Self-assembly of tetramers of 5,6-dihydroxyindole explains the primary physical properties of eumelanin: Experiment, simulation, and design

ACS Nano

Volumn 7, Issue 2, 2013, Pages 1524-1532

  Chen, Chun Teh ^a   Ball, Vincent ^b,c,d,e   De Almeida Gracio, José Joaquim ^f,g   Singh, Manoj Kumar ^f,g   Toniazzo, Valérie ^b   Ruch, David ^a,b   Buehler, Markus J ^a  

^a Massachusetts Institute of Technology   (United States)

^b LUXEMBOURG INSTITUTE OF SCIENCE AND TECHNOLOGY   (Luxembourg)

^c UNIVERSITÉ DE STRASBOURG   (France)

^d INSERM   (France)

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

^f UNIVERSITY OF AVEIRO   (Portugal)

^g UNIVERSITY OF AVEIRO   (Portugal)

Author keywords

electrical conductivity; eumelanin; mechanical properties; molecular dynamics; self assembly

Indexed keywords

BROAD BANDS; DENSITY FUNCTIONAL THEORY CALCULATIONS; DRY AND WET CONDITIONS; ELECTRICAL CONDUCTIVITY; EUMELANIN FILMS; EUMELANINS; EXPERIMENTAL OBSERVATION; FREE RADICAL SCAVENGING; INTERLAYER DISTANCE; ISOTROPIC MATERIALS; LAYER-BY-LAYER FILMS; MASS DENSITIES; NON-COVALENT; NON-RADIATIVE RELAXATION; ORDERS OF MAGNITUDE; PHYSICOCHEMICAL PROPERTY; QUANTUM-MECHANICAL STUDY; SECONDARY STRUCTURES; STRUCTURAL AND MECHANICAL PROPERTIES; SUPRAMOLECULAR ORGANIZATIONS; TETRAMERS; TRANSMISSION ELECTRON MICROSCOPE; YOUNG'S MODULUS;

ABSORPTION SPECTROSCOPY; DENSITY (SPECIFIC GRAVITY); DENSITY FUNCTIONAL THEORY; ELASTIC MODULI; ELECTRIC CONDUCTIVITY; MECHANICAL PROPERTIES; MOLECULAR DYNAMICS; MOLECULES; OLIGOMERS; QUANTUM THEORY; SELF ASSEMBLY; TRANSMISSION ELECTRON MICROSCOPY;

STRUCTURAL DESIGN;

5,6 DIHYDROXYINDOLE; 5,6-DIHYDROXYINDOLE; EUMELANIN; INDOLE DERIVATIVE; MELANIN; POLYMER;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; DRUG DESIGN; ELECTRIC CONDUCTIVITY; PHYSICAL PHENOMENA;

DRUG DESIGN; ELECTRIC CONDUCTIVITY; INDOLES; MELANINS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PHYSICAL PROCESSES; POLYMERS;

EID: 84874444535     PISSN: 19360851     EISSN: 1936086X     Source Type: Journal    
DOI: 10.1021/nn305305d     Document Type: Article

References (38)

1. Meredith, P.; Sarna, T. The Physical and Chemical Properties of Eumelanin Pigm. Cell Res. 2006, 19, 572-594
2. 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
3. Ball, V.; Del Frari, D.; Michel, M.; Buehler, M.; Toniazzo, V.; Singh, M.; Gracio, J.; Ruch, D. Deposition Mechanism and Properties of Thin Polydopamine Films for High Added Value Applications in Surface Science at the Nanoscale BioNanoScience 2012, 2, 16-34
4. Peles, D. N.; Hong, L.; Hu, D.-N.; Ito, S.; Nemanich, R. J.; Simon, J. D. Human Iridal Stroma Melanosomes of Varying Pheomelanin Contents Possess a Common Eumelanic Outer Surface J. Phys. Chem. B 2009, 113, 11346-11351
5. Jastrzebska, M.; Kocot, A.; Vij, J. K.; Zalewska-Rejdak, J.; Witecki, T. Dielectric Studies on Charge Hopping in Melanin Polymer J. Mol. Struct. 2002, 606, 205-210
6. Liu, Y.; Hong, L.; Kempf, V. R.; Wakamatsu, K.; Ito, S.; Simon, J. D. Ion-Exchange and Adsorption of Fe(III) by Sepia Melanin Pigm. Cell Res. 2004, 17, 262-269
7. Kollias, N.; Sayre, R. M.; Zeise, L.; Chedekel, M. R. New Trends in Photobiology: Photoprotection by Melanin J. Photochem. Photobiol., B 1991, 9, 135-160
8. Clancy, C. M. R.; Nofsinger, J. B.; Hanks, R. K.; Simon, J. D. A Hierarchical Self-Assembly of Eumelanin J. Phys. Chem. B 2000, 104, 7871-7873
9. Pezzella, A.; d'Ischia, M.; Napolitano, A.; Palumbo, A.; Prota, G. An Integrated Approach to the Structure of Sepia Melanin. Evidence for a High Proportion of Degraded 5,6-Dihydroxyindole-2-carboxylic Acid Units in the Pigment Backbone Tetrahedron 1997, 53, 8281-8286
10. Cheng, J. I. N.; Moss, S. C.; Eisner, M.; Zschack, P. X-ray Characterization of Melanins-I Pigm. Cell Res. 1994, 7, 255-262
11. Cheng, J. I. N.; Moss, S. C.; Eisner, M. X-ray Characterization of Melanins-II Pigm. Cell Res. 1994, 7, 263-273
12. Zajac, G. W.; Gallas, J. M.; Cheng, J.; Eisner, M.; Moss, S. C.; Alvarado-Swaisgood, A. E. The Fundamental Unit of Synthetic Melanin: A Verification by Tunneling Microscopy of X-ray Scattering Results Biochim. Biophys. Acta 1994, 1199, 271-278
13. Gallas, J. M.; Littrell, K. C.; Seifert, S.; Zajac, G. W.; Thiyagarajan, P. Solution Structure of Copper Ion-Induced Molecular Aggregates of Tyrosine Melanin Biophys. J. 1999, 77, 1135-1142
14. Clancy, C. M. R.; Simon, J. D. Ultrastructural Organization of Eumelanin from Sepia Officinalis Measured by Atomic Force Microscopy Biochemistry 2001, 40, 13353-13360
15. 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
16. 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, 10.1002/adfm.201202127
17. Napolitano, A.; Pezzella, A.; Prota, G.; Seraglia, R.; Traldi, P. Structural Analysis of Synthetic Melanins from 5,6-Dihydroxyindole by Matrix-Assisted Laser Desorption/Ionization Mass Spectrometry Rapid Commun. Mass Spectrom. 1996, 10, 468-472
18. Stark, K. B.; Gallas, J. M.; Zajac, G. W.; Eisner, M.; Golab, J. T. Spectroscopic Study and Simulation from Recent Structural Models for Eumelanin: II. Oligomers J. Phys. Chem. B 2003, 107, 11558-11562
19. Stark, K. B.; Gallas, J. M.; Zajac, G. W.; Eisner, M.; Golab, J. T. Spectroscopic Study and Simulation from Recent Structural Models for Eumelanin: I. Monomer, Dimers J. Phys. Chem. B 2003, 107, 3061-3067
20. Kaxiras, E.; Tsolakidis, A.; Zonios, G.; Meng, S. Structural Model of Eumelanin Phys. Rev. Lett. 2006, 97, 218102
21. Meng, S.; Kaxiras, E. Theoretical Models of Eumelanin Protomolecules and Their Optical Properties Biophys. J. 2008, 94, 2095-2105
22. Bridelli, M. G. Self-Assembly of Melanin Studied by Laser Light Scattering Biophys. Chem. 1998, 73, 227-239
23. Miyasaka, Y.; Nakamura, A.; Temmyo, J. Graphite Thin Films Consisting of Nanograins of Multilayer Graphene on Sapphire Substrates Directly Grown by Alcohol Chemical Vapor Deposition Jpn. J. Appl. Phys. 2011, 50, 04DH12
24. Park, J. H.; Aluru, N. R. Self-Assembly of Graphenes Surf. Sci. 2011, 605, 1616-1620
25. Watt, A. A. R.; Bothma, J. P.; Meredith, P. The Supramolecular Structure of Melanin Soft Matter 2009, 5, 3754-3760
26. Herlinger, E.; Jameson, R. F.; Linert, W. Spontaneous Autoxidation of Dopamine J. Chem. Soc., Perkin Trans. 2 1995, 259-263
27. Raper, H. S. The Tyrosinase-Tyrosine Reaction. VI. Production from Tyrosine of 5:6-Dihydroxyindole and 5:6-Dihydroxyindole-2-carboxylic Acid-The Precursors of Melanin Biochem. J. 1927, 21, 89-96
28. Bernsmann, F.; Ponche, A.; Ringwald, C.; Hemmerlé, J.; Raya, J.; Bechinger, B.; Voegel, J.-C.; Schaaf, P.; Ball, V. Characterization of Dopamine-Melanin Growth on Silicon Oxide J. Phys. Chem. C 2009, 113, 8234-8242
29. Zeise, L.; Addison, R. B.; Chedekel, M. R. Bio-Analytical Studies of Eumelanins. I. Characterization of Melanin the Particle Pigm. Cell Res. 1992, 2, 48-53
30. Moses, D. N.; Mattoni, M. A.; Slack, N. L.; Waite, J. H.; Zok, F. W. Role of Melanin in Mechanical Properties of Glycera Jaws Acta Biomater. 2006, 2, 521-530
31. Swift, J. A. Speculations on the Molecular Structure of Eumelanin Int. J. Cosmet. Sci. 2009, 31, 143-150
32. Bhushan, B. Springer Handbook of Nanotechnology, 2 nd ed.; Springer: Berlin, 2007.
33. Hatton, R. A.; Blanchard, N. P.; Stolojan, V.; Miller, A. J.; Silva, S. R. P. Nanostructured Copper Phthalocyanine-Sensitized Multiwall Carbon Nanotube Films Langmuir 2007, 23, 6424-6430
34. Ball, V. Impedance Spectroscopy and Zeta Potential Titration of Dopa-Melanin Films Produced by Oxidation of Dopamine Colloids Surf., A 2010, 363, 92-97
35. Decher, G. Fuzzy Nanoassemblies: Toward Layered Polymeric Multicomposites Science 1997, 277, 1232-1237
36. Lee, H.; Dellatore, S. M.; Miller, W. M.; Messersmith, P. B. Mussel-Inspired Surface Chemistry for Multifunctional Coatings Science 2007, 318, 426-430
37. Gaedt, K.; Höltje, H.-D. Consistent Valence Force-Field Parameterization of Bond Lengths and Angles with Quantum Chemical Ab Initio Methods Applied to Some Heterocyclic Dopamine D3-Receptor Agonists J. Comput. Chem. 1998, 19, 935-946
38. Il'ichev, Y. V.; Simon, J. D. Building Blocks of Eumelanin: Relative Stability and Excitation Energies of Tautomers of 5,6-Dihydroxyindole and 5,6-Indolequinone J. Phys. Chem. B 2003, 107, 7162-7171