Chemiluminescence of Cypridina Luciferin Analogs. Part 3. MCLA Chemiluminescence with Singlet Oxygen Generated by the Retro-Diels-Alder Reaction of a Naphthalene Endoperoxide

Photochemistry and Photobiology

Volumn 68, Issue 2, 1998, Pages 143-149

  Fujimori, Ken ^a   Komiyama, Tomoko ^a   Tabata, Hideo ^a   Nojima, Takayuki ^b   Ishiguro, Katsuya ^b   Sawaki, Yasuhiko ^b   Tatsuzawa, Hidetaka ^c   Nakano, Minoru ^d  

^a UNIVERSITY OF TSUKUBA   (Japan)

^b NAGOYA UNIVERSITY   (Japan)

^c MARINE BIOTECHNOLOGY INSTITUTE   (Japan)

^d JAPAN IMMUNORESEARCH LABORATORIES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BETULACEAE; CYPRIDINA; CYPRIDINA LUCIFERIN;

EID: 0000473989     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1751-1097.1998.tb02481.x     Document Type: Article

References (33)

1. Deadwyler, G., P. D. Sima, Y. Fu and J. R. Kanofsky (1997) Singlet oxygen-mediated inactivation of acetylcholinesterase: a comparison of purified enzyme in solution and enzyme bound to K564 leukemia cells. Photochem. Photobiol. 65, 884-894.
2. Foote, C. S. (1976) Photosensitized oxidation and singlet oxygen: consequences in biological systems. In Free Radicals in Biology, Vol. 2 (Edited by W. A. Pryor), pp. 85-133. Academic Press, New York.
3. Khan, A. U., P. D. Macio, M. H. G. Medeiros and T. Wilson (1992) Spermine and spermidine protection of plasmid DNA against single-strand breaks induced by singlet oxygen. Proc. Natl. Acad. USA 89, 11428-11430.
4. Nagano, T., T. Tanaka, H. Mizuki and M. Hirobe (1994) Toxicity of singlet oxygen generated thermolytically in Escherichia coli. Chem. Pharm. Bull. 42, 883-887.
5. Kanofsky, J. E. (1989) Singlet oxygen production by biological systems. Chem. Biol. Interact. 70, 1-28.
6. Kanofsky, J. R., H. Hoogland, R. Weber and S. J. Weiss (1988) Singlet oxygen production by human eosinophils. J. Biol. Chem. 263, 9692-9696.
7. g) molecular oxygen in solutions. Chem. Phys. Lett. 81, 443-445.
8. Uehara, K., K. Hori, M. Nakano and S. Koga (1991) Highly sensitive chemiluminescence method for determining myeloperoxidase in human polymorphonuclear leukocytes. Anal. Biochem. 199, 191-196.
9. Koga, S., M. Nakano and K. Uehara (1991) Mechanism for the generation of superoxide anion and singlet oxygen during heme compound-catalyzed linoleic acid hydroperoxide decomposition. Arch. Biochem. Biophys. 289, 223-229.
10. Nakano, M. (1990) Determination of superoxide radical and singlet based on chemiluminescence of luciferin analogs. Methods Enzymol. 186, 585-591.
11. Mashiko, S., N. Suzuki, S. Koga, M. Nakano, T. Ashino, I. Mizumoto and H. Inaba (1991) Measurement of rate constants for quenching singlet oxygen with a Cypridina luciferin analog (2-methyl-6-[p-methoxyphenyl]-3,7-dinydroimidazo [1,2-a]pyrazin-3-one) and sodium azide. J. Biolumin. Chemilumin. 6, 69-72.
12. Saito, I., T. Matsuura and K. Inoue (1981) Formation of superoxide ion from singlet oxygen. On the use of a water-soluble singlet oxygen source. J. Am. Chem. Soc. 103, 188-190.
13. Macio, P. D. and H. Sies (1989) Quantification of singlet oxygen generated by thermolysis of 3,3′-(1,4-naphthylidine) dipropionate. Monomol and dimol photoemission and the effects of 1,4-diazabicyclo[2,2,2]octane. J. Am. Chem. Soc. 111, 2909-2914.
14. Turro, N. J., M.-F. Chow and J. Rigaudy (1981) Mechanism of thermolysis of endoperoxides of aromatic compounds. Activation parameters, magnetic field, and magnetic isotope effects. J. Am. Chem. Soc. 103, 7218-7224.
15. Wasserman, H. H. and D. L. Larsen (1972) Formation of 1,4-endoperoxides from the dye-sensitized photo-oxygenation of alkyl-naphthalenes. J. Chem. Soc. Chem. Commun. 253-254.
16. Fujimori, K., H. Nakajima, K. Akutsu, M. Mitani, H. Sawada and M. Nakayama (1993) Chemiluminescence of Cypridina luciferin analogues. Part 1. Effect of pH on rates of spontaneous autoxidation of CLA in aqueous buffer solutions. J. Chem. Soc. Perkin Trans. 2, 2405-2409.
17. Akutsu, K., H. Nakajima and K. Fujimori (1995) Chemiluminescence of Cypridina luciferin analogues. Part 1. Kinetic studies on the reaction of 2-methyl-6-phenylimidazo[1,2-a]pyrazin-3(7H)-one (CLA) with superoxide: hydroperoxyl radical is an actual active species to initiate the reaction. J. Chem. Soc. Perkin Trans. 2, 1699-1706.
18. Teranishi, K., K. Ueda, H. Nakao, M. Hisamatsu and T. Yamada (1994) Synthesis of hydroperoxide via photooxygenation for a model aequorin bioluminescence. Tetrahedron Lett. 35, 8181-8184.
19. Usami, K. and M. Isobe (1995) Two luminescent intermediates of coelenterazine analog, peroxide and dioxetanone, prepared by direct photo-oxygenation at low temperature. Tetrahedron Lett. 36, 8613-8616.
20. Usami, K. and M. Isobe (1996) Chemiluminescence characters of hydroperoxide and dioxetanone of coelenterate luciferin analog prepared by low-temperature photooxygenation. Chem. Lett. 215-216.
21. Usami, K. and M. Isobe (1996) Low-temperature photooxygenation of coelenterate luciferin analog - synthesis and proof of 1,2-dioxetanone as luminescence intermediates. Tetrahedron 52, 1201-1209.
22. Goto, T., S. Inoue, S. Sugiura, K. Nishikawa, M. Isobe and Y. Abe (1968) Cypridina bioluminescence V. Structure of emitting species in the luminescence of Cypridina luciferin and its released compounds. Tetrahedron Lett. 37, 4035-4038.
23. Nojima, T., K. Ishiguro and Y. Sawaki (1997) Mechanistic study on the reaction of phenyldiazomethanes with singlet oxygen - formation and cycloreversion of 1,2,3,4-dioxadiazole intermediates. J. Org. Chem. 62, 6911-6917.
24. - chemiluminescence upon UV laser photolysis of an aromatic endoperoxide in aqueous solution. Chem. Phys. Lett. 129, 463-467.
25. Long, C. A. and D. R. Kearns (1975) Radiationless decay of singlet molecular oxygen in solution. II. Temperature dependence and solvent effects. J. Am. Chem Soc. 97, 2018-2020.
26. Teranishi, K., M. Hisamatsu and T. Yamada (1996) Studies on the mechanism of chemiluminescence: synthesis and chemiluminescent properties of the 5-hydroperoxide analogue of coelenterate luciferin. Tetrahedron Lett. 37, 8425-8428.
27. Goto, T. (1988) Oxidation of luciferin in bioluminescence and chemiluminescence. In The Role of Oxygen in Chemistry and Biochemistry (Edited by W. Ando and Y. Moro-oka), pp. 353-366. Elsevier, Amsterdam.
28. Teranishi, K., M. Hisamatsu and T. Yamada (1997) Synthesis and chemiluminescent properties of the peroxy acid compound as an intermediate of coelenterate luciferin luminescence. Tetrahedron Lett. 38, 2689-2692.
29. Matheson, I. B. C., R. D. Etheridge, N. R. Kratowich and J. Lee (1975) The quenching of singlet oxygen by amino acids and proteins. Photochem. Photobiol. 21, 165-171.
30. Toya, Y., S. Nakatsuka and T. Goto (1985) Structure of Cypridina biluciferyl, a dimer of Cypridina luciferiyl radical having bioluminescence activity. Tetrahedron Lett. 26, 239-242.
31. Frimer, A. A. (1983) Singlet oxygen in peroxide chemistry. In The Chemistry of Organic Peroxide (Edited by S. Patai), pp. 201-234. John Wiley and Sons, Chichester.
32. Wintgens, V., J. C. Scaiano, S. M. Linden and D. C. Neckers (1989) Transient phenomena in the laser flash photolysis of rose bengal C-2′ ethyl ester. J. Org. Chem. 54, 5242-5250.
33. Sawyer, D. T. and E. J. Nanni Jr. (1981) Redox chemistry of dioxygen species and their chemical reactivity. In Oxygen and Oxy-radicals in Chemistry and Biochemistry (Edited by M. A. J. Rogers and E. L. Powers), pp. 15-44. Academic Press, New York.