Design, synthesis and evaluation of 3-quinoline carboxylic acids as new inhibitors of protein kinase CK2

References

• Pinna LA. Casein kinase 2: an ‘eminence grise’ in cellular regulation? Biochim Biophys Acta 1990;1054:267–84
   PubMed Web of Science ®Google Scholar
• Faust M, Montenarh M. Subcellular localization of protein kinase CK2. A key to its function? Cell Tissue Res 2000;301:329–40
   PubMed Web of Science ®Google Scholar
• Piazza F, Manni S, Ruzzene M, et al. Protein kinase CK2 in hematologic malignancies: reliance on a pivotal cell survival regulator by oncogenic signaling pathways. Leukemia 2012;26:1174–9
   PubMed Web of Science ®Google Scholar
• Sarno S, Pinna LA. Protein kinase CK2 as a druggable target. Mol BioSyst 2008;4:889–94
   PubMed Web of Science ®Google Scholar
• Murtaza I, Wang HX, Feng X, et al. Down-regulation of catalase and oxidative modification of protein kinase CK2 lead to the failure of apoptosis repressor with caspase recruitment domain to inhibit cardiomyocyte hypertrophy. J Biol Chem 2008;283:5996–6004
   PubMed Web of Science ®Google Scholar
• Singh NN, Ramji DP. Protein kinase CK2, an important regulator of the inflammatory response? J Mol Med (Berl) 2008;86:887–97
   PubMed Web of Science ®Google Scholar
• Trembley JH, Chen Z, Unger G, et al. Emergence of protein kinase CK2 as a key target in cancer therapy. Biofactors 2010;36:187–95
   PubMed Web of Science ®Google Scholar
• Meggio F, Pinna LA. One-thousand-and-one substrates of protein kinase CK2? FASEB J 2003;17:349–68
   PubMed Web of Science ®Google Scholar
• Siddiqui-Jain A, Drygin D, Streiner N, et al. CX-4945, an orally bioavailable selective inhibitor of protein kinase CK2, inhibits prosurvival and angiogenic signaling and exhibits antitumor efficacy. Cancer Res 2010;70:10288–98
   PubMed Web of Science ®Google Scholar
• Pierre F, Chua PC, O’Brien SE, et al. Discovery and SAR of 5-(3-chlorophenylamino)benzo[c] [2,6]naphthyridine-8-carboxylic Acid (CX-4945), the first clinical stage inhibitor of protein kinase CK2 for the treatment of cancer. J Med Chem 2011;54:635–54
   PubMed Web of Science ®Google Scholar
• ClinicalTrials.gov Identifier: NCT02128282
   Google Scholar
• Meth-Cohn O, Narine B. A versatile new synthesis of quinolines and related fused pyridines. Tet Lett 1978;23:2045–8
   Google Scholar
• Rao KR, Bhanumathi N, Sattur PB. Synthesis of novel quino[2,3-b][1,5]benzodiazepin-12-ones. J Het Chem 1991;28:1339–40
   Web of Science ®Google Scholar
• Patent; Rigel Pharmaceuticals, Inc.; WO2005/30774 2005; A1
   Google Scholar
• Morris GM, Huey R, Lindstrom W, et al. Autodock4 and AutoDockTools4: automated docking with selective receptor flexibility. J Comp Chem 2009;16:2785–91
   Web of Science ®Google Scholar
• Shoichet BK, Stroud RM, Santi DV, et al. Structure-based discovery of inhibitors of thymidylate synthase. Science 1993;259:1445–50
   PubMed Web of Science ®Google Scholar
• Bodian DL, Yamasaki RB, Buswell RL, et al. Inhibition of the fusion-inducing conformational change of influenza hemagglutinin by benzoquinones and hydroquinones. Biochemistry 1993;32:2967–78
   PubMed Web of Science ®Google Scholar
• Ring CS, Sun E, McKerrow JH, et al. Structure-based inhibitor design by using protein models for the development of antiparasitic agents. Proc Natl Acad Sci USA 1993;90:3583–7
   PubMed Web of Science ®Google Scholar
• Ewing TJ, Makino S, Skillman AG, Kuntz ID. DOCK 4.0: search strategies for automated molecular docking of flexible molecule databases. J Comput Aided Mol Des 2001;15:411–28
   PubMed Web of Science ®Google Scholar
• Battistutta R, Cozza G, Pierre F, et al. Unprecedented selectivity and structural determinants of a new class of protein kinase CK2 inhibitors in clinical trials for the treatment of cancer. Biochemistry 2011;50:8478–88
   PubMed Web of Science ®Google Scholar
• Pedretti A, Villa L, Vistoli G. VEGA – an open platform to develop chemobioinformatics applications, using plug-in architecture and script programming. J Comput Aided Mol Des 2004;18:167–73
   PubMed Web of Science ®Google Scholar
• Lindahl E, Hess B, van der Spoel D. GROMACS 3.0: a package for molecular simulation and trajectory analysis. J Mol Mod 2001;7:306–17
   Web of Science ®Google Scholar
• http://www.net-sci.org/Science/Compchem/featurel4.html
   Google Scholar
• Bursulaya BD, Totrov M, Abagyan R, Brooks CL III. Comparative study of several algorithms for flexible ligand docking. J Comput Aided Mol Des 2003;17:755
   PubMed Web of Science ®Google Scholar
• Yakovenko OY, Oliferenko AA, Golub AG, et al. Rational design of protein kinase inhibitors. Ukr Bioorg Acta 2007;1:52
   Google Scholar
• Yakovenko OY, Li YY, Oliferenko AA, et al. Ab initio parameterization of YFF1, a universal force field for drug-design applications. J Mol Model 2012;18:663
   PubMed Web of Science ®Google Scholar
• Yakovenko O, Oliferenko AA, Bdzhola VG, et al. Kirchhoff atomic charges fitted to multipole moments: implementation for a virtual screening system. J Comput Chem 2008;29:1332
   PubMed Web of Science ®Google Scholar
• http://accelrys.com
   Google Scholar
• Hastie CJ, McLauchlan HJ, Cohen P. Assay of protein kinases using radiolabeled ATP: a protocol. Nat Protoc 2006;1:968–71
   PubMed Web of Science ®Google Scholar
• Golub AG, Yakovenko OY, Bdzhola VG, et al. Evaluation of 3-Carboxy-4(1H)-quinolones as Inhibitors of Human Protein Kinase CK2. J Med Chem 2006;49:6443–50
   PubMed Web of Science ®Google Scholar
• Synyugin AR, Chekanov MO, Nyporko OY, et al. New 2-quinolinone derivatives: synthesis and CK2 inhibitor activity. Ukr Bioorg Acta 2012;1:51–60
   Google Scholar
• Synyugin АR, Chekanov MO, Lukashov SS, Yarmoluk SM. Synthesis of 3-(quinoline-2-on-3-yl)propanoic acids. Ukr Bioorg Acta 2010;2:58–62
   Google Scholar
• Suzuki Y, Oishi S, Takei Y, et al. Design and synthesis of a novel class of CK2 inhibitors: application of copper- and gold-catalysed cascade reactions for fused nitrogen heterocycles. Org Biomol Chem 2012;10:4907–15
   PubMed Web of Science ®Google Scholar