Staurosporine analogues from microbial and synthetic sources and their biological activities

Current Medicinal Chemistry

Volumn 20, Issue 31, 2013, Pages 3872-3902

  Park, B S ^b   Abdel Azeem, A Z ^c   Al Sanea, M M ^c   Yoo, K H ^a   Tae, J S ^b   Lee, S H ^a  

^a Korea Institute of Science and Technology   (South Korea)

^b Yonsei University   (South Korea)

^c University of Science and Technology (UST)   (South Korea)

Author keywords

Biological activity; Cancer; Kinase inhibitor; Phosphorylation; Staurosporine analogues

Indexed keywords

1'' [5'' [(METHOXYCARBONYL)AMINO] 2'' METHYL] PHENYLAMINOCARBONYLSTAUROSPORINE; 2 [1 (3 DIMETHYLAMINOPROPYL) 3 INDOLYL] 3 (3 INDOLYL)MALEIMIDE; 4' DEMETHYLAMINO 4' HYDROXYSTAUROSPORINE; 6 FORMYLAMINO 12,13 DIHYDRO 1,11 DIHYDROXY 5H INDOLO[2,3 A]PYRROLO[3,4 C]CARBAZOLE 5,7(6H) DIONE 13 GLUCOSIDE; 7 HYDROXYSTAUROSPORINE; ANGIOGENESIS INHIBITOR; CEP 751; CISPLATIN; DOXORUBICIN; EDOTECARIN; ENZASTAURIN; HOLYRINE A; HOLYRINE B; K 252A; K 252B; K 252C; K 252D; LESTAURTINIB; MIDOSTAURIN; MLR 52; PACLITAXEL; RK 1409; RK 1409B; RK 286D; RUBOXISTAURIN; STAUROSPORINE DERIVATIVE; TACROLIMUS; TAN 999; UNCLASSIFIED DRUG; UNINDEXED DRUG; ZHD 0501;

ANTIANGIOGENIC ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; COMPETITIVE INHIBITION; DRUG ACTIVITY; DRUG CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; IC 50; MAXIMUM TOLERATED DOSE; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PHAGOCYTOSIS; STRUCTURE ACTIVITY RELATION;

ANIMALS; HUMANS; INDOLES; PROTEIN KINASE INHIBITORS;

EID: 84887922218     PISSN: 09298673     EISSN: 1875533X     Source Type: Journal    
DOI: 10.2174/09298673113209990176     Document Type: Article

References (120)

1. Buss, A.D.; Cox, B.; Waigh, R.D. In Burger's medicinal chemistry and drug discovery, 6th ed.; Volume 1: Drug Discovery; Abraham, D.J., Ed.; Wiley: Hoboken, NJ, 2003; Chapter 20, 847-900.
2. Butler, M.S. The role of natural product chemistry in drug discovery, J. Nat. Prod., 2004, 67, 2141-2153.
3. Demain, A. L.; Sanchez, S. Microbial drug discovery: 80 years of progress, J. Antibiot., 2009, 62, 5-16.
4. Li, J.W.-H.; Vederas, J.C. Drug discovery and natural products: End of an era or an endless frontier, Science, 2009, 325, 161-165.
5. Brewer, S. In Biodiversity: New leads for the pharmaceutical and agrochemical industries, Wrigley, S.K.; Hayes, M.A.; Thomas, R.; Chrystal, E.J.T.; Nicholson, N., Ed.; The Royal Society of Chemistry, 2000, The relationship between natural products and synthetic chemistry in the discovery process, 59-65.
6. Gani, O.A.B.S.M.; Engh, R.A. Protein kinase inhibition of clinically important staurosporine analogue. Nat. Prod. Rep., 2010, 27, 489-498.
7. Omura, S.; Iwai, Y.; Hirano, A.; Nakagawa, A.; Awaya, J.; Tsuchya, H.; Takahashi, Y.; Masuma, R. A New alkaloid AM-2282 of Streptomyces origin. Taxonomy, fermentation, isolation and preliminary characterization. J. Antibiot., 1977, 30(4), 275-282.
8. Furusaki, A.; Hashiba, N.; Matsumoto, T.; Hirano, A.; Iwai, Y.; Mura, S. X-Ray crystal structure of staurosporine: a new alkaloid from a Streptomyces strain. Chem. Commun., 1978, (18), 800-801.
9. Tamaoki, T.; Nomoto, H.; Takahashi, I.; Kato, Y.; Morimoto, M.; Tomita, F. Staurosporine, a potent inhibitor of phospholipid/Ca2+ dependent protein kinase. Biochem. Biophys. Res. Commun., 1986, 135(2), 397-402.
10. Meggio, F.; Deana, A.D.; Ruzzene, M.; Brunati, A.M.; Cesaro, L.; Guerra, B.; Meyer, T.; Mett, H.; Fabbro, D.; Furet, P.; Dobrowolska, G.; Pinna, L.A. Different susceptibility of protein kinases to staurosporine inhibition. Kinetic studies and molecular bases for the resistance of protein kinase CK2. Eur. J. Biochem., 1995, 234(1), 317-322.
11. Meyer, T.; Regenass, U.; Fabbro, D.; Alteri, E.; Röusel, J.; Möller, M.; Caravatti, G.; Matter, A. A derivative of staurosporine (CGP 41 251) shows selectivity for protein kinase C inhibition and in vitro antiproliferative as well as in vivo antitumor activity. Int. J. Cancer, 1989, 43(5), 851-856.
12. Gschwendt, M.; Kittstein, W.; Marks, F. Elongation factor-2 kinase: effective inhibition by the novel protein kinase inhibitor rottlerin and relative insensitivity towards staurosporine. FEBS Letters, 1994, 338(1), 85-88.
13. Yanagihara, N.; Tachikawa, E.; Izumi, F.; Yasugawa, S.; Yamamoto, H.; Miyamoto, E. Staurosporine: An effective inhibitor for Ca2+/Calmodulindependent protein kinase II. J. Neurochem., 1991, 56(1), 294-298.
14. Nakano, H.; Kobayashi, E.; Takahashi, I.; Tamaoki, T.; Kuzuu, Y.; Iba, H. Staurosporine inhibits tyrosine-specific protein kinase activity of Rous sarcoma virus transforming protein p60. J. Antibiot., 1987, 40(5), 706-708.
15. Fujita-Yamaguchi, Y.; Kathuria, S. Characterization of receptor tyrosine-specific protein kinases by the use of inhibitors. Staurosporine is a 100-times more potein inhibitor of insulin receptor than IGF-I receptor. Biochem. Biophys. Res. Commun., 1988, 157(3), 955-962.
16. Caravatti, G.; Meyer, T.; Fredenhagen, A.; Trinks, U.; Mett, H.; Fabbro, D. Inhibitory activity and selectivity of staurosporine derivatives towards protein kinase C. Bioorg. Med. Chem. Lett., 1994, 4(3), 399-404.
17. Zhao, B.; Bower, M.J.; McDevitt, P.J.; Zhao, H.; Davis, S.T.; Johanson, K.O.; Green, S.M.; Concha, N.O.; Zhou, B.B. Structural basis for Chk1 inhibition by UCN-01. J. Biol. Chem., 2002, 277(48), 46609-46615.
18. Atwell, S.; Adams, J.M.; Badger, J.; Buchanan, M.D.; Feil, I.K.; Froning, K.J.; Gao, X.; Hendle, J.; Keegan, K.; Leon, B.C.; Muller-Dieckmann, H.J.; Nienaber, V.L.; Noland, B.W.; Post, K.; Rajashankar, K.R.; Ramos, A.; Russell, M.; Burley, S.K.; Buchanan, S.G. A novel mode of Gleevec binding is revealed by the structure of spleen tyrosine kinase. J. Biol. Chem., 2004, 279(53), 55827-55832.
19. Fernández, A.; Maddipati, S. A priori inference of cross reactivity for drug-targeted kinases. J. Med. Chem., 2006, 49(11), 3092-3100.
20. Karaman, M.W.; Herrgard, S.; Treiber, D.K.; Gallant, P.; Atteridge, C.E.; Campbell, B.T.; Chan, K.W.; Ciceri, P.; Davis, M.I.; Edeen, P.T.; Faraoni, R.; Floyd, M.; Hunt, J.P.; Lockhart, D.J.; Milanov, Z.V.; Morrison, M.J.; Pallares, G.; Patel, H.K.; Pritchard, S.; Wodicka, L.M.; Zarrinkar, P.P. A quantitative analysis of kinase inhibitor selectivity. Nat. Biotechnol., 2008, 26(1), 127-132.
21. De Azevedo, W.F. Jr.; Canduri, F.; Fadel, V.; Teodoro, L.G.; Hial, V.; Gomes, R.A. Molecular model for the binary complex of uropepsin andpepstatin. Biochem. Biophys. Res. Commun., 2001, 287(1), 277-281.
22. Canduri, F.; Teodoro, L.G.; Fadel, V.; Lorenzi, C.C.; Hial, V.; Gomes, R.A.; Neto, J.R.; de Azevedo, W.F. Jr. Structure of human uropepsin at 2.45 resolution. Acta Crystallogr. D Biol. Crystallogr., 2001, 57(Pt 11), 1560-1570.
23. Cohen, P. The development and therapeutic potential of protein kinase inhibitors. Curr. Opin. Chem. Biol., 1999, 3(4), 459-465.
24. Kim, S.H.; Schulze-Gahmen, U.; Brandsen, J.; de Azevedo Junior, W.F. Structural basis for chemical inhibition of CDK2. Prog. Cell Cycle Res., 1996, 2, 137-145.
25. De Azevedo, W.F.; Leclerc, S.; Meijer, L.; Havlicek, L.; Strnad, M.; Kim, S.H. Inhibition of cyclin-dependent kinases by purine analogues: crystal structure of human cdk2 complexed with roscovitine. Eur. J. Biochem., 1997, 243(1-2), 518-526.
26. De Azevedo, W.F. Jr.; Mueller-Dieckmann, H.J.; Schulze-Gahmen, U.; Worland, P.J.; Sausville, E.; Kim, S.H. Structural basis for specificity and potency of a flavonoid inhibitor of human CDK2, a cell cycle kinase. Proc. Natl. Acad. Sci. U S A., 1996, 93(7), 2735-2740.
27. De Azevedo, W.F. Jr.; Canduri, F.; da Silveira, N.J. Structural basis for inhibition of cyclin-dependent kinase 9 by flavopiridol. Biochem. Biophys. Res. Commun., 2002, 293(1), 566-571.
28. Filgueira de Azevedo, W. Jr.; Gaspar, R.T.; Canduri, F.; Camera, J.C. Jr.; Freitas da Silveira, N.J. Molecular model of cyclindependent kinase 5 complexed with roscovitine. Biochem. Biophys. Res. Commun., 2002, 297(5), 1154-1158.
29. Canduri, F.; Uchoa, H.B.; de Azevedo, W.F. Jr. Molecular models of cyclin-dependent kinase 1 complexed with inhibitors. Biochem. Biophys. Res. Commun., 2004, 324(2), 661-666.
30. Krystof, V.; Cankar, P.; Frysová, I.; Slouka, J.; Kontopidis, G.; Dzubák, P.; Hajdúch, M.; Srovnal, J.; de Azevedo, W.F. Jr.; Orság, M.; Paprskárová, M.; Rolcík, J.; Látr, A.; Fischer, P.M.; Strnad, M. 4-Arylazo-3,5-diamino-1H-pyrazole CDK inhibitors: SAR study, crystal structure in complex with CDK2, selectivity, and cellular effects. J. Med, Chem., 2006, 49(22), 6500-6509.
31. Fabbro, D.; Cowan-Jacob, S.W.; Möbitz, H.; Georg, M.B. In kinase inhibitors, Volume 975, Methods in Molecular Biology, Bernhard, K.; Ed., Humana Press, 2012; Ch 1, Targeting cancer with smallmolecular-weight kinase inhibitors, 1-34.
32. Etienne, C.L. Synthetic efforts and activity profile of staurosporine, a potent inhibitor of protein kinase C, 1997, http://www.chem.umn.edu/studsem/ abstract9697/etienne42997/etis em.html.
33. Moody, C.J.; Kulsum F. Rahimtoola, K.F.; Porter, B.; Barry, C.; Ross, C.B. Synthesis of the staurosporine aglycon. J. Org. Chem., 1992, 57, 2105-2114.
34. Wood, J.L.; Stoltz, B.M.; Dietrich, H.-J. Total synthesis of (+)-and (-)-K252a. J. Am. Chem. Soc., 1995, 117, 10413-10414.
35. Xie G.; Lown, W.J. A facile synthesis of staurosporine aglycone. Tetrahedron. Lett, 1994, 35, 5555-5558.
36. Ganesan Gobi Rajeshwaran, G.G.; Mohanakrishnan, A.K. Synthetic studies on indolocarbazoles: Total synthesis of staurosporine aglycon, Org. Lett., 2011, 13, 1418-1421.
37. Link, J.T.; Raghavan, S.; Gallant, M.; Danishefsky, S.J.; Chou, T.C.; Ballas, L.M. Staurosporine and ent-staurosporine: The first total syntheses, prospects for a regioselective approach, and activity profiles. J. Am. Chem. Soc., 1996, 118(12), 2825-2842.
38. Link, J.T.; Raghavan, S.; Danishefsky, S.J. First total synthesis of staurosporine and ent-staurosporine J. Am. Chem. Soc., 1995, 117, 552-523.
39. Link, J.T.; Danishefsky, S.J. Epoxides derived from pyranosyl dienes: Unusually stable glycosyl donors. Tetrahedron Lett., 1994, 35, 9131-9134.
40. Link, J.T.; Danishefsky, S.J. Regioselective imide reduction: An issue in the total synthesis of staurosporine. Tetrahedron Lett., 1994, 35, 9135-9138.
41. Onaka, H.; Taniguchi, S.; Igarashi, Y.; Furumai, T. Characterization of the biosynthetic gene cluster of rebeccamycin from Lechevalieria aerocolonigenes ATCC 39243. Biosci. Biotechnol. Biochem., 2003, 67(1), 127-138.
42. Onaka, H.; Taniguchi, S.I.; Igarashi, Y.; Furumai, T. Cloning of the staurosporine biosynthetic gene cluster from Streptomyces sp. TPA0274 and its heterologous expression in Streptomyces lividans. J. Antibiot., 2002, 55(12), 1063-1071.
43. Sánchez, C.; Butovich, I.A.; Braña, A.F.; Rohr, J.; Méndez, C.; Salas, J.A. The biosynthetic gene cluster for the antitumor rebeccamycin: characterization and generation of indolocarbazole derivatives. Chem. Biol., 2002, 9(4), 519-531.
44. Meksuriyen, D.; Cordell, G.A. Biosynthesis of staurosporine, 2. Incorporation of tryptophan. J. Nat. Prod., 1988, 51(5), 893-899.
45. Nakano, H.; Omura, S. Chemical biology of natural indolocarbazole products: 30 years since the discovery of staurosporine. J. Antibiot., 2009, 62(1), 17-26.
46. Kase, H.; Iwahashi, K.; Matsuda, Y. K-252a, A potent inhibitor of protein kinase C from microbial origin. J. Antibiot., 1986, 39(8), 1059-1065.
47. Nakanishi, S.; Matsuda, Y.; Iwahashi, K.; Kase, H. K-252b, c and d, potent inhibitors of protein kinase C from microbial origin. J. Antibiot., 1986, 39(8), 1066-1071.
48. Nye, S.H.; Squinto, S.P.; Glass, D.J.; Stitt, T.N.; Hantzopoulos, P.; Macchi, M.J.; Lindsay, N.S.; Ip, N.Y.; Yancopoulos, G.D. K252a and staurosporine selectively block autophosphorylation of neurotrophin receptors and neurotrophin-mediated responses. Mol. Biol. Cell, 1992, 3(6), 677-686.
49. Schiering, N.; Knapp, S.; Marconi, M.; Flocco, M.M.; Cui, J.; Perego, R.; Rusconi, L.; Cristiani, C. Crystal structure of the tyrosine kinase domain of the hepatocyte growth factor receptor c-Met and its complex with the microbial alkaloid K-252a. Proc. Natl. Acad. Sci. U.S.A., 2003, 100(22), 12654-12659.
50. Fischmann, T.O.; Smith, C.K.; Mayhood, T.W.; Myers, J.E.; Reichert, P.; Mannarino, A.M.; Carr, D.; Zhu, H.; Wong, J.; Yang, R.-S.; Le, Y.H.; Madison, V.S. Crystal structures of MEK1 and binary and ternary complexes with nucleotides and inhibitors. Biochemistry, 2009, 48(12), 2661-2674.
51. Osada, H.; Takahashi, H.; Tsunoda, K.; Kusakabe, H.; Isono, K. A new inhibitor of protein kinase C, RK-286C (4'-demethylamino-4'- hydroxystaurosporine). I: Screening, taxonomy, fermentation and biological activity. J. Antibiot., 1990, 43(2), 163-167.
52. Takahashi, H.; Osada, H.; Uramoto, M.; Isono, K. A new inhibitor of protein kinase C, RK-286C (4'-demethylamino-4'-hydroxystaurosporine). II: Isolation, physico-chemical properties and structure. J. Antibiot., 1990, 43(2), 168-173.
53. Osada, H.; Satake, M.; Koshino, H.; Onose, R.; Isono, K. A new indolocarbazole antibiotic, RK-286 D. J. Antibiot., 1992, 45(2), 278-279.
54. Osada, H.; Magae, J.; Watanabe, C.; Isono, K. Rapid screening method for inhibitors of protein kinase C. J. Antibiot., 1988, 41(7), 925-931.
55. Koshino, H.; Osada, H.; Amano, S.; Onose, R.; Isono, K. A new inhibitor of protein kinase C, RK-1409 B (4'-demethylamino-4'-hydroxy-3'-epistaurosporine) . J. Antibiot., 1992, 45(9), 1428-1428.
56. McAlpine, J.B.; Karwowski, J.P; Jackson, M.; Mullally, M.M; Hochlowski, J.E; Premachandran, U.; Burres, N.S. MLR-52, (4'-demethylamino-4',5'- dihydroxystaurosporine), a new inhibitor of protein kinase C with immunosuppressive activity. J. Antibiot., 1994, 47(3), 281-288.
57. Pirsch, J.D.; Miller, J.; Deierhoi, M.H.; Vincenti, F.; Filo, R.S. A comparison of tacrolimus (FK506) and cyclosporine for immunosuppression after cadaveric renal transplantation 1. Transplantation, 1997, 63(7), 977-983.
58. Williams, D.E.; Bernan, V.S.; Ritacco, F.V.; Maiese, W.M.; Greenstein, M.; Andersen, R.J. Holyrines A and B, possible intermediates in staurosporine biosynthesis produced in culture by a marine actinomycete obtained from the North Atlantic Ocean. Tetrahedron Lett., 1999, 40(40), 7171-7174.
59. Canedo Hernandez, L.M.; de la Fuente Blanco, J.A.; Baz, J.P; Fernandez Puentes, J.L.; Millan, F.R.; Vazquez, F.E.; FernandezChimeno, R.I.; Gravalos, D.G. 4-NMethyl5-hydroxystaurosporine and 5-hydroxystaurosporine, new indolocarbazole alkaloids from a marine Micromonospora sp. strain. J. Antibiot., 2000, 53(9), 895-902.
60. Han, X.-X.; Cui, C.-B.; Gu, Q.-Q.; Zhu, W.-M.; Liu, H.-B.; Gu, J.-Y.; Osada, H. ZHD-0501, A novel naturally occurring staurosporine analog from Actinomadura sp. 007. Tetrahedron Lett., 2005, 46(36), 6137-6140
61. Wang, H.Y.; Cai, B.; Cui, C.B.; Zhang, D.Y.; Yang, B.F. Vitexicarpin, a flavonoid from Vitex trifolia L., induces apoptosis in K562 cells via mitochondria-controlled apoptotic pathway. Yao. Xue. Xue. Bao., 2005, 40(1), 27-31.
62. Li, X.B.; Tang, J.S.; Gao, H.; Ding, R.; Li, J.; Hong, K.; Yao, X.S. A new staurosporine analogue from Actinomycetes Streptomyces sp.(172614). J. Nat. Prod., 2011, 13(8), 765-769.
63. Kinnel, R.B.; Scheuer, P.J. 11-Hydroxystaurosporine: A highly cytotoxic, powerful protein kinase C inhibitor from a tunicate. J. Org. Chem., 1992, 57(23), 6327-6329.
64. Takahashi, I.; Asano, K.; Kawamoto, I.; Tamaoki, T.; Nakano, H. UCN-01 and UCN-02, new selective inhibitors of protein kinase C. I. Screening, producing organism and fermentation. J. Antibiot., 1989, 42(4), 564-570.
65. Takahashi, I.; Saitoh, Y.; Yoshida, M.; Sano, H.; Nakano, H.; Morimoto, M.; Tamaoki, T. UCN-01 and UCN-02, new selective inhibitors of protein kinase C. II. Purification, physico-chemical properties, structural determination and biological activities. J. Antibiot., 1989, 42(4), 571-576.
66. Zhao, B.; Bower, M.J.; McDevitt, P.J.; Zhao, H.; Davis, S.T.; Johanson, K.O.; Green, S.M.; Concha, N.O.; Zhou, B.B.S. Structural basis for Chk1 inhibition by UCN-01. J. Biol. Chem., 2002, 277(48), 46609-46615.
67. Komander, D.; Kular, G.S.; Bain, J.; Elliott, M.; Alessi, D.R.; Van Aalten, D.M.F. Structural basis for UCN-01 (7-hydroxystaurosporine) specificity and PDK1 (3-phosphoinositidedependent protein kinase-1) inhibition. Biochem. J., 2003, 375, 255-262.
68. Jiang, X.; Zhao, B.; Britton, R.; Lim, L.Y.; Leong, D.; Sanghera, J.S.; Zhou, B.B.S.; Piers, E.; Andersen, R.J.; Roberge, M. Inhibition of Chk1 by the G2 DNA damage checkpoint inhibitor isogranulatimide. Mol. Cancer Ther., 2004, 3(10), 1221-1227.
69. Osada, H.; Koshino, H.; Kudo, T.; Onose, R.; Isono, K. A new inhibitor of protein kinase C. RK-1409(7-oxostaurosporine). I. Taxonomy and biological activity. J. Antibiot., 1992, 45(2), 189-194.
70. Koshino, H.; Osada, H.; Isono, K. A new inhibitor of protein kinase C, RK-1409 (7-oxostaurosporine). II. Fermentation, isolation, physico-chemical properties and structure. J. Antibiot., 1992, 45(2), 195-198.
71. Tanida, S.; Takizawa, M.; Takahashi, T.; Tsubotani, S.; Harada, S. TAN-999 and TAN-l030A, new indolocarbazole alkaloids with macrophage-activating properties. J. Antibiot, 1989, 42(11), 1619-1630.
72. Tsubotani, S.; Tanida, S.; Harada, S. Structure determination of indolocarbazole alkaloids by NMR spectroscopy. Tetrahedron, 1991, 47(22), 3565-3574.
73. Barrabee, E.B.; Horan, A.C.; Gentile, F.A.; Patel, M.G. Indolocarbazoles from saccharothrix aerocolonigenes subsp. copiosa subsp. NOV.SCC 1951 ATCC 53856, WO Patent 91/09034, 27 June, 1991.
74. Salas, A.P; Reillo, C.S; Braña, A.F; Fernández, C.M; Salas Fernández, J.A.; Vara, F.M. Glycosylated indolecarbazoels, method for obtaining same and uses thereof. US Patent 0136753, 2011.
75. Cai, Y.; Fredenhagen, A.; Hug, P.; Peter, H.H. A nitro analogue of staurosporine and other minor metabolites produced by a Streptomyces longisporoflavus strain. J. Antibiot., 1995, 48(2), 143-148.
76. Cai, Y.; Fredenhagen, A.; Hug, P.; Meyer, T.; Peter, H.H. Further minor metabolites of staurosporine produced by a Streptomyces longisporoflavus strain. J. Antibiot., 1996, 49(6), 519-526.
77. Cai, Y.; Fredenhagen, A.; Hug, P.; Peter, H.H. The staurosporine producing strain Streptomyces longisporoflavus produces metabolites related to K252a. Proposal for biosynthetic intermediates of K252a. J. Antibiot., 1996, 49(10), 1060-1062.
78. Cantrell, C.L.; Groweiss, A.; Gustafson, K.R.; Boyd, M.R. A new staurosporine analog from the prosobranch mollusk Coriocella nigra. Nat. Prod. Lett., 1999, 14(1), 39-46.
79. Schupp, P.; Eder, C.; Proksch, P.; Wray, V.; Schneider, B.; Herderich, M.; Paul, V. Staurosporine derivatives from the ascidian Eudistoma toealensis and its predatory flatworm pseudoceros sp. J. Nat. Prod., 1999, 62(7), 959-962.
80. Schupp, P.; Proksch, P.; Wray, V. Further new staurosporine derivatives from the ascidian Eudistoma toealensis and its predatory flatworm pseudoceros sp. J. Nat. Prod., 2002, 65(3), 295-298.
81. Schupp, P.; Steube, K.; Meyer, C.; Proksch, P. Anti-proliferative effects of new staurosporine derivatives isolated from a marine ascidian and its predatory flatworm. Cancer Lett., 2001, 174(2), 165-172.
82. Ubukata, M.; Tamehiro, N.; Matsuura, N.; Nakajima, N. Indocardazostatin, a novel inhibitor of NGF-induced neurite outgrowth from rat pheochromocytoma PC12 cells. J. Antibiot., 1999, 52(10), 921-924.
83. Matsuura, N.; Tamehiro, N.; Andoh, T.; Kawashima, A.; Ubukata, M. Indocarbazostatin and indocarbazostatin B, novel inhibitors of NGF-induced neuronal differentiation in PC12 cells. I. Screening, taxonomy, fermentation and biological activities. J. Antibiot., 2002, 55(4), 355-362.
84. Tamehiro, N.; Matsuura, N.; Feng, Y.; Nakajima, N.; Ubukata, M. Indocarbazostatin and indocarbazostatin B, novel inhibitors of NGF-induced neuronal differentiation in PC12 cells. II. Isolation, physicochemical properties and structural elucidation. J. Antibiot., 2002, 55(4), 363-370.
85. Meyer, T.; Regenass, U.; Fabbro, D.; Alteri, E.; Röusel, J.; Möller, M.; Caravatti, G.; Matter, A. A derivative of staurosporine (CGP 41 251) shows selectivity for protein kinase C inhibition and in vitro antiproliferative as well as in vivo antitumor activity. Int. J. Cancer, 1989, 43(5), 851-856.
86. Weisberg, E.; Boulton, C.; Kelly, L.M.; Manley, P.; Fabbro, D.; Meyer, T.; Gilliland, D.G.; Griffin, J.D. Inhibition of mutant FLT3 receptors in leukemia cells by the small molecule tyrosine kinase inhibitor PKC412. Cancer Cell, 2002, 1(5), 433-443.
87. Yamada, R.; Fukuda, K.; Kawanishi, M.; Ohmori, Y.; Nasu, M.; Seto, M.; Sasaki, Y.; Sunazuka, T.; Zhuorong, L.; Funato, N. Synthesis and activity of staurosporine analogs with a lactone functionality. Bioorg. Med. Chem. Lett., 1996, 6(16), 1893-1896.
88. Li, Z.; Sunazuka, T.; Yamada, R.; Kato, Y.; Enomoto, A.; Hayashi, M.; Harigaya, Y.; Omura, S. Synthesis and antiangiogenic activity of staurosporine derivatives. J. Antibiot., 2000, 53(4), 426-429.
89. Boggon, T.J.; Li, Y.; Manley, P.W.; Eck, M.J. Crystal structure of the Jak3 kinase domain in complex with a staurosporine analog. Blood, 2005, 106(3), 996-1002.
90. Zhu, X.; Kim, J.L.; Newcomb, J.R.; Rose, P.E.; Stover, D.R.; Toledo, L.M.; Zhao, H.; Morgenstern, K.A. Structural analysis of the lymphocyte-specific kinase Lck in complex with non-selective and Src family selective kinase inhibitors. Structure, 1999, 7(6), 651-661.
91. Malaviya, R.; Zhu, D.; Dibirdik, I.; Uckun, F.M. Targeting Janus kinase 3 in mast cells prevents immediate hypersensitivity reactions and anaphylaxis. J. Biol. Chem., 1999, 274(38), 27028-27038.
92. Rochman, Y.; Spolski, R.; Leonard, W.J. New insights into the regulation of T cells by c family cytokines. Nat. Rev. Immunol., 2009, 9(7), 480-490.
93. Walters, D.K.; Mercher, T.; Gu, T.L.; O'Hare, T.; Tyner, J.W.; Loriaux, M.; Goss, V.L.; Lee, K.A.; Eide, C.A.; Wong, M.J.; Stoffregen, E.P.; McGreevey, L.; Nardone, J.; Moore, S.A.; Crispino, J.; Boggon, T.J.; Heinrich, M.C.; Deininger, M.W.; Polakiewicz, R.D.; Gilliland D.G.; Druker, B.J. Activating alleles of JAK3 in acute megakaryoblastic leukemia. Cancer Cell, 2006, 10(1), 65-75.
94. El-Deeb, I.M.; Jung, S.-J.; Park, B.-S.; Yoo, Y.-J.; Choi, K.-H.; Yang, Y.-M.; Lee, S.-W.; Kim, I.-T.; Han, D.-K.; Lee, S.H. A highly selective staurosporine derivative designed by a new selectivity filter. Bull. Kor. Chem. Soc., 2011, 32(5), 1709-1714.
95. Kase, H.; Iwahashi, K.; Nakanishi, S.; Matsuda, Y.; Yamada, K.; Takahashi, M.; Murakata, C.; Sato, A.; Kaneko, M. K-252 compounds, novel and potent inhibitors of protein kinase C and cyclic nucleotide-dependent protein kinases. Biochem. Biophys. Res. Commun., 1987, 142(2), 436-440.
96. George, D.J.; Dionne, C.A.; Jani, J.; Angeles, T.; Murakata, C.; Lamb, J.; Isaacs, J.T. Sustained in vivo regression of Dunning H rat prostate cancers treated with combinations of androgen ablation and Trk tyrosine kinase inhibitors, CEP-751 (KT-6587) or CEP-701 (KT-5555). Cancer Res., 1999, 59(10), 2395-2401.
97. Rubin, J.B.; Segal, R.A. Growth, survival and migration: the Trk to cancer. Signal Transduction in Cancer, 2004, 115, 1-18.
98. Levis, M.; Allebach, J.; Tse, K.-F.; Zheng, R.; Baldwin, B.R.; Smith, B.D.; Jones-Bolin, S.; Ruggeri, B.; Dionne, C.; Small, D. A FLT3-targeted tyrosine kinase inhibitor is cytotoxic to leukemia cells in vitro and in vivo. Blood, 2002, 99(11), 3885-3891.
99. Murakata, C.; Kaneko, M.; Gessner, G.; Angeles, T.S.; Ator, M.A.; O'Kane, T.M.; McKenna, B.A.W.; Thomas, B.A.; Mathiasen, J.R.; Saporito, M.S.; Bozyczko-Coyne, D.; Hudkins, R.L. Mixed lineage kinase activity of indolocarbazole analogues. Bioorg. Med. Chem. Lett., 2002, 12(2), 147-150.
100. Bozyczko-Coyne, D.; Saporito, M.S.; Hudkins, R.L. Targeting the JNK pathway for therapeutic benefit in CNS disease. CNS Neurol. Disord. Drug Targets., 2002, 1(1), 31-49.
101. Takahashi, I.; Kobayashi, E.; Nakano, H.; Murakata, C.; Saitoh, H.; Suzuki, K.; Tamaoki, T. Potent selective inhibition of 7-O-methyl UCN-01 against protein kinase C. J. Pharmacol. Exp. Ther., 1990, 255(3), 1218-1221.
102. Toullec, D.; Pianetti, P.; Coste, H.; Bellevergue, P.; Grand-Perret, T.; Ajakane, M.; Baudet, V.; Boissin, P.; Boursier, E.; Loriolle, F. The bisindolylmaleimide GF 109203X is a potent and selective inhibitor of protein kinase C. J. Biol.Chem., 1991, 266(24), 15771-15781.
103. Alessi, D.R. The protein kinase C inhibitors Ro318220 and GF109203X are equally potent inhibitors of MAPKAP kinase-1 (Rsk-2) and p70S6 kinase. FEBS Letters, 1997, 402(2), 121-123.
104. Davies, S.P.; Reddy, H.; Caivano, M.; Cohen, P. Specificity and mechanism of action of some commonly used protein kinase inhibitors. Biochem. J., 2000, 351, 95-105.
105. McCombie, S.W.; Bishop, R.W.; Carr, D.; Dobek, E.; Kirkup, M.P.; Kirschmeier, P.; Lin, S.-I.; Petrin, J.; Rosinski, K.; Shankar, B.B.; Wilson, O. Indolocarbazoles. 1. Total synthesis and protein kinase inhibiting characteristics of compounds related to K-252c. Bioorg. Med. Chem. Lett., 1993, 3(8), 1537-1542.
106. Jackson, J.R.; Gilmartin, A.; Imburgia, C.; Winkler, J.D.; Marshall, L.A.; Roshak, A. An indolocarbazole inhibitor of human checkpoint kinase (Chk1) abrogates cell cycle arrest caused by DNA damage. Cancer Res., 2000, 60(3), 566-572.
107. Arakawa, H.; Iguchi, T.; Morita, M.; Yoshinari, T.; Kojiri, K.; Suda, H.; Okura, A.; Nishimura, S. Novel Indolocarbazole compound 6-N-Formylamino-12,13- dihydro-1,11-dihydroxy-13-(-d-glucopyranosyl)-5H-indolo[2,3-a] pyrro[3,4-c]carbazole-5,7(6H)-dione (NB-506): Its potent antitumor activities in mice. Cancer Res., 1995, 55(6), 1316-1320.
108. Yoshinari, T.; Matsumoto, M.; Arakawa, H.; Okada, H.; Noguchi, K.; Suda, H.; Okura, A.; Nishimura, S. Novel antitumor indolocarbazole compound 6-N-formylamino-12,13-dihydro-1,11-dihydroxy-13-(-d-glucopyranosyl)-5H-indolo [2,3-a] pyrrolo[3, 4-c] carbazole-5,7 (6H)-dione (NB-506): induction of topoisomerase I-mediated DNA cleavage and mechanisms of cell line-selective cytotoxicity. Cancer Res., 1995, 55(6), 1310-1315.
109. Arakawa, H.; Morita, M.; Kodera, T.; Okura, A.; Ohkubo, M.; Morishima, H.; Nishimura, S. In vivo Antitumor activity of a novel indolocarbazole compound, J107088, on murine and human tumors transplanted into mice. Cancer Sci., 1999, 90(10), 1163-1170.
110. Yoshinari, T.; Ohkubo, M.; Fukasawa, K.; Egashira, S.-I.; Hara, Y.; Matsumoto, M.; Nakai, K.; Arakawa, H.; Morishima, H.; Nishimura, S. Mode of action of a new indolocarbazole anticancer agent, J-107088, targeting topoisomerase I. Cancer Res., 1999, 59(17), 4271-4275.
111. Joy, S.V.; Scates, A.C.; Bearelly, S.; Dar, M.; Taulien, C.A.; Goebel, J.A.; Cooney, M.J. Ruboxistaurin, a protein kinase C inhibitor, as an emerging treatment for diabetes microvascular complications. Ann. Pharmacother., 2005, 39(10), 1693-1699.
112. Jirousek, M.R.; Gillig, J.R.; Gonzalez, C.M.; Heath, W.F.; McDonald III, J.H.; Neel, D.A.; Rito, C.J.; Singh, U.; Stramm, L.E.; Melikian-Badalian, A.; Baevsky, M.; Ballas, L.M.; Hall, S.E.; Winneroski, L.L.; Faul, M.M. (S)-13-[(Dimethylamino)methyl]-10,11,14,15-tetrahydro-4,9:16,21-dimetheno-1H, 13H-dibenzo[e,k] pyrrolo [3,4-h] [1,4,13] oxadiazacyclohexadecene-1,3(2H)-dione (LY333531) and related analogues: Isozyme selective inhibitors of protein kinase C. J. Med. Chem., 1996, 39(14), 2664-2671.
113. Tamaki, K.; Shotwell, J.B.; White, R.D.; Drutu, I.; Petsch, D.T.; Nheu, T.V.; He, H.; Hirokawa, Y.; Maruta, H.; Wood, J.L. Efficient syntheses of novel C2'-alkylated (±)-K252a analogues. Org. Lett., 2001, 3(11), 1689-1692.
114. Al-awar, R.S.; Ray, J.E.; Hecker, K.A.; Joseph, S.; Huang, J.; Shih, C.; Brooks, H.B.; Spencer, C.D.; Watkins, S.A.; Schultz, R.M.; Considine, E.L.; Faul, M.M.; Sullivan, K.A.; Kolis, S.P.; Carr, M.A.; Zhang, F. Preparation of novel aza-1,7-annulated indoles and their conversion to potent indolocarbazole kinase inhibitors. Bioorg. Med. Chem. Lett., 2004, 14(15), 3925-3928.
115. Davis, P.D.; Hill, C.H.; Lawton, G.; Nixon, J.S.; Wilkinson, S.E.; Hurst, S.A.; Keech, E.; Turner, S.E. Inhibitors of protein kinase C. 1. 2,3-bisarylmaleimides. J. Med. Chem., 1992, 35(1), 177-184.
116. Bullock, A.N.; Debreczeni, J.É.; Fedorov, O.Y.; Nelson, A.; Marsden, B.D.; Knapp, S. Structural basis of inhibitor specificity of the human protooncogene proviral insertion site in moloney murine leukemia virus (PIM-1) kinase. J. Med. Chem., 2005, 48(24), 7604-7614
117. Bartlett, S.; Nelson, A. Evaluation of alternative approaches for the synthesis of macrocyclic bisindolylmaleimides. Org. Biomol. Chem., 2004, 2, 2874-2883.
118. Valdman, A.; Fang, X.; Pang, S.T.; Ekman, P.; Egevad, L. Pim1 expression in prostatic intraepithelial neoplasia and human prostate cancer. The Prostate, 2004, 60(4), 367-371.
119. Faul, M.M.; Gillig, J.R.; Jirousek, M.R.; Ballas, L.M.; Schotten, T.; Kahl, A.; Mohr, M. Acyclic N-(azacycloalkyl) bisindolylmaleimides: Isozyme selective inhibitors of PKC. Bioorg. Med. Chem. Lett., 2003, 13, 1857-1859.
120. Salas, A.P.; Reillo, C.S.; Braña, A.F.; Fernández, C.M.; Salas Fernández, J.A.; Varas, F.M. Glycosylated indolecarbazoles, method for obtaining same and uses thereof, US Patent 20,110,136,753, 2011.