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Volumn 84, Issue 3, 2008, Pages 600-607

Structural effects on the electronic absorption properties of 5,6-dihydroxyindole oligomers: The potential of an integrated experimental and DFT approach to model eumelanin optical properties

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EID: 84962469610     PISSN: 00318655     EISSN: 17511097     Source Type: Journal    
DOI: 10.1111/j.1751-1097.2007.00249.x     Document Type: Article
Times cited : (39)

References (50)
  • 1
    • 0002281576 scopus 로고    scopus 로고
    • The chemistry of melanins and related metabolites
    • Edited by J. J. Nordlund, R. E. Boissy, V. J. Hearing, R. A. King and J. P. Ortonne, Oxford University Press, New York
    • Prota, G., M. d’Ischia and A. Napolitano (1998) The chemistry of melanins and related metabolites. In The Pigmentary System: Its Physiology and Pathophysiology (Edited by J. J. Nordlund, R. E. Boissy, V. J. Hearing, R. A. King and J. P. Ortonne), pp. 307–332. Oxford University Press, New York.
    • (1998) The Pigmentary System: Its Physiology and Pathophysiology , pp. 307-332
    • Prota, G.1    D’Ischia, M.2    Napolitano, A.3
  • 2
    • 33750541700 scopus 로고    scopus 로고
    • The physical and chemical properties of eumelanin
    • Meredith, P. and T. Sarna (2006) The physical and chemical properties of eumelanin. Pigment Cell Res. 19, 572–594.
    • (2006) Pigment Cell Res , vol.19 , pp. 572-594
    • Meredith, P.1    Sarna, T.2
  • 3
    • 0037902622 scopus 로고    scopus 로고
    • A chemist’s view of melanogenesis
    • Ito, S. (2003) A chemist’s view of melanogenesis. Pigment Cell Res. 16, 230–236.
    • (2003) Pigment Cell Res , vol.16 , pp. 230-236
    • Ito, S.1
  • 4
    • 0034798327 scopus 로고    scopus 로고
    • Variation in melanin content and composition in type V and VI photoexposed and photoprotected human skin: The dominant role of DHI
    • Alaluf, S., A. Heath, N. Carter, D. Atkins, H. Mahalingam, K. Barrett, R. Kolb and N. Smit (2001) Variation in melanin content and composition in type V and VI photoexposed and photoprotected human skin: The dominant role of DHI. Pigment Cell Res. 14, 337–347.
    • (2001) Pigment Cell Res , vol.14 , pp. 337-347
    • Alaluf, S.1    Heath, A.2    Carter, N.3    Atkins, D.4    Mahalingam, H.5    Barrett, K.6    Kolb, R.7    Smit, N.8
  • 6
    • 33751213726 scopus 로고    scopus 로고
    • The chemical structure of melanin
    • Simon, J D. and S. Ito (2004) The chemical structure of melanin. Reply. Pigment Cell Res. 17, 423–424.
    • (2004) Reply. Pigment Cell Res , vol.17 , pp. 423-424
    • Simon, J.D.1    Ito, S.2
  • 7
    • 0035818451 scopus 로고    scopus 로고
    • Ultrastructural organization of eumelanin from Sepia officinalis measured by atomic force microscopy
    • Clancy, C. M. R. and J. D. Simon (2001) Ultrastructural organization of eumelanin from Sepia officinalis measured by atomic force microscopy. Biochemistry 40, 13353–13360.
    • (2001) Biochemistry , vol.40 , pp. 13353-13360
    • Clancy, C.M.R.1    Simon, J.D.2
  • 8
    • 0028491919 scopus 로고
    • X-ray characterization of melanins—II
    • Cheng, J., S. C. Moss and M. Eisner (1994) X-ray characterization of melanins—II. Pigment Cell Res. 7, 263–273.
    • (1994) Pigment Cell Res , vol.7 , pp. 263-273
    • Cheng, J.1    Moss, S.C.2    Eisner, M.3
  • 9
    • 2542425585 scopus 로고    scopus 로고
    • A first-principles density-functional calculations of the electronic and vibrational structure of the key melanin monomers
    • Powell, B. J., T. Baruah, N. Bernstein, K. Brake, R. H. McKenzie, P. Meredith and M. R. Pederson (2004) A first-principles density-functional calculations of the electronic and vibrational structure of the key melanin monomers. J. Chem. Phys. 120, 8608–8615.
    • (2004) J. Chem. Phys , vol.120 , pp. 8608-8615
    • Powell, B.J.1    Baruah, T.2    Bernstein, N.3    Brake, K.4    McKenzie, R.H.5    Meredith, P.6    Pederson, M.R.7
  • 10
    • 11444251796 scopus 로고    scopus 로고
    • 5,6-dihydroxyindole-2-carboxylic acid (DHI-CA): A first principles density-functional study
    • Powell, B. J. (2005) 5,6-dihydroxyindole-2-carboxylic acid (DHI-CA): A first principles density-functional study. Chem. Phys. Lett. 402, 111–115.
    • (2005) Chem. Phys. Lett , vol.402 , pp. 111-115
    • Powell, B.J.1
  • 11
    • 0038055976 scopus 로고    scopus 로고
    • Spectroscopic study and simulation from recent structural models for eumelanin: I. Monomer, dimers
    • 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. 107, 3061–3067.
    • (2003) J. Phys. Chem , vol.107 , pp. 3061-3067
    • Stark, K.B.1    Gallas, J.M.2    Zajac, G.W.3    Eisner, M.4    Golab, J.T.5
  • 12
    • 34247361971 scopus 로고    scopus 로고
    • Photophysics of eumelanin: Ab initio studies on the electronic spectroscopy and photo-chemistry of 5,6-dihydroxyindole
    • Sobolewski, A. L. and W. Domcke (2007) Photophysics of eumelanin: Ab initio studies on the electronic spectroscopy and photo-chemistry of 5,6-dihydroxyindole. Chem. Phys. Chem. 8, 756–762.
    • (2007) Chem. Phys. Chem , vol.8 , pp. 756-762
    • Sobolewski, A.L.1    Domcke, W.2
  • 14
    • 33845582917 scopus 로고    scopus 로고
    • Mid-infrared absorption spectrum of 5,6-dihydroxyindole-2-carboxylic acid
    • Okuda, H., A. Nakamura, K. Wakamatsu, S. Ito and T. Sota (2007) Mid-infrared absorption spectrum of 5,6-dihydroxyindole-2-carboxylic acid. Chem. Phys. Lett. 433, 355–359.
    • (2007) Chem. Phys. Lett , vol.433 , pp. 355-359
    • Okuda, H.1    Nakamura, A.2    Wakamatsu, K.3    Ito, S.4    Sota, T.5
  • 15
    • 0042705196 scopus 로고    scopus 로고
    • Building blocks of eumelanin: Relative stability and excitation energies of tautomers of 5,6-dihydroxyindole and 5,6-indolequinone
    • 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. B 107, 7162–7171.
    • (2003) J. Phys. Chem. B , vol.107 , pp. 7162-7171
    • Il’Ichev, Y.V.1    Simon, J.D.2
  • 16
    • 0038626622 scopus 로고    scopus 로고
    • Electronic properties of random polymers: Modeling optical spectra of melanins
    • Bochenek, K. and E. Gudowska-Nowak (2003) Electronic properties of random polymers: Modeling optical spectra of melanins. Acta Phys. Pol. B 34, 2775–2790.
    • (2003) Acta Phys. Pol. B , vol.34 , pp. 2775-2790
    • Bochenek, K.1    Gudowska-Nowak, E.2
  • 17
    • 0242270639 scopus 로고    scopus 로고
    • Spectroscopic study and simulation from recent structural models for eumelanin: II
    • 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: II. Oligomers. J. Phys. Chem. B 107, 11558–11562.
    • (2003) Oligomers. J. Phys. Chem. B , vol.107 , pp. 11558-11562
    • Stark, K.B.1    Gallas, J.M.2    Zajac, G.W.3    Eisner, M.4    Golab, J.T.5
  • 18
    • 13444311039 scopus 로고    scopus 로고
    • Effect of stacking and redox state on optical absorption spectra of melanins-comparison of theoretical and experimental results
    • Stark, K. B., J. M. Gallas, G. W. Zajac, J. T. Golab, S. Gidanian, T. McIntire and P. J. Farmer (2005) Effect of stacking and redox state on optical absorption spectra of melanins-comparison of theoretical and experimental results. J. Phys. Chem. B 109, 1970– 1977.
    • (2005) J. Phys. Chem. B , vol.109
    • Stark, K.B.1    Gallas, J.M.2    Zajac, G.W.3    Golab, J.T.4    Gidanian, S.5    McIntire, T.6    Farmer, P.J.7
  • 20
    • 33646194551 scopus 로고    scopus 로고
    • Chemical and structural disorder in eumelanins—A possible explanation for broad band absorbance
    • Tran, M. L., B. J. Powell and P. Meredith (2006) Chemical and structural disorder in eumelanins—A possible explanation for broad band absorbance. Biophys. J. 90, 743–752.
    • (2006) Biophys. J , vol.90 , pp. 743-752
    • Tran, M.L.1    Powell, B.J.2    Meredith, P.3
  • 22
    • 84961976124 scopus 로고    scopus 로고
    • Short-lived quinonoid species from 5,6-dihydroxyindole dimers en route to eumelanin polymers: Integrated chemical, pulse radiolytic, and quantum mechanical investigation
    • Pezzella, A., L. Panzella, O. Crescenzi, A. Napolitano, S. Navaratnam, 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.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 15490-15498
    • Pezzella, A.1    Panzella, L.2    Crescenzi, O.3    Napolitano, A.4    Navaratnam, S.5    Edge, R.6    Land, E.J.7    Barone, V.8    D’Ischia, M.9
  • 23
    • 34147117162 scopus 로고    scopus 로고
    • The first 5,6-dihydroxyindole tetramer by oxidation of 5,5',6,6,-tetrahydroxy-2,4'-biindolyl and unexpected issue of positional reactivity en route to eumelanin-related polymers
    • 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 unexpected issue of positional reactivity en route to eumelanin-related polymers. Org. Lett. 9, 1411–1414.
    • (2007) Org. Lett , vol.9 , pp. 1411-1414
    • Panzella, L.1    Pezzella, A.2    D’Ischia, M.3
  • 26
    • 0001475454 scopus 로고    scopus 로고
    • Toward reliable density functional methods without adjustable parameters: The PBE0 model
    • Adamo, C. and V. Barone (1999) Toward reliable density functional methods without adjustable parameters: The PBE0 model. J. Chem. Phys. 110, 6158–6170.
    • (1999) J. Chem. Phys , vol.110 , pp. 6158-6170
    • Adamo, C.1    Barone, V.2
  • 27
    • 7744246251 scopus 로고    scopus 로고
    • Absorption and fluorescence spectra of uracil in the gas phase and in aqueous solution: A TD-DFT quantum mechanical study
    • Improta, R. and V. Barone (2004) Absorption and fluorescence spectra of uracil in the gas phase and in aqueous solution: A TD-DFT quantum mechanical study. J. Am. Chem. Soc. 126, 14320–14321.
    • (2004) J. Am. Chem. Soc , vol.126 , pp. 14320-14321
    • Improta, R.1    Barone, V.2
  • 28
    • 0036462496 scopus 로고    scopus 로고
    • Quantum mechanical study of the conformational behavior of proline and 4R-hydroxyproline dipeptide analogues in vacuum and in aqueous solution
    • Benzi, C., R. Improta, G. Scalmani and V. Barone (2002) Quantum mechanical study of the conformational behavior of proline and 4R-hydroxyproline dipeptide analogues in vacuum and in aqueous solution. J. Comp. Chem. 23, 341–350.
    • (2002) J. Comp. Chem , vol.23 , pp. 341-350
    • Benzi, C.1    Improta, R.2    Scalmani, G.3    Barone, V.4
  • 29
    • 0037197256 scopus 로고    scopus 로고
    • Conformational analysis of the tyrosine dipeptide analogue in the gas phase and in aqueous solution by a density functional ⁄ continuum solvent model
    • Langella, E., N. Rega, R. Improta, O. Crescenzi and V. Barone (2002) Conformational analysis of the tyrosine dipeptide analogue in the gas phase and in aqueous solution by a density functional ⁄ continuum solvent model. J. Comp. Chem. 23, 650–661.
    • (2002) J. Comp. Chem , vol.23 , pp. 650-661
    • Langella, E.1    Rega, N.2    Improta, R.3    Crescenzi, O.4    Barone, V.5
  • 30
    • 84962360895 scopus 로고    scopus 로고
    • Understanding the role of stereoelectronic effects in determining collagen stability. 2. A quantum mechanical ⁄ molecular mechanical study of (proline-proline-glycine)n polypeptides
    • Improta, R., F. Mele, O. Crescenzi, C. Benzi and V. Barone (2002) Understanding the role of stereoelectronic effects in determining collagen stability. 2. A quantum mechanical ⁄ molecular mechanical study of (proline-proline-glycine)n polypeptides. J. Am. Chem. Soc. 124, 7857–7865.
    • (2002) J. Am. Chem. Soc , vol.124 , pp. 7857-7865
    • Improta, R.1    Mele, F.2    Crescenzi, O.3    Benzi, C.4    Barone, V.5
  • 31
    • 33746925603 scopus 로고    scopus 로고
    • Ab initio investigation of the n → π* transitions in thiocarbonyl dyes
    • Jacquemin, D., V. Wathelet and E. A. Perpete (2006) Ab initio investigation of the n → π* transitions in thiocarbonyl dyes. J. Phys. Chem. A 110, 9145–9152.
    • (2006) J. Phys. Chem. A , vol.110 , pp. 9145-9152
    • Jacquemin, D.1    Wathelet, V.2    Perpete, E.A.3
  • 34
    • 84962440857 scopus 로고    scopus 로고
    • 17 O) spectra of acetone in aqueous solution. An integrated Car-Parrinello and DFT ⁄ PCM approach
    • 17 O) spectra of acetone in aqueous solution. An integrated Car-Parrinello and DFT ⁄ PCM approach. J. Phys. Chem. B 109, 445–453.
    • (2005) J. Phys. Chem. B , vol.109 , pp. 445-453
    • Crescenzi, O.1    Pavone, M.2    De Angelis, F.3    Barone, V.4
  • 35
    • 0242345989 scopus 로고    scopus 로고
    • Computation of the acetone ultraviolet spectrum in gas phase and in aqueous solution by a mixed discrete ⁄ continuum model
    • Aquilante, F., M. Cossi, O. Crescenzi, G. Scalmani and V. Barone (2003) Computation of the acetone ultraviolet spectrum in gas phase and in aqueous solution by a mixed discrete ⁄ continuum model. Mol. Phys. 101, 1945–1953.
    • (2003) Mol. Phys , vol.101 , pp. 1945-1953
    • Aquilante, F.1    Cossi, M.2    Crescenzi, O.3    Scalmani, G.4    Barone, V.5
  • 36
    • 0002466981 scopus 로고    scopus 로고
    • A TDDFT study of the electronic spectrum of s-tetrazine in the gas-phase and in aqueous solution
    • Adamo, C. and V. Barone (2000) A TDDFT study of the electronic spectrum of s-tetrazine in the gas-phase and in aqueous solution. Chem. Phys. Lett. 330, 152–160.
    • (2000) Chem. Phys. Lett , vol.330 , pp. 152-160
    • Adamo, C.1    Barone, V.2
  • 37
    • 33645949559 scopus 로고
    • Self-consistent molecular orbital methods. XXIII. A polarization-type basis set for second-row elements
    • For a general introduction to basis sets see: Foresman, J. B. and A. Frisch (1996) Exploring Chemistry with Electronic Structure Methods. Gaussian, Inc, Pittsburg, PA
    • Francl, M. M., W. J. Pietro, W. J. Hehre, J. S. Binkley, M. S. Gordon, D. J. DeFrees and J. A. Pople (1982) Self-consistent molecular orbital methods. XXIII. A polarization-type basis set for second-row elements. J. Chem. Phys. 77, 3654–3665. For a general introduction to basis sets see: Foresman, J. B. and A. Frisch (1996) Exploring Chemistry with Electronic Structure Methods. Gaussian, Inc, Pittsburg, PA.
    • (1982) J. Chem. Phys , vol.77 , pp. 3654-3665
    • Francl, M.M.1    Pietro, W.J.2    Hehre, W.J.3    Binkley, J.S.4    Gordon, M.S.5    Defrees, D.J.6    Pople, J.A.7
  • 38
    • 84961986752 scopus 로고    scopus 로고
    • New developments in the polarizable continuum model for quantum mechanical and classical calculations on molecules in solution
    • Cossi, M., G. Scalmani, N. Rega and V. Barone (2002) New developments in the polarizable continuum model for quantum mechanical and classical calculations on molecules in solution. J. Chem. Phys. 117, 43–54.
    • (2002) J. Chem. Phys , vol.117 , pp. 43-54
    • Cossi, M.1    Scalmani, G.2    Rega, N.3    Barone, V.4
  • 40
    • 84962428748 scopus 로고    scopus 로고
    • Achieving linear-scaling computational cost for the polarizable continuum model of solvation
    • Scalmani, G., V. Barone, K. N. Kudin, C. S. Pomelli, G. E. Scuseria and M. J. Frisch (2004) Achieving linear-scaling computational cost for the polarizable continuum model of solvation. Theor. Chem. Acc. 111, 90–100.
    • (2004) Theor. Chem. Acc , vol.111 , pp. 90-100
    • Scalmani, G.1    Barone, V.2    Kudin, K.N.3    Pomelli, C.S.4    Scuseria, G.E.5    Frisch, M.J.6
  • 41
    • 84961981991 scopus 로고    scopus 로고
    • A new definition of cavities for the computation of solvation free energies by the polarizable continuum model
    • Barone, V., M. Cossi and J. Tomasi (1997) A new definition of cavities for the computation of solvation free energies by the polarizable continuum model. J. Chem. Phys. 107, 3210–3221.
    • (1997) J. Chem. Phys , vol.107 , pp. 3210-3221
    • Barone, V.1    Cossi, M.2    Tomasi, J.3
  • 42
    • 0032533083 scopus 로고    scopus 로고
    • An efficient implementation of time-dependent density-functional theory for the calculation of excitation energies of large molecules
    • Stratmann, R. E., G. E. Scuseria and M. J. Frisch (1998) An efficient implementation of time-dependent density-functional theory for the calculation of excitation energies of large molecules. J. Chem. Phys. 109, 8218–8224.
    • (1998) J. Chem. Phys , vol.109 , pp. 8218-8224
    • Stratmann, R.E.1    Scuseria, G.E.2    Frisch, M.J.3
  • 43
    • 0030570285 scopus 로고    scopus 로고
    • Treatment of electronic excitations within the adiabatic approximation of time dependent density functional theory
    • Bauernschmitt, R. and R. Ahlrichs (1996) Treatment of electronic excitations within the adiabatic approximation of time dependent density functional theory. Chem. Phys. Lett. 256, 454–464.
    • (1996) Chem. Phys. Lett , vol.256 , pp. 454-464
    • Bauernschmitt, R.1    Ahlrichs, R.2
  • 44
    • 0000287603 scopus 로고    scopus 로고
    • Molecular excitation energies to high-lying bound states from time-dependent density-functional response theory: Characterization and correction of the time-dependent local density approximation ionization threshold
    • Casida, M. E., C. Jamorski, K. C. Casida and D. R. Salahub (1998) Molecular excitation energies to high-lying bound states from time-dependent density-functional response theory: Characterization and correction of the time-dependent local density approximation ionization threshold. J. Chem. Phys. 108, 4439–4449.
    • (1998) J. Chem. Phys , vol.108 , pp. 4439-4449
    • Casida, M.E.1    Jamorski, C.2    Casida, K.C.3    Salahub, D.R.4
  • 45
    • 21444444464 scopus 로고    scopus 로고
    • Accurate excitation energies from time-dependent density functional theory: Assessing the PBE0 model
    • Adamo, C., G. E. Scuseria and V. Barone (1999) Accurate excitation energies from time-dependent density functional theory: Assessing the PBE0 model. J. Chem. Phys. 111, 2889–2899.
    • (1999) J. Chem. Phys , vol.111 , pp. 2889-2899
    • Adamo, C.1    Scuseria, G.E.2    Barone, V.3
  • 46
    • 84962426273 scopus 로고    scopus 로고
    • Time-dependent density functional theory for molecules in liquid solutions
    • Cossi, M. and V. Barone (2001) Time-dependent density functional theory for molecules in liquid solutions. J. Chem. Phys. 115, 4708–4717.
    • (2001) J. Chem. Phys , vol.115 , pp. 4708-4717
    • Cossi, M.1    Barone, V.2
  • 48
    • 22444440100 scopus 로고    scopus 로고
    • Structure-property relationships for electron-vibrational coupling in conjugated organic oligomeric systems
    • O’Neill, L. and H. J. Byrne (2005) Structure-property relationships for electron-vibrational coupling in conjugated organic oligomeric systems. J. Phys. Chem. B. 109, 12685–12690.
    • (2005) J. Phys. Chem. B , vol.109 , pp. 12685-12690
    • O’Neill, L.1    Byrne, H.J.2
  • 49
    • 33847615576 scopus 로고    scopus 로고
    • Effective method to compute Franck-Condon integrals for optical spectra of large molecules in solution
    • Santoro, F., R. Improta, A. Lami, J. Bloino and V. Barone (2007) Effective method to compute Franck-Condon integrals for optical spectra of large molecules in solution. J. Chem. Phys. 126(8), 084509.
    • (2007) J. Chem. Phys , vol.126 , Issue.8 , pp. 084509
    • Santoro, F.1    Improta, R.2    Lami, A.3    Bloino, J.4    Barone, V.5
  • 50
    • 33846403719 scopus 로고    scopus 로고
    • Ab initio calculations of absorption spectra of large molecules in solution: Coumarin C153
    • Improta, R., V. Barone and F. Santoro (2007) Ab initio calculations of absorption spectra of large molecules in solution: Coumarin C153. Angew. Chem. Int. Edit. 46, 405–408.
    • (2007) Angew. Chem. Int. Edit , vol.46 , pp. 405-408
    • Improta, R.1    Barone, V.2    Santoro, F.3


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