The reaction mechanism for the high quantum yield of Cypridina (Vargula) bioluminescence supported by the chemiluminescence of 6-aryl-2-methylimidazo[1, 2-a]pyrazin-3(7H)-ones (Cypridina luciferin analogues)

Photochemical and Photobiological Sciences

Volumn 7, Issue 2, 2008, Pages 197-207

  Hirano, Takashi ^a   Takahashi, Yuto ^a   Kondo, Hiroyuki ^a   Maki, Shojiro ^a   Kojima, Satoshi ^a   Ikeda, Hiroshi ^b   Niwa, Haruki ^a  

^a UNIVERSITY OF ELECTRO COMMUNICATIONS   (Japan)

^b Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,1,3,3 TETRAMETHYLGUANIDINE; ACETAMIDE DERIVATIVE; ACETIC ACID; BENZENE DERIVATIVE; DIGLYME; DIMETHYL SULFOXIDE; GUANIDINE DERIVATIVE; IMIDAZOLE DERIVATIVE; INDOLE DERIVATIVE; LUCIFERIN; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOLUMINESCENCE; CHEMOLUMINESCENCE; CYPRIDINA; DECOMPOSITION; FLUORESCENCE; LUMINESCENCE; NATIVE SPECIES; NONHUMAN; PRIORITY JOURNAL; QUANTUM YIELD; REACTION ANALYSIS;

CYPRIDINA; CYPRIDINA LUCIFERIN; VARGULA;

EID: 39049118380     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/b713374j     Document Type: Article

References (39)

1. O. Shimomura T. Goto Y. Hirata Crystalline Cypridina luciferin Bull. Chem. Soc. Jpn. 1957 30 929
2. O. Shimomura F. H. Johnson T. Masugi Cypridina bioluminescence-Light- emitting oxyluciferin-luciferase complex Nature 1969 164 1299
3. T. Goto Chemistry of bioluminescence Pure Appl. Chem. 1968 17 421
4. O. Shimomura F. H. Johnson Introduction to the Cypridina system Methods Enzymol. 1978 57 331
5. O. Shimomura, in Bioluminescence: Chemical Principles and Methods, World Scientific, Singapore, 2006
6. F. H. Johnson O. Shimomura Y. Saiga L. C. Gershman G. T. Reynolds J. R. Waters Quantum efficiency of Cypridina luminescence, with a note on that of Aequorea J. Cell. Comp. Physiol. 1962 60 85
7. O. Shimomura F. H. Johnson Mechanisms in quantum yield of Cypridina bioluminescence Photochem. Photobiol. 1970 12 291
8. Y. Kishi T. Goto Y. Hirata O. Shimomura F. H. Johnson Cypridina bioluminescence I. Structure of Cypridina luciferin Tetrahedron Lett. 1966 3427
9. Y. Kishi T. Goto S. Inoue S. Sugiura H. Kishimoto Cypridina bioluminescence 3. Total synthesis of Cypridina luciferin Tetrahedron Lett. 1966 3445
10. T. Hirano Y. Gomi T. Takahashi K. Kitahara F. Q. Chen I. Mizoguchi S. Kyushin M. Ohashi Chemiluminescence of coelenterazine analogs - Structure of emitting species Tetrahedron Lett. 1992 39 5771
11. R. Saito T. Hirano H. Niwa M. Ohashi Substituent effects on the chemiluminescent properties of coelenterazine analogues Chem. Lett. 1998 1711
12. H. Kondo T. Igarashi S. Maki H. Niwa H. Ikeda T. Hirano Substituent effects on the kinetics for the chemiluminescence reaction of 6-arylimidazo[1,2-a]pyrazin-3(7H)-ones (Cypridina luciferin analogues): support for the single electron transfer (SET)-oxygenation mechanism with triplet molecular oxygen Tetrahedron Lett. 2005 46 7701
13. Y. Takahashi H. Kondo S. Maki H. Niwa H. Ikeda T. Hirano Chemiluminescence of 6-aryl-2-methylimidazo[1,2-a]pyrazin-3(7H)-ones in DMSO-TMG and in diglyme-acetate buffer: support for the chemiexcitation process to generate the singlet-excited state of neutral oxyluciferin in a high quantum yield in the Cypridina (Vargula) bioluminescence mechanism Tetrahedron Lett. 2006 47 6057
14. T. Hirano, Y. Takahashi, H. Kondo, H. Ikeda, S. Maki and H. Niwa, Mechanistic study on the Cypridina (Vargula) bioluminescence reaction, in Proceedings of the 14th International Symposium on Bioluminescence and Chemiluminescence, ed., A. A. Szalay,,, P. J. Hill,,, L. J. Kricka, and, P. E. Stanley,, World Scientific, Singapore, 2006, pp. 11-14
15. F. McCapra Y. C. Chang Chemiluminescence of a Cypridina luciferin analogue J. Chem. Soc., Chem. Commun. 1967 1011
16. T. Goto S. Inoue S. Sugiura Cypridina bioluminescence 4. Synthesis and chemiluminescence of 3,7-dihydroimidazo[1,2-a]pyrazin-3-one and its 2-methyl derivative Tetrahedron Lett. 1968 3873
17. T. Goto H. Fukatsu Cypridina bioluminescence 7. Chemiluminescence in micelle solutions - A model system for Cypridina bioluminescence Tetrahedron Lett. 1969 4299
18. O. Shimomura F. H. Johnson Mechanism of luminescent oxidation of Cypridina luciferin Biochem. Biophys. Res. Commun. 1971 44 340
19. K. Usami M. Isobe Low-temperature photooxygenation of coelenterate luciferin analog synthesis and proof of 1,2-dioxetanone as luminescence intermediate Tetrahedron 1996 52 12061
20. F. H. Johnson, H.-D. Stachel, E. C. Taylor, O. Shimomura, Chemiluminescence and fluorescence of Cypridina luciferin and of some new indole compounds in dimethylsufoxide, in Bioluminescence in Progress, Princeton University Press, Princeton, 1966, pp. 67-82
21. T. Goto S. Inoue S. Sugiura K. Nishikawa M. Isobe Y. Abe Cypridina bioluminescence V. Structure of emitting species in luminescence of Cypridina luciferin and its related compounds Tetrahedron Lett. 1968 4035
22. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. G. Johnson, W. Chen, M. W. Wong, C. Gonzalez and J. A. Pople, GAUSSIAN 03, Gaussian, Inc., Wallingford, CT, 2004
23. A. D. Becke Density-functional thermochemistry 3. The role of exact exchange J. Chem. Phys. 1993 98 5648
24. C. T. Lee W. T. Yang R. G. Parr Development of the Colle-Salventti correlation-energy formula into a functional of the electron-density Phys. Rev. B 1988 37 785
25. P. J. Stephens F. J. Devlin C. F. Chabalowski M. J. Frisch Ab-initio calculation of vibrational absorption and circular-dichroism spectra using density-functional force-fields J. Phys. Chem. 1994 98 11623
26. R. Dennington, II, T. Keith, J. Millam, K. Eppinnett, W. L. Hovell and R. Gilliland, Semichem, Inc., Shawnee Mission, KS, 2003
27. S. Inoue S. Sugiura H. Kakoi T. Goto Cypridina bioluminescence 6. A new route for synthesis of Cypridina luciferin and its analogs Tetrahedron Lett. 1969 1609
28. Y. Toya T. Kayano K. Sato T. Goto Synthesis and chemiluminescence properties of 6-(4-methoxyphenyl)-2-methylimidazo[1,2-a]pyrazin-3(7H)-one and 2-methy-6-(2-naphthyl)imidazo[1,2-a]pyrazin-3(7H)-one Bull. Chem. Soc. Jpn. 1992 65 2475
29. J. Lee H. H. Seliger Quantum yields of luminol chemiluminescence reaction in aqueous and aprotic solvents Photochem. Photobiol. 1972 15 227
30. C. Reichardt, in Solvents and Solvent Effects in Organic Chemistry, 3rd edn, Wiley-VCH, Weinheim, 2003
31. E. Lippert Habilitationsschrift zur Erlangung der Lehrberichtigung (Venia Legendi) für das Fach physikalische Chemie ander Techischen-Hochschle- Stuttgart-spektroskopische Bestimmung des Dipolmomentes aromatischer verbindungen im ersten angeregten Singulettzustand Z. Electrochem. 1957 61 962
32. N. Mataga Y. Kaifu M. Koizumi Solvent effects upon fluorescence spectra and the dipolemoments of excited molecules Bull. Chem. Soc. Jpn. 1956 29 465
33. S. Sumalekshmy K. R. Gopidas Photoinduced intramolecular charge transfer in donor-acceptor substituted tetrahydropyrenes J. Phys. Chem. B 2004 108 3705
34. M. Maus W. Rettig D. Bonafoux R. Lapouyade Photoinduced intramolecular charge transfer in a series of differently twisted donor-acceptor biphenyls as revealed by fluorescence J. Phys. Chem. A 1999 103 3388
35. H. Isobe M. Okamura 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
36. G. J. Kavarnos N. J. Turro Photosensitization by reversible electron-transfer - Theories, experimental evidence, and examples Chem. Rev. 1986 86 401
37. N. J. Turro, in Modern Molecular Photochemistry, University Science Books, Sausalito, CA, 1991
38. H. Nakamura M. Aizawa D. Takeuchi A. Murai O. Shimomura Convergent and short-step syntheses of dl-Cypridina luciferin and its analogues based on Pd-mediated cross couplings Tetrahedron Lett. 2000 41 2185
39. T. Nakatsu S. Ichiyama J. Hiratake A. Saldanha N. Kobashi K. Sakata H. Kato Structural basis for the spectral difference in luciferase bioluminescence Nature 2006 440 372