Comparison of chemical characteristics of the first and the second cysteine-rich domains of protein kinase C

Bioorganic and Medicinal Chemistry

Volumn 5, Issue 8, 1997, Pages 1725-1737

  Irie, Kazuhiro ^a   Yanai, Yoshiaki ^a   Oie, Kentaro ^a   Ishizawa, Junya ^a   Nakagawa, Yu ^a   Ohigashi, Hajime ^a   Wender, Paul A ^b   Kikkawa, Ushio ^c  

^a KYOTO UNIVERSITY   (Japan)

^b STANFORD UNIVERSITY   (United States)

^c KOBE UNIVERSITY   (Japan)

Author keywords

Cysteine rich domain; Indolactam; Phorbol ester; Protein kinase C; Zinc finger

Indexed keywords

CYSTEINE; LACTAM; PHORBOL DIBUTYRATE; PHORBOL ESTER; PROTEIN KINASE C;

ARTICLE; BINDING AFFINITY; BINDING SITE; CONFORMATIONAL TRANSITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTEIN BINDING; PROTEIN DOMAIN; PROTEIN STRUCTURE; SIGNAL TRANSDUCTION; TUMOR PROMOTION;

AMINO ACID SEQUENCE; ANIMALS; BINDING SITES; CARCINOGENS; CIRCULAR DICHROISM; CYSTEINE; ISOENZYMES; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; PHORBOL 12,13-DIBUTYRATE; PROTEIN CONFORMATION; PROTEIN KINASE C; RATS; ZINC;

EID: 0030792726     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(97)00116-8     Document Type: Article

References (58)

1. Nishizuka, Y. Nature 1984, 308, 693.
2. For reviews, see: Marks, F.; Gschwendt, M. Mutation Res. 1995, 333, 161; Newton, A. C. J. Biol. Chem. 1995, 270, 28,495; Nishizuka, Y. FASEB J. 1995, 9, 484.
3. For reviews, see: Marks, F.; Gschwendt, M. Mutation Res. 1995, 333, 161; Newton, A. C. J. Biol. Chem. 1995, 270, 28,495; Nishizuka, Y. FASEB J. 1995, 9, 484.
4. For reviews, see: Marks, F.; Gschwendt, M. Mutation Res. 1995, 333, 161; Newton, A. C. J. Biol. Chem. 1995, 270, 28,495; Nishizuka, Y. FASEB J. 1995, 9, 484.
5. Ono, Y.; Fujii, T.; Igarashi, K.; Kuno, T.; Tanaka, C.; Kikkawa, U.; Nishizuka, Y. Proc. Natl. Acad. Sci. USA 1989, 86, 4868.
6. Burns, D. J.; Bell, R. M. J. Biol. Chem. 1991, 266, 18,330.
7. Quest, A. F. G.; Bell, R. M. J. Biol. Chem. 1994, 269, 20,000.
8. Yanai, Y.; Irie, K.; Ohigashi, H.; Wender, P. A. Bioorg. Med. Chem. Lett. 1997, 7, 117.
9. Szallasi, Z.; Bogi, K.; Gohari, S.; Biro, T.; Acs, P.; Blumberg, P. M. J. Biol. Chem. 1996, 277, 18,299.
10. Dekker, L. V.; Parker, P. J. Trends Biochem. Sci. 1994, 19, 73.
11. Hommel, U.; Zurini, M.; Luyten, M. Nat. Struct. Biol. 1994, 7, 383.
12. Ichikawa, S.; Hatanaka, H.; Takeuchi, Y.; Ohno, S.; Inagaki, F. J. Biochem. 1995, 117, 566.
13. Zhang, G.; Kazanietz, M. G.; Blumberg, P. M.; Hurley, J. H. Cell 1995, 81, 917.
14. Irie, K.; Ishii, T.; Ohigashi, H.; Wender, P. A.; Miller, B. L.; Takeda, N. J. Org. Chem. 1996, 61, 2164.
15. Irie, K.; Isaka, T.; Iwata, Y.; Yanai, Y.; Nakamura, Y.; Koizumi, F.; Ohigashi, H.; Wender, P. A.; Satomi, Y.; Nishino, H. J. Am. Chem. Soc. 1996, 118, 10,733.
16. Slater, S. J.; Ho, C.; Kelly, M. B.; Larkin, J. D.; Taddeo, F. J.; Yeager, M. D.; Stubbs, C. D. J. Biol. Chem. 1996, 271, 4627.
17. Hannun, Y. A.; Bell, R. M. Meth. Enzymol. 1987, 141, 287.
18. Bazzi, M. D.; Nelsestuen, G. L. Biochemistry 1989, 28, 3577.
19. Wender, P. A.; Irie, K.; Miller, B. L. Proc. Natl. Acad. Sci. USA 1995, 92, 239.
20. Hubbard, S. R.; Bishop, W. R.; Kirschmeier, P.; George, S. J.; Cramer, S. P.; Hendrickson, W. A. Science 1991, 254, 1776.
21. Quest, A. F. G.; Bloomenthal, J.; Bardes, E. S. G.; Bell, R. M. J. Biol. Chem. 1992, 267, 10193.
22. For reviews, see: Klug, A.; Schwabe, J. W. R. FASEB J. 1995, 9, 597; Schwabe, J. W. R.; Klug, A. Nat. Struct. Biol. 1994, 1, 345.
23. For reviews, see: Klug, A.; Schwabe, J. W. R. FASEB J. 1995, 9, 597; Schwabe, J. W. R.; Klug, A. Nat. Struct. Biol. 1994, 1, 345.
24. Sharkey, N. A.; Blumberg, P. M. Cancer Res. 1985, 45, 19.
25. Omichinski, J. G.; Clore, G. M.; Schaad, O.; Felsenfeld, G.; Trainor, C.; Appella, E.; Stahl, S. J.; Gronenborn, A. M. Science 1993, 261, 438.
26. Kazanietz, M. G.; Barchi, J. J.; Omichinski, J. G.; Blumberg, P. M. J. Biol. Chem. 1995, 270, 14679.
27. Dimitrijevic, S. M.; Ryves, W. J.; Parker, P. J.; Evans, F. J. Mol. Pharmacol. 1995, 48, 259.
28. Quest, A. F. G.; Bardes, E. S. G.; Bell, R. M. J. Biol. Chem. 1994, 269, 2953.
29. Kazanietz, M. G.; Areces, L. B.; Bahador, A.; Mischak, H.; Goodnight, J.; Mushinski, J. F.; Blumberg, P. M. Mol. Pharmacol. 1993, 44, 298.
30. Inoue, Y.; Saijoh, K.; Sumino, K. Pharmacol. Toxicol. 1988, 62, 278.
31. Markovac, J.; Goldstein, G. W. Nature 1988, 334, 71.
32. Saijoh, K.; Inoue, Y.; Katsuyama, H.; Sumino, K. Pharmacol. Toxicol. 1988, 63, 221.
33. Speizer, L. A.; Watson, M. J.; Kanter, J. R.; Brunton, L. L. J. Biol. Chem. 1989, 264, 5581.
34. Saijoh, K.; Fukunaga, T.; Katsuyama, H.; Lee, M. J.; Sumino, K. Environ. Res. 1993, 63, 264.
35. Murakami, K.; Feng, G.; Chen, S. G. J. Pharmacol. Exp. Ther. 1993, 264, 757.
36. Long, G. J.; Rosen, J. F.; Schanne, F. A. X. J. Biol. Chem. 1994, 269, 834.
37. Rajanna, B.; Chetty, C. S.; Rajanna, S.; Hall, E.; Fail, S.; Yallapragada, P. R. Toxicol. Lett. 1995, 81, 197.
38. Matthies, H. J. G.; Palfrey, H. C.; Hirning, L. D.; Miller, R. J. J. Neurosci. 1987, 7, 1198.
39. Nichols, R. A.; Haycock, J. W.; Wang, J. K. T.; Greengard, P. J. Neurochem. 1987, 48, 615.
40. Weiss, S.; Ellis, J.; Hendley, D. D.; Lenox, R. H. J. Neurochem. 1989, 52, 530.
41. For a review, see: Nishizuka, Y. Science 1992, 258, 607.
42. Krizek, B. A.; Berg, J. M. Inorg. Chem. 1992, 31, 2984.
43. Irie, K.; Yanai, Y.; Ohigashi, H.; Wender, P. A. Bioorg. Med. Chem. Lett. 1996, 6, 353.
44. Irie, K.; Yanai, Y.; Oie, K.; Ohigashi, H.; Wender, P. A. Bioorg. Med. Chem. Lett. 1997, 7, 965.
45. Yang, J. T.; Wu, C.-S. C.; Martinez, H. M. Methods Enzymol. 1986, 130, 208.
46. Hecker, E.; Adolf, W.; Hergenhahn, M.; Schmidt, R.; Sorg, B. In Cellular Interactions by Environmental Tumor Promoters; Fujiki, H., Hecker, E., Moore, R. E., Sugimura, T., Weinstein, I. B. Eds.; Japan Scientific Society Press: Tokyo/ VNU Science Press: Utrecht, 1984; pp 3-36.
47. Shieh, H.-L.; Hansen, H.; Zhu, J.; Riedel, H. Mol. Carcinogen. 1995, 12, 166.
48. Kawai, T.; Ichinose, T.; Takeda, M.; Tomioka, N.; Endo, Y.; Yamaguchi, K.; Shuto, K.; Itai, A. J. Org. Chem. 1992, 57, 6150.
49. Endo, Y.; Shudo, K.; Itai, A.; Hasegawa, M.; Sakai, S. Tetrahedron 1986, 42, 5905.
50. Caution: Indolactams are tumor promoters and should be handled with special care.
51. Nakatsuka, S.; Masuda, T.; Sakai, K.; Goto, T. Tetrahedron Lett. 1986, 47, 5735.
52. Endo, Y.; Shudo, K.; Okamoto, T. Chem. Pharm. Bull. 1982, 30, 3457.
53. 1H NMR, EI-MS, and high-resolution (HR) EI-MS.
54. Endo, Y.; Ohno, M.; Hirano, M.; Itai, A.; Shudo, K. J. Am. Chem. Soc. 1996, 118, 1841.
55. Kozikowski, A. P.; Ma, D.; Pang, Y.-P.; Shum, P.; Likic, V.; Mishra, P. K.; Macura, S.; Basu, A.; Lazo, J. S.; Ball, R. G. J. Am. Chem. Soc. 1993, 115, 3957.
56. Irie, K.; Koshimizu, K. Mem. Coll. Agric., Kyoto Univ. 1988, 132, 1.
57. Kikkawa, U.; Ono, Y.; Ogita, K.; Fujii, T.; Asaoka, Y.; Sekiguchi, K.; Kosaka, Y.; Igarashi, K.; Nishizuka, Y. FEBS Lett. 1987, 217, 227.
58. James, H. G. In SAS User's Guide; Jane, T. H., Kathryn, A. C., Eds.; SAS Institute: Cary, NC, 1979; pp 357-360.