Synthetic Caged DAG-lactones for Photochemically Controlled Activation of Protein Kinase C

ChemBioChem

Volumn 12, Issue 4, 2011, Pages 535-539

  Nomura, Wataru ^a   Narumi, Tetsuo ^a   Ohashi, Nami ^a   Serizawa, Yuki ^a   Lewin, Nancy E ^b   Blumberg, Peter M ^b   Furuta, Toshiaki ^a,c   Tamamura, Hirokazu ^a  

^a TOKYO MEDICAL AND DENTAL UNIVERSITY   (Japan)

^b NATIONAL CANCER INSTITUTE   (United States)

^c TOHO UNIVERSITY   (Japan)

Author keywords

Cage compounds; Diacylglycerol; Drug design; Enzymes; Proteins

Indexed keywords

6 BROMO 7 HYDROXYCOUMARIN; 6 BROMO 7 METHOXYCOUMARIN; COUMARIN DERIVATIVE; DIACYLGLYCEROL; LACTONE; PROTEIN KINASE C; PROTEIN KINASE C DELTA; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; BIOLOGICAL ACTIVITY; DERIVATIZATION; ENZYME ACTIVATION; LIGAND BINDING; NONHUMAN; PHARMACOPHORE; PHOTOACTIVATION; PHOTOCHEMISTRY; PHOTOLYSIS; PRIORITY JOURNAL; PROTEIN FUNCTION; SIGNAL TRANSDUCTION;

ANIMALS; DIGLYCERIDES; ENZYME ACTIVATION; HUMANS; LACTONES; LIGHT; MODELS, BIOLOGICAL; MOLECULAR STRUCTURE; PHOTOCHEMISTRY; PROTEIN KINASE C; SIGNAL TRANSDUCTION;

EID: 79952033233     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.201000670     Document Type: Article

References (42)

1. G. Dormán, G. D. Prestwich, Trends Biotechnol. 2000, 18, 64-77;
2. G. Mayer, A. Heckel, Angew. Chem. 2006, 118, 5020-5042; Angew. Chem. Int. Ed. 2006, 45, 4900-4921;
3. H.-M. Lee, D. R. Larson, D. S. Lawrence, ACS Chem. Biol. 2009, 4, 409-427;
4. E. J. Quann, E. Merino, T. Furuta, M. Huse, Nat. Immunol. 2009, 10, 627-637.
5. Y. Nishizuka, Science 1992, 258, 607-614;
6. A. C. Newton, J. Biol. Chem. 1995, 270, 28495-28498.
7. T. Watanabe, Y. Ono, Y. Taniyama, K. Hazama, K. Igarashi, K. Ogita, U. Kikkawa, Y. Nishizuka, Proc. Natl. Acad. Sci. USA 1992, 89, 10159-10163.
8. H. Mischak, J. H. Pierce, J. Goodnight, M. G. Kazanietz, P. M. Blumberg, J. F. Mushinski, J. Biol. Chem. 1993, 268, 20110-20115.
9. C. Li, E. Wernig, M. Leitges, Y. Hu, Q. Xu, FASEB J. 2003, 17, 2106-2108.
10. T. Ghayur, M. Hugunin, R. V. Talanian, S. Ratnofsky, C. Quinlan, Y. Emoto, P. Pandey, R. Datta, Y. Huang, S. Kharbanda, H. Allen, R. Kamen, W. Wong, D. Kufe, J. Exp. Med. 1996, 184, 2399-2404;
11. D. L. Alkon, M.-K. Sun, T. J. Nelson, Trends Pharmacol. Sci. 2007, 28, 51-60.
12. Q. J. Wang, Trends Pharmacol. Sci. 2006, 27, 317-323.
13. V. E. Marquez, P. M. Blumberg, Acc. Chem. Res. 2003, 36, 434-443.
14. K. Nacro, B. Bienfait, J. Lee, K.-C. Han, J.-H. Kang, S. Benzaria, N. E. Lewin, D. K. Bhattacharyya, P. M. Blumberg, V. E. Marquez, J. Med. Chem. 2000, 43, 921-944;
15. H. Tamamura, B. Beinfait, K. Nacro, N. E. Lewin, P. M. Blumberg, V. E. Marquez, J. Med. Chem. 2000, 43, 3210-3217.
16. T. Furuta, S. S.-H. Wang, J. L. Dantzker, T. M. Dore, W. J. Bybee, E. M. Callaway, W. Denk, R. Y. Tsien, Proc. Natl. Acad. Sci. USA 1999, 96, 1193-1200;
17. H. Ando, T. Furuta, R. Y. Tsien, H. Okamoto, Nat. Genet. 2001, 28, 317-325;
18. H. J. Montgomery, B. Perdicakis, D. Fishlock, G. A. Lajoie, E. Jervis, J. G. Guillemette, Bioorg. Med. Chem. 2002, 10, 1919-1927;
19. W. Lin, D. S. Lawrence, J. Org. Chem. 2002, 67, 2723-2726;
20. M. Lu, O. D. Fedoryak, B. R. Moister, T. M. Dore, Org. Lett. 2003, 5, 2119-2122;
21. A. Z. Suzuki, T. Watanabe, M. Kawamoto, K. Nishiyama, H. Yamashita, M. Ishii, M. Iwamura, T. Furuta, Org. Lett. 2003, 5, 4867-4870.
22. T. Furuta, T. Watanabe, S. Tanabe, J. Sakyo, C. Matsuba, Org. Lett. 2007, 9, 4717-4720.
23. X. P. Huang, R. Sreekumar, J. R. Patel, J. W. Walker, Biophys. J. 1996, 70, 2448-2457;
24. V. G. Robu, E. S. Pfeiffer, S. L. Robia, R. C. Balijepalli, Y. Pi, T. J. Kamp, J. W. Walker, J. Biol. Chem. 2003, 278, 48154-48161.
25. Y. Kishi, R. R. Rando, Acc. Chem. Res. 1998, 31, 163-172;
26. P. A. Wender, C. M. Cribbs, K. F. Koehler, N. A. Sharkey, C. L. Herald, Y. Kamano, G. R. Petit, P. M. Blumberg, Proc. Natl. Acad. Sci. USA 1998, 95, 7197-7201;
27. S. Wang, G. W. A. Milne, M. C. Nicklaus, V. E. Marquez, J. Lee, P. M. Blumberg, J. Med. Chem. 1994, 37, 1326-1338.
28. H. Tamamura, D. M. Sugano, N. E. Lewin, P. M. Blumberg, V. E. Marquez, J. Med. Chem. 2004, 47, 644-655;
29. K. Malolanarasimhan, N. Kedei, D. M. Sigano, J. A. Kelley, C. C. Lai, N. E. Lewin, R. J. Surawski, V. A. Pavlyukovets, S. H. Garfield, S. Wincovitch, P. M. Blumberg, V. E. Marquez, J. Med. Chem. 2007, 50, 962-978.
30. D. M. Sigano, M. L. Peach, K. Nacro, Y. Choi, N. E. Lewin, M. C. Nicklaus, P. M. Blumberg, V. E. Marquez, J. Med. Chem. 2003, 46, 1571-1579.
31. N. A. Sharkey, P. M. Blumberg, Cancer Res. 1985, 45, 19-24;
32. M. G. Kazanietz, K. W. Krausz, P. M. Blumberg, J. Biol. Chem. 1992, 267, 20878-20886.
33. L. Li, P. S. Lorenzo, K. Bogi, P. M. Blumberg, S. H. Yupsa, Mol. Cell. Biol. 1999, 19, 8547-8558.
34. T. Furuta, H. Torigai, M. Sugimoto, M. Iwamura, J. Org. Chem. 1995, 60, 3953-3956;
35. B. Schade, V. Hagen, R. Schmidt, R. Herbrich, E. Krause, T. Eckardt, J. Bendig, J. Org. Chem. 1999, 64, 9109-9117.
36. T. Furuta, A. Momotake, M. Sugimoto, M. Hatayama, M. Iwamura, Biochem. Biophys. Res. Commun. 1996, 228, 193-198;
37. T. Furuta, M. Iwamura, Methods Enzymol. 1998, 291, 50-63.
38. T. Eckardt, V. Hagen, B. Schade, R. Schmidt, C. Schweitzer, J. Bendig, J. Org. Chem. 2002, 67, 703-710.
39. V. Hagen, J. Bendig, S. Frings, T. Eckardt, S. Helm, D. Reuter, U. B. Kaupp, Angew. Chem. 2001, 113, 1077-1080; Angew. Chem. Int. Ed. 2001, 40, 1045-1048;
40. V. Hagen, S. Frings, J. Bendig, D. Lorenz, B. Wiesner, U. B. Kaupp, Angew. Chem. 2002, 114, 3775-3777; Angew. Chem. Int. Ed. 2002, 41, 3625-3628.
41. D. Geißler, W. Kresse, B. Wiesner, J. Bendig, H. Kettenmann, V. Hagen, ChemBioChem 2003, 4, 162-170;
42. V. Hagen, S. Frings, B. Wiesner, S. Helm, U. B. Kaupp, J. Bendig, ChemBioChem 2003, 4, 434-442.