Synthesis of [3H]-labeled bioactive lipid a analogs and their use for detection of lipid A-binding proteins on murine macrophages

Bulletin of the Chemical Society of Japan

Volumn 74, Issue 11, 2001, Pages 2189-2197

  Fukase, Koichi ^a   Kirikae, Teruo ^a   Kirikae, Fumiko ^a   Liu, Wen Chi ^a   Oikawa, Masato ^a   Suda, Yasuo ^a   Kurosawa, Motohiro ^a   Fukase, Yoshiyuki ^a   Yoshizaki, Hiroaki ^a   Kusumoto, Shoichi ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL MEMBRANES; NITROCELLULOSE; PROTEINS; RADIOACTIVITY; SYNTHESIS (CHEMICAL);

MURINE MACROPHAGES;

LIPIDS;

LIPID A DERIVATIVE; LIPID BINDING PROTEIN; PYROXYLIN;

ANIMAL CELL; ARTICLE; BINDING SITE; CELL MEMBRANE; ESCHERICHIA COLI; LIPOGENESIS; MOUSE; NONHUMAN; PERITONEUM MACROPHAGE; POLYACRYLAMIDE GEL ELECTROPHORESIS; PROTEIN ANALYSIS; PROTEIN PROTEIN INTERACTION; RADIOACTIVITY;

EID: 0035788492     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.74.2189     Document Type: Article

References (42)

1. Parts of this work were presented at a) 6th Conference of the International Endotoxin Society, Paris (France), August 2000: K. Fukase, T. Kirikae, F. Kirikae, M. Oikawa, Y. Suda, W.-C. Liu, M. Kurosawa, and S. Kusumoto, J. Endotoxin Res., 6, 156, Abst. No. P 125 (2000); b) 41st Symposium on the Chemistry of Natural Products, Nagoya (Japan), October 1999: M. Oikawa, W.-C. Liu, H. Furuta, T Shintaku, H. Sekljic, N. Fukuda, Y. Fukase, Y. Suda, K. Fukase, and S. Kusumoto.
2. Parts of this work were presented at a) 6th Conference of the International Endotoxin Society, Paris (France), August 2000: K. Fukase, T. Kirikae, F. Kirikae, M. Oikawa, Y. Suda, W.-C. Liu, M. Kurosawa, and S. Kusumoto, J. Endotoxin Res., 6, 156, Abst. No. P 125 (2000); b) 41st Symposium on the Chemistry of Natural Products, Nagoya (Japan), October 1999: M. Oikawa, W.-C. Liu, H. Furuta, T Shintaku, H. Sekljic, N. Fukuda, Y. Fukase, Y. Suda, K. Fukase, and S. Kusumoto.
3. Parts of this work were presented at a) 6th Conference of the International Endotoxin Society, Paris (France), August 2000: K. Fukase, T. Kirikae, F. Kirikae, M. Oikawa, Y. Suda, W.-C. Liu, M. Kurosawa, and S. Kusumoto, J. Endotoxin Res., 6, 156, Abst. No. P 125 (2000); b) 41st Symposium on the Chemistry of Natural Products, Nagoya (Japan), October 1999: M. Oikawa, W.-C. Liu, H. Furuta, T Shintaku, H. Sekljic, N. Fukuda, Y. Fukase, Y. Suda, K. Fukase, and S. Kusumoto.
4. E. T. Rietschel, T. Kirikae, F. U. Schade, U. Mamat, G. Schmidt, H. Loppnow, A. J. Ulmer, U. Zähringer, U. Seydel, F. Di Padova, M. Schreier, and H. Brade, FASEB J., 8, 217 (1994).
5. E. T. Rietschel and H. Brade, Sci. Am., 267, 54 (1992).
6. a) M. Imoto, H. Yoshimura, M. Yamamoto, T. Shimamoto, S. Kusumoto, and T. Shiba, Tetrahedron Lett., 25, 2667 (1984).
7. M. Imoto, H. Yoshimura, M. Yamamoto, T. Shimamoto, S. Kusumoto, and T. Shiba, Bull. Chem. Soc. Jpn., 60, 2197 (1987).
8. a) M. Imoto, H. Yoshimura, M. Yamamoto, N. Sakaguchi, S. Kusumoto, and T. Shiba, Tetrahedron Lett., 26, 1545 (1985).
9. b) M. Imoto, H. Yoshimura, T. Shimamoto, N. Sakaguchi, S. Kusumoto, and T. Shiba, Bull. Chem. Soc. Jpn., 60, 2205 (1987).
10. E. T. Rietschel, H. Brade, O. Holst, L. Brade, S. Müller-Loennies, U. Mamat, U. Zähringer, F. Beckmann, U. Seydel, K. Brandenburg, A. J. Ulmer, T. Mattem, H. Heine, J. Schletter, H. Loppnow, U. Schönbeck, H.-D. Flad, S. Hauschildt, U. F. Schade, F. Di Padova, S. Kusumoto, and R. R. Schumann, Bacterial Endotoxin: Chemical Constitution, Biological Recognition, Host Response, and Immunological Detoxification, in "Current Topics in Microbiology and Immunology, Vol. 216, Pathology of Septic Shock," ed by E. T. Rietschel and H. Wagner, Springer-Verlag, Berlin Heidelberg (1996), pp. 39.
11. H. Loppnow, H. Brade, I. Durrbaum, C. A. Dinarello, S. Kusumoto, E. T. Rietschel, and H. D. Flad, J. Immunol., 142, 3229 (1989).
12. a) T. Kusama, T. Soga, E. Shioya, K. Nakayama, H. Nakajima, Y. Osada, Y. Ono, S. Kusumoto, and T. Shiba, Chem. Pharm. Bull., 38, 3366 (1990).
13. b) A. J. Ulmer, A. H. Heine, W. Feist, S. Kusumoto, T. Kusama, H. Brade, U. Schade, E. T. Rietschel, and H.-D. Flad, Infect. Immun., 60, 3309 (1992).
14. T. Kusama, T. Soga, Y. Ono, E. Kumazawa, E. Shioya, K. Nakayama, K. Uoto, and Y. Osada, Chem. Pharm. Bull., 39, 3244 (1991).
15. W.-C. Liu, M. Oikawa, K. Fukase, Y. Suda, and S. Kusumoto, Bull. Chem. Soc. Jpn., 72, 1377 (1999).
16. K. Fukase, Y. Fukase, M. Oikawa, W.-C. Liu, Y. Suda, and S. Kusumoto, Tetrahedron, 54, 4033 (1998).
17. M. J. Fenton and D. T. Golenbock, J. Leukoc. Biol., 64, 25 (1998).
18. R. Medzhitov and C. A. Janeway Jr., Proc. Natl. Acad. Sci. U.S.A., 95, 429 (1998).
19. R. B. Yang, M. R. Mark, A. Gray, A. Huang, M. H. Xie, M. Zhang, A. Goddard, W. I. Wood, A. L. Gurney, and P. J. Godowski, Nature, 395, 284 (1998).
20. C. J. Kirschning, H. Wesche, T. Merrill Ayres, and M. Rothe, J. Exp. Med., 188, 2091 (1998).
21. A. Poltorak, X. He, I. Smimova, M. Y. Liu, C. V. Huffel, X. Du, D. Birdwell, E. Alejos, M. Silva, C. Galanos, M. Freudenberg, P. Ricciardi-Castagnoli, B. Layton, and B. Beutler, Science, 282, 2085 (1998).
22. J. C. Chow, D. W. Young, D. T. Golenbock, W. J. Christ, and F. Gusovsky, J. Bio. Chem., 274, 10689 (1999).
23. E. Lien, T. K. Means, H. Heine, A. Yoshimura, S. Kusumoto, K. Fukase, M. J. Fenton, M. Oikawa, N. Qureshi, B. Monks, R. W. Finberg, R. R. Ingalls, and D. T. Golenbock, J. Clin. Invest., 105, 497 (2000).
24. K. Hoshino, O. Takeuchi, T. Kawai, H. Sanjo, T. Ogawa, Y. Takeda, K. Takeda, and S. Akira, J. Immunol., 162, 3749 (1999).
25. S. T. Qureshi, L. Larivière, G. Leveque, S. Clermont, K. J. Moore, P. Gros, and D. Malo, J. Exp. Med., 189, 615 (1999).
26. S. Akashi, R. Shimazu, H. Ogata, Y. Nagai, K. Takeda, M. Kimoto, and K. Miyake, J. Immunol., 164, 3471 (2000).
27. O. Takeuchi, K. Hoshino, T. Kawai, H. Sanjo, H. Takada, T. Ogawa, and S. Akira, Immunity, 11, 443 (1999).
28. R. Schwandner, R. Dziarski, H. Wesche, M. Rothe, and C. J. Kirschning, J. Biol. Chem., 274, 17406 (1999). Our group demonstrated that Enterococcus hirae lipoteichoic acid itself has no immunostimulating activity but an unidentified immunopotentiator comprised in lipoteichoic acid fraction is responsible for the activity:
29. D. M. Underhill, A. Ozinsky, and K. D. Smith, A. Aderem, Proc. Natl. Acad. Sci. U.S.A., 96, 14459 (1999).
30. M. Hirschfeld, C. J. Kirschning, R. Schwandner, H. Wesche, J. H. Weis, R. M. Wooten, and J. J. Weis, J. Immunol., 163, 2382 (1999).
31. T. Kirikae, F. Kirikae, K. Tominaga, N. Qureshi, S. Yamamoto, and M. Nakano, J. Endotoxin Res., 4, 115 (1997).
32. T. Kirikae, F. Kirikae, H. Iwai, N. Qureshi, K. Fukase, S. Kusumoto, and M. Nakano, J. Endotoxin Res., 5, 62 (1999).
33. K. Fukase, M. Oikawa, Y. Suda, W.-C. Liu, Y. Fukase, T. Shintaku, H. Sekljic, H. Yoshizaki, and S. Kusumoto, J. Endotoxin Res., 5, 46 (1999).
34. M. Oikawa, A. Wada, H. Yoshizaki, K. Fukase, and S. Kusumoto, Bull. Chem. Soc. Jpn., 70, 1435 (1997).
35. D. Thom, A. J. Powell, C. W. Lloyd, and D. A. Rees, Biochem. J., 168, 187 (1977).
36. K. Fukase, I. Kinoshita, Y. Suda, Y. Aoki, W.-C. Liu, M. Oikawa, M. Kurosawa, U. Zähringer, U. Seydel, E. T. Rietschel, and S. Kusumoto, Synlett, 1996, 252.
37. C. A. Aurell and A. O. Wistrom, Biochem. Biophys. Res. Commun., 253, 119 (1998).
38. F. Nomura, S. Akashi, Y. Sakao, S. Sato, T. Kawai, M. Matsumoto, K. Nakanishi, M. Kimoto, K. Miyake, K. Takeda, and S. Akira, J. Immunol., 161, 3476 (2000).
39. P. A. Detmers, N. Thieblemont, T. Vasselon, R. Pironkova, D. S. Miller, and S. D. Wright, J. Immunol., 157, 5589 (1996).
40. N. Thiéblemont and S. D. Wright, J. Exp. Med., 185, 2095 (1997).
41. A. Lentschat, V. T. El-Samalouti, J. Schletter, S. Kusumoto, L. Brade, E. T. Rietschel, J. Gerdes, M. Ernst, H. Flad, and A. J. Ulmer, Infect. Immun., 67, 2515 (1999).
42. V. T. El-Samalouti, J. Schletter, I. Chyla, A. Lentschat, U. Mamat, L. Brade, H. D. Flad, A. J. Ulmer, and L. Hamann, FEMS Immunol. Med. Microbiol., 23, 259 (1999).