Protein kinase C βiI in diabetic complications: Survey of structural, biological and computational studies

Expert Opinion on Therapeutic Targets

Volumn 16, Issue 3, 2012, Pages 325-344

  Sobhia, M Elizabeth ^a   Grewal, Baljinder K ^a   Bhat, Jyotsna ^a   Rohit, Shishir ^a   Punia, Vijay ^a  

^a NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

Author keywords

Diabetes; Homology modeling; in silico; Molecular dynamics; Pharmacophore modeling; PKC II; QSAR; SAR

Indexed keywords

12 (2 CYANOETHYL) 6,7,12,13 TETRAHYDRO 13 METHYL 5 OXOINDOLO[2,3 A]PYRROLO[3,4 C]CARBAZOLE; 2 [1 (3 AMIDINOTHIOPROPYL) 1H INDOL 3 YL] 3 (1 METHYL 1H INDOL 3 YL)MALEIMIDE; 2 [1 (3 DIMETHYLAMINOPROPYL) 3 INDOLYL] 3 (3 INDOLYL)MALEIMIDE; 3 (1 METHYL 1H INDOL 3 YL) 4 (2 NITROPHENYL) 1 PYRROLE 2,5 DIONE; 3 (1 METHYL 1H INDOL 3 YL) 4 [1 [4 (PYRIDIN 2 YL)CYCLOHEXYL] 1H INDOL 3 YL] 1H PYRROLE 2,5 DIONE; 3 (5 CHLORO 1 METHYL 1H INDOL 3 YL) 4 (1 METHYL 1H INDOL 3 YL) 1H PYRROLE 2,5 DIONE; 3 [1 [3 (1H IMIDAZOL 1 YL)PROPYL] 1H INDOL 3 YL] 4 (PHENYLAMINO) 1H PYRROLE 2,5 DIONE; 3 [1 [3 (DIMETHYLAMINO)PROPYL) 1H INDOL 3 YL] 4 [1 (THIOPHEN 2 YL) 1H INDOL 3 YL] 1H PYRROLE 2,5 DIONE; 3 [2 (AMINOMETHYL) 2,3 DIHYDRO 1H PYRROLO[1,2A]INDOL 9 YL] 4 (PHENYLAMINO) 1H PYRROLE 2,5 DIONE; 3 [3 [4 (1 METHYL 1H INDOL 3 YL) 2,5 DIOXO 2,5 DIHYDRO 1H PYRROL 3 YL] 1H INDOL 1 YL]PROPYLCARBAMIMIDOTHIOATE; 3 [8 (AMINOMETHYL) 6,7,8,9 TETRAHYDROPYRIDO[1,2 A]INDOL 10 YL] 4 (1H INDOL 3 YL) 1H PYRROLE 2,5 DIONE; 7 HYDROXYSTAUROSPORINE; ACRIDINE YELLOW GOLD; APRINOCARSEN; BISINDOLYLMALEIMIDE; BRYOSTATIN 1; CALPHOSTIN C; CGS 41251; G 06976; INDOLYLINDAZOLYLMALEIMIDE DERIVATIVE; ISOQUININOLINE H7; KW 2401; LESTAURTINIB; MIDASTOURIN; MIDOSTAURIN; PROTEIN KINASE C BETA; PROTEIN KINASE C BETA II; PROTEIN KINASE C BETA INHIBITOR; RUBOXISTAURIN; SAFINGOL; SANGIVAMTYCIN; SPHINGOSINE; STAUROSPORINE; UNCLASSIFIED DRUG;

CRYSTAL STRUCTURE; DIABETES MELLITUS; DIABETIC MICROANGIOPATHY; DIABETIC NEPHROPATHY; DIABETIC RETINOPATHY; ENZYME ACTIVATION; ENZYME LOCALIZATION; HUMAN; INSULIN RESISTANCE; MOLECULAR DOCKING; MOLECULAR DYNAMICS; NONHUMAN; PHARMACOPHORE; PROTEIN FUNCTION; REVIEW; STRUCTURE ACTIVITY RELATION;

ANIMALS; DIABETES COMPLICATIONS; HUMANS; MODELS, MOLECULAR; PROTEIN CONFORMATION; PROTEIN KINASE C; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84858206920     PISSN: 14728222     EISSN: 17447631     Source Type: Journal    
DOI: 10.1517/14728222.2012.667804     Document Type: Review

References (71)

1. Newton AC. Protein kinase C: structure, function, and regulation. J Biol Chem 1995;270:28495-8
2. Koya D, King GL. Protein kinase C activation and the development of diabetic complications. Diabetes 1998;47:859-66 (Pubitemid 28255657)
3. Idris I, Gray S, Donnelly R. Protein kinase C activation: isozyme-specific effects on metabolism and cardiovascular complications in diabetes. Diabetologia 2001;44:659-73 (Pubitemid 32846021)
4. Nishizuka Y. Studies and perspectives of protein kinase C. Science 1986;233:305-12
5. Avignon A, Sultan A. PKC-epsilon inhibition: a new therapeutic approach for diabetic complications? Diabetes Metab 2006;32:205-13 (Pubitemid 43966743)
6. Kubo K, Ohno S, Suzuki K. Primary structures of human protein kinase C betaI and betaII differ only in their C-terminal sequences. FEBS Lett 1987;223:138-42 (Pubitemid 17150655)
7. Das Evcimen N, King GL. The role of protein kinase C activation and the vascular complications of diabetes. Pharmacol Res 2007;55:498-510 (Pubitemid 46962309)
8. Wheeler GD. Ruboxistaurin (Eli Lilly). IDrugs 2003;6:159-63
9. Aiello LP. The potential role of PKC beta in diabetic retinopathy and macular edema. Surv Ophthalmol 2002;47:S263-9 (Pubitemid 36351246)
10. Tanaka M, Sagawa S, Hoshi J, et al. Synthesis of anilino- monoindolylmaleimides as potent and selective PKC beta inhibitors. Bioorg Med Chem Lett 2004;14:5171-4 (Pubitemid 39233388)
11. Zhang HC, Derian CK, McComsey DF, et al. Novel indolylindazolylmaleimides as inhibitors of protein kinase C-beta synthesis, biological activity, and cardiovascular safety. J Med Chem 2005;48:1725-8 (Pubitemid 40396306)
12. Pinton P, Tsuboi T, Ainscow EK, et al. Dynamics of glucose-induced membrane recruitment of protein kinase C betaII in living pancreatic islet beta-cells. J Biol Chem 2002;277:37702-10
13. Inoguchi T, Battan R, Handler E, et al. Preferential elevation of protein kinase C isoform betaII and diacylglycerol levels in the aorta and heart of diabetic rats: differential reversibility to glycemic control by islet cell transplantation. Proc Natl Acad Sci 1992;89:11059-63
14. Kikkawa R, Haneda M, Uzu T, et al. Translocation of protein kinase Calpha and zeta in rat glomerular mesangial cells cultured under high glucose conditions. Diabetologia 1994;37:838-41 (Pubitemid 24247856)
15. Gurusamy N, Watanabe K, Ma M, et al. Inactivation of 14-3-3 protein exacerbates cardiac hypertrophy and fibrosis through enhanced expression of protein kinase C beta2 in experimental diabetes. Biol Pharm Bull 2005;28:957-62 (Pubitemid 40880296)
16. Idris I, Donnelly R. Protein kinase C inhibition: a novel therapeutic strategy for diabetic microangiopathy. Diab Vasc Dis Res 2006;3:172-8 (Pubitemid 44902483)
17. Shiba T, Inoguchi T, Sportsman JR, et al. Correlation of diacylglycerol level and protein kinase C activity in rat retina to retinal circulation. Am J Physiol Endocrinol Metab 1993;265:E783-93
18. Jirousek MR, Gillig JR, Gonzalez CM, et al. (S)-13-(dimethylamino)methyl- 10,11,14,15-tetrahydro-4,9:16, 21-dimetheno-1H, 13H-dibenzoe,kpyrrolo 3,4-h1,4,13oxadiazacyclohexadecene-1,3(2H)-dione (LY333531) and related analogues: isozyme selective inhibitors of protein kinase C beta. J Med Chem 1996;39:2664-71 (Pubitemid 26240333)
19. Takagi C, Bursell SE, Lin YW, et al. Regulation of retinal hemodynamics in diabetic rats by increased expression and action of endothelin-1. Invest Ophthalmol Vis Sci 1996;37:2504-18 (Pubitemid 26391288)
20. Aiello LP, Avery RL, Arrigg PG, et al. Vascular endothelial growth factor in ocular fluid of patients with diabetic retinopathy and other retinal disorders. N Engl J Med 1994;331:1480-7 (Pubitemid 24356306)
21. McCarty MF. A central role for protein kinase C overactivity in diabetic glomerulosclerosis: implications for prevention with antioxidants, fish oil, and ACE inhibitors. Med Hypotheses 1998;50:155-65
22. Igwe OJ, Chronwall BM. Hyperalgesia induced by peripheral inflammation is mediated by protein kinase C betaII isozyme in the rat spinal cord. Neuroscience 2001;104:875-90 (Pubitemid 32607437)
23. Piontek J, Brandt R. Differential and regulated binding of cAMP-dependent protein kinase and protein kinase C isoenzymes to gravin in human model neurons. J Biol Chem 2003;278:38970-9
24. Hulver MW, Dohm GL. The molecular mechanism linking muscle fat accumulation to insulin resistance. Proc Nutr Soc 2004;63:375-80 (Pubitemid 38787493)
25. Itani S, Ruderman N, Schmieder F, Boden G. Lipid-induced insulin resistance in human muscle is associated with changes in diacylglycerol, protein kinase C, and IkB-alpha. Diabetes 2002;51:2005-11 (Pubitemid 34729001)
26. Cortright RN, Azevedo Jr JL, Zhou Q, et al. Protein kinase C modulates insulin action in human skeletal muscle. Am J Physiol Endocrinol Metab 2000;278:E553-62 (Pubitemid 30149401)
27. Osterhoff MA, Heuer S, Pfeiffer M, et al. Identification of a functional protein kinase Cbeta promoter polymorphism in humans related to insulin resistance. Mol Genet Metab 2008;93:210-15
28. Mima A, Ohshiro Y, Kitada M, et al. Glomerular-specific protein kinase C-beta-induced insulin receptor substrate-1 dysfunction and insulin resistance in rat models of diabetes and obesity. Kidney Int 2011;79:883-96
29. Kawai Y, Ishizuka T, Kajita K, et al. Inhibition of PKCbeta improves glucocorticoid-induced insulin resistance in rat adipocytes. IUBMB Life 2002;54:365-70 (Pubitemid 36298257)
30. Huang W, Bansode R, Mehta M, Mehta KD. Loss of protein kinase Cbeta function protects mice against diabetes induced obesity and development of hepatic steatosis and insulin resistance. Hepatology 2009;49:1525-36
31. Gould CM, Newton AC. The life and death of protein kinase C. Curr Drug Targets 2008;9:614-25
32. Steinberg SF. Structural basis of protein kinase C isoform function. Physiol Rev 2008;88:1341-78
33. Mellor H, Parker PJ. The extended protein kinase C superfamily. Biochem J 1998;332:281-92 (Pubitemid 28271856)
34. Kiley SC, Parker PJ. Differential localization of protein kinase C isozymes in U937 cells: evidence for distinct isozyme functions during monocyte differentiation. J Cell Sci 1995;108:1003-16
35. Blobe GC, Stribling DS, Fabbro D, et al. Protein kinase C betaII specifically binds to and is activated by F-actin. J Biol Chem 1996;271:15823-30 (Pubitemid 26225363)
36. Grodsky N, Li Y, Bouzida D, et al. Structure of the catalytic domain of human protein kinase C betaII complexed with a bisindolylmaleimide inhibitor. Biochemistry (Mosc) 2006;45:13970-81 (Pubitemid 44846186)
37. Leonard TA, Rozycki B, Saidi LF, et al. Crystal structure and allosteric activation of protein kinase C betaII. Cell 2011;144:55-66
38. Standaert ML, Musunuru K, Yamada K, et al. Insulin-stimulated phosphatidylcholine hydrolysis, diacylglycerol/protein kinase C signalling, and hexose transport in pertussis toxin-treated BC3H-1 myocytes. Cell Signal 1994;6:707-16 (Pubitemid 24329986)
39. Banci L, Cavallaro G, Kheifets V, et al. Molecular dynamics characterization of the C2 domain of protein kinase C-beta. J Biol Chem 2002;277:12988-97 (Pubitemid 34952667)
40. Newton AC. Regulation of the ABC kinases by phosphorylation: protein kinase C as a paradigm. Biochem J 2003;370:361-71 (Pubitemid 36315124)
41. Shen GX, Way KJ, Jacobs JR, King GL. Applications of inhibitors for protein kinase C and their isoforms. Methods Mol Biol 2003;233:397-422
42. Davies SP, Reddy H, Caivano M, Cohen P. Specificity and mechanism of action of some commonly used protein kinase inhibitors. Biochem J 2000;351:95-105
43. Cabanis A, Gressier B, Brunet C, et al. Effect of the protein kinase C inhibitor GF 109 203X on elastase release and respiratory burst of human neutrophils. Gen Pharmacol Vasc Syst 1996;27:1409-14 (Pubitemid 26419703)
44. Wang Y, Yin OQP, Graf P, et al. Dose-and time-dependent pharmacokinetics of midostaurin in patients with diabetes mellitus. J Clin Pharmacol 2008;48:763-75 (Pubitemid 351713159)
45. Wang Y, Yang H, Liu H, et al. Effect of staurosporine on the mobility and invasiveness of lung adenocarcinoma A549 cells: an in vitro study. BMC Cancer 2009;9(1):174
46. Goekjian PG. Staurosporine as an early lead:an overview of kinase inhibitors inspired by the iindolocarbazole alkaloids. Dosis 2006;22:124-51
47. Alakananda B. The potential of protein kinase C as a target for anticancer treatment. Pharmacol Ther 1993;59:257-80
48. Toullec D, Pianetti P, Coste H, et al. The bisindolylmaleimide GF 109203X is a potent and selective inhibitor of protein kinase C. J Biol Chem 1991;266:15771-81 (Pubitemid 21907725)
49. Davis PD, Hill CH, Lawton G, et al. Inhibitors of protein kinase C. 1. 2, 3-bisarylmaleimides. J Med Chem 1992;35:177-84
50. Davis PD, Elliott LH, Harris W, et al. Inhibitors of protein kinase C. 2. Substituted bisindolylmaleimides with improved potency and selectivity. J Med Chem 1992;35:994-1001
51. Bit RA, Davis PD, Elliott LH, et al. Inhibitors of protein kinase C. 3. Potent and highly selective bisindolylmaleimides by conformational restriction. J Med Chem 1993;36:21-9 (Pubitemid 23040140)
52. Faul MM, Gillig JR, Jirousek MR, et al. Acyclic N-(azacycloalkyl) bisindolylmaleimides: isozyme selective inhibitors of PKCbeta. Bioorg Med Chem Lett 2003;13:1857-9 (Pubitemid 36577128)
53. Tanaka M, Sagawa S, Hoshi J, et al. Synthesis, SAR studies, and pharmacological evaluation of 3-anilino-4-(3-indolyl) maleimides with conformationally restricted structure as orally bioavailable PKCbeta-selective inhibitors. Bioorg Med Chem 2006;14:5781-94 (Pubitemid 44080593)
54. Wagner J, von Matt P, Sedrani R, et al. Discovery of 3-(1 H-Indol-3-yl)-4-2-(4-methylpiperazin-1-yl) quinazolin-4-yl pyrrole-2, 5-dione (AEB071), a potent and selective inhibitor of protein kinase C isotypes. J Med Chem 2009;52:6193-6
55. Li H, Hong Y, Nukui S, et al. Identification of novel pyrrolopyrazoles as protein kinase C betaII inhibitors. Bioorg Med Chem Lett 2011;21:584-7
56. Zhang HC, White KB, Ye H, et al. Macrocyclic bisindolylmaleimides as inhibitors of protein kinase C and glycogen synthase kinase-3. Bioorg Med Chem Lett 2003;13:3049-53 (Pubitemid 36993634)
57. Zhang HC, Ye H, Conway BR, et al. 3-(7-Azaindolyl)-4-arylmaleimides as potent, selective inhibitors of glycogen synthase kinase-3. Bioorg Med Chem Lett 2004;14:3245-50 (Pubitemid 38624601)
58. Zhang HC, Bonaga LVR, Ye H, et al. Novel bis (indolyl) maleimide pyridinophanes that are potent, selective inhibitors of glycogen synthase kinase-3. Bioorg Med Chem Lett 2007;17:2863-8 (Pubitemid 46636245)
59. Graff JR, McNulty AM, Hanna KR, et al. The protein kinase Cbeta-selective inhibitor, enzastaurin (LY317615. HCl), suppresses signaling through the AKT pathway, induces apoptosis, and suppresses growth of human colon cancer and glioblastoma xenografts. Cancer Res 2005;65:7462-9 (Pubitemid 41161281)
60. Chothia C, Lesk AM. The relation between the divergence of sequence and structure in proteins. EMBO J 1986;5:823-6
61. Lengauer T, Rarey M. Computational methods for biomolecular docking. Curr Opin Struct Biol 1996;6:402-6 (Pubitemid 26197442)
62. Allen MP. Introduction to molecular dynamics simulation. Comput Soft Matter Synthetic Polymers Proteins 2004;23:1-28
63. Selassie CD. History of quantitative structure-activity relationships. Burger's Med Chem Drug Discov 2003;1:1-48
64. Dror O, Shulman-Peleg A, Nussinov R, Wolfson HJ. Predicting molecular interactions in silico: I. A guide to pharmacophore identification and its applications to drug design. Curr Med Chem 2004;11:71-90 (Pubitemid 38081736)
65. Tang S, Xiao V, Wei L, et al. Protein kinase C isozymes and their selectivity towards ruboxistaurin. Proteins Struct Funct Bioinform 2008;72:447-60 (Pubitemid 351809179)
66. Kumar H, Kumar R, Grewal BK, Sobhia ME. Insights into the structural requirements of PKC betaII inhibitors based on HQSAR and CoMSIA analyses. Chem Biol Drug Des 2011;78:283-8
67. Sri Divya P, Grewal B, Elizabeth Sobhia M. 2D and 3D QSAR analyses to predict favorable substitution sites in anilino-monoindolylmaleimides acting as PKCbetaII selective inhibitors. Med Chem Res 2011;20:1188-99
68. Jain K, Sobhia ME. Targeting PKC-beta II by peptides and peptidomimetics derived from RACK 1: an in silico approach. Mol Inform 2011;30:45-62
69. Jain K, Ajay D, Sobhia ME. Targeting PKC-betaII and PKB connection: design of dual inhibitors. Mol Inform 2011;30:329-44
70. Ghoreschi K, Laurence A, O'Shea JJ. Selectivity and therapeutic inhibition of kinases: to be or not to be? Nat Immunol 2009;10:356-60
71. Liu Q, Chen X, MacDonnell SM, et al. Protein kinase Calpha, but not PKCbeta or PKCgamma, regulates contractility and heart failure susceptibility. Circ Res 2009;105(2):194-200