Mechanisms for ultrafast nonradiative relaxation in electronically excited eumelanin constituents

Biophysical Journal

Volumn 95, Issue 9, 2008, Pages 4396-4402

  Meng, Sheng ^a   Kaxiras, Efthimios ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EUMELANIN; INDOLE; INDOLE DERIVATIVE; MELANIN; PROTON;

ARTICLE; CHEMISTRY; DIMERIZATION; ELECTRON; METABOLISM; OPTICS; QUANTUM THEORY; TIME;

DIMERIZATION; ELECTRONS; INDOLES; MELANINS; OPTICS AND PHOTONICS; PROTONS; QUANTUM THEORY; TIME FACTORS;

EID: 58149144255     PISSN: 00063495     EISSN: 15420086     Source Type: Journal    
DOI: 10.1529/biophysj.108.135756     Document Type: Article

References (54)

1. Kollias, N., R. M. Sayre, L. Zeise, and M. R. Chedekel. 1991. Photoprotection by melanin. J. Photochem. Photobiol. B. 9:135-160.
2. Seagle, B. L., E. M. Gasyna, W. F. Mieler, and J. R. Norris, Jr. 2006. Photoprotection of human retinal pigment epithelium cells against blue light-induced apoptosis by melanin free radicals from Sepia officinalis. Proc. Natl. Acad. Sci. USA. 103:16644-16648.
3. Meredith, P., and T. Sarna. 2006. The physical and chemical properties of eumelanin. Pigment Cell Res. 19:572-594.
4. Meredith, P., and J. Riesz. 2004. Radiative relaxation quantum yields for synthetic eumelanin. Photochem. Photobiol. 79:211-216.
5. Nofsinger, J. B., S. E. Forest, and J. D. Simon. 1999. Explanation for the disparity among absorption and action spectra of eumelanin. J. Phys. Chem. 103:11428-11432.
6. Nofsinger, J. B., and J. D. Simon. 2001. Radiative relaxation of Sepia eumelanin is affected by aggregation. Photochem. Photobiol. 74:31-37.
7. Dadachova, E., R. A. Bryan, X. Huang, T. Moadel, A. D. Schweitzer, P. Aisen, J. D. Nosanchuk, and A. Casadevall. 2007. Ionizing radiation changes the electronic properties of melanin and enhances the growth of melanized fungi. PloS ONE. 2:e457.
8. Warshel, A. 1976. Bicycle-pedal model for 1st step in vision process. Nature. 260:679-683.
9. Olsen, S., J. Riesz, I. Mahadevan, A. Coutts, B. J. Powell, R. H. McKenzie, S. C. Smith, and P. Meredith. 2007. Convergent proton transfer photocycles violate mirror-image symmetry in a key melanin monomer. J. Am. Chem. Soc. 129:6672-6673.
10. Bush,W. D., J. Carguilo, F. A. Zucca, A. Albertin, L. Zecca, G. S. Edwards, R. J. Nemanich, and J. D. Simon. 2006. The surface oxidation potential of human neuromelanin reveals a spherical architecture with a pheomelanin core and a eumelanin surface. Proc. Natl. Acad. Sci. USA. 103:14785-14789.
11. Ito, S. 2003. A chemist's view of melanogenesis. Pigment Cell Res. 16:230-236.
12. Il'ichev, Y. V., and J. D. Simon. 2003. Building blocks of eumelanin: relative stability and excitation energies of tautomers of 5,6-dihydroxyindole and 5,6-indolequinone. J. Phys. Chem. 107:7162-7171.
13. Kaxiras, E., A. Tsolakidis, G. Zonios, and S. Meng. 2006. Structural model of eumelanin. Phys. Rev. Lett. 97:218102.
14. Meng, S., and E. Kaxiras. 2008. Theoretical models of eumelanin protomolecules and their optical properties. Biophys. J. 94:2095-2105.
15. Runge, E., and E. K. U. Gross. 1984. Density-functional theory for time-dependent systems. Phys. Rev. Lett. 52:997-1000.
16. Soler, J. M., E. Artacho, J. D. Gale, A. García, J. Junquera, P. Ordejón, and D. Sánchez-Portal. 2002. The SIESTA method for ab initio order-N materials simulation. J. Phys. Condens. Matter. 14:2745-2779.
17. Junquera, J., O. Paz, D. Sanchez-Portal, and E.Artacho. 2001.Numerical atomic orbitals for linear-scaling calculations. Phys. Rev. B. 64:235111.
18. Casida, M. E. 1996. Recent Developments and Applications in Density Functional Theory. J. M. Seminario, editor. Elsevier, Amsterdam, The Netherlands.
19. Tavernelli, I., U. F. Rohrig, and U. Rothlisberger. 2005. Molecular dynamics in electronically excited states using time-dependent density functional theory. Mol. Phys. 103:963-981.
20. Tateyama, Y., N. Oyama, T. Ohno, and Y. Miyamoto. 2006. Real-time propagation time-dependent density functional theory study on the ring-opening transformation of the photoexcited crystalline benzene. J. Chem. Phys. 124:124507.
21. Castro, A., M. A. L. Marques, J. A. Alonso, G. F. Bertsch, and A. Rubio. 2004. Excited states dynamics in time-dependent density functional theory - high-field molecular dissociation and harmonic generation. Eur. Phys. J. D. 28:211-218.
22. Isborn, C. M., X. Li, and J. C. Tully. 2007. Time-dependent density functional theory Ehrenfest dynamics: collisions between atomic oxygen and graphite clusters. J. Chem. Phys. 126:134307.
23. Meng, S., and E. Kaxiras. 2008. Real-time, local basis-set implementation of time-dependent density functional theory for excited state dynamics simulations. J. Chem. Phys. 129:054110.
24. Hack, M. D., and D. G. Truhlar. 2000. Nonadiabatic trajectories at an exhibition. J. Phys. Chem. A. 104:7917-7926.
25. Tully, J. C. 1990. Molecular-dynamics with electronic-transitions. J. Chem. Phys. 93:1061-1071.
26. Zhu, C. Y., S. Nangia, A. W. Jasper, and D. G. Truhlar. 2004. Coherent switching with decay of mixing: an improved treatment of electronic coherence for non-Born-Oppenheimer trajectories. J. Chem. Phys. 121: 7658-7670.
27. Ben-Nun, M., and T. J. Martinez. 2002. Ab initio quantum molecular dynamics. Adv. Chem. Phys. 121:439-512.
28. Troullier, N., and J. L. Martins. 1991. Efficient pseudopotentials for plane-wave calculations. Phys. Rev. B. 43:1993-2006.
29. Ceperley, D. M., and B. J. Alder. 1980. Ground-state of the electron-gas by a stochastic method. Phys. Rev. Lett. 45:566-569.
30. Tsolakidis, A., and E. Kaxiras. 2005. A TDDFT study of the optical response of DNA bases, base pairs, and their tautomers in the gas phase. J. Phys. Chem. A. 109:2373-2380.
31. Dreuw, A., and M. Head-Gordon. 2004. Failure of time-dependent density functional theory for long-range charge-transfer excited states: the zincbacteriochlorin-bacteriochlorin and bacteriochlorophyll-spheroidene complexes. J. Am. Chem. Soc. 126:4007-4016.
32. Linstrom, P. J., and W. G. Mallard, editors. 2005. N. I. S. T. Chemistry WebBook. NIST Standard Reference Database 69. http://webbook.nist.gov.
33. Weiss, R. M., and A. Warshel. 1979.New view of the dynamics of singlet cis-trans photoisomerization. J. Am. Chem. Soc. 101:6131-6133.
34. Desouter-Lecomte, M., and J. C. Lorquet. 1979. Non-adiabatic interactions in unimolecular decay. 4. Transition probability as a function of the Massey parameter. J. Chem. Phys. 71:4391-4403.
35. Frutos, L. M., T. Andruniów, F. Santoro, N. Ferré, and M. Olivucci. 2007. Tracking the excited-state time evolution of the visual pigment with multiconfigurational quantum chemistry. Proc. Natl. Acad. Sci. USA. 104:7764-7769.
36. Tanner, C., C. Manca, and S. Leutwyler. 2003. Probing the threshold to H atom transfer along a hydrogen-bonded ammonia wire. Science. 302:1736-1739.
37. Coe, J. D., B. G. Levine, and T. J. Martinez. 2007. Ab initio molecular dynamics of excited-state intramolecular proton transfer using multi-reference perturbation theory. J. Phys. Chem. A. 111:11302-11310.
38. Paterson, M. J., M. A. Robb, L. Blancafort, and A. D. DeBellis. 2005. Mechanism of an exceptional class of photostabilizers: a seam of conical intersection parallel to excited state intramolecular proton transfer (ESIPT) in o-hydroxyphenyl-(1,3,5)-triazine. J. Chem. Phys. A. 109:7527-7537.
39. Coe, J. D., and T. J. Martinez. 2005. Competitive decay at two- and three-state conical intersections in excited-state intramolecular proton transfer. J. Am. Chem. Soc. 127:4560-4561.
40. Levine, B. G., C. Ko, J. Quenneville, and T. J. Martinez. 2006. Conical intersections and double excitations in time-dependent density functional theory. Mol. Phys. 104:1039-1051.
41. Löwdin, P.-O. 1965. Quantum genetics and the aperiodic solid. Some Aspects on the biological problems of heredity, mutations, ageing and tumours in view of the quantum theory of the DNA molecule. Adv. Quantum Chem. 2:213-361.
42. Groenhof, G., L. V. Schafer, M. Boggio-Pasqua, M. Goette, H. Grubmüller, and M. A. Robb. 2007. Ultrafast deactivation of an excited cytosine-guanine base pair in DNA. J. Am. Chem. Soc. 129:6812-6819.
43. Hudock, H. R., B. G. Levine, A. L. Thompson, H. Satzger, D. Townsend, N. Gador, S. Ullrich, A. Stolow, and T. J. Martinez. 2007. Ab initio molecular dynamics and time-resolved photoelectron spectroscopy of electronically excited uracil and thymine. J. Phys. Chem. A. 111:8500-8508.
44. Tahara, T., and S. Takeuchi. 2007. The answer to concerted versus step-wise controversy for the double proton transfer mechanism of 7-azaindole dimer in solution. Proc. Natl. Acad. Sci. USA. 104:5285-5290.
45. Kwon, O.-H., and A. H. Zewail. 2007. Double proton transfer dynamics of model DNA base pairs in the condensed phase. Proc. Natl. Acad. Sci. USA. 104:8703-8708.
46. Kato, M., A. V. Pisliakov, and A. Warshel. 2006. The barrier for proton transport in aquaporins as a challenge for electrostatic models: the role of protein relaxation in mutational calculations. Proteins Struct. Funct. Bioinform. 64:829-844.
47. Warshel, A., and Z. T. Chu. 2001. Nature of the surface crossing process in bacteriorhodopsin: computer simulations of the quantum dynamics of the primary photochemical event. J. Phys. Chem. B. 105:9857-9871.
48. Stark, K. B., J. M. Gallas, G. W. Zajac,M. Eisner, and J. T. Golab. 2003. Spectroscopic study and simulation from recent structural models for eumelanin. I. Monomer, dimers. J. Phys. Chem. B. 107:3061-3067.
49. Pezzella, A., L. Panzella, O. Crescenzi, A. Napolitano, S. Navaratman, R. Edge, E. J. Land, V. Barone, and M. d'Ischia. 2006. Short-lived quinonoid species from 5,6-dihydroxyindole dimers en route to eumelanin polymers: integrated chemical, pulse radiolytic, and quantum mechanical investigation. J. Am. Chem. Soc. 128:15490-15498.
50. McGinness, J., P. Corry, and P. Proctor. 1974. Amorphous semiconductor switching in melanins. Science. 183:853-855.
51. Cheng, J., S. C. Moss, M. Eisner, and P. Zschack. 1994. X-ray characterization of melanins - II. Pigment Cell Res. 7:263-273.
52. Tran, M. L., B. J. Powell, and P. Meredith. 2006. Chemical and structural disorder in eumelanins: a possible explanation for broadband absorbance. Biophys. J. 90:743-752.
53. Butcher, J. 2007. Spectroscopy of eumelanin monomers and dimers. Masters thesis. University of Queensland, Brisbane, Australia.
54. Panzella, L., A. Pezzella, A. Napolitano, and M. d'Ischia. 2007. The first 5,6-dihydroxyindole tetramer by oxidation of 5,5′,6,6′- tetrahydroxy-2,4′-biindolyl and an unexpected issue of positional reactivity en route to eumelanin-related polymers. Org. Lett. 7:1411-1414.