Probing the membrane targeting C1 subdomains of PKC with bivalent ligands

Current Topics in Medicinal Chemistry

Volumn 7, Issue 4, 2007, Pages 355-362

  Nowak, Ireneusz ^a  

^a Brigham Young University   (United States)

Author keywords

Benzolactam; Bivalent; Diacylglycerol; Modulator; Phorbol esters; PKC

Indexed keywords

2 PYRROLIDONE DERIVATIVE; BRYOSTATIN; INDOLACTAM V; INDOLE DERIVATIVE; LACTAM DERIVATIVE; PHORBOL ESTER DERIVATIVE; PROTEIN KINASE C; PROTEIN KINASE C ACTIVATOR; PROTEIN KINASE C ALPHA; PROTEIN KINASE C BETA; PROTEIN KINASE C DELTA; PROTEIN KINASE C GAMMA; PROTEIN KINASE C INHIBITOR; PROTEIN KINASE C IOTA;

BINDING AFFINITY; CELL MEMBRANE; DRUG DESIGN; DRUG EFFICACY; DRUG POTENCY; DRUG PROTEIN BINDING; DRUG SELECTIVITY; DRUG SYNTHESIS; DRUG TARGETING; ENZYME ACTIVATION; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME STRUCTURE; HUMAN; HYDROPHILICITY; LIPOPHILICITY; NONHUMAN; PROTEIN DOMAIN; PROTEIN EXPRESSION; PROTEIN FAMILY; PROTEIN FUNCTION; PROTEIN TRANSPORT; REVIEW; SIGNAL TRANSDUCTION; STRUCTURE ACTIVITY RELATION;

LIGANDS; MOLECULAR PROBES; PROTEIN KINASE C;

EID: 33847627060     PISSN: 15680266     EISSN: None     Source Type: Journal    
DOI: 10.2174/156802607779941260     Document Type: Review

References (52)

1. Manning, G.; Whyte, D.B.; Martinez, R.; Hunter, T.; Sudarsanam, S. The protein kinase complement of the human genome. Science 2002, 298, 1912-1934.
2. Nishizuka, Y. Studies and perspectives of protein kinase C. Science 1986, 233, 305-312.
3. Newton, A.C. Regulation of protein kinase C. Curr. Opin. Cell. Biol. 1997, 9, 161-167.
4. Parekh, D.B.; Ziegler, W.; Parker, P.J. Multiple pathways control protein kinase C phosphorylation. EMBO J. 2000, 19, 496-503.
5. Giorgione, J.R.; Lin, J.-H.; McCammon, A.; Newton, A.C. Increased membrane affinity of the C1 domain of protein kinase C δ compensates for the lack of involvement of its C2 domain in membrane recruitment. J. Biol. Chem. 2006, 282, 1660-1669.
6. Song, J.S.; Swann, P.G.; Szallasi, Z.; Blank, U.; Blumberg, P.M.; Rivera, J. Tyrosine phosphorylation-dependent and -independent associations of protein kinase C-δ with Src family kinases in the RBL-2H3 mast cell line: regulation of Src family kinase activity by protein kinase C-δ. Oncogene 1998, 16, 3357-3368.
7. Zhang, G.; Kazanietz, M.G.; Blumberg, M.P.; Hurley, J.H.Crystal structure of the Cys2 activator-binding domain of protein kinase C δ in complex with phorbol ester. J.H. Cell 1995, 81, 917-924.
8. Johnson, J.; Giorgione, J.; Newton, A.C. The C1 and C2 domains of protein kinase C are independent membrane targeting modules, with specificity for phosphatidylserine conferred by the C1 domain. Biochemistry 2000, 39, 11360-11369.
9. Nalefski, E.A.; Falke, J.J. The C2 domain calcium-binding motif: structural and functional diversity. Protein Sci. 1996, 5, 2375-2390.
10. Hurley, J.H.; Newton, A.C; Parker, P.J.; Blumberg, P.M.; Nishizuka, Y. Taxonomy and function of C1 protein kinase C homology domains. Protein Sci. 1997, 6, 477-480.
11. Kikkawa, U.; Takai, Y.; Tanaka, Y.; Miyake, R.; Nishizuka, Y. Protein kinase C as a possible receptor protein of tumor-promoting phorbol esters. J. Biol. Chem. 1983, 258, 11442-11445.
12. König, B.; DiNitto, P.A.; Blumberg, P.M. Stoichiometric binding of diacylglycerol to the phorbol ester receptor. J. Cell. Biochem. 1985, 29, 37-44.
13. Hannun, Y.A.; Bell, R.M. Phorbol ester binding and activation of protein kinase C on triton X-100 mixed micelles containing phosphatidylserine. J. Biol. Chem. 1986, 261, 9341-9347.
14. Mosior, M.; Newton, A.C. Calcium-independent binding to interfacial phorbol esters causes protein kinase C to associate with membranes in the absence of acidic lipids. Biochemistry 1986, 35, 1612-1623.
15. Slater, S.J.; Ho, C.; Kelly, M.B.; Larkin, J.D.; Taddeo, F.J.; Yeager, M.D.; Stubbs, C.D. Protein kinase C α contains two activator binding sites that bind phorbol esters and diacylglycerols with opposite affinities. J. Biol. Chem. 1996, 271, 4627-4631.
16. Szalasi, Z.; Bogi, K.; Gohari, S.; Biro, T.; Acs, P.; Blumberg, P.M. Non-equivalent roles for the first and second zinc fingers of protein kinase C δ. J. Biol. Chem. 1996, 271, 18299-18301.
17. Bogi, K.; Lorenzo, P.S.; Acs, P.; Szallasi, Z.; Wagner, G.S.; Blumberg, P.M. Comparison of the roles of the C1a and C1b domains of protein kinase C α in ligand induced translocation in NIH 3T3 cells. FEBS Lett. 1999, 456, 27-30.
18. Hunn, M.; Quest, A.F.G. Cysteine-rich regions of protein kinase C δ are functionally non-equivalent. Differences between cysteine-rich regions of non-calcium-dependent protein kinase C δ and calcium-dependent protein kinase C γ. FEBS Lett. 1997, 400, 226-232.
19. Quest, A.F.G.; Bell, R.M. The regulatory region of protein kinase C γ. Studies of phorbol ester binding to individual and combined functional segments expressed as glutathione S-transferase fusion proteins indicate a complex mechanism of regulation by phospholipids, phorbol esters, and divalent cations. J. Biol. Chem. 1994, 269, 20000-20012.
20. Irie, K.; Yanai, Y.; Oie, K.; Ishizawa, J.; Nakagawa, Y.; Ohigashi, H.; Wender, P.A.; Kikkawa, U. Comparison of chemical characteristics of the first and the second cysteine-rich domains of protein kinase C γ. Bioorg. Med. Chem. 1997, 5, 1725-1737.
21. Bogi, K.; Lorenzo, P.S.; Szallasi, Z.; Acs, P.; Wagner, G.S; Blumberg, P.M. Differential selectivity of ligands for the C1a and C1b phorbol ester binding domains of protein kinase C δ: possible correlation with tumor-promoting activity. Cancer Res. 1998, 58, 1423-1428.
22. Lorenzo, P.S.; Bogi, K.; Hughes, K.M.; Beheshti, M.; Battacharyya, D.; Garfield, S.H.; Petit, G.R.; Blumberg, P.M. Differential roles of the tandem C1 domains of protein kinase C δ in the biphasic down-regulation induced by bryostatin 1. Cancer Res. 1999, 59, 6137-6144.
23. Stahelin, R.V.; Digman, M.A.; Medkova, M.; Ananthanarayanan, B.; Rafter, J.D.; Melovic, H.R.; Cho, W. Mechanism of diacylglycerol-induced membrane targeting and activation of protein kinase C δ. J. Biol. Chem. 2004, 279, 29501-29512.
24. Ananthanarayanan, B.; Stahelin, R.V.; Digman, M.A.; Cho, W. Activation mechanisms of conventional protein kinase C isoforms are determined by the ligand affinity and conformational flexibility of their C1 domains. J. Biol. Chem. 2003, 278, 46886-46894.
25. Makowske, M.; Rosen, O.M. Complete activation of protein kinase C by an antipeptide antibody directed against the pseudosubstrate prototope. J. Biol. Chem. 1989, 264, 16155-16159.
26. Orr, J.W.; Keranen, L.M.; Newton, A.C. Reversible exposure of the pseudosubstrate domain of protein kinase C by phosphatidylserine and diacylglycerol. J. Biol. Chem. 1992, 267, 15263-15266.
27. Orr, J.W.; Newton, A.C. Intrapeptide regulation of protein kinase C. J. Biol. Chem. 1994, 269, 8383-8387.
28. Mellor, H.; Parker, P.J. The extended protein kinase C superfamily. Biochem. J. 1998, 332, 281-292.
29. Hofmann, J. The potential for isoenzyme-selective modulation of protein kinase C FASEB J. 1997, 11, 649-669.
30. Irie, K.; Oie, K.; Nakahara, A.; Yanai, Y.; Ohigashi, H.; Wender, P.A.; Fukuda, H.; Konishi, H.; Kikkawa U. Molecular basis for protein kinase C isozyme selective binding: The synthesis, folding, and phorbol ester binding of cysteine-rich domains of a protein kinase C isozymes. J. Am. Chem. Soc. 1998, 120, 9159-9167.
31. Irie, K.; Nakahara, A.; Nakagawa, Y.; Ohigashi, H.; Shindo, M.; Fukuda, H.; Konishi, H.; Kikkawa, U.; Kashiwagi, K.; Saito, N. Establishment of a binding assay for protein kinase C isozymes using synthetic C1 peptides and development of new medicinal leads with protein kinase C isozyme and C1 domain selectivity. Pharmacol. Ther. 2002, 93, 271-281.
32. Hurley, J. H.; Newton, A. C.; Parker, P. J.; Blumberg, P. M.; Nishizuka, Y. Taxonomy and function of C1 protein kinase C homology domains. Protein Sci. 1997, 6, 477-480.
33. Wender, P.A.; Koehler, M.F.T.; Wright, D.L.; Irie, K. Mapping phorbol ester binding domains of protein kinase C (PKC): the design, synthesis, and biological activity of novel phorbol ester dimers. Synthesis 1999, 1401-1406.
34. Giorgione, J.; Hysell, M.; Harvey, D.F.; Newton, A.C. Contribution of the C1A and A1B domains to the membrane interaction of protein kinase C. Biochemistry 2003, 42, 1194-11202.
35. Sodeoka, M.; Arai, M.A.; Adachi, K.; Uotsu, K.; Shibasaki, M. Rational design, synthesis, and evaluation of a new type of PKC inhibitor. J. Am. Chem. Soc. 1998, 120, 457-458.
36. Johnson, J.E.; Zimmerman, M.L.; Daleke, D.L.; Newton, A.C. Lipid structure and not membrane structure is the major determinant in the regulation of protein kinase C by phosphatidylserine. Biochemistry 1998, 37, 12020-12025.
37. Kazanietz, M.G.; Areces, L.B.; Bahador, A.; Mischak, H.; Goodnight, J.; Mushinski, J.F.; Blumberg, P.M. Characterization of ligand and substrate specificity for the calcium-dependent and calcium-independent protein kinase C isozymes. Mal. Pharmacol. 1993, 44, 298-307
38. Teng, K.; Marquez, V.E.; Milne, G.W.A.; Barchi, J.J.; Jr.; Kazanietz, M.G.; Lewin, N.E.; Blumberg, P.M.; Abushanab, E. Conformationally constrained analogs of diacylglycerol. Interaction of γ-lactones with the phorbol ester receptor of protein kinase C. J. Am. Chem. Soc. 1992, 114, 1059-1070.
39. Lee, J.; Wang, S.; Milne, G.W.A.; Sharma, R.; Lewin, N.E.; Blumberg, P.M.; Marquez, V.E. Conformationally constrained analogs of diacylglycerol. 11. Ultrapotent protein kinase C ligands based on a chiral 5-disubstituted tetrahydro-2-furanone template. J. Med. Chem. 1996, 39, 29-35.
40. Nacro, K.; Bienfait, B.; Lee, J.; Han, K.-C.; Kang, J.-H.; Benzaria, S.; Lewin, N.E.; Bhattacharyya, D.K.; Blumberg, P.M. Marquez, V.E. Conformationally constrained analogs of diacylglycerol (DAG). 16. How much structural complexity is necessary for recognition and high binding affinity to protein kinase C? J. Med. Chem. 2000, 43, 921-944.
41. Baba, Y.; Ogoshi, Y.; Hirai, G.; Yanagisawa, T.; Nagamatsu, K.; Mayumi, S.; Yuichi, H.; Sodeoka, M. Design, synthesis, and structure-activity relationship of new isobenzofuranone ligands of protein kinase C. Bioorg. Med. Chem. Lett. 2004, 14, 2963-2967.
42. Baba, Y.; Mayumi, S.; Hirai, G.; Kawasaki, H.; Ogoshi, Y.; Yanagisawa, T.; Hashimoto, M.; Sodeoka, M. Evaluation of series of isobenzofuranone dimers as PKC α ligands: implication for the distance between the two ligand binding sites. Bioorg. Med. Chem. Lett. 2004, 14, 2969-2972.
43. De Vries, D.J.; Harald, C.L.; Pettit, G.R.; Blumberg, P.M. Demonstration of sub-nanomolar affinity of bryostatin 1 for the phorbol ester receptor in rat brain. Biochem. Pharmacol. 1988, 37, 4069-4073.
44. Rando, R.R.; Kishi, Y. Structural basis of protein kinase C activation by diacylglycerols and tumor promoters. Biochemistry 1992, 31, 2211-2218.
45. Endo, Y.; Ohno, M.; Hirano, M.; Itai, A.; Shudo, K; Synthesis, conformation, and biological activity of teleocidin mimics, benzolactams. A clarification of the conformational flexibility problem in structure-activity studies of teleocidins. J. Am. Chem. Soc. 1996, 118, 1841-1855.
46. Sridhar, J.; Wei, Z.-L.; Nowak, I.; Lewin, N.E.; Ayres, J.A.; Pearce, L.V.; Blumberg, P.M.; Kozikowski, A.P. New bivalent PKC ligands linked by a carbon spacer: enhancement in binding affinity. J. Med. Chem. 2003, 46, 4196-4204.
47. Kozikowski, A.P.; Nowak, I.; Petukhov, P.A.; Etcheberrigaray, R.; Mohamed, A.; Tan, M.; Levin, N.; Hennings, H.; Pearce, L.L.; Blumberg, P.M. New amide-bearing benzolactam-based PKC modulators induce enhanced secretion of the amyloid precursor protein metabolite sAPPα. J. Med Chem. 2003, 46, 364-373
48. Qiao, L.; Wang, S.; George C.; Lewin N.E.; Blumberg, P.M.; Kozikowski, A.P. Structure-based design of a new class of protein kinase C modulators. J. Am. Chem. Soc. 1998, 120, 6629-6630.
49. Qiao, L.; Zhao, L.Y.; Rong, S.B.; Wu, X.W.; Wang, S.; Fujii, T.; Kazanietz, M.G.; Rauser, L.; Savage, J.; Roth, B.L.; Anderson, J.F.; Kozikowski, A.P. Rational design, synthesis and biological evaluation of rigid pyrrolidone analogues as potential inhibitors of prostate cancer cell growth. Bioorg. Med. Chem. Lett. 2001, 11, 955-959.
50. Kozikowski, A.P.; Nowak, I.; Petukhov, P.A.; Etcheberrigaray, R.; Mohamed, A.; Tan, M.; Levin,N.; Hennings, H.; Pearce, L.L.; Blumberg, P.M. New amide-bearing benzolactam-based PKC modulators induce enhanced secretion of the amyloid precursor protein metabolite sAPP α. J. Med. Chem. 2003, 46, 364-373.
51. Wang, Q. J.; Fang, T.W.; Fenick, D.; Garfield, S.; Bienfait, B.; Marquez, V.E.; Blumberg, P.M. The lipophilicity of phorbol esters as a critical factor in determining the pattern of translocation of protein kinase C δ fused to green fluorescent protein. J. Biol. Chem. 2000, 275, 12136-12146.
52. Qin, D.; Sullivan, R.; Berkowitz, W.F.; Bittman, R.; Rotenberg, S.A. Inhibition of protein kinase C by dequalinium analogues: dependence on linker length and geometry. J. Med. Chem. 2000, 43, 1413-1417.