Theoretical fingerprinting of the photophysical properties of four firefly bioluminophores

Photochemical and Photobiological Sciences

Volumn 12, Issue 11, 2013, Pages 2028-2035

  Pinto Da Silva, Luís ^a   Esteves Da Silva, Joaquim C G ^a  

^a UNIVERSITY OF PORTO   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE; OXYLUCIFERIN; PYRAZINE DERIVATIVE;

ANIMAL; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; FIREFLY; LUMINESCENCE; METABOLISM; PEPTIDE MAPPING; PHOTOCHEMISTRY; QUANTUM THEORY;

ANIMALS; FIREFLIES; INDOLES; LUMINESCENT MEASUREMENTS; MOLECULAR STRUCTURE; PEPTIDE MAPPING; PHOTOCHEMICAL PROCESSES; PYRAZINES; QUANTUM THEORY;

EID: 84886930678     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/c3pp50203a     Document Type: Article

References (49)

1. S. M. Marques J. C. G. Esteves da Silva Firefly bioluminescence: a mechanistic approach of luciferase catalyzed reactions IUBMB Life 2009 61 3523
2. V. R. Viviani F. G. Arnoldi A. J. Neto T. L. Oehlmeyer E. J. Bechara Y. Ohmiya The structural origin and biological function of pH-sensitivity in firefly luciferases Photochem. Photobiol. Sci. 2008 7 159
3. L. Pinto da Silva J. C. G. Esteves da Silva Computational Studies of the Luciferase Light-Emitting Product: Oxyluciferin J. Chem. Theor. Comput. 2011 7 809
4. L. Pinto da Silva J. C. G. Esteves da Silva Firefly chemiluminescence and bioluminescence: efficient generation of excited states ChemPhysChem 2012 13 2257
5. M. Matsumoto Advanced chemistry of dioxetane-based chemiluminescent substrates originating from bioluminescence J. Photochem. Photobiol., C 2004 5 27
6. I. Navizet Y. J. Liu N. Ferré D. Roca-Sanjuán R. Lindh The chemistry of bioluminescence: an analysis of chemical functionalities ChemPhysChem 2011 12 3064
7. S. P. Schmidt G. B. Schuster Dioxethanone chemiluminescence by chemically-initiated electron exchange pathway-efficient generation of excited singlet-states J. Am. Chem. Soc. 1978 100 1966
8. H. Isobe Y. Takano M. Okumura S. Kuramitsu K. Yamaguchi Mechanistic insights in charge-transfer-induced luminescence of 1,2-dioxetanones with a substituent of low oxidation potential J. Am. Chem. Soc. 2005 127 8667
9. L. Yue Y. J. Liu W. H. Fang Mechanistic insight into the chemiluminescent decomposition of firefly dioxetanone J. Am. Chem. Soc. 2012 134 11632
10. L. Pinto da Silva J. C. G. Esteves da Silva Interstate crossing-induced chemiexcitation as the reason for the chemiluminescence of dioxetanones ChemPhysChem 2013 14 1071
11. Y. Ando K. Niwa N. Yamada T. Enomoto T. Irie H. Kubota Y. Ohmiya H. Akiyama Firefly bioluminescence quantum yield and colour change by pH-sensitive green emission Nat. Photonics 2008 2 44
12. K. Niwa Y. Ichino S. Kumata Y. Nakajima Y. Hiraishi D. Kato V. R. Viviani Y. Ohmiya Quantum Yields and Kinetics of the Firefly Bioluminescence Reaction of Beetle Luciferases Photochem. Photobiol. 2010 86 1046
13. A. Roda M. Guardigli P. Pasini M. Mirasole Bioluminescence and chemiluminescence in drug screening Anal. Bioanal. Chem. 2003 377 826
14. A. Roda P. Pasini M. Mirasoli E. Michelini M. Guardigli Biotechnological applications of bioluminescence and chemiluminescence Trends Biotechnol. 2004 22 295
15. A. Roda M. Guardigli Analytical chemiluminescence and bioluminescence: latest achievements and new horizons Anal. Bioanal. Chem. 2012 402 69
16. V. Villalobos S. Naik D. Piwnica-Worms Current state of imaging protein-protein interactions in vivo with genetically encoded reporters Annu. Rev. Biomed. Eng. 2007 9 321
17. J. Brogan F. Li W. Li Z. He Q. Huang C. Y. Li Imaging molecular pathways: reporter geners Radiat. Res. 2012 177 508
18. H. Takakura K. Sasakura T. Ueno Y. Urano T. Terai K. Hanaoka T. Tsuboi T. Nagano Development of Luciferin Analogues Bearing an Amino Group and Their Application as BRET Donors Chem.-Asian. J. 2010 5 2053
19. M. K. So C. Xu A. M. Loening S. S. Ganbhir J. Rao Self-illuminating quantum dot conjugates for in vivo imaging Nat. Biotechnol. 2006 24 339
20. N. Ma A. F. Marshall J. Rao J. Am. Chem. Soc. 2010 132 6884
21. B. R. Branchini J. C. Rosenberg D. M. Ablamsky K. P. Taylor T. L. Southworth S. J. Linder Sequential bioluminescence resonance energy transfer-fluororescence resonance energy transfer-based ratiometric protease assays with fusion proteins of firefly luciferase and red fluorescent protein Anal. Biochem. 2011 414 239
22. L. Pinto da Silva J. C. G. Esteves da Silva TD-DFT/Molecular Mechanics Study of the Photinus pyralis Bioluminescence system J. Phys. Chem. B 2012 116 2008
23. L. Pinto da Silva J. C. G. Esteves da Silva Study on the Effects of Intermolecular Interactions on Firefly Multicolor Bioluminescence ChemPhysChem 2011 12 3002
24. L. Pinto da Silva J. C. G. Esteves da Silva Computational Investigation of the Effect of pH on the Color of Firefly Bioluminescence by DFT ChemPhysChem 2011 12 951
25. C. I. Song Y. M. Rhee Dynamics on the electronically excited state surface of the bioluminescent firefly luciferase-oxyluciferin system J. Am. Chem. Soc. 2011 133 12040
26. P. Naumov Y. Ozawa K. Ohkubo S. Fukuzumi Structure and spectroscopy of oxyluciferin, the light emitter of the firefly bioluminescence J. Am. Chem. Soc. 2009 131 11590
27. T. Hirano Y. Hasumi K. Ohtsuka S. Maki H. Niwa M. Yamaji D. Hashizume Spectroscopic studies of the light-color modulation mechanism of firefly (beetle) bioluminescence J. Am. Chem. Soc. 2009 131 2385
28. C. G. Min A. M. Ren J. F. Guo L. Y. Zou J. D. Goddard C. C. Sun Theoretical investigation on the origin of yellow-green firefly bioluminescence by time-dependent density functional theory ChemPhysChem 2010 11 2199
29. B. F. Milne M. A. Marques F. Nogueira Fragment molecular orbital investigation of the role of AMP protonation in firefly luciferase pH-sensitivity Phys. Chem. Chem. Phys. 2010 12 14285
30. L. Pinto da Silva J. C. G. Esteves da Silva Theoretical Modulation of the Color of Light Emitted by Firefly Oxyluciferin J. Comput. Chem. 2011 32 2654
31. K. Stochkel C. N. Hansen J. Houmoller L. M. Nielsen M. Linares P. Norman F. Nogueira O. V. Maltsev L. Hintermann S. B. Nielsen P. Naumov B. F. Milne On the influence of water on the electronic structure of firefly oxyluciferin anions from absorption spectroscopy of bare and monohydrated ions in vacuo J. Am. Chem. Soc. 2013 135 6485
32. D. Cai M. A. Marques F. Nogueira Accurate color tuning of firefly chromophore by modulation of local polarization electrostatic fields J. Phys. Chem. B 2010 115 329
33. D. Cai M. A. L. Marques B. F. Milne F. Nogueira Bioheterojunction Effect on Fluorescence Origin and Efficiency Improvement of Firefly Chromophores J. Phys. Chem. Lett. 2010 1 2781
34. I. Navizet D. Roca-Sanjuán L. Yue Y. J. Liu N. Ferré R. Lindh Are the bio- and chemiluminescence states of the firefly oxyluciferin the same as the fluorescence state? Photochem. Photobiol. 2013 89 319
35. M. J. Frisch, et al., Gaussian 09, Revision A.02, Gaussian, Inc., Wallingford CT, 2009
36. C. Adamo V. Barone Toward reliable density functional methods without adjustable parameters: The PBE0 model J. Chem. Phys. 1999 110 6158
37. L. Pinto da Silva J. C. G. Esteves da Silva Analysis of the performance of DFT functionals in the study of light emission by oxyluciferin analogs Int. J. Quantum Chem. 2013 113 45
38. D. Jacquemin E. A. Perpète I. Ciofini C. Adamo Assessment of the omega B97 family for excited-state calculations Theor. Chem. Acc. 2011 128 127
39. D. Jacquemin V. Wathelet E. A. Perpète C. Adamo Extensive TD-DFT Benchmark: Singlet-Excited States of Organic Molecules J. Chem. Theor. Comput. 2009 5 2420
40. Y. Zhao D. G. Truhlar Density functional for spectroscopy: No long-range self-interaction error, good performance for Rydberg and charge-transfer states, and better performance on average than B3LYP for ground states J. Phys. Chem. A 2006 110 13126
41. Y. Zhao D. G. Truhlar Density functionals with broad applicability in chemistry Acc. Chem. Res. 2008 41 157
42. C. C. Woodroofe P. L. Meisnheimer D. H. Klaubert Y. Kovic J. C. Rosenberg C. E. Behney T. L. Southworth B. R. Branchini Novel Heterocyclic Analogues of Firefly Luciferin Biochemistry 2012 51 9807 9813
43. N. R. Conley A. Dragulescu-Andrasi J. Rao W. E. Moerner A Selenium Analogue of Firefly D-Luciferin with Red-Shifted Bioluminescence Emission Angew. Chem., Int. Ed. 2012 51 3350
44. S. F. Chen Y. J. Liu I. Navizet N. Ferré W. H. Fang R. Lindh Systematic Theoretical Investigation on the Light Emitter of Firefly J. Chem. Theor. Comput. 2011 7 798
45. B. R. Branchini M. H. Murtiashaw R. A. Magyar N. C. Portier M. C. Ruggiero J. G. Stroh Yellow-Green and red firefly bioluminescence from 5,5-dimethyloxyluciferin J. Am. Chem. Soc. 2002 124 2112
46. P. Naumov M. Kochunnoonny Spectral-structural effects of the keto-enol-enolate and phenol-phenolate equilibria of oxyluciferin J. Am. Chem. Soc. 2010 132 11566
47. K. M. Solntsev S. P. Laptenok P. Naumov Photoinduced dynamics of oxyluciferin analogues: unusual enol "super" photoacidity and evidence for keto-enol isomerization J. Am. Chem. Soc. 2012 134 16452
48. L. Pinto da Silva R. Simkovitch D. Huppert J. C. G. Esteves da Silva Oxyluciferin Photoacidity: The Missing Element for Solving the Keto-Enol Mystery? ChemPhysChem 2013 10.1002/cphc.201300402
49. A. R. Allouche Gabedit-A Graphical User Interface for Computational Chemistry Softwares J. Comput. Chem. 2011 32 174