure of poly(dopamine) Langmuir 2012, 28, 6428-6435
10. Hong, S.; Na, Y. S.; Choi, S.; Song, I. T.; Kim, W. Y.; Lee, H. Non-covalent self-assembly and covalent polymerisation co-contribute to polydopamine formation Adv. Funct. Mater. 2012, 22, 4711-4717
11. Lee, H.; Dellatore, S. M.; Miller, W. M.; Messersmith, P. B. Mussel-inspired surface chemistry for multifunctional coatings Science 2007, 318, 426-430
12. Kang, S. M.; Rho, J.; Choi, I. S.; Messersmith, P. B.; Lee, H. Norepinephrine: Material-independent, multifunctional surface modification reagent J. Am. Chem. Soc. 2009, 131, 13224-13225
13. Wei, Q.; Zhang, F.; Li, J.; Li, B.; Zhao, C. Oxydant-induced dopamine polymerization for multifunctional coatings Polym. Chem. 2010, 1, 1430-1433
14. Bernsmann, F.; Ball, V.; Addiego, F.; Ponche, A.; Michel, M.; Gracio, J.; Toniazzo, V.; Ruch, D. Dopamine-melanin film deposition depends on the used oxidant and buffer solution Langmuir 2011, 27, 2819-2825
15. Dreyer, D. R.; Miller, D. J.; Freeman, B. D.; Paul, D. R.; Bielawski, C. W. Perspectives on poly(dopamine) Chem. Sci. 2013, 4, 3796-3802
16. D'Ischia, M.; Napolitano, A.; Pezzella, A.; Land, E. J.; Ramsden, C. A.; Riley, P. A. 5,6-Didroxyindoles and indole-5,6-diones Adv. Heterocycl. Chem. 2005, 89, 1-63
17. Szpoganicz, B.; Gidanian, S.; Kong, P.; Farmer, P. Metal binding by melanins: studies of colloidal dihydroxyindole-melanin, and its complexation by Cu(II) and Zn(II) ions J. Inorg. Biochem. 2002, 89, 45-53
18. El-Ayaan, U.; Herlinger, E.; Jameson, R. F.; Linert, W. J. Chem. Soc., Dalton Trans. 1997, 2813-2817
19. Bridelli, M. G. Metal binding by melanins: studies of colloidal dihydroxyindole-melanin, and its complexation by Cu(II) and Zn(II) ions Biophys. Chem. 1998, 73, 227-239
20. Chen, C.-T.; Ball, V.; Gracio, J. J. A.; Singh, M. K.; Toniazzo, V.; Ruch, D.; Buehler, M. J. Self-assembly of tetramers of 5,6-dihydroxyindole explains the primary physical properties of eumelanin: Experiment, simulation, and design ACS Nano 2013, 7, 1524-1532
21. Ball, V. Impedance spectroscopy and zeta potential titration of dopa-melanin films produced by oxidation of dopamine Colloids Surf., A 2010, 363, 92-97
22. Del Frari, D.; Bour, J.; Ball, V.; Toniazzo, V.; Ruch, D. Degradation of polydopamine coatings by sodium hypochlorite: A process depending on the substrate and the film synthesis method Polym. Degrad. Stab. 2012, 97, 1844-1849
23. Meredith, P.; Powell, B. J.; Riesz, J.; Nighswander-Rempel, S. P.; Pederson, M. R.; Moore, E. G. Towards structure-property-function relationships for eumelanin Soft Matter 2006, 2, 37-44
24. Pop-Georgievski, O.; Popelka, S.; Houska, M.; Chvostová, D.; Proks, V.; Rypáček, F. Poly(ethyleneoxide) layers grafted to dopamine-melanin anchoring layer: stability and resistance to protein adsorption Biomacromolecules 2011, 12, 3232-3242
25. Arzillo, M.; Mangiapia, G.; Pezzella, A.; Heenan, R. K.; Radulescu, A.; Paduano, L.; d'Ischia, M. Eumelanin buildup on the nanoscale: aggregate growth/assembly and visible absorption development in biomimetic 5,6-dihydroxyindole polymerization Biomacromolecules 2012, 13, 2379-2390
26. Kawatsura, K.; Takeshima, N.; Imaoku, T.; Takahiro, K.; Mokuno, Y.; Horino, Y.; Sekioka, T.; Terasawa, M. High-resolution X-ray spectroscopy for copper and copper oxides and a new WDX system using an ion microbeam Nucl. Instrum. Methods Phys. Res., Sect. B 2002, 193, 877-882
27. Sakai, A.; Ninomiya, S.; Hiraoka, K. XPS depth analysis of CuO by electrospray droplet impact Surf. Interface Anal. 2012, 44, 938-941
28. Watt, A. A. R.; Bothma, J. P.; Meredith, P. The supramolecular structure of melanin Soft Matter 2009, 5, 3754-3760
29. Meng, S.; Kaxiras, E. Theoretical models of eumelanin protomolecules and their optical properties Biophys. J. 2008, 94, 2095-2105
30. Gallas, J. M.; Littrell, K. C.; Seifert, S.; Zajac, G. W.; Thyagarajan, P. Solution structure of copper ion-induced molecular aggregates of tyrosine melanin Biophys. J. 1999, 77, 1135-1142
31. Ito, S.; Wakamatsu, K. Chemical degradation of melanins: Application to identification of dopamine-melanin Pigm. Cell Res. 1998, 11, 120-126