Chemi- and bioluminescence of coelenterazine analogues possessing an adamantylmethyl group

Tetrahedron

Volumn 53, Issue 38, 1997, Pages 12903-12916

  Hirano, Takashi ^a   Negishi, Ryo ^a   Yamaguchi, Mihoko ^a   Chen, Feng Qi ^a   Ohmiya, Yoshihiro ^b   Tsuji, Frederick I ^a,c   Ohashi, Mamoru ^a  

^a UNIVERSITY OF ELECTRO COMMUNICATIONS   (Japan)

^b SHIZUOKA UNIVERSITY   (Japan)

^c UNIVERSITY OF CALIFORNIA SAN DIEGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADAMANTANE DERIVATIVE; PYRAZINE DERIVATIVE;

ARTICLE; BIOLUMINESCENCE; CHEMOLUMINESCENCE; IN VITRO STUDY; MOLECULAR DYNAMICS; PHOTOCHEMISTRY; PRIORITY JOURNAL;

EID: 0030815159     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00812-0     Document Type: Article

References (35)

1. a) Shimomura, O.; Johnson, F. H.; Saiga, Y. J. Cell. Comp. Physiol., 1962, 59, 223 (1962);
2. b) Johnson, F. H.; Shimomura, O. Methods Enzymol., 1978, 57, 71.
3. Ohmiya, Y.; Hirano, T. Chem. & Biol., 1996, 3, 337.
4. Shimomura, O.; Johnson, F. H. Tetrahedron Lett., 1973, 2963.
5. Shimomura, O.; Johnson, F. H. Nature (London), 1975, 256, 236 (1975).
6. a) Shimomura, O.; Musicki, B.; Kishi, Y. Biochem. J., 1988, 251, 405;
7. b) Shimomura, O.; Musicki, B.; Kishi, Y. Biochem. J., 1989, 267, 913;
8. c) Shimomura, O,; Inouye, S.; Musicki, B.; Kishi, Y. Biochem. J., 1990, 270, 309;
9. d) Shimomura, O. Cell Calcium, 1991, 12, 635;
10. e) Shimomura, O.: Musicki, B.; Kishi, Y.; Inouye, S. Cell Calcium, 1993, 14, 373; O Shimomura, O.; Kishi, Y.; Inouye, S. Biochem. J., 1993, 296, 549;
11. e) Shimomura, O.: Musicki, B.; Kishi, Y.; Inouye, S. Cell Calcium, 1993, 14, 373; O Shimomura, O.; Kishi, Y.; Inouye, S. Biochem. J., 1993, 296, 549;
12. g) Shimomura, O. Biochem. J., 1995, 306, 537.
13. a) Chen, F. -Q.; Gomi, Y.; Hirano, T.; Ohashi, M.; Ohmiya, Y.; Tsuji, F. I. J. Chem. Soc., Perkin Trans, 1, 1992, 1607;
14. b) Ohmiya, Y.; Teranishi, K.; Akutagawa, M.; Ohashi, M.; Tsuji, F. I. Chem, Lett., 1993, 2149.
15. Shimomura O.; Johnson, F. H. Nature (London), 1970, 227, 1356.
16. Teranishi K.; Goto, T. Chem. Lett., 1989, 1423.
17. Inouye, S.; Noguchi, M.; Sasaki, Y.; Takagi, Y.; Miyata, T.; Imanaga, S.; Miyata, T.; Tsuji, F. I. Proc. Natl Acad. Sci. USA, 1985, 82, 3154.
18. Preliminary communication, Hirano, T.; Negishi, R.; Yamaguchi, M.; Chen, F. -Q.; Ohmiya, Y.; Tsuji, F. I.; Ohashi, M. J. Chem. Soc., Chem. Commun., 1995, 1335.
19. Bochmann, M.; Wilkinson, G.; Young, G. B. J. Chem. Soc., Dalton Trans., 1980, 1979.
20. Kishi, Y.; Tanino, H.; Goto, T. Tetrahedron Lett., 1972, 2747.
21. Inoue, S.; Sugiura, S.; Kakoi, H.; Hashizume, K.; Goto, T.; Iio, H. Chem. Lett., 1975, 141.
22. a) McCapra F.; Chang, Y. C. J. Chem. Soc. Chem. Commun., 1967, 1011;
23. b) McCapra F.; Manning, M. J. J. Chem. Soc. Chem. Commun., 1973, 467.
24. Goto, T.; Inouye, S.; Sugiura, S.; Nishikawa, K.; Isobe, M.; Abe, Y. Tetrahedron Lett., 1968, 4035.
25. Hori, K.; Wampler, J. E.; Cormier, M. J. J. Chem. Soc. Chem. Commun., 1973, 492.
26. Hirano, T.; Gomi, Y.; Takahashi, T.; Kitahara, K.; Chen, F. -Q.; Mizoguchi, I.; Kyushin, S.; Ohashi, M. Tetrahedron Lett., 1992, 33, 5771.
27. Recently, the chemiluminescent properties of 2-hydroperoxide and 1,2-dioxetanone of a coelenterazi ne analogue (2-tert-buty1-6-(p-methoxyphenyl)-8-benzyl-3,7-dihydroimidazo[1,2-a]pyrazin-3- one) were reported; Usami, K.; Isobe, M, Tetrahedron, 1996, 52, 12061. The chemiluminescence spectra of this coelenterazine analogue and its 2-hydroperoxide in diglyme containing acetate buffer (pH 5.6, 0.5% v/v) are similar to that of coelenterazine 1 in diglyme containing acetate buffer (pH 5.6,0.66% v/v).
28. Tsuji, F. I.; Inouye, S.; Goto, T.; Sakaki, Y. Proc. Natl. Acad. Sci. USA, 1986, 83, 8107.
29. Shimomura O.; Shimomura, A. FEBS Lett., 1982, 138, 201.
30. Hirano, T.; Mizoguchi, I.; Yamaguchi, M.; Chen, F. -Q.; Ohashi, M.; Ohmiya, Y.; Tsuji, F. I. J. Chem. Soc., Chem. Commun., 1994, 165.
31. Chen, F. Q.; Zheng, J. L.; Hirano, T.; Niwa, H.; Ohmiya, Y.; Ohashi, M. J. Chem. Soc., Perkin Trans, 1, 1995, 2129.
32. a) Kurose, K.; Inouye, S.; Sasaki, Y.; Tsuji, F. I. Proc. Natl. Acad. Sci. USA, 1989, 86, 80;
33. b) Ohmiya Y.; Tsuji, F. I. FEBS Lett., 1993, 320, 267.
34. a) Inouye, S.; Aoyama, S.; Miyata, T.; Tsuji, F. I.; Sakaki, Y. J. Biochem., 1989, 105, 473;
35. b) Inouye, S.; Zenno, S.; Sakaki, Y.; Tsuji, F. I. Protein Expression Purif., 1991, 2, 122.