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Current Medicinal Chemistry

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ISSN (Online): 1875-533X

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Review Article

Recent Advances in the Development of Casein Kinase 1 Inhibitors

Author(s): Sha-Sha Li, Yue-Hui Dong and Zhao-Peng Liu*

Volume 28, Issue 8, 2021

Published on: 13 July, 2020

Page: [1585 - 1604] Pages: 20

DOI: 10.2174/0929867327666200713185413

Price: $65

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Abstract

Background: The casein kinase 1 (CK1) family is involved in regulating many cellular processes, including membrane trafficking, DNA damage repair, cytoskeleton dynamics, cytoskeleton maintenance and apoptosis. CK1 isoforms, especially CK1δ and CK1ε have emerged as important therapeutic targets for severe disorders such as Alzheimer’s disease (AD), amyotrophic lateral sclerosis (ALS), familial advanced sleep phase syndrome and cancer. Due to the importance of CK1 for the pathogenesis of disorders, there are great interests in the development of CK1 inhibitors.

Methods: Using SciFinder® as a tool, the publications about the biology of CK1 and the recent developments of CK1 inhibitors were surveyed with an exclusion of those published as patents.

Results: This review presents the current state of knowledge on the development of CK1 inhibitors, including both synthetic small molecular inhibitors that were divided into 7 categories according to structural features, and the natural compounds. An overview of the advancement of CK1 inhibitors was given, with the introduction of various existing CK1 inhibitors, their inhibitory activities, and the structure-activity relationships.

Conclusion: Through physicochemical characterization and biological investigations, it is possible to understand the structure-activity relationship of CK1 inhibitors, which will contribute to better design and discovery of potent and selective CK1 inhibitors as potential agents for severe disorders such as AD, ALS and cancer.

Keywords: Casein kinase 1 (CK1), inhibitor, chemical, small molecules, anticancer agents, drug design.

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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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