메뉴 건너뛰기




Volumn 243, Issue , 2012, Pages 7-16

TDDFT investigation of fluorescence properties of luciferin and oxyluciferin analogs bearing an amino group

Author keywords

Bio heterojunction analysis; Luciferin analog; Oxyluciferin analog; TDDFT calculation

Indexed keywords


EID: 84862984798     PISSN: 10106030     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jphotochem.2012.05.024     Document Type: Article
Times cited : (12)

References (55)
  • 1
    • 10644240820 scopus 로고
    • The chemical mechanism and evolutionary development of beetle bioluminescence
    • K.V. Wood The chemical mechanism and evolutionary development of beetle bioluminescence Photochemistry and Photobiology 62 1995 662 673
    • (1995) Photochemistry and Photobiology , vol.62 , pp. 662-673
    • Wood, K.V.1
  • 2
    • 0036865977 scopus 로고    scopus 로고
    • The origin, diversity, and structure function relationships of insect luciferases
    • DOI 10.1007/PL00012509
    • V.R. Viviani The origin, diversity and structure-function relationships of insect luciferases Cellular and Molecular Life Sciences 59 2002 1833 1850 (Pubitemid 36015859)
    • (2002) Cellular and Molecular Life Sciences , vol.59 , Issue.11 , pp. 1833-1850
    • Viviani, V.R.1
  • 5
    • 79959754307 scopus 로고    scopus 로고
    • Theoretical modulation of the color of light emitted by firefly oxyluciferin
    • L.P.D. Silva, and J.C.G.E.D. Silva Theoretical modulation of the color of light emitted by firefly oxyluciferin Journal of Computational Chemistry 32 2011 2654 2664
    • (2011) Journal of Computational Chemistry , vol.32 , pp. 2654-2664
    • Silva, L.P.D.1    Silva, J.C.G.E.D.2
  • 6
    • 78651421262 scopus 로고    scopus 로고
    • Accurate color tuning of firefly chromophore by modulation of local polarization electrostatic fields
    • D. Cai, M.A.L. Marques, and F. Nogueira Accurate color tuning of firefly chromophore by modulation of local polarization electrostatic fields Journal of Physical Chemistry B 115 2011 329 332
    • (2011) Journal of Physical Chemistry B , vol.115 , pp. 329-332
    • Cai, D.1    Marques, M.A.L.2    Nogueira, F.3
  • 8
    • 81255209257 scopus 로고    scopus 로고
    • Study on the effects of intermolecular interactions on firefly multicolor bioluminescence
    • L.P.D. Silva, and J.C.G.E.D. Silva Study on the effects of intermolecular interactions on firefly multicolor bioluminescence ChemPhysChem 12 2011 3002 3008
    • (2011) ChemPhysChem , vol.12 , pp. 3002-3008
    • Silva, L.P.D.1    Silva, J.C.G.E.D.2
  • 9
    • 0037905684 scopus 로고    scopus 로고
    • Theoretical study of the amazing firefly bioluminescence: The formation and structures of the light emitters
    • DOI 10.1021/ja021255a
    • G. Orlova, J.D. Goddard, and L.Y. Brovko Theoretical study of the amazing firefly bioluminescence: the formation and structures of the light emitters Journal of the American Chemical Society 125 2003 6962 6971 (Pubitemid 36682795)
    • (2003) Journal of the American Chemical Society , vol.125 , Issue.23 , pp. 6962-6971
    • Orlova, G.1    Goddard, J.D.2    Brovko, L.Yu.3
  • 12
    • 0002552327 scopus 로고
    • The chemi- and bioluminescence of firefly luciferin: An efficient chemical production of electronically excited states
    • E.H. White, E. Rapaport, H.H. Seliger, and T.A. Hopkins The chemi- and bioluminescence of firefly luciferin: an efficient chemical production of electronically excited states Bioorganic Chemistry 1 1971 92 122
    • (1971) Bioorganic Chemistry , vol.1 , pp. 92-122
    • White, E.H.1    Rapaport, E.2    Seliger, H.H.3    Hopkins, T.A.4
  • 13
    • 79961134132 scopus 로고    scopus 로고
    • Dynamics on the electronically excited state surface of the bioluminescent firefly luciferase-oxyluciferin system
    • C. Song, and Y.M. Rhee Dynamics on the electronically excited state surface of the bioluminescent firefly luciferase-oxyluciferin system Journal of the American Chemical Society 133 2011 12040 12041
    • (2011) Journal of the American Chemical Society , vol.133 , pp. 12040-12041
    • Song, C.1    Rhee, Y.M.2
  • 15
    • 79953202877 scopus 로고    scopus 로고
    • Computational investigation of the effect of ph on the color of firefly bioluminescence by DFT
    • L.P.D. Silva, and J.C.G.E.D. Silva Computational investigation of the effect of ph on the color of firefly bioluminescence by DFT ChemPhysChem 12 2011 951 960
    • (2011) ChemPhysChem , vol.12 , pp. 951-960
    • Silva, L.P.D.1    Silva, J.C.G.E.D.2
  • 17
    • 79953720833 scopus 로고    scopus 로고
    • Molecular enigma of multicolor bioluminescence of firefly luciferase
    • S. Hosseinkhani Molecular enigma of multicolor bioluminescence of firefly luciferase Cellular and Molecular Life Sciences 68 2011 1167 1182
    • (2011) Cellular and Molecular Life Sciences , vol.68 , pp. 1167-1182
    • Hosseinkhani, S.1
  • 18
    • 82955173084 scopus 로고    scopus 로고
    • The chemistry of bioluminescence: An analysis of chemical functionalities
    • I. Navizet, Y.J. Liu, N. Ferré, D. Roca-Sanjuán, and R. Lindh The chemistry of bioluminescence: an analysis of chemical functionalities ChemPhysChem 12 2011 3064 3076
    • (2011) ChemPhysChem , vol.12 , pp. 3064-3076
    • Navizet, I.1    Liu, Y.J.2    Ferré, N.3    Roca-Sanjuán, D.4    Lindh, R.5
  • 19
    • 68849087538 scopus 로고    scopus 로고
    • Structure and spectroscopy of oxyluciferin, the light emitter of the firefly bioluminescence
    • P. Naumov, Y. Ozawa, K. Ohkubo, and S. Fukuzumi Structure and spectroscopy of oxyluciferin, the light emitter of the firefly bioluminescence Journal of the American Chemical Society 131 2009 11590 11605
    • (2009) Journal of the American Chemical Society , vol.131 , pp. 11590-11605
    • Naumov, P.1    Ozawa, Y.2    Ohkubo, K.3    Fukuzumi, S.4
  • 20
    • 77955783230 scopus 로고    scopus 로고
    • Spectral-structural effects of the keto-enol-enolate and phenol-phenolate equilibria of oxyluciferin
    • P. Naumov, and M. Kochunnoonny Spectral-structural effects of the keto-enol-enolate and phenol-phenolate equilibria of oxyluciferin Journal of the American Chemical Society 132 2010 11566 11579
    • (2010) Journal of the American Chemical Society , vol.132 , pp. 11566-11579
    • Naumov, P.1    Kochunnoonny, M.2
  • 21
    • 79960978025 scopus 로고    scopus 로고
    • Multireference theoretical studies on the solvent effect of firefly multicolor bioluminescence
    • S.F. Chen, L. Yue, Y.J. Liu, and R. Lindh Multireference theoretical studies on the solvent effect of firefly multicolor bioluminescence International Journal of Quantum Chemistry 111 2011 3371 3377
    • (2011) International Journal of Quantum Chemistry , vol.111 , pp. 3371-3377
    • Chen, S.F.1    Yue, L.2    Liu, Y.J.3    Lindh, R.4
  • 23
    • 0032451343 scopus 로고    scopus 로고
    • Luciferase and recombinant luciferase labels
    • R.L. Price, D.J. Squirrell, M.J. Murphy, D.J. Squirrell, and M.J. Murphy Luciferase and recombinant luciferase labels Journal of Clinical Ligand Assay 21 1999 349 357 (Pubitemid 29149092)
    • (1998) Journal of Clinical Ligand Assay , vol.21 , Issue.4 , pp. 349-357
    • Price, R.L.1    Squirrell, D.J.2    Murphy, M.J.3
  • 24
    • 0033935716 scopus 로고    scopus 로고
    • Application of bioluminescence and chemiluminescence in biomedical sciences
    • L.J. Kricka Application of bioluminescence and chemiluminescence in biomedical sciences Methods in Enzymology 305 2000 333 345 (Pubitemid 30421276)
    • (2000) Methods in Enzymology , vol.305 , pp. 333-345
    • Kricka, L.J.1
  • 25
    • 0033631082 scopus 로고    scopus 로고
    • Detection of luciferase having two kinds of luminescent colour based on optical filter procedure: Application to an enzyme immunoassay
    • H. Ohkuma, K. Abe, Y. Kosaka, and M. Maeda Detection of luciferase having two kinds of luminescent colour based on optical filter procedure: application to an enzyme immunoassay Luminescence 15 2000 21 27
    • (2000) Luminescence , vol.15 , pp. 21-27
    • Ohkuma, H.1    Abe, K.2    Kosaka, Y.3    Maeda, M.4
  • 26
    • 0036363666 scopus 로고    scopus 로고
    • Imaging of light emission from the expression of luciferases in living cells and organisms: A review
    • L.F. Greer, and A.A. Szalay Imaging of light emission from the expression of luciferases in living cells and organisms: a review Luminescence 17 2002 43 74
    • (2002) Luminescence , vol.17 , pp. 43-74
    • Greer, L.F.1    Szalay, A.A.2
  • 27
    • 33748759854 scopus 로고    scopus 로고
    • The catalytic machinery of chondroitinase ABC I utilizes a calcium coordination strategy to optimally process dermatan sulfate
    • DOI 10.1021/bi0605484
    • V. Prabhakar, I. Capila, R. Raman, A. Srinivasan, C.J. Bosques, K. Pojasek, M.A. Wrick, and R. Sasisekharan The catalytic machinery of chondroitinase ABC I utilizes a calcium coordination strategy to optimally process dermatan sulfate Biochemistry 45 2006 11130 11139 (Pubitemid 44413660)
    • (2006) Biochemistry , vol.45 , Issue.37 , pp. 11130-11139
    • Prabhakar, V.1    Capila, I.2    Raman, R.3    Srinivasan, A.4    Bosques, C.J.5    Pojasek, K.6    Wrick, M.A.7    Sasisekharan, R.8
  • 28
    • 0036405345 scopus 로고    scopus 로고
    • Advances in in vivo bioluminescence imaging of gene expression
    • DOI 10.1146/annurev.bioeng.4.111901.093336
    • C.H. Contag, and M.H. Bachmann Advances in in vivo bioluminescence imaging of gene expression Annual Review of Biomedical Engineering 4 2002 235 260 (Pubitemid 35217421)
    • (2002) Annual Review of Biomedical Engineering , vol.4 , pp. 235-260
    • Contag, C.H.1    Bachmann, M.H.2
  • 29
    • 70350049958 scopus 로고    scopus 로고
    • Colo-tuning of firefly luciferase bioluminescence by modification of enzyme and substrate structure: New opportunities for optical imaging
    • E. Santaniello, and G. Meroni Colo-tuning of firefly luciferase bioluminescence by modification of enzyme and substrate structure: new opportunities for optical imaging Minerva Biotechnologica 21 2009 77 86
    • (2009) Minerva Biotechnologica , vol.21 , pp. 77-86
    • Santaniello, E.1    Meroni, G.2
  • 30
    • 0036865977 scopus 로고    scopus 로고
    • The origin, diversity, and structure function relationships of insect luciferases
    • DOI 10.1007/PL00012509
    • V.R. Viviani The origin, diversity, and structure function relationships of insect luciferases Cellular and Molecular Life Sciences 59 2002 1833 1850 (Pubitemid 36015859)
    • (2002) Cellular and Molecular Life Sciences , vol.59 , Issue.11 , pp. 1833-1850
    • Viviani, V.R.1
  • 31
    • 0033944664 scopus 로고    scopus 로고
    • Chemical synthesis of firefly luciferin analogs and inhibitors
    • B.R. Branchini Chemical synthesis of firefly luciferin analogs and inhibitors Mehtods in Enzymology 305 2000 188 195 (Pubitemid 30421266)
    • (2000) Methods in Enzymology , vol.305 , pp. 188-195
    • Branchini, B.R.1
  • 34
    • 33748785208 scopus 로고    scopus 로고
    • Luciferin derivatives for enhanced in vitro and in vivo bioluminescence assays
    • DOI 10.1021/bi060475o
    • R. Shinde, J. Perkins, and C.H. Contag Luciferin derivatives for enhanced in vitro and in vivo bioluminescence assays Biochemistry 45 2006 11103 11112 (Pubitemid 44413657)
    • (2006) Biochemistry , vol.45 , Issue.37 , pp. 11103-11112
    • Shinde, R.1    Perkins, J.2    Contag, C.H.3
  • 35
    • 52949105772 scopus 로고    scopus 로고
    • N-Alkylated 6′-aminoluciferins are bioluminescent substrates for ultra-glo and quantilum luciferase: New potential scaffolds for bioluminescent assays
    • C.C. Woodroofe, J.W. Shultz, M.G. Wood, J. Osterman, J.J. Cali, W.J. Daily, P.L. Meisenheimer, and D.H. Klaubert N-Alkylated 6′-aminoluciferins are bioluminescent substrates for ultra-glo and quantilum luciferase: new potential scaffolds for bioluminescent assays Biochemistry 47 2008 10383 10393
    • (2008) Biochemistry , vol.47 , pp. 10383-10393
    • Woodroofe, C.C.1    Shultz, J.W.2    Wood, M.G.3    Osterman, J.4    Cali, J.J.5    Daily, W.J.6    Meisenheimer, P.L.7    Klaubert, D.H.8
  • 37
    • 19444363758 scopus 로고    scopus 로고
    • In vivo imaging of S-TRAIL-mediated tumor regression and apoptosis
    • DOI 10.1016/j.ymthe.2005.01.017, PII S1525001605000304
    • K. Shah, C.H. Tung, X.O. Breakefield, and R. Weissleder In vivo imaging of S-TRAIL-mediated tumor regression and apoptosis Molecular Therapy 11 2005 926 931 (Pubitemid 40724111)
    • (2005) Molecular Therapy , vol.11 , Issue.6 , pp. 926-931
    • Shah, K.1    Tung, C.-H.2    Breakefield, X.O.3    Weissleder, R.4
  • 40
    • 34250223468 scopus 로고    scopus 로고
    • A homogeneous assay to measure live and dead cells in the same sample by detecting different protease markers
    • DOI 10.1016/j.ab.2007.04.007, PII S0003269707002278
    • A.L. Niles, R.A. Moravec, P.E. Hesselberth, M.A. Scurria, W.J. Daily, and T.L. Riss A homogeneous assay to measure live and dead cells in the same sample by detecting different protease markers Analytical Biochemistry 366 2007 197 206 (Pubitemid 46898209)
    • (2007) Analytical Biochemistry , vol.366 , Issue.2 , pp. 197-206
    • Niles, A.L.1    Moravec, R.A.2    Eric Hesselberth, P.3    Scurria, M.A.4    Daily, W.J.5    Riss, T.L.6
  • 43
    • 77957910759 scopus 로고    scopus 로고
    • Bioheterojunction effect on fluorescence origin and efficiency improvement of firefly chromophores
    • D. Cai, M.A.L. Marques, B.F. Milne, and F. Nogueira Bioheterojunction effect on fluorescence origin and efficiency improvement of firefly chromophores The Journal of Physical Chemistry Letters 1 2010 2781 2787
    • (2010) The Journal of Physical Chemistry Letters , vol.1 , pp. 2781-2787
    • Cai, D.1    Marques, M.A.L.2    Milne, B.F.3    Nogueira, F.4
  • 47
    • 0022816745 scopus 로고
    • The dielectric constant of a folded protein
    • M.K. Gilson, and B.H. Honig The dielectric constant of a folded protein Biopolymers 25 1986 2097 2119
    • (1986) Biopolymers , vol.25 , pp. 2097-2119
    • Gilson, M.K.1    Honig, B.H.2
  • 48
    • 84961976154 scopus 로고    scopus 로고
    • Modeling electron transfer in biochemistry: A quantum chemical study of charge separation in rhodobacter sphaeroides and photosystem II
    • M.R.A. Blomberg, P.E.M. Siegbahn, and G.T. Babcock Modeling electron transfer in biochemistry: a quantum chemical study of charge separation in rhodobacter sphaeroides and photosystem II Journal of the American Chemical Society 120 1998 8812
    • (1998) Journal of the American Chemical Society , vol.120 , pp. 8812
    • Blomberg, M.R.A.1    Siegbahn, P.E.M.2    Babcock, G.T.3
  • 49
    • 84961980743 scopus 로고
    • COSMO: A new approach to dielectric screening in solvents with explicit expressions for the screening energy and its gradient
    • A. Klamt, and G. Schüürmann COSMO: a new approach to dielectric screening in solvents with explicit expressions for the screening energy and its gradient Journal of the Chemical Society, Perkin Transactions 2 25 1993 799 805
    • (1993) Journal of the Chemical Society, Perkin Transactions , vol.2 , Issue.25 , pp. 799-805
    • Klamt, A.1    Schüürmann, G.2
  • 51
    • 77957306415 scopus 로고    scopus 로고
    • Robust light emission from cyclic alkylaminoluciferin substrates for firefly luciferase
    • G.R. Reddy, W.C. Thompson, and S.C. Miller Robust light emission from cyclic alkylaminoluciferin substrates for firefly luciferase Journal of the American Chemical Society 132 2010 13586 13587
    • (2010) Journal of the American Chemical Society , vol.132 , pp. 13586-13587
    • Reddy, G.R.1    Thompson, W.C.2    Miller, S.C.3
  • 52
    • 34548427946 scopus 로고    scopus 로고
    • Red light in chemiluminescence and yellow-green light in bioluminescence: Color-tuning mechanism of firefly, Photinus pyralis, studied by the symmetry-adapted cluster-configuration interaction method
    • DOI 10.1021/ja0611691
    • N. Nakatani, J. Hasegawa, and H. Nakatsuji Red light in chemiluminescence and yellow-green light in bioluminescence: color-tuning mechanism of firefly, Photinus pyralis, studied by the symmetry-adapted cluster-configuration interaction method Journal of the American Chemical Society 129 2007 8756 8765 (Pubitemid 47492063)
    • (2007) Journal of the American Chemical Society , vol.129 , Issue.28 , pp. 8756-8765
    • Nakatani, N.1    Hasegawa, J.-Y.2    Nakatsuji, H.3
  • 54
    • 0029882210 scopus 로고    scopus 로고
    • Influence of chain length and derivatization on the lowest singlet and triplet states and intersystem crossing in oligothiophenes
    • DOI 10.1021/ja9531135
    • D. Beljonne, J. Cornil, R.H. Friend, R.A.J. Janssen, and J.L. Brédas Influence of chain length and derivatization on the lowest singlet and triplet states and intersystem crossing in oligothiophenes Journal of the American Chemical Society 118 1996 6453 6461 (Pubitemid 26247699)
    • (1996) Journal of the American Chemical Society , vol.118 , Issue.27 , pp. 6453-6461
    • Beljonne, D.1    Cornil, J.2    Friend, R.H.3    Janssen, R.A.J.4    Bredas, J.L.5
  • 55
    • 0001635103 scopus 로고    scopus 로고
    • Density functional theory calculations of the visible spectrum of chlorophyll a
    • PII S0009261499001943
    • D. Sundholm Density functional theory calculations of the visible spectrum of chlorophyll a Chemical Physics Letters 302 1999 480 484 (Pubitemid 129593889)
    • (1999) Chemical Physics Letters , vol.302 , Issue.5-6 , pp. 480-484
    • Sundholm, D.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.