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Review Article

酪蛋白激酶1抑制剂开发的最新进展

卷 28, 期 8, 2021

发表于: 13 July, 2020

页: [1585 - 1604] 页: 20

弟呕挨: 10.2174/0929867327666200713185413

价格: $65

摘要

背景：酪蛋白激酶1（CK1）家族参与调节许多细胞过程，包括膜运输，DNA损伤修复，细胞骨架动力学，细胞骨架维持和细胞凋亡。 CK1亚型，尤其是CK1δ和CK1ε已成为严重疾病的重要治疗靶标，例如阿尔茨海默氏病（AD），肌萎缩性侧索硬化症（ALS），家族性晚期睡眠期综合征和癌症。由于CK1在疾病的发病机理中的重要性，因此人们对CK1抑制剂的开发非常感兴趣。 方法：使用SciFinderR作为工具，对有关CK1生物学和CK1抑制剂最新发展的出版物进行了调查，但不包括以专利形式发表的出版物。 结果：这篇综述介绍了CK1抑制剂发展的最新知识，包括根据结构特征分为7类的合成小分子抑制剂和天然化合物。概述了CK1抑制剂的研究进展，并介绍了各种现有的CK1抑制剂，它们的抑制活性以及构效关系。 结论：通过理化特性和生物学研究，可能了解CK1抑制剂的结构-活性关系，这将有助于更好地设计和发现有效的和选择性的CK1抑制剂，作为严重疾病如AD，ALS和癌症的潜在药物。

关键词: 酪蛋白激酶1（CK1）、抑制剂、化学物质、小分子、抗癌药物、药物设计。

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[1]
Johnson, L.N. Protein kinase inhibitors: contributions from structure to clinical compounds. Q. Rev. Biophys., 2009, 42(1), 1-40.
[http://dx.doi.org/10.1017/S0033583508004745] [PMID: 19296866]
[2]
Flotow, H.; Roach, P.J. Role of acidic residues as substrate determinants for casein kinase I. J. Biol. Chem., 1991, 266(6), 3724-3727.
[PMID: 1995625]
[3]
Meggio, F.; Perich, J.W.; Marin, O.; Pinna, L.A. The comparative efficiencies of the Ser(P)-, Thr(P)- and Tyr(P)-residues as specificity determinants for casein kinase-1. Biochem. Biophys. Res. Commun., 1992, 182(3), 1460-1465.
[http://dx.doi.org/10.1016/0006-291X(92)91898-Z] [PMID: 1540189]
[4]
Graves, P.R.; Haas, D.W.; Hagedorn, C.H.; DePaoli-Roach, A.A.; Roach, P.J. Molecular cloning, expression, and characterization of a 49-kilodalton casein kinase I isoform from rat testis. J. Biol. Chem., 1993, 268(9), 6394-6401.
[PMID: 8454611]
[5]
Rowles, J.; Slaughter, C.; Moomaw, C.; Hsu, J.; Cobb, M.H. Purification of casein kinase I and isolation of cDNAs encoding multiple casein kinase I-like enzymes. Proc. Natl. Acad. Sci. USA, 1991, 88(21), 9548-9552.
[http://dx.doi.org/10.1073/pnas.88.21.9548] [PMID: 1946367]
[6]
Gross, S.D.; Anderson, R.A. Casein kinase I: spatial organization and positioning of a multifunctional protein kinase family. Cell. Signal., 1998, 10(10), 699-711.
[http://dx.doi.org/10.1016/S0898-6568(98)00042-4] [PMID: 9884021]
[7]
Tapia, C.; Featherstone, T.; Gómez, C.; Taillon-Miller, P.; Allende, C.C.; Allende, J.E. Cloning and chromosomal localization of the gene coding for human protein kinase CK1. FEBS Lett., 1994, 349(2), 307-312.
[http://dx.doi.org/10.1016/0014-5793(94)00679-2] [PMID: 8050587]
[8]
Xu, R.M.; Carmel, G.; Sweet, R.M.; Kuret, J.; Cheng, X. Crystal structure of casein kinase-1, a phosphate-directed protein kinase. EMBO J., 1995, 14(5), 1015-1023.
[http://dx.doi.org/10.1002/j.1460-2075.1995.tb07082.x] [PMID: 7889932]
[9]
Longenecker, K.L.; Roach, P.J.; Hurley, T.D. Three-dimensional structure of mammalian casein kinase I: molecular basis for phosphate recognition. J. Mol. Biol., 1996, 257(3), 618-631.
[http://dx.doi.org/10.1006/jmbi.1996.0189] [PMID: 8648628]
[10]
Hantschel, O.; Superti-Furga, G. Regulation of the c-Abl and Bcr-Abl tyrosine kinases. Nat. Rev. Mol. Cell Biol., 2004, 5(1), 33-44.
[http://dx.doi.org/10.1038/nrm1280] [PMID: 14708008]
[11]
Peifer, C.; Abadleh, M.; Bischof, J.; Hauser, D.; Schattel, V.; Hirner, H.; Knippschild, U.; Laufer, S. 3,4-Diaryl-isoxazoles and -imidazoles as potent dual inhibitors of p38alpha mitogen activated protein kinase and casein kinase 1delta. J. Med. Chem., 2009, 52(23), 7618-7630.
[http://dx.doi.org/10.1021/jm9005127] [PMID: 19591487]
[12]
Fu, Z.; Chakraborti, T.; Morse, S.; Bennett, G.S.; Shaw, G. Four casein kinase I isoforms are differentially partitioned between nucleus and cytoplasm. Exp. Cell Res., 2001, 269(2), 275-286.
[http://dx.doi.org/10.1006/excr.2001.5324] [PMID: 11570820]
[13]
Tuazon, P.T.; Traugh, J.A. Casein kinase I and II--multipotential serine protein kinases: structure, function, and regulation. Adv. Second Messenger Phosphoprotein Res., 1991, 23, 123-164.
[PMID: 1997039]
[14]
Longenecker, K.L.; Roach, P.J.; Hurley, T.D. Crystallographic studies of casein kinase I delta toward a structural understanding of auto-inhibition. Acta Crystallogr. D Biol. Crystallogr., 1998, 54(Pt 3), 473-475.
[http://dx.doi.org/10.1107/S0907444997011724] [PMID: 9761932]
[15]
Taylor, S.S.; Knighton, D.R.; Zheng, J.; Sowadski, J.M.; Gibbs, C.S.; Zoller, M.J. A template for the protein kinase family. Trends Biochem. Sci., 1993, 18(3), 84-89.
[http://dx.doi.org/10.1016/0968-0004(93)80001-R] [PMID: 8480367]
[16]
Shanware, N.P.; Hutchinson, J.A.; Kim, S.H.; Zhan, L.; Bowler, M.J.; Tibbetts, R.S. Casein kinase 1-dependent phosphorylation of familial advanced sleep phase syndrome-associated residues controls PERIOD 2 stability. J. Biol. Chem., 2011, 286(14), 12766-12774.
[http://dx.doi.org/10.1074/jbc.M111.224014] [PMID: 21324900]
[17]
Etchegaray, J-P.; Machida, K.K.; Noton, E.; Constance, C.M.; Dallmann, R.; Di Napoli, M.N.; DeBruyne, J.P.; Lambert, C.M.; Yu, E.A.; Reppert, S.M.; Weaver, D.R. Casein kinase 1 delta regulates the pace of the mammalian circadian clock. Mol. Cell. Biol., 2009, 29(14), 3853-3866.
[http://dx.doi.org/10.1128/MCB.00338-09] [PMID: 19414593]
[18]
Walton, K.M.; Fisher, K.; Rubitski, D.; Marconi, M.; Meng, Q-J.; Sládek, M.; Adams, J.; Bass, M.; Chandrasekaran, R.; Butler, T.; Griffor, M.; Rajamohan, F.; Serpa, M.; Chen, Y.; Claffey, M.; Hastings, M.; Loudon, A.; Maywood, E.; Ohren, J.; Doran, A.; Wager, T.T. Selective inhibition of casein kinase 1 epsilon minimally alters circadian clock period. J. Pharmacol. Exp. Ther., 2009, 330(2), 430-439.
[http://dx.doi.org/10.1124/jpet.109.151415] [PMID: 19458106]
[19]
Vielhaber, E.; Eide, E.; Rivers, A.; Gao, Z.H.; Virshup, D.M. Nuclear entry of the circadian regulator mPER1 is controlled by mammalian casein kinase I epsilon. Mol. Cell. Biol., 2000, 20(13), 4888-4899.
[http://dx.doi.org/10.1128/MCB.20.13.4888-4899.2000] [PMID: 10848614]
[20]
Desagher, S.; Osen-Sand, A.; Montessuit, S.; Magnenat, E.; Vilbois, F.; Hochmann, A.; Journot, L.; Antonsson, B.; Martinou, J.C. Phosphorylation of bid by casein kinases I and II regulates its cleavage by caspase 8. Mol. Cell, 2001, 8(3), 601-611.
[http://dx.doi.org/10.1016/S1097-2765(01)00335-5] [PMID: 11583622]
[21]
Beyaert, R.; Vanhaesebroeck, B.; Declercq, W.; Van Lint, J.; Vandenabele, P.; Agostinis, P.; Vandenheede, J.R.; Fiers, W. Casein kinase-1 phosphorylates the p75 tumor necrosis factor receptor and negatively regulates tumor necrosis factor signaling for apoptosis. J. Biol. Chem., 1995, 270(40), 23293-23299.
[http://dx.doi.org/10.1074/jbc.270.40.23293] [PMID: 7559483]
[22]
Brockman, J.L.; Gross, S.D.; Sussman, M.R.; Anderson, R.A. Cell cycle-dependent localization of casein kinase I to mitotic spindles. Proc. Natl. Acad. Sci. USA, 1992, 89(20), 9454-9458.
[http://dx.doi.org/10.1073/pnas.89.20.9454] [PMID: 1409656]
[23]
Knippschild, U.; Gocht, A.; Wolff, S.; Huber, N.; Löhler, J.; Stöter, M. The casein kinase 1 family: participation in multiple cellular processes in eukaryotes. Cell. Signal., 2005, 17(6), 675-689.
[http://dx.doi.org/10.1016/j.cellsig.2004.12.011] [PMID: 15722192]
[24]
Sillibourne, J.E.; Milne, D.M.; Takahashi, M.; Ono, Y.; Meek, D.W. Centrosomal anchoring of the protein kinase CK1delta mediated by attachment to the large, coiled-coil scaffolding protein CG-NAP/AKAP450. J. Mol. Biol., 2002, 322(4), 785-797.
[http://dx.doi.org/10.1016/S0022-2836(02)00857-4] [PMID: 12270714]
[25]
Zyss, D.; Ebrahimi, H.; Gergely, F. Casein kinase I delta controls centrosome positioning during T cell activation. J. Cell Biol., 2011, 195(5), 781-797.
[http://dx.doi.org/10.1083/jcb.201106025] [PMID: 22123863]
[26]
Behrend, L.; Milne, D.M.; Stöter, M.; Deppert, W.; Campbell, L.E.; Meek, D.W.; Knippschild, U. IC261, a specific inhibitor of the protein kinases casein kinase 1-delta and -epsilon, triggers the mitotic checkpoint and induces p53-dependent postmitotic effects. Oncogene, 2000, 19(47), 5303-5313.
[http://dx.doi.org/10.1038/sj.onc.1203939] [PMID: 11103931]
[27]
Stöter, M.; Bamberger, A.M.; Aslan, B.; Kurth, M.; Speidel, D.; Löning, T.; Frank, H.G.; Kaufmann, P.; Löhler, J.; Henne-Bruns, D.; Deppert, W.; Knippschild, U. Inhibition of casein kinase I delta alters mitotic spindle formation and induces apoptosis in trophoblast cells. Oncogene, 2005, 24(54), 7964-7975.
[http://dx.doi.org/10.1038/sj.onc.1208941] [PMID: 16027726]
[28]
Drewes, G.; Ebneth, A.; Mandelkow, E.M. MAPs, MARKs and microtubule dynamics. Trends Biochem. Sci., 1998, 23(8), 307-311.
[http://dx.doi.org/10.1016/S0968-0004(98)01245-6] [PMID: 9757832]
[29]
Hanger, D.P.; Byers, H.L.; Wray, S.; Leung, K-Y.; Saxton, M.J.; Seereeram, A.; Reynolds, C.H.; Ward, M.A.; Anderton, B.H. Novel phosphorylation sites in tau from Alzheimer brain support a role for casein kinase 1 in disease pathogenesis. J. Biol. Chem., 2007, 282(32), 23645-23654.
[http://dx.doi.org/10.1074/jbc.M703269200] [PMID: 17562708]
[30]
Knippschild, U.; Wolff, S.; Giamas, G.; Brockschmidt, C.; Wittau, M.; Würl, P.U.; Eismann, T.; Stöter, M. The role of the casein kinase 1 (CK1) family in different signaling pathways linked to cancer development. Onkologie, 2005, 28(10), 508-514.
[http://dx.doi.org/10.1159/000087137] [PMID: 16186692]
[31]
Dumaz, N.; Milne, D.M.; Meek, D.W. Protein kinase CK1 is a p53-threonine 18 kinase which requires prior phosphorylation of serine 15. FEBS Lett., 1999, 463(3), 312-316.
[http://dx.doi.org/10.1016/S0014-5793(99)01647-6] [PMID: 10606744]
[32]
Sakaguchi, K.; Saito, S.; Higashimoto, Y.; Roy, S.; Anderson, C.W.; Appella, E. Damage-mediated phosphorylation of human p53 threonine 18 through a cascade mediated by a casein 1-like kinase. Effect on Mdm2 binding. J. Biol. Chem., 2000, 275(13), 9278-9283.
[http://dx.doi.org/10.1074/jbc.275.13.9278] [PMID: 10734067]
[33]
Kulikov, R.; Winter, M.; Blattner, C. Binding of p53 to the central domain of Mdm2 is regulated by phosphorylation. J. Biol. Chem., 2006, 281(39), 28575-28583.
[http://dx.doi.org/10.1074/jbc.M513311200] [PMID: 16870621]
[34]
Inuzuka, H.; Tseng, A.; Gao, D.; Zhai, B.; Zhang, Q.; Shaik, S.; Wan, L.; Ang, X.L.; Mock, C.; Yin, H.; Stommel, J.M.; Gygi, S.; Lahav, G.; Asara, J.; Xiao, Z-X.J.; Kaelin, W.G. Jr.; Harper, J.W.; Wei, W. Phosphorylation by casein kinase I promotes the turnover of the Mdm2 oncoprotein via the SCF(beta-TRCP) ubiquitin ligase. Cancer Cell, 2010, 18(2), 147-159.
[http://dx.doi.org/10.1016/j.ccr.2010.06.015] [PMID: 20708156]
[35]
Huart, A-S.; MacLaine, N.J.; Narayan, V.; Hupp, T.R. Exploiting the MDM2-CK1α protein-protein interface to develop novel biologics that induce UBL-kinase-modification and inhibit cell growth. PLoS One, 2012, 7(8)e43391
[http://dx.doi.org/10.1371/journal.pone.0043391] [PMID: 22916255]
[36]
Huart, A-S.; MacLaine, N.J.; Meek, D.W.; Hupp, T.R. CK1alpha plays a central role in mediating MDM2 control of p53 and E2F-1 protein stability. J. Biol. Chem., 2009, 284(47), 32384-32394.
[http://dx.doi.org/10.1074/jbc.M109.052647] [PMID: 19759023]
[37]
Knippschild, U.; Milne, D.M.; Campbell, L.E.; DeMaggio, A.J.; Christenson, E.; Hoekstra, M.F.; Meek, D.W. p53 is phosphorylated in vitro and in vivo by the delta and epsilon isoforms of casein kinase 1 and enhances the level of casein kinase 1 delta in response to topoisomerase-directed drugs. Oncogene, 1997, 15(14), 1727-1736.
[http://dx.doi.org/10.1038/sj.onc.1201541] [PMID: 9349507]
[38]
Tarapore, P.; Fukasawa, K. Loss of p53 and centrosome hyperamplification. Oncogene, 2002, 21(40), 6234-6240.
[http://dx.doi.org/10.1038/sj.onc.1205707] [PMID: 12214254]
[39]
Bao, Y.; Hata, Y.; Ikeda, M.; Withanage, K. Mammalian hippo pathway: from development to cancer and beyond. J. Biochem., 2011, 149(4), 361-379.
[http://dx.doi.org/10.1093/jb/mvr021] [PMID: 21324984]
[40]
Pan, D. The hippo signaling pathway in development and cancer. Dev. Cell, 2010, 19(4), 491-505.
[http://dx.doi.org/10.1016/j.devcel.2010.09.011] [PMID: 20951342]
[41]
Klaus, A.; Birchmeier, W. Wnt signalling and its impact on development and cancer. Nat. Rev. Cancer, 2008, 8(5), 387-398.
[http://dx.doi.org/10.1038/nrc2389] [PMID: 18432252]
[42]
Rubin, L.L.; de Sauvage, F.J. Targeting the Hedgehog pathway in cancer. Nat. Rev. Drug Discov., 2006, 5(12), 1026-1033.
[http://dx.doi.org/10.1038/nrd2086] [PMID: 17139287]
[43]
Cheong, J.K.; Virshup, D.M. Casein kinase 1: complexity in the family. Int. J. Biochem. Cell Biol., 2011, 43(4), 465-469.
[http://dx.doi.org/10.1016/j.biocel.2010.12.004] [PMID: 21145983]
[44]
Shin, S.; Wolgamott, L.; Roux, P.P.; Yoon, S-O. Casein kinase 1ε promotes cell proliferation by regulating mRNA translation. Cancer Res., 2014, 74(1), 201-211.
[http://dx.doi.org/10.1158/0008-5472.CAN-13-1175] [PMID: 24247720]
[45]
Masuda, K.; Ono, M.; Okamoto, M.; Morikawa, W.; Otsubo, M.; Migita, T.; Tsuneyoshi, M.; Okuda, H.; Shuin, T.; Naito, S.; Kuwano, M. Downregulation of Cap43 gene by von Hippel-Lindau tumor suppressor protein in human renal cancer cells. Int. J. Cancer, 2003, 105(6), 803-810.
[http://dx.doi.org/10.1002/ijc.11152] [PMID: 12767066]
[46]
Yang, W.S.; Stockwell, B.R. Inhibition of casein kinase 1-epsilon induces cancer-cell-selective, PERIOD2-dependent growth arrest. Genome Biol., 2008, 9(6), R92.
[http://dx.doi.org/10.1186/gb-2008-9-6-r92] [PMID: 18518968]
[47]
Relles, D.; Sendecki, J.; Chipitsyna, G.; Hyslop, T.; Yeo, C.J.; Arafat, H.A. Circadian gene expression and clinicopathologic correlates in pancreatic cancer. J. Gastrointest. Surg., 2013, 17(3), 443-450.
[http://dx.doi.org/10.1007/s11605-012-2112-2] [PMID: 23254314]
[48]
Sinnberg, T.; Menzel, M.; Kaesler, S.; Biedermann, T.; Sauer, B.; Nahnsen, S.; Schwarz, M.; Garbe, C.; Schittek, B. Suppression of casein kinase 1alpha in melanoma cells induces a switch in beta-catenin signaling to promote metastasis. Cancer Res., 2010, 70(17), 6999-7009.
[http://dx.doi.org/10.1158/0008-5472.CAN-10-0645] [PMID: 20699366]
[49]
Rodriguez, N.; Yang, J.; Hasselblatt, K.; Liu, S.; Zhou, Y.; Rauh-Hain, J.A.; Ng, S-K.; Choi, P-W.; Fong, W-P.; Agar, N.Y.R.; Welch, W.R.; Berkowitz, R.S.; Ng, S-W. Casein kinase I epsilon interacts with mitochondrial proteins for the growth and survival of human ovarian cancer cells. EMBO Mol. Med., 2012, 4(9), 952-963.
[http://dx.doi.org/10.1002/emmm.201101094] [PMID: 22707389]
[50]
Flajolet, M.; He, G.; Heiman, M.; Lin, A.; Nairn, A.C.; Greengard, P. Regulation of Alzheimer’s disease amyloid-beta formation by casein kinase I. Proc. Natl. Acad. Sci. USA, 2007, 104(10), 4159-4164.
[http://dx.doi.org/10.1073/pnas.0611236104] [PMID: 17360493]
[51]
Giamas, G.; Stebbing, J.; Vorgias, C.E.; Knippschild, U. Protein kinases as targets for cancer treatment. Pharmacogenomics, 2007, 8(8), 1005-1016.
[http://dx.doi.org/10.2217/14622416.8.8.1005] [PMID: 17716234]
[52]
Rena, G.; Bain, J.; Elliott, M.; Cohen, P. D4476, a cell-permeant inhibitor of CK1, suppresses the site-specific phosphorylation and nuclear exclusion of FOXO1a. EMBO Rep., 2004, 5(1), 60-65.
[http://dx.doi.org/10.1038/sj.embor.7400048] [PMID: 14710188]
[53]
Hu, Y.; Song, W.; Cirstea, D.; Lu, D.; Munshi, N.C.; Anderson, K.C. CSNK1α1 mediates malignant plasma cell survival. Leukemia, 2015, 29(2), 474-482.
[http://dx.doi.org/10.1038/leu.2014.202] [PMID: 24962017]
[54]
Järås, M.; Miller, P.G.; Chu, L.P.; Puram, R.V.; Fink, E.C.; Schneider, R.K.; Al-Shahrour, F.; Peña, P.; Breyfogle, L.J.; Hartwell, K.A.; McConkey, M.E.; Cowley, G.S.; Root, D.E.; Kharas, M.G.; Mullally, A.; Ebert, B.L. Csnk1a1 inhibition has p53-dependent therapeutic efficacy in acute myeloid leukemia. J. Exp. Med., 2014, 211(4), 605-612.
[http://dx.doi.org/10.1084/jem.20131033] [PMID: 24616378]
[55]
Arey, R.; McClung, C.A. An inhibitor of casein kinase 1 ε/δ partially normalizes the manic-like behaviors of the ClockΔ19 mouse. Behav. Pharmacol., 2012, 23(4), 392-396.
[http://dx.doi.org/10.1097/FBP.0b013e32835651fd] [PMID: 22743604]
[56]
Perreau-Lenz, S.; Vengeliene, V.; Noori, H.R.; Merlo-Pich, E.V.; Corsi, M.A.; Corti, C.; Spanagel, R. Inhibition of the casein-kinase-1-ε/δ/prevents relapse-like alcohol drinking. Neuropsychopharmacology, 2012, 37(9), 2121-2131.
[http://dx.doi.org/10.1038/npp.2012.62] [PMID: 22549116]
[57]
Li, D.; Herrera, S.; Bubula, N.; Nikitina, E.; Palmer, A.A.; Hanck, D.A.; Loweth, J.A.; Vezina, P. Casein kinase 1 enables nucleus accumbens amphetamine-induced locomotion by regulating AMPA receptor phosphorylation. J. Neurochem., 2011, 118(2), 237-247.
[http://dx.doi.org/10.1111/j.1471-4159.2011.07308.x] [PMID: 21564097]
[58]
Meng, Q-J.; Maywood, E.S.; Bechtold, D.A.; Lu, W-Q.; Li, J.; Gibbs, J.E.; Dupré, S.M.; Chesham, J.E.; Rajamohan, F.; Knafels, J.; Sneed, B.; Zawadzke, L.E.; Ohren, J.F.; Walton, K.M.; Wager, T.T.; Hastings, M.H.; Loudon, A.S.I. Entrainment of disrupted circadian behavior through inhibition of casein kinase 1 (CK1) enzymes. Proc. Natl. Acad. Sci. USA, 2010, 107(34), 15240-15245.
[http://dx.doi.org/10.1073/pnas.1005101107] [PMID: 20696890]
[59]
Halekotte, J.; Witt, L.; Ianes, C.; Krüger, M.; Bührmann, M.; Rauh, D.; Pichlo, C.; Brunstein, E.; Luxenburger, A.; Baumann, U.; Knippschild, U.; Bischof, J.; Peifer, C. Optimized 4,5-diarylimidazoles as potent/selective inhibitors of protein kinase CK1 delta and their structural relation to p38 alpha MAPK. Molecules, 2017, 22(4), 522.
[http://dx.doi.org/10.3390/molecules22040522] [PMID: 28338621]
[60]
Andrzejewska, M.; Pagano, M.A.; Meggio, F.; Brunati, A.M.; Kazimierczuk, Z. Polyhalogenobenzimidazoles: synthesis and their inhibitory activity against casein kinases. Bioorg. Med. Chem., 2003, 11(18), 3997-4002.
[http://dx.doi.org/10.1016/S0968-0896(03)00403-6] [PMID: 12927861]
[61]
Hua, Z.; Huang, X.; Bregman, H.; Chakka, N.; DiMauro, E.F.; Doherty, E.M.; Goldstein, J.; Gunaydin, H.; Huang, H.; Mercede, S.; Newcomb, J.; Patel, V.F.; Turci, S.M.; Yan, J.; Wilson, C.; Martin, M.W. 2-Phenylamino-6-cyano-1H-benzimidazole-based isoform selective casein kinase 1 gamma (CK1γ) inhibitors. Bioorg. Med. Chem. Lett., 2012, 22(17), 5392-5395.
[http://dx.doi.org/10.1016/j.bmcl.2012.07.046] [PMID: 22877629]
[62]
Bischof, J.; Leban, J.; Zaja, M.; Grothey, A.; Radunsky, B.; Othersen, O.; Strobl, S.; Vitt, D.; Knippschild, U. 2-Benzamido-N-(1H-benzo[d]imidazol-2-yl)thiazole-4-carboxamide derivatives as potent inhibitors of CK1δ/ε. Amino Acids, 2012, 43(4), 1577-1591.
[http://dx.doi.org/10.1007/s00726-012-1234-x] [PMID: 22331384]
[63]
Richter, J.; Bischof, J.; Zaja, M.; Kohlhof, H.; Othersen, O.; Vitt, D.; Alscher, V.; Pospiech, I.; García-Reyes, B.; Berg, S.; Leban, J.; Knippschild, U. Difluoro-dioxolo-benzoimidazol-benzamides as potent inhibitors of CK1δ and ε with nanomolar inhibitory activity on cancer cell proliferation. J. Med. Chem., 2014, 57(19), 7933-7946.
[http://dx.doi.org/10.1021/jm500600b] [PMID: 25191940]
[64]
Salado, I.G.; Redondo, M.; Bello, M.L.; Perez, C.; Liachko, N.F.; Kraemer, B.C.; Miguel, L.; Lecourtois, M.; Gil, C.; Martinez, A.; Perez, D.I. Protein kinase CK-1 inhibitors as new potential drugs for amyotrophic lateral sclerosis. J. Med. Chem., 2014, 57(6), 2755-2772.
[http://dx.doi.org/10.1021/jm500065f] [PMID: 24592867]
[65]
Benek, O.; Hroch, L.; Aitken, L.; Gunn-Moore, F.; Vinklarova, L.; Kuca, K.; Perez, D.I.; Perez, C.; Martinez, A.; Fisar, Z.; Musilek, K. 1-(Benzo[d]thiazol-2-yl)-3-phenylureas as dual inhibitors of casein kinase 1 and ABAD enzymes for treatment of neurodegenerative disorders. J. Enzyme Inhib. Med. Chem., 2018, 33(1), 665-670.
[http://dx.doi.org/10.1080/14756366.2018.1445736] [PMID: 29536773]
[66]
García-Reyes, B.; Witt, L.; Jansen, B.; Karasu, E.; Gehring, T.; Leban, J.; Henne-Bruns, D.; Pichlo, C.; Brunstein, E.; Baumann, U.; Wesseler, F.; Rathmer, B.; Schade, D.; Peifer, C.; Knippschild, U. Discovery of inhibitor of Wnt production 2 (IWP-2) and related compounds as selective ATP-competitive inhibitors of casein kinase 1 (CK1) delta/epsilon. J. Med. Chem., 2018, 61(9), 4087-4102.
[http://dx.doi.org/10.1021/acs.jmedchem.8b00095] [PMID: 29630366]
[67]
Luxenburger, A.; Schmidt, D.; Ianes, C.; Pichlo, C.; Krüger, M.; von Drathen, T.; Brunstein, E.; Gainsford, G.J.; Baumann, U.; Knippschild, U.; Peifer, C. Design, synthesis and biological evaluation of isoxazole-based CK1 inhibitors modified with chiral pyrrolidine scaffolds. Molecules, 2019, 24(5), 873.
[http://dx.doi.org/10.3390/molecules24050873] [PMID: 30832206]
[68]
Cruz, J.C.; Tsai, L.H. Cdk5 deregulation in the pathogenesis of Alzheimer’s disease. Trends Mol. Med., 2004, 10(9), 452-458.
[http://dx.doi.org/10.1016/j.molmed.2004.07.001] [PMID: 15350898]
[69]
Takashima, A. GSK-3 is essential in the pathogenesis of Alzheimer’s disease. J. Alzheimers Dis., 2006, 9(3)(Suppl.), 309-317.
[http://dx.doi.org/10.3233/JAD-2006-9S335] [PMID: 16914869]
[70]
Oumata, N.; Bettayeb, K.; Ferandin, Y.; Demange, L.; Lopez-Giral, A.; Goddard, M-L.; Myrianthopoulos, V.; Mikros, E.; Flajolet, M.; Greengard, P.; Meijer, L.; Galons, H. Roscovitine-derived, dual-specificity inhibitors of cyclin-dependent kinases and casein kinases 1. J. Med. Chem., 2008, 51(17), 5229-5242.
[http://dx.doi.org/10.1021/jm800109e] [PMID: 18698753]
[71]
Bibian, M.; Rahaim, R.J.; Choi, J.Y.; Noguchi, Y.; Schürer, S.; Chen, W.; Nakanishi, S.; Licht, K.; Rosenberg, L.H.; Li, L.; Feng, Y.; Cameron, M.D.; Duckett, D.R.; Cleveland, J.L.; Roush, W.R. Development of highly selective casein kinase 1δ/1ε (CK1δ/ε) inhibitors with potent antiproliferative properties. Bioorg. Med. Chem. Lett., 2013, 23(15), 4374-4380.
[http://dx.doi.org/10.1016/j.bmcl.2013.05.075] [PMID: 23787102]
[72]
Monastyrskyi, A.; Nilchan, N.; Quereda, V.; Noguchi, Y.; Ruiz, C.; Grant, W.; Cameron, M.; Duckett, D.; Roush, W. Development of dual casein kinase 1δ/1ε (CK1δ/ε) inhibitors for treatment of breast cancer. Bioorg. Med. Chem., 2018, 26(3), 590-602.
[http://dx.doi.org/10.1016/j.bmc.2017.12.020] [PMID: 29289448]
[73]
Bryant, C.D.; Parker, C.C.; Zhou, L.; Olker, C.; Chandrasekaran, R.Y.; Wager, T.T.; Bolivar, V.J.; Loudon, A.S.; Vitaterna, M.H.; Turek, F.W.; Palmer, A.A. Csnk1e is a genetic regulator of sensitivity to psychostimulants and opioids. Neuropsychopharmacology, 2012, 37(4), 1026-1035.
[http://dx.doi.org/10.1038/npp.2011.287] [PMID: 22089318]
[74]
Yang, L-L.; Li, G-B.; Yan, H-X.; Sun, Q-Z.; Ma, S.; Ji, P.; Wang, Z-R.; Feng, S.; Zou, J.; Yang, S-Y. Discovery of N6-phenyl-1H-pyrazolo[3,4-d]pyrimidine-3,6-diamine derivatives as novel CK1 inhibitors using common-feature pharmacophore model based virtual screening and hit-to-lead optimization. Eur. J. Med. Chem., 2012, 56, 30-38.
[http://dx.doi.org/10.1016/j.ejmech.2012.08.007] [PMID: 22944772]
[75]
Huart, A-S.; Saxty, B.; Merritt, A.; Nekulova, M.; Lewis, S.; Huang, Y.; Vojtesek, B.; Kettleborough, C.; Hupp, T.R. A Casein kinase 1/Checkpoint kinase 1 pyrazolo-pyridine protein kinase inhibitor as novel activator of the p53 pathway. Bioorg. Med. Chem. Lett., 2013, 23(20), 5578-5585.
[http://dx.doi.org/10.1016/j.bmcl.2013.08.046] [PMID: 24007918]
[76]
Mente, S.; Arnold, E.; Butler, T.; Chakrapani, S.; Chandrasekaran, R.; Cherry, K.; DiRico, K.; Doran, A.; Fisher, K.; Galatsis, P.; Green, M.; Hayward, M.; Humphrey, J.; Knafels, J.; Li, J.; Liu, S.; Marconi, M.; McDonald, S.; Ohren, J.; Paradis, V.; Sneed, B.; Walton, K.; Wager, T. Ligand-protein interactions of selective casein kinase 1δ inhibitors. J. Med. Chem., 2013, 56(17), 6819-6828.
[http://dx.doi.org/10.1021/jm4006324] [PMID: 23919824]
[77]
Wager, T.T.; Galatsis, P.; Chandrasekaran, R.Y.; Butler, T.W.; Li, J.; Zhang, L.; Mente, S.; Subramanyam, C.; Liu, S.; Doran, A.C.; Chang, C.; Fisher, K.; Grimwood, S.; Hedde, J.R.; Marconi, M.; Schildknegt, K. Identification and profiling of a selective and brain penetrant radioligand for in vivo target occupancy measurement of casein kinase 1 (CK1) inhibitors. ACS Chem. Neurosci., 2017, 8(9), 1995-2004.
[http://dx.doi.org/10.1021/acschemneuro.7b00155] [PMID: 28609096]
[78]
Xu, R.M.; Carmel, G.; Kuret, J.; Cheng, X. Structural basis for selectivity of the isoquinoline sulfonamide family of protein kinase inhibitors. Proc. Natl. Acad. Sci. USA, 1996, 93(13), 6308-6313.
[http://dx.doi.org/10.1073/pnas.93.13.6308] [PMID: 8692811]
[79]
Kim, S.Y.; Dunn, I.F.; Firestein, R.; Gupta, P.; Wardwell, L.; Repich, K.; Schinzel, A.C.; Wittner, B.; Silver, S.J.; Root, D.E.; Boehm, J.S.; Ramaswamy, S.; Lander, E.S.; Hahn, W.C. CK1epsilon is required for breast cancers dependent on beta-catenin activity. PLoS One, 2010, 5(2)e8979
[http://dx.doi.org/10.1371/journal.pone.0008979] [PMID: 20126544]
[80]
Brockschmidt, C.; Hirner, H.; Huber, N.; Eismann, T.; Hillenbrand, A.; Giamas, G.; Radunsky, B.; Ammerpohl, O.; Bohm, B.; Henne-Bruns, D.; Kalthoff, H.; Leithäuser, F.; Trauzold, A.; Knippschild, U. Anti-apoptotic and growth-stimulatory functions of CK1 delta and epsilon in ductal adenocarcinoma of the pancreas are inhibited by IC261 in vitro and in vivo. Gut, 2008, 57(6), 799-806.
[http://dx.doi.org/10.1136/gut.2007.123695] [PMID: 18203806]
[81]
Kurihara, T.; Sakurai, E.; Toyomoto, M.; Kii, I.; Kawamoto, D.; Asada, T.; Tanabe, T.; Yoshimura, M.; Hagiwara, M.; Miyata, A. Alleviation of behavioral hypersensitivity in mouse models of inflammatory pain with two structurally different casein kinase 1 (CK1) inhibitors. Mol. Pain, 2014, 10(17), 17.
[http://dx.doi.org/10.1186/1744-8069-10-17] [PMID: 24612480]
[82]
Esvan, Y.J.; Zeinyeh, W.; Boibessot, T.; Nauton, L.; Théry, V.; Knapp, S.; Chaikuad, A.; Loaëc, N.; Meijer, L.; Anizon, F.; Giraud, F.; Moreau, P. Discovery of pyrido[3,4-g]quinazoline derivatives as CMGC family protein kinase inhibitors: Design, synthesis, inhibitory potency and X-ray co-crystal structure. Eur. J. Med. Chem., 2016, 118, 170-177.
[http://dx.doi.org/10.1016/j.ejmech.2016.04.004] [PMID: 27128181]
[83]
Karthikeyan, C.; Jharia, P.; Waiker, D.K.; Nusbaum, A.C.; Amawi, H.; Kirwen, E.M.; Christman, R.; Arudra, S.K.C.; Meijer, L.; Tiwari, A.K.; Trivedi, P.N. -(1H-Pyrazol-3-yl)quinazolin-4-amines as a novel class of casein kinase 1δ/ε inhibitors: synthesis, biological evaluation and molecular modeling studies. Bioorg. Med. Chem. Lett., 2017, 27(12), 2663-2667.
[http://dx.doi.org/10.1016/j.bmcl.2017.04.080] [PMID: 28487075]
[84]
Loidreau, Y.; Deau, E.; Marchand, P.; Nourrisson, M-R.; Loge, C.; Coadou, G.; Loaec, N.; Meijer, L.; Besson, T. Synthesis and molecular modelling studies of 8-arylpyrido 3 ',2 ':4,5 thieno 3,2-d pyrimidin-4-amines as multitarget Ser/Thr kinases inhibitors. Eur. J. Med. Chem., 2015, 92, 124-134.
[http://dx.doi.org/10.1016/j.ejmech.2014.12.038] [PMID: 25549552]
[85]
Silveira-Dorta, G.; Sousa, I.J.; Fernandes, M.X.; Martín, V.S.; Padrón, J.M. Synthesis and identification of unprecedented selective inhibitors of CK1ε. Eur. J. Med. Chem., 2015, 96, 308-317.
[http://dx.doi.org/10.1016/j.ejmech.2015.03.046] [PMID: 25899335]
[86]
Myrianthopoulos, V.; Lozach, O.; Zareifi, D.; Alexopoulos, L.; Meijer, L.; Gorgoulis, V.G.; Mikros, E. Combined virtual and experimental screening for CK1 inhibitors identifies a modulator of p53 and reveals important aspects of in silico screening performance. Int. J. Mol. Sci., 2017, 18(10), 2102.
[http://dx.doi.org/10.3390/ijms18102102] [PMID: 28984824]
[87]
Liu, Y-M.; Chen, C-H.; Yeh, T-K.; Liou, J-P. Synthesis and evaluation of novel 7H-pyrrolo-[2,3-d]pyrimidine derivatives as potential anticancer agents. Future Med. Chem., 2019, 11(9), 959-974.
[http://dx.doi.org/10.4155/fmc-2018-0564] [PMID: 30789758]
[88]
Yokoyama, T.; Okano, M.; Noshita, T.; Funayama, S.; Ohtsuki, K. Characterization of (-)-matairesinol as a potent inhibitor of casein kinase I in vitro. Biol. Pharm. Bull., 2003, 26(3), 371-374.
[http://dx.doi.org/10.1248/bpb.26.371] [PMID: 12612451]
[89]
Gompel, M.; Leost, M.; De Kier Joffe, E.B.; Puricelli, L.; Franco, L.H.; Palermo, J.; Meijer, L. Meridianins, a new family of protein kinase inhibitors isolated from the ascidian Aplidium meridianum. Bioorg. Med. Chem. Lett., 2004, 14(7), 1703-1707.
[http://dx.doi.org/10.1016/j.bmcl.2004.01.050] [PMID: 15026054]
[90]
Baunbaek, D.; Trinkler, N.; Ferandin, Y.; Lozach, O.; Ploypradith, P.; Rucirawat, S.; Ishibashi, F.; Iwao, M.; Meijer, L. Anticancer alkaloid lamellarins inhibit protein kinases. Mar. Drugs, 2008, 6(4), 514-527.
[http://dx.doi.org/10.3390/md20080026] [PMID: 19172192]
[91]
Meijer, L.; Thunnissen, A.M.; White, A.W.; Garnier, M.; Nikolic, M.; Tsai, L.H.; Walter, J.; Cleverley, K.E.; Salinas, P.C.; Wu, Y.Z.; Biernat, J.; Mandelkow, E.M.; Kim, S.H.; Pettit, G.R. Inhibition of cyclin-dependent kinases, GSK-3beta and CK1 by hymenialdisine, a marine sponge constituent. Chem. Biol., 2000, 7(1), 51-63.
[http://dx.doi.org/10.1016/S1074-5521(00)00063-6] [PMID: 10662688]
[92]
Esposito, G.; Bourguet-Kondracki, M-L.; Mai, L.H.; Longeon, A.; Teta, R.; Meijer, L.; Van Soest, R.; Mangoni, A.; Costantino, V.; Chloromethylhalicyclamine, B. a marine-derived protein kinase CK1 delta/epsilon inhibitor. J. Nat. Prod., 2016, 79(11), 2953-2960.
[http://dx.doi.org/10.1021/acs.jnatprod.6b00939] [PMID: 27933894]
[93]
Sprouse, J.; Reynolds, L.; Kleiman, R.; Tate, B.; Swanson, T.A.; Pickard, G.E. Chronic treatment with a selective inhibitor of casein kinase I δ/ε yields cumulative phase delays in circadian rhythms. Psychopharmacology (Berl.), 2010, 210(4), 569-576.
[http://dx.doi.org/10.1007/s00213-010-1860-5] [PMID: 20407760]
[94]
Sprouse, J.; Reynolds, L.; Swanson, T.A.; Engwall, M. Inhibition of casein kinase I ε/δ produces phase shifts in the circadian rhythms of Cynomolgus monkeys. Psychopharmacology (Berl.), 2009, 204(4), 735-742.
[http://dx.doi.org/10.1007/s00213-009-1503-x] [PMID: 19277609]
[95]
Smadja Storz, S.; Tovin, A.; Mracek, P.; Alon, S.; Foulkes, N.S.; Gothilf, Y. Casein kinase 1δ activity: a key element in the zebrafish circadian timing system. PLoS One, 2013, 8(1)e54189
[http://dx.doi.org/10.1371/journal.pone.0054189] [PMID: 23349822]
[96]
Joshi, K.; Goyal, S.; Grover, S.; Jamal, S.; Singh, A.; Dhar, P.; Grover, A. Novel group-based QSAR and combinatorial design of CK-1δ inhibitors as neuroprotective agents. BMC Bioinformatics, 2016, 17(19)(Suppl. 19), 515.
[http://dx.doi.org/10.1186/s12859-016-1379-9] [PMID: 28155653]

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