Spectroscopic studies of the light-color modulation mechanism of firefly (Beetle) bioluminescence

Journal of the American Chemical Society

Volumn 131, Issue 6, 2009, Pages 2385-2396

  Hirano, Takashi ^a   Hasumi, Yosuke ^a   Ohtsuka, Kazuhiro ^a   Maki, Shojiro ^a   Niwa, Haruki ^a   Yamaji, Minoru ^b   Hashizume, Daisuke ^c  

^a UNIVERSITY OF ELECTRO COMMUNICATIONS   (Japan)

^b GUNMA UNIVERSITY   (Japan)

^c RIKEN   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

COLOR; DENSITY FUNCTIONAL THEORY; FLUORESCENCE; LIGHT EMISSION; MODULATION; NEGATIVE IONS; PHOSPHORESCENCE; SOLVENTS; SPECTROSCOPIC ANALYSIS;

ACTIVE SITE; CONJUGATE ACID; CONTACT ION PAIRS; COVALENT CHARACTER; DENSITY FUNCTIONAL THEORY CALCULATIONS; EMISSION MAXIMA; EMISSION PROPERTIES; EXCITED SINGLET STATE; FLUORESCENCE LIFETIME MEASUREMENTS; FLUORESCENCE MAXIMA; H-BONDS; ION PAIRS; LIGHT EMITTERS; MODEL COMPOUND; POLAR SOLVENTS; PROTONATED; SITE ENVIRONMENTS; SOLVENT POLARITY; SPECTROSCOPIC PROPERTY; SPECTROSCOPIC STUDIES; WILD TYPES;

BIOLUMINESCENCE;

ANION; BASE; LUCIFERASE; LUCIFERIN; PHENOL DERIVATIVE; SOLVENT; 5,5-DIMETHYLOXYLUCIFERIN; FIREFLY LUCIFERASE;

ARTICLE; BEETLE; BIOLUMINESCENCE; CALCULATION; CHEMICAL BOND; COLOR; CONJUGATE; DENSITY FUNCTIONAL THEORY; FLUORESCENCE; MODULATION; SPECTROSCOPY; WILD TYPE; ANIMAL; CHEMISTRY; FIREFLY; LUMINESCENCE; QUANTUM THEORY; SPECTROFLUOROMETRY; THERMODYNAMICS; ULTRAVIOLET SPECTROPHOTOMETRY;

ANIMALS; FIREFLIES; FIREFLY LUCIFERIN; LUCIFERASES, FIREFLY; LUMINESCENCE; QUANTUM THEORY; SPECTROMETRY, FLUORESCENCE; SPECTROPHOTOMETRY, ULTRAVIOLET; THERMODYNAMICS;

EID: 67849102207     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja808836b     Document Type: Article

References (95)

1. In this paper, we use the term "firefly (beetle) bioluminescence" for the bioluminescence of fireflies, click beetles, and railroad worms. The word "beetle bioluminescence" has also been used.
2. McElroy, W. D.; DeLuca, M. In Bioluminescence in Action; Herring, P. J., Ed.; Academic Press: London, 1978; pp 109-127.
3. Shimomura, O. In Bioluminescence: Chemical Principles and Methods; World Scientific Publishing: Singapore, 2006; pp 1-29.
4. Fraga, H. Photochem. Photobiol. Sci. 2008, 7, 146-158.
5. McElroy, W. D. Proc. Natl. Acad. Sci. U.S.A. 1947, 33, 342-345.
6. (a) Seliger, H. H.; McElroy, W. D. Biochem. Biophys. Res. Commun. 1959, 1, 21-24.
7. (b) Seliger, H. H.; McElroy, W. D. Arch. Biochem. Biophys. 1960, 88, 136-141.
8. Seliger, H. H.; McElroy, W. D. Proc. Natl. Acad. Sci. U.S.A. 1964, 52, 75-81.
9. (a) Wood, K. V.; Lam, Y. A.; Seliger, H. H.; McElroy, W. D. Science 1989, 244, 700-703.
10. (b) Wood, K. V.; Lam, Y. A.; McElroy, W. D. J. Biolumin. Chemilumin. 1989, 4, 289-301.
11. Viviani, V. R. Cell. Mol. Life Sci. 2002, 59, 1833-1850.
12. DeLuca, M.; McElroy, W. D. Methods Enzymol. 1978, 57, 3-15.
13. (a) de Wet, J. R.; Wood, K. V.; Helinski, D. R.; DeLuca, M. Proc. Natl. Acad. Sci. U.S.A. 1985, 82, 7870-7873.
14. (b) de Wet, J. R.; Wood, K. V.; Helinski, D. R.; DeLuca, M. Methods Enzymol. 1986, 133, 3-14.
15. Greer, L. F.; Szalay, A. A. Luminescence 2002, 17, 43-74.
16. Contag, C. H.; Bachmann, M. H. Annu. Rev. Biomed. Eng. 2002, 4, 235-260.
17. Ando, Y.; Niwa, K.; Yamada, N.; Enomoto, T.; Irie, T.; Kubota, H.; Ohmiya, Y.; Akiyama, H. Nat. Photonics 2008, 2, 44-47.
18. Conti, E.; Franks, N. P.; Brick, P. Structure 1996, 4, 287-298.
19. Nakatsu, T.; Ichiyama, S.; Hiratake, J.; Saldanha, A.; Kobashi, N.; Sakata, K.; Kato, H. Nature 2006, 440, 372-376.
20. (a) White, E. H.; Rapaport, E.; Hopkins, T. A.; Seliger, H. H. J.Am. Chem. Soc. 1969, 91, 2178-2180.
21. (b) White, E. H.; Steinmetz, M. G.; Miano, J. D.; Wildes, P. D.; Morland, R. J. Am. Chem. Soc. 1980, 102, 3199-3208.
22. White, E. H.; Rapaport, E.; Seliger, H. H.; Hopkins, T. A. Bioorg. Chem. 1971, 1, 92-122.
23. White, E. H.; Roswell, D. F. Photochem. Photobiol. 1991, 53, 131-136.
24. (a) McCapra, F.; Gilfoyle, D. J.; Young, D. W.; Church, N. J.; Spencer, P. In Bioluminescence and Chemiluminescence. Fundamentals and Applied Aspects; Campbell, A. K., Kricka, L. J., Stanley, P. E., Eds.; Wiley: Chichester, U.K., 1994; pp 387-391.
25. (b) McCapra, F. In Bioluminescence and Chemiluminescence: Molecular Reporting with Photons; Hastings, J. W., Kricka, L. J., Stanley, P. E., Eds.; Wiley: Chichester, U.K., 1997; pp 7-15.
26. Branchini, B. R.; Murtiashaw, M. H.; Magrar, R. A.; Portier, N. C.; Ruggiero, M. C.; Stroh, J. G. J. Am. Chem. Soc. 2002, 124, 2112-2113.
27. Branchini, B. R.; Southworth, T. L.; Murtiashaw, M. H.; Magrar, R. A.; Gonzalez, S. A.; Ruggiero, M. C.; Stroh, J. G. Biochemistry 2004, 43, 7255-7262.
28. Morton, R. A.; Hopkins, T. A.; Seliger, H. H. Biochemistry 1969, 8, 1598-1607.
29. DeLuca, M. Biochemistry 1969, 8, 160-166.
30. Hopkins, T. A.; Seliger, H. H.; White, E. H.; Cass, M. W. J. Am. Chem. Soc. 1967, 89, 7148-7150.
31. McCapra, F.; Chang, Y. C.; Francois, V. P. Chem. Commun. 1968, 22-23.
32. Shimomura, O.; Goto, T.; Johnson, F. H. Proc. Natl. Acad. Sci. U.S.A. 1977, 74, 2799-2802.
33. Wannlund, J.; DeLuca, M.; Stempel, K.; Boyer, P. D. Biochem. Biophys. Res. Commun. 1978, 81, 987-992.
34. (a) Suzuki, N.; Sato, M.; Nishikawa, K.; Goto, T. Tetrahedron Lett. 1969, 10, 4683-4684.
35. (b) Suzuki, N.; Sato, M.; Okada, K.; Goto, T. Tetrahedron 1972, 28, 4065-4074.
36. (a) Gandelman, O. A.; Brovko, L. Y.; Ugarova, N. N.; Shchegolev, A. A. Biochemistry (Moscow) 1990, 55, 785-789.
37. (b) Gandelman, O. A.; Brovko, L. Y.; Ugarova, N. N.; Chikishev, A. Y.; Shkurimov, A. P. J. Photochem. Photobiol., B 1993, 19, 187-191.
38. Suzuki, N.; Ueyama, T.; Izawa, Y.; Toya, Y.; Goto, T. Heterocycles 1983, 20, 1027-1030.
39. (a) Leontieva, O. V.; Vlasova, T. N.; Ugarova, N. N. Biochemistry (Moscow) 2006, 71, 51-55.
40. (b) Vlasova, T. N.; Leontieva, O. V.; Ugarova, N. N. Biochemistry (Moscow) 2006, 71, 555-559.
41. We have employed an approach of characterizing the excited molecule of the light emitter to explain the color modulation mechanism of jellyfish bioluminescence:
42. (a) Hirano, T.; Mizoguchi, I.; Yamaguchi, M.; Chen, F. Q.; Ohashi, M.; Ohmiya, Y.; Tsuji, F. I. Chem. Commun. 1995, 165-167.
43. (b) Saito, R.; Hirano, T.; Niwa, H.; Ohashi, M. Perkin Trans. 2 1997, 1711-1716.
44. Imai, Y.; Shibata, T.; Maki, S.; Niwa, H.; Ohashi, M.; Hirano, T. J. Photochem. Photobiol., A 2001, 146, 95-107.
45. Mori, K.; Maki, S.; Niwa, H.; Ikeda, H.; Hirano, T. Tetrahedron 2006, 62, 6272-6288.
46. We presented some of the data in this paper at a meeting of the Chemical Society of Japan (CSJ) on March 29, 2008: Hasumi, Y.; Ohtsuka, K.; Kojima, S.; Maki, S.; Niwa, H.; Hirano, T. Abstr. PapsChem. Soc. Jpn. 2008, 88, 1626.
47. Suzuki, N.; Goto, T. Agric. Biol. Chem. 1972, 36, 2213-2221.
48. Reichardt, C. In Solvents and Solvent Effects in Organic Chemistry, 3rd ed.; Wiley-VCH: Weinheim, Germany, 2003.
49. Lippert, E. Z. Electrochem. 1957, 61, 962-975.
50. Mataga, N.; Kaifu, Y.; Koizumi, M. Bull. Chem. Soc. Jpn. 1956, 29, 465-471.
51. (a) Kosower, E. M.; Tanizawa, K. Chem. Phys. Lett. 1972, 16, 419-425.
52. (b) Kosower, E. M.; Dodiuk, H.; Tanizawa, K.; Ottolenghi, M.; Orbach, N. J. Am. Chem. Soc. 1975, 97, 2167-2178.
53. Hirano, T.; Takahashi, Y.; Kondo, H.; Maki, S.; Kojima, S.; Ikeda, H.; Niwa, H. Photochem. Photobiol. Sci. 2008, 7, 197-207.
54. Laurence, C.; Berthelot, M.; Graton, J. The Chemistry of Phenols, Part 1; Rappoport, Z., Ed.; Wiley: Chichester, U.K., 2003; pp 529-603.
55. Pines, E. The Chemistry of Phenols, Part 1; Rappoport, Z., Ed.; Wiley: Chichester, U.K., 2003; pp 491 - 527.
56. Matsuzaki, A.; Nagakura, S.; Yoshihara, K. Bull. Chem. Soc. Jpn. 1974, 47, 1152-1157.
57. Tolbert, L. M.; Nesselroth, S. M. J. Phys. Chem. 1991, 95, 10331-10336.
58. Willis, K. J.; Szabo, A. G. J. Phys. Chem. 1991, 95, 1585-1589.
59. Ions and Ion Pairs in Organic Reactions; Szwarc, M., Ed.; Wiley - Interscience: New York, 1972; Vol. 1.
60. Kolthoff, I. M.; Chantooni, M. K., Jr.; Bhowmik, S. J. Am. Chem. Soc. 1968, 90, 23-28.
61. Galezowski, W.; Jarczewski, A.; Stanczyk, M.; Brzezinski, B.; Bartl, F.; Zundel, G. J. Chem. Soc., Faraday Trans. 1997, 93, 2515-2518.
62. Orlova, G.; Goddard, J. D.; Brovko, L. Y. J. Am. Chem. Soc. 2003, 125, 6962-6971.
63. Frisch, M. J.; et al. Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
64. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
65. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev.B1988, 37, 785-789.
66. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623-11627.
67. (a) Ren, A.-M.; Goddard, J. D. J. Photochem. Photobiol., B 2005, 81, 163-170.
68. (b) Yang, T.; Goddard, J. D. J. Phys. Chem. A 2007, 111, 4489-4497.
69. Seliger, H. H.; Buck, J. B.; Fasyie, W. G.; McElroy, W. D. J. Gen. Physiol. 1964, 48, 95-104.
70. (a) Viviani, V. R.; Bechara, E. J. H. Photochem. Photobiol. 1993, 58, 615-622.
71. (b) Viviani, V. R.; Bechara, E. J. H. Ann. Entomol. Soc. Am. 1997, 90, 389-398.
72. Viviani, V. R.; Bechara, E. J. H.; Ohmiya, Y. Biochemistry 1999, 38, 8271-8279.
73. Kishi, Y.; Matsuura, S.; Inoue, S.; Shimomura, O.; Goto, T. Tetrahedron Lett. 1968, 9, 2847-2850.
74. Viviani, V. R.; Arnoldi, F. G. C.; Venkatesh, B.; Silva Neto, A. J.; Ogawa, F. G. T.; Oehlmeyer, T. L.; Ohmiya, Y. J. Biochem. 2006, 140, 467-474.
75. Branchini, B. R.; Magyar, R. A.; Murtiashaw, M. H.; Anderson, S. M.; Zimmer, M. Biochemistry 1998, 37, 15311-15319.
76. Berg, J. M.; Tymoczko, J. L., Stryer. L. Biochemistry, 6th ed.; Freeman: New York, 2006.
77. (a) Viviani, V. R.; Ohmiya, Y. Photochem. Photobiol. 2000, 72, 267-271.
78. (b) Viviani, V. R.; Uchida, A.; Viviani, W.; Ohmiya, Y. Photochem. Photobiol. 2002, 76, 538-544.
79. Viviani, V. R.; Arnoldi, F. G. C.; Ogawa, F. T.; Brochetto-Braga, M. Luminescence 2007, 22,362-369.
80. Branchini, B. R.; Magyar, R. A.; Murtiashaw, M. H.; Portier, N. C. Biochemistry 2001, 40, 2410-2418.
81. Homer, R. B.; Johnson, C. D. The Chemistry ofAmides; Zabicky, J., Ed.; Wiley-Interscience: London, 1970; pp 187-243.
82. Wu, Z.; Fenselau, C. J. Am. Soc. Mass Spectrom. 1992, 3, 863-866.
83. Wu, J.; Lebrilla, C. B. J. Am. Chem. Soc. 1993, 115, 3270-3275.
84. Zhang, K.; Zimmerman, D. M.; Chung-Phillips, A.; Cassady, C. J. J. Am. Chem. Soc. 1993, 115, 10812-10822.
85. Viviani, V. R.; Arnoldi, F. G. C.; Neto, A. J. S.; Oehlmeyer, T. L.; Bechara, E. J. H.; Ohmiya, Y. Photochem. Photobiol. Sci. 2008, 7, 159-169.
86. Kajiyama, N.; Nakano, E. Protein Eng. 1991, 4, 691-693.
87. Mamaev, S. V.; Laikhter, A. L.; Arslan, T.; Hecht, S. M. J. Am. Chem. Soc. 1996, 118, 7243-7244.
88. Ugarova, N. N.; Brovko, L. Y. Luminescence 2002, 17, 321-330.
89. Viviani, V. R.; Ohmiya, Y. Luminescence 2006, 21, 262-267.
90. Turro, N. J. Modern Molecular Photochemistry; University Science Books: Sausalito, CA, 1991.
91. Nakatani, N.; Hasegawa, J.; Nakatsuji, H. J. Am. Chem. Soc. 2007, 129, 8756-8765.
92. Liu, Y.-J.; De Vico, L.; Lindh, R. J. Photochem. Photobiol., A 2008, 194, 261-267.
93. Eaton, D. F. Pure. Appl. Chem. 1988, 7, 1107-1114.
94. Yamaji, M. Photochem. Photobiol. Sci. 2008, 7, 711-717.
95. Dennington, R., II; Keith, T.; Millam, J.; Eppinnett, K.; Hovell, W. L.; Gilliland, R. GaussView, version 3.09; Semichem, Inc.: Shawnee Mission, KS, 2003.