Advanced chemistry of dioxetane-based chemiluminescent substrates originating from bioluminescence

Journal of Photochemistry and Photobiology C: Photochemistry Reviews

Volumn 5, Issue 1, 2004, Pages 27-53

  Matsumoto, Masakatsu ^a,b,c,d  

^a KANAGAWA UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

^c SAGAMI CHEMICAL RESEARCH CENTER   (Japan)

^d FUJIREBIO INC   (Japan)

Author keywords

Bioluminescence; Charge transfer; Chemiexcitation process; Chemiluminescence; CIEEL; Dioxetane; Electron transfer

Indexed keywords

CARBONYL PRODUCTS; THERMOLYSIS;

BIOCHEMISTRY; BIOLUMINESCENCE; CHEMILUMINESCENCE;

PHOTOCHEMICAL REACTIONS;

EID: 2442495183     PISSN: 13895567     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jphotochemrev.2004.02.001     Document Type: Review

References (156)

1. McCapra F. Q. Rev. 20:1966;485
2. White E.H., Harding M.J.C. Photochem. Photobiol. 4:1965;1129
3. F. McCapra, J. Chem. Soc., Chem. Commun. (1968) 155.
4. Kopecky K.R., Mumford C. Can. J. Chem. 47:1969;709
5. F. McCapra, K.D. Perring, in: J.R. Burr (Ed.), Chemi- and Bioluminescence, Dekker, New York, 1985, p. 359.
6. W.D. McElroy, M. DeLuca, in: J.R. Burr (Ed.), Chemi- and Bioluminescence Dekker, New York, 1985, p. 387.
7. Hastings J.W. Photochem. Photobiol. 62:1995;599
8. Wilson T. Photochem. Photobiol. 62:1995;601
9. Mager H.I.X., Tu S.-C. Photochem. Photobiol. 62:1995;607
10. Wood K.V. Photochem. Photobiol. 62:1995;662
11. Wada N. Recent Res. Dev. Photochem. Photobiol. 5:2001;19
12. M. Ohashi, in: K. Ogura (Ed.), Dynamic Aspects of Natural Products Chemistry, Kodansha, Tokyo, 1997, p. 269.
13. Hirano T., Ohashi M. J. Synth. Org. Chem. (Jpn. Yuki Gosei Kyoukai Shi). 54:1996;596
14. Schuster G.B. Acc. Chem. Res. 12:1979;366
15. F. McCapra, K.D. Perring, in: J.R. Burr (Ed.), Chemi- and Bioluminescence, Dekker, New York, 1985, p. 259.
16. W. Adam, in: S. Patai (Ed.), The Chemistry of Peroxide, Wiley, New York, 1983, p. 829.
17. W. Adam, in: A. Hassner (Ed.), Small Ring Heterocycles, Wiley, New York, 1986, p. 351.
18. W. Adam, M. Heil, T. Mosandl, C.R. Saha-Möller, in: W. Ando (Ed.), Organic Peroxides, Wiley, New York, 1992, p. 221.
19. C.R. Saha-Möller, W. Adam, in: A. Padwa (Ed.), Comprehensive Heterocyclic Chemistry. II. A Review of the Literature 1982-1995, Pergamon Press, New York, 1996, p. 1041.
20. 2, vol. II, CRC Press, Florida, 1985, p. 37.
21. E.H. White, D.F. Roswell, in: J.R. Burr (Ed.), Chemi- and Bioluminescence, Dekker, New York, 1985, p. 215.
22. A.G. Mohan, in: J.R. Burr (Ed.), Chemi- and Bioluminescence, Dekker, New York, 1985, p. 245.
23. A.C. Balwin, in: S. Patai (Ed.), The Chemistry of Peroxide, Wiley, New York, 1983, p. 97.
24. Richardson W.H., O'Neal H.E. J. Am. Chem. Soc. 94:1972;8665
25. Turro N.J., Lechtken P. J. Am. Chem. Soc. 95:1973;264
26. Richardson W.H., Montgomery F.C., Yelvington M.B., O'Neal H.E. J. Am. Chem. Soc. 96:1974;7525
27. Adam W., Baader W.J. J. Am. Chem. Soc. 107:1985;410
28. Richardson W.H. J. Org. Chem. 54:1989;4677
29. Reguero M., Bernardi F., Bottoni A., Olivucci M., Robb M.A. J. Am. Chem. Soc. 113:1991;1566
30. Wilson T., Halpern A.M. J. Phys. Org. Chem. 8:1995;359
31. Vasil'ev R.F. J. Biolumin. Chemilumin. 13:1998;69
32. Takano Y., Tsunesada T., Isobe H., Yoshioka Y., Yamaguchi K., Saito I. Bull. Chem. Soc. Jpn. 72:1999;213
33. Wilsey S., Bernardi F., Olivucci M., Robb M.A., Murphy S., Adam W. J. Phys. Chem. A. 103:1999;1669
34. Tanaka C., Tanaka J. J. Phys. Chem. A. 104:2000;2078
35. McCapra F. Methods Enzymol. 305:2000;3
36. Kazakov V.P., Voloshin A.I., Shavaleev N.M. J. Photochem. Photobiol. A: Chem. 119:1998;177
37. Koo J.-Y., Schuster G.B. J. Am. Chem. Soc. 99:1977;6107
38. Koo J.-Y., Schuster G.B. J. Am. Chem. Soc. 100:1978;4496
39. Hercules D.M. Science. 145:1964;808
40. Chandross E.A., Sonntag F.I. J. Am. Chem. Soc. 86:1964;3179
41. Santhanam K.S.V., Bard A.J. J. Am. Chem. Soc. 87:1965;139
42. Catalani L.H., Wilson T. J. Am. Chem. Soc. 111:1989;2633
43. McCapra F. J. Photochem. Photobiol. A: Chem. 51:1990;21
44. Schmidt S.P., Schuster G.B. J. Am. Chem. Soc. 102:1980;306
45. Adam W., Cueto O. J. Am. Chem. Soc. 101:1979;6511
46. Handley R.S., Stern A.J., Schaap A.P. Tetrahedron Lett. 26:1985;3183
47. Akhavan-Tafti H., Eickholt R.A., Arghavani Z., Schaap A.P. J. Am. Chem. Soc. 119:1997;245
48. F. McCapra, A. Burford, J. Chem. Soc., Chem. Commun. (1976) 607.
49. Zaklika K.A., Thayer A.L., Schaap A.P. J. Am. Chem. Soc. 100:1978;4916
50. Zaklika K.A., Kissel T., Thayer A.L., Burns P.A., Schaap A.P. Photochem. Photobiol. 30:1979;35
51. Schaap A.P., Gagnon S.D., Zaklika K.A. Tetrahedron Lett. 23:1982;2943
52. T. Goto, H. Nakamura, J. Chem. Soc., Chem. Commun. (1978) 781.
53. Nakamura H., Goto T. Photochem. Photobiol. 30:1978;27
54. Schaap A.P., Gagnon S.D. J. Am. Chem. Soc. 104:1982;3504
55. Schaap A.P., Chen T.-S., Handley R.S., DeSilva R., Giri B.P. Tetrahedron Lett. 28:1987;1155
56. Schaap A.P., Handley R.S., Giri B.P. Tetrahedron Lett. 28:1987;935
57. Edwards B., Sparks A., Voyta J.C., Bronstein I. J. Biolumin. Chemilumin. 5:1990;1
58. Adam W., Bronstein I., Edwards B., Engel T., Reinhardt D., Schneider F.W., Trofimov A.V., Vasil'ev R.F. J. Am. Chem. Soc. 118:1996;10400
59. Beck S., Köster H. Anal. Chem. 62:1990;2258
60. Trofimov A.V., Vasil'ev R.F., Mielke K., Adam W. Photochem. Photobiol. 62:1995;35
61. Trofimov A.V., Mielke K., Vasil'ev R.F., Adam W. Photochem. Photobiol. 63:1996;463
62. 2, vol. II, CRC Press, Florida, 1985 (Chapter 5).
63. Adam W., Reinhardt D., Saha-Möller C.R. Analyst. 121:1996;1527
64. H. Numan, J.H. Wieringa, H. Wynberg, J. Hess, A. Vos, J. Chem. Soc., Chem. Commun. (1977) 591.
65. Schuster G.B., Turro N.J., Steinmetzer H.-C., Schaap A.P., Faler G., Adam W., Liu J.-C. J. Am. Chem. Soc. 97:1975;7110
66. Hess J., Vos A. Acta Crystallogr. B. 33:1977;3527
67. K. Ishimaru, Japanese Patent Kokai P2002-20382A (2002).
68. N.-Y. Wang, Patent WO94/10258 (1994).
69. B.P. Giri, US Patent 1998-99693P (1998).
70. M. Matsumoto, H. Suganuma, Y. Katao, H. Mutoh, J. Chem. Soc., Chem. Commun. (1995) 431.
71. Watanabe N., Suganuma H., Kobayashi H., Mutoh H., Katao Y., Matsumoto M. Tetrahedron. 55:1999;4287
72. M. Matsumoto, H. Suganuma, J. Chem. Soc., Chem. Commun. (1994) 2449.
73. Matsumoto M., Kobayashi H., Matsubara J., Watanabe N., Yamashita S., Oguma D., Kitano Y., Ikawa H. Tetrahedron Lett. 37:1996;397
74. Matsumoto M., Watanabe N., Kobayashi H., Suganuma H., Matsubara J., Kitano Y., Ikawa H. Tetrahedron Lett. 37:1996;5939
75. Matsumoto M., Kitano Y., Kobayashi H., Ikawa H. Tetrahedron Lett. 37:1996;8191
76. Liden A., Roussel C., Liljefors T., Chanon M., Carter R.E., Metzger J., Sandström J. J. Am. Chem. Soc. 98:1976;2853
77. P. Lechtken, G. Reissenweber, P. Grumbmüller, Tetrahedron Lett. (1977) 2881.
78. Kopecky K.R., Lockwood P.A., Gomez R.R., Ding J.-Y. Can. J. Chem. 59:1981;851
79. M. Matsumoto, N. Watanabe, H. Kobayashi, unpublished results.
80. Matsumoto M., Watanabe N., Kasuga N.C., Hamada F., Tadokoro K. Tetrahedron Lett. 38:1997;2863
81. Gollnick K., Knutzen-Mies K. J. Org. Chem. 56:1991;4017
82. M. Matsumoto, H. Murakami, N. Watanabe, J. Chem. Soc., Chem. Commun. (1998) 2319.
83. Baumstark A.L., Parker A.N. J. Heterocycl. Chem. 29:1992;791
84. Adam W., Fell R., Schultz M.H. Tetrahedron. 49:1993;2227
85. Adam W., Qian X., Saha-Möller C.R. Tetrahedron. 49:1993;417
86. Matsumoto M., Ito Y., Murakami M., Watanabe N. Luminescence. 17:2002;305
87. K. Fujimori, K. Wakasugi, M. Matsumoto, Chem. Lett. (2002) 762.
88. Matsumoto M., Watanabe N., Shiono T., Suganuma H., Matsubara J. Tetrahedron Lett. 38:1997;5825
89. Lee C., Singer L.A. J. Am. Chem. Soc. 102:1980;3823
90. Matsumoto M., Suganuma H., Azami M., Aoshima N., Mutoh H. Heterocycles. 41:1995;2419
91. McCapra F. Tetrahedron Lett. 34:1993;6941
92. Adam W., Trofimov A.V. J. Org. Chem. 65:2000;6474
93. Matsumoto M., Watanabe N., Kobayashi H., Azami M., Ikawa H. Tetrahedron Lett. 38:1997;411
94. Watanabe N., Kobayashi H., Azami M., Matsumoto M. Tetrahedron. 55:1999;6831
95. Edwards B., Sparks A., Voyta J.C., Strong R., Murphy O., Bronstein I. J. Org. Chem. 55:1990;6225
96. Matsumoto M., Hiroshima T., Chiba S., Isobe R., Watanabe N., Kobayashi H. Luminescence. 14:1999;345
97. Matsumoto M., Ito Y., Matsubara J., Sakuma T., Mizoguchi Y., Watanabe N. Tetrahedron Lett. 42:2001;2349
98. Matsumoto M., Murayama J., Nishiyama M., Mizoguchi Y., Sakuma T., Watanabe N. Tetrahedron Lett. 43:2002;1523
99. Yang N.C., Feit E.D., Hui M.H., Turro N.J., Dalton J.C. J. Am. Chem. Soc. 92:1970;6974
100. Baumstark A.L., Willson C.E. Tetrahedron Lett. 22:1981;4363
101. A.L. Baumstark, C.E. Willson, Tetrahedron Lett. (1979) 2569.
102. Ohashi M., Takanashi M., Watanabe N., Matsumoto M., Saisu T., Niwa H. Eur. J. Mass Spectrom. 7:2001;441
103. Nery A.L.P., Röpke S., Catalani L.H., Baader W.J. Tetrahedron Lett. 40:1999;2443
104. Nery A.L.P., Weiß D., Catalani L.H., Baader W.J. Tetrahedron. 56:2000;5317
105. Matsumoto M., Azami M. Terahedron Lett. 38:1997;8947
106. Matsumoto M., Ishihara T., Watanabe N., Hiroshima T. Terahedron Lett. 40:1999;4571
107. Adam W., Bronstein I., Trofimov A.V., Vasil'ev R.F. J. Am. Chem. Soc. 121:1999;958
108. Burshtein A.I. Chem. Phys. 289:2003;251
109. Adam W., Matsumoto M., Trofimov A.V. J. Am. Chem. Soc. 122:2000;8631
110. C. Tanaka, J. Tanaka, M. Matsumoto, in: Proceedings of the 83rd Annual Meeting of the Chemical Society of Japan, Tokyo, 2003 (Abstract 4C2-03).
111. S. Singh, E.F. Ullman, J. Chem. Soc., Chem. Commun. (2003) 1756.
112. M. Matsumoto, Y. Mizuno, M. Maeda, N. Watanabe, in: Proceedings of the Symposium on Photochemistry, Simane, 2003.
113. Mariscal A., Garcia A., Carnero M., Gomez M., Fernandez-Crehuet J. Biotechniques. 16:1994;888
114. Buxton R.C., Edwards B., Juo R.R., Voyta J.C., Bethell R. Anal. Biochem. 280:2000;291
115. J.D. Stevenson, A. Dietel, N.R. Thomas, J. Chem. Soc., Chem. Commun. (1999) 2105.
116. Matsumoto M., Mizoguchi Y., Motoyama T., Watanabe N. Tetrahedron Lett. 42:2001;8869
117. Adam W., Bronstein I., Trofimov A.V. J. Phys. Chem. A. 102:1998;5406
118. Adam W., Matsumoto M., Trofimov A.V. J. Org. Chem. 65:2000;2078
119. Schaap A.P., Akhavan H., Romano R.J. Clin. Chem. 35:1989;1863
120. B. Edwards, A. Sparks, J.C. Voyta, I. Bronstein, in: A.K. Campbell, L.J. Lricka, P.E. Stanley (Eds.), Bioluminescence and Chemiluminescence: Fundamentals and Applied Aspects, Wiley, Chichester, 1994, p. 56.
121. Matsumoto M., Arai N., Watanabe N. Tetrahedron Lett. 37:1996;8535
122. Matsumoto M., Sakuma T., Watanabe N. Luminescence. 16:2001;275
123. I. Bronstein, B. Edwards, Patent WO 2000006164.
124. Matsumoto M., Sakuma T., Watanabe N. Tetrahedron Lett. 43:2002;8955
125. Schaap A.P., Burns P.A., Zaklika K.A. J. Am. Chem. Soc. 99:1977;1270
126. Zaklika K.A., Burns P.A., Schaap A.P. J. Am. Chem. Soc. 100:1978;318
127. Sabelle S., Renard P.-Y., Pecorella K., de Suzzoni-Dèzard S., Crèminon C., Grassi J., Mioskowski C. J. Am. Chem. Soc. 124:2002;4874
128. Sabelle S., Hydrio J., Leclerc E., Mioskowski C., Renard P.-Y. Tetrahedron Lett. 43:2002;3645
129. M. Matsumoto, K. Ueda, T. Mizuno, N. Watanabe, in: Proceedings of the 81st Annual Meeting of the Chemical Society of Japan, Tokyo, 2002 (Abstract 3PC066).
130. M. Matsumoto, T. Mizuno, N. Watanabe, J. Chem. Soc., Chem. Commun. (2003) 482.
131. M. Matsumoto, H. Murakami, N. Watanabe, in: Proceedings of the 72nd Annual Meeting of the Chemical Society of Japan, Tokyo, 1997 (Abstract 2J242).
132. Adam W., Reinhardt D. J. Chem. Soc., Perkin Trans. 2:1994;1503
133. White E.H., Harding M.J.C. Photochem. Photobiol. 4:1965;1129
134. M. Kimura, H. Nishikawa, H. Kura, H. Lim, H. White, Chemistry. Lett. (1993) 505.
135. Imanishi T., Ueda Y., Tainaka R., Miyashita K., Hoshino N. Tetrahedron Lett. 38:1997;841
136. Imanishi T., Ueda Y., Tainaka R., Kuni N., Minagawa M., Hoshino N., Miyashita K. Heterocycles. 47:1998;829
137. Adam W., Reinhardt D. J. Chem. Soc., Perkin Trans. 2:1997;1453
138. Sakanishi K., Nugroho M.B., Kato Y., Yamazaki N. Tetrahedron Lett. 35:1994;3559
139. Sakanishi K., Kato Y., Mizukoshi E., Shimizu K. Tetrahedron Lett. 35:1994;4789
140. Imanishi T., Ueda Y., Minagawa M., Hoshino N., Miyashita K. Tetrahedron Lett. 38:1997;3967
141. N. Watanabe, M. Matsumoto, F. Nagamatsu, submitted for publication.
142. Watanabe N., Nagashima Y., Yamazaki T., Matsumoto M. Tetrahedron. 59:2003;4811
143. White E.H., Rapaport E., Hopkins T.A., Seliger H.H. J. Am. Chem. Soc. 91:1969;2178
144. White E.H., Rapaport E., Hopkins T.A., McElroy W.D. Bioorg. Chem. 1:1971;92
145. White E.H., Steinmetz M.G., Miano J.D., Wildes P.D., Morland R. J. Am. Chem. Soc. 102:1980;3199
146. White E.H., Roswell D.F. Photochem. Photobiol. 53:1991;131
147. Morton R.A., Hopkins T.A., Seliger H.H. Biochemistry. 8:1969;1598
148. F. McCapra, D.J. Gilfoyle, D.W. Young, N.J. Church, P. Spencer, in: A.K. Campbell, L.J. Kricka, P.E. Stanley (Eds.), Bioluminescence and Chemiluminescence: Fundamentals and Applied Aspects, Wiley, Chichester, 1994, p. 387.
149. F. McCapra, in: J.W. Hastings, L.J. Kricka, P.E. Stanley (Eds.), Bioluminescence and Chemiluminescence: Molecular Reporting with Photons, Wiley, Chichester, 1997, p. 7.
150. Branchini B.R., Murtiashaw M.H., Magyar R.A., Portier N.C., Ruggiero M.C., Stroh J.G. J. Am. Chem. Soc. 124:2002;2112
151. Orlova G., Goddard J.D., Brovko L.Y. J. Am. Chem. Soc. 125:2003;6962
152. M. Matsumoto, D. Kasai, N. Watanabe, H. Ijuin, in: Proceedings of the Symposium on Photochemistry, Simane, to be submitted.
153. Mayer A., Neuenhofer S. Angew. Chem. Int. Ed. Engl. 33:1994;1044
154. Kricka L.J. Methods Enzymol. 305:2000;333
155. Roda A., Pasini P., Guardigli M., Baraldini M., Musiani M., Mirasoli M. Fresenius J. Anal. Chem. 366:2000;752
156. Palilis L.P., Calokerinos A.C. Anal. Chim. Acta. 413:2000;175