Flavone inspired discovery of benzylidenebenzofuran-3(2H)-ones (aurones) as potent inhibitors of human protein kinase CK2
[Display omitted] •New substituted benzylidenebenzofuran-3(2H)-ones were synthesized.•41 aurones inhibited CK2 with IC50 in nanomolar range of values.•The most promising compound 12m (BFO13) has an IC50 = 3.6 nM with CLipE = 4.94. In this work, we describe the design, synthesis and SAR studies of 2-...
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| Published in: | Bioorganic chemistry Vol. 102; p. 104062 |
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| Main Authors: | , , , , , , , , |
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01-09-2020
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| Abstract | [Display omitted]
•New substituted benzylidenebenzofuran-3(2H)-ones were synthesized.•41 aurones inhibited CK2 with IC50 in nanomolar range of values.•The most promising compound 12m (BFO13) has an IC50 = 3.6 nM with CLipE = 4.94.
In this work, we describe the design, synthesis and SAR studies of 2-benzylidenebenzofuran-3-ones (aurones), a new family of potent inhibitors of CK2. A series of aurones have been synthesized. These compounds are structurally related to the synthetic flavones and showed nanomolar activities towards CK2. Biochemical tests revealed that 20 newly synthesized compounds inhibited CK2 with IC50 values in the nanomolar range. Further property-based optimization of aurones was performed, yielding a series of CK2 inhibitors with enhanced lipophilic efficiency. The most potent compound 12m (BFO13) has CLipE = 4.94 (CLogP = 3.5; IC50 = 3.6 nM) commensurable with the best known inhibitors of CK2. |
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| AbstractList | [Display omitted]
•New substituted benzylidenebenzofuran-3(2H)-ones were synthesized.•41 aurones inhibited CK2 with IC50 in nanomolar range of values.•The most promising compound 12m (BFO13) has an IC50 = 3.6 nM with CLipE = 4.94.
In this work, we describe the design, synthesis and SAR studies of 2-benzylidenebenzofuran-3-ones (aurones), a new family of potent inhibitors of CK2. A series of aurones have been synthesized. These compounds are structurally related to the synthetic flavones and showed nanomolar activities towards CK2. Biochemical tests revealed that 20 newly synthesized compounds inhibited CK2 with IC50 values in the nanomolar range. Further property-based optimization of aurones was performed, yielding a series of CK2 inhibitors with enhanced lipophilic efficiency. The most potent compound 12m (BFO13) has CLipE = 4.94 (CLogP = 3.5; IC50 = 3.6 nM) commensurable with the best known inhibitors of CK2. In this work, we describe the design, synthesis and SAR studies of 2-benzylidenebenzofuran-3-ones (aurones), a new family of potent inhibitors of CK2. A series of aurones have been synthesized. These compounds are structurally related to the synthetic flavones and showed nanomolar activities towards CK2. Biochemical tests revealed that 20 newly synthesized compounds inhibited CK2 with IC values in the nanomolar range. Further property-based optimization of aurones was performed, yielding a series of CK2 inhibitors with enhanced lipophilic efficiency. The most potent compound 12m (BFO13) has CLipE = 4.94 (CLogP = 3.5; IC = 3.6 nM) commensurable with the best known inhibitors of CK2. |
| ArticleNumber | 104062 |
| Author | Yarmoluk, S.M. Bdzhola, V.G. Protopopov, M.V. Borysenko, I.P. Starosyla, S.A. Lukashov, S.S. Bilokin, Y.V. Vdovin, V.S. Prykhod'ko, A.O. |
| Author_xml | – sequence: 1 givenname: M.V. surname: Protopopov fullname: Protopopov, M.V. email: mykola.protopopov@gmail.com, mykola.protopopov@imbg.org.ua organization: Institute of Molecular Biology and Genetics, NAS of Ukraine, 150 Zabolotnogo St., 03143 Kyiv, Ukraine – sequence: 2 givenname: V.S. surname: Vdovin fullname: Vdovin, V.S. organization: Institute of Molecular Biology and Genetics, NAS of Ukraine, 150 Zabolotnogo St., 03143 Kyiv, Ukraine – sequence: 3 givenname: S.A. surname: Starosyla fullname: Starosyla, S.A. organization: Institute of Molecular Biology and Genetics, NAS of Ukraine, 150 Zabolotnogo St., 03143 Kyiv, Ukraine – sequence: 4 givenname: I.P. surname: Borysenko fullname: Borysenko, I.P. organization: Institute of Molecular Biology and Genetics, NAS of Ukraine, 150 Zabolotnogo St., 03143 Kyiv, Ukraine – sequence: 5 givenname: A.O. surname: Prykhod'ko fullname: Prykhod'ko, A.O. organization: Institute of Molecular Biology and Genetics, NAS of Ukraine, 150 Zabolotnogo St., 03143 Kyiv, Ukraine – sequence: 6 givenname: S.S. surname: Lukashov fullname: Lukashov, S.S. organization: Institute of Molecular Biology and Genetics, NAS of Ukraine, 150 Zabolotnogo St., 03143 Kyiv, Ukraine – sequence: 7 givenname: Y.V. surname: Bilokin fullname: Bilokin, Y.V. organization: OTAVA Ltd., 400 Applewood Crescent, Unit 100, Vaughan, Ontario L4K 0C3, Canada – sequence: 8 givenname: V.G. surname: Bdzhola fullname: Bdzhola, V.G. organization: Institute of Molecular Biology and Genetics, NAS of Ukraine, 150 Zabolotnogo St., 03143 Kyiv, Ukraine – sequence: 9 givenname: S.M. surname: Yarmoluk fullname: Yarmoluk, S.M. organization: Institute of Molecular Biology and Genetics, NAS of Ukraine, 150 Zabolotnogo St., 03143 Kyiv, Ukraine |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/32683178$$D View this record in MEDLINE/PubMed |
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| Cites_doi | 10.1172/JCI34616 10.1006/bbrc.2000.3319 10.1016/j.bmc.2013.08.013 10.1016/j.chembiol.2005.08.015 10.1021/jm500943z 10.1039/C6SC02335E 10.1021/acschembio.5b00235 10.1016/j.bmc.2012.02.017 10.1042/bj20030674 10.1023/B:JCAM.0000035186.90683.f2 10.1021/jm070909t 10.1038/nprot.2006.149 10.1158/1078-0432.CCR-06-1602 10.1038/sj.onc.1204411 10.1021/acs.jmedchem.8b01766 10.1038/s41598-019-52141-5 10.1002/jcc.21256 10.1016/j.jsb.2011.12.007 10.1039/C7SC05122K 10.1016/j.ejmech.2016.03.004 10.1006/bbrc.1994.1904 10.1016/j.pain.2005.02.025 10.1096/fj.02-0473rev 10.1016/j.ejmech.2015.04.032 10.1007/s00109-008-0352-0 10.1080/17460441.2017.1344210 10.3390/ph8020279 10.1007/s11010-011-0945-8 10.1182/blood-2010-04-277947 10.3390/ph10010009 10.1021/acs.jmedchem.8b00077 10.4155/fmc.12.208 10.1107/S0108270194007973 10.1016/j.bmc.2018.05.011 10.1016/S1389-1723(02)80184-0 10.1021/bi2008382 10.1016/j.febslet.2010.11.019 10.1016/j.bmcl.2009.05.062 10.3390/ph10040098 10.3390/ph10010008 10.1016/j.bbapap.2007.10.009 10.1107/S1600536811041869 10.1016/j.ejmech.2010.12.025 10.1021/bi300531c 10.1016/j.bmc.2017.04.037 10.1182/blood-2005-11-013672 10.1002/1097-0347(200007)22:4<341::AID-HED5>3.0.CO;2-3 10.1107/S1600536811016217 10.1002/pros.2990240105 |
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| Keywords | Protein kinase CK2 inhibitor 2-benzylidenebenzofuran-3-ones Virtual screening Aurone In vitro biochemical assay Molecular docking |
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| References | Golub, Bdzhola, Briukhovetska, Balanda, Kukharenko, Kotey, Ostrynska, Yarmoluk (b0095) 2011; 46 Jin, Ju, Cheong, Ae, Jin, Woo, Yoo (b0045) 2007; 13 Hochscherf, Lindenblatt, Witulski, Birus, Aichele, Marminon, Bouaziz, Le Borgne, Jose, Niefind (b0125) 2017; 10 Meggio, Pinna (b0005) 2003; 17 Martins, Lúcio, Silva, Anderes, Gameiro, Silva, Barata (b0055) 2010; 116 Morris, Ruth, Lindstrom, Sanner, Belew, Goodsell, Olson (b0250) 2009; 30 Haneda, Furuya, Asai, Morikawa, Ohtsuki (b0070) 2000; 275 Ryckmans, Edwards, Horne, Correia, Owen, Thompson, Tran, Tutt, Young (b0235) 2009; 19 Freeman-Cook, Hoffman, Johnson (b0240) 2013; 5 Yenice, Davis, Goueli, Akdas, Limas, Ahmed (b0030) 1994; 24 Stalter, Siemer, Becht, Ziegler, Remberger, Issinger (b0020) 1994; 202 Golub, Bdzhola, Kyshenia, Sapelkin, Prykhod’ko, Kukharenko, Ostrynska, Yarmoluk (b0120) 2011; 356 Pedretti, Villa, Vistoli (b0255) 2004; 18 Hastie, McLauchlan, Cohen (b0260) 2006; 1 Lolli, Cozza, Mazzorana, Tibaldi, Cesaro, Donella-Deana, Meggio, Venerando, Franchin, Sarno, Battistutta, Pinna (b0110) 2012; 51 De Fusco, Brear, Iegre, Georgiou, Sore, Hyvönen, Spring (b0175) 2017; 25 Ruzzene, Pinna (b0010) 1804; 2010 Kufareva, Bestgen, Brear, Prudent, Laudet, Moucadel, Ettaoussi, Sautel, Krimm, Engel, Filhol, Le Borgne, Lomberget, Cochet, Abagyan (b0185) 2019; 9 Piazza, Ruzzene, Gurrieri, Montini, Bonanni, Chioetto, Di Maira, Barbon, Cabrelle, Zambello, Adami, Trentin, Pinna, Semenzato (b0040) 2006; 108 Battistutta, Mazzorana, Sarno, Kazimierczuk, Zanotti, Pinna (b0080) 2005; 12 Brear, De Fusco, Hadje Georgiou, Francis-Newton, Stubbs, Sore, Venkitaraman, Abell, Spring, Hyvönen (b0170) 2016; 7 Niefind, Bischoff, Golub, Bdzhola, Balanda, Prykhod’ko, Yarmoluk (b0215) 2017; 10 Nakanishi, Murata, Nagata, Kurono, Kinoshita, Yasue, Miyazaki, Takei, Nakamura, Sakurai, Iwamoto, Nishiwaki, Nakaniwa, Sekiguchi, Hirasawa, Tsujimoto, Kitaura (b0190) 2015; 96 Satyanarayana Reddy, Ravi Kumar, Venkata Prasad, Gopikrishna, Anand Solomon (b0210) 2011; 67 Guerra, Bischoff, Bdzhola, Yarmoluk, Issinger, Golub, Niefind (b0225) 2015; 10 Tsopelas, Giaginis, Tsantili-Kakoulidou (b0245) 2017; 12 Reddy, Ravikumar, Prasad, Krishna, Solomon (b0205) 2011; 67 Brear, North, Iegre, Hadje Georgiou, Lubin, Carro, Green, Sore, Hyvönen, Spring (b0165) 2018; 26 Golub, Bdzhola, Ostrynska, Kyshenia, Sapelkin, Prykhod’ko, Kukharenko, Yarmoluk (b0115) 2013; 21 Alchab, Ettouati, Bouaziz, Bollacke, Delcros, Gertzen, Gohlke, Pinaud, Marchivie, Guillon, Fenet, Jose, Borgne (b0140) 2015; 8 Faust, Tawfic, Davis, Bubash, Ahmed (b0025) 2000; 22 Ostrynska, Balanda, Bdzhola, Golub, Kotey, Kukharenko, Gryshchenko, Briukhovetska, Yarmoluk (b0100) 2016; 115 Iegre, Brear, De Fusco, Yoshida, Mitchell, Rossmann, Carro, Sore, Hyvönen, Spring (b0180) 2018; 9 Ferguson, Sheth, Basso, Paliwal, Gray, Fischmann, Le (b0150) 2011; 585 Singh, Ramji (b0060) 2008; 86 Landesman-Bollag, Romieu-Mourez, Song, Sonenshein, Cardiff, Seldin (b0035) 2001; 20 Papinutto, Ranchio, Lolli, Pinna, Battistutta (b0085) 2012; 177 Li, Shi, Liang, Clark (b0065) 2005; 115 Bestgen, Krimm, Kufareva, Kamal, Seetoh, Abell, Hartmann, Abagyan, Cochet, Le Borgne, Engel, Lomberget (b0160) 2019; 62 Daya-Makin, Sanghera, Mogentale, Lipp, Parchomchuk, Hogg, Pelech (b0015) 1994; 54 Haidar, Bouaziz, Marminon, Laitinen, Poso, Le Borgne, Jose (b0130) 2017; 10 Sarno, De Moliner, Ruzzene, Pagano, Battistutta, Bain, Fabbro, Schoepfer, Elliott, Furet, Meggio, Zanotti, Pinna (b0090) 2003; 374 Chilin, Battistutta, Bortolato, Cozza, Zanatta, Poletto, Mazzorana, Zagotto, Uriarte, Guiotto, Pinna, Meggio, Moro (b0075) 2008; 51 Hundsdörfer, Hemmerling, Götz, Totzke, Bednarski, Le Borgne, Jose (b0145) 2012; 20 Johnson, Gallego, Edwards (b0230) 2018; 61 Battistutta, Cozza, Pierre, Papinutto, Lolli, Sarno, Obrien, Siddiqui-Jain, Haddach, Anderes, Ryckman, Meggio, Pinna (b0155) 2011; 50 Golub, Yakovenko, Prykhod’ko, Lukashov, Bdzhola, Yarmoluk (b0105) 2008; 1784 Goud, Panneerselvam, Zacharias, Desiraju (b0200) 1995; 51 Jabor Gozzi, Bouaziz, Winter, Daflon-Yunes, Aichele, Nacereddine, Marminon, Valdameri, Zeinyeh, Bollacke, Guillon, Lacoudre, Pinaud, Cadena, Jose, Le Borgne, Di Pietro (b0135) 2015; 58 Silva, Yunes, Cardoso, Martins, Jotta, Abecasis, Nowill, Leslie, Cardoso, Barata (b0050) 2008; 118 Vdovin, Lukashov, Borysenko, Fesun, Yarmoluk (b0220) 2015; 1 Nakayama (b0195) 2002; 94 De Fusco (10.1016/j.bioorg.2020.104062_b0175) 2017; 25 Faust (10.1016/j.bioorg.2020.104062_b0025) 2000; 22 Nakayama (10.1016/j.bioorg.2020.104062_b0195) 2002; 94 Tsopelas (10.1016/j.bioorg.2020.104062_b0245) 2017; 12 Nakanishi (10.1016/j.bioorg.2020.104062_b0190) 2015; 96 Lolli (10.1016/j.bioorg.2020.104062_b0110) 2012; 51 Ruzzene (10.1016/j.bioorg.2020.104062_b0010) 1804; 2010 Li (10.1016/j.bioorg.2020.104062_b0065) 2005; 115 Vdovin (10.1016/j.bioorg.2020.104062_b0220) 2015; 1 Golub (10.1016/j.bioorg.2020.104062_b0095) 2011; 46 Freeman-Cook (10.1016/j.bioorg.2020.104062_b0240) 2013; 5 Battistutta (10.1016/j.bioorg.2020.104062_b0155) 2011; 50 Martins (10.1016/j.bioorg.2020.104062_b0055) 2010; 116 Silva (10.1016/j.bioorg.2020.104062_b0050) 2008; 118 Papinutto (10.1016/j.bioorg.2020.104062_b0085) 2012; 177 Satyanarayana Reddy (10.1016/j.bioorg.2020.104062_b0210) 2011; 67 Meggio (10.1016/j.bioorg.2020.104062_b0005) 2003; 17 Iegre (10.1016/j.bioorg.2020.104062_b0180) 2018; 9 Bestgen (10.1016/j.bioorg.2020.104062_b0160) 2019; 62 Singh (10.1016/j.bioorg.2020.104062_b0060) 2008; 86 Haneda (10.1016/j.bioorg.2020.104062_b0070) 2000; 275 Yenice (10.1016/j.bioorg.2020.104062_b0030) 1994; 24 Hochscherf (10.1016/j.bioorg.2020.104062_b0125) 2017; 10 Stalter (10.1016/j.bioorg.2020.104062_b0020) 1994; 202 Piazza (10.1016/j.bioorg.2020.104062_b0040) 2006; 108 Jin (10.1016/j.bioorg.2020.104062_b0045) 2007; 13 Alchab (10.1016/j.bioorg.2020.104062_b0140) 2015; 8 Ostrynska (10.1016/j.bioorg.2020.104062_b0100) 2016; 115 Sarno (10.1016/j.bioorg.2020.104062_b0090) 2003; 374 Haidar (10.1016/j.bioorg.2020.104062_b0130) 2017; 10 Ferguson (10.1016/j.bioorg.2020.104062_b0150) 2011; 585 Landesman-Bollag (10.1016/j.bioorg.2020.104062_b0035) 2001; 20 Ryckmans (10.1016/j.bioorg.2020.104062_b0235) 2009; 19 Morris (10.1016/j.bioorg.2020.104062_b0250) 2009; 30 Guerra (10.1016/j.bioorg.2020.104062_b0225) 2015; 10 Pedretti (10.1016/j.bioorg.2020.104062_b0255) 2004; 18 Hundsdörfer (10.1016/j.bioorg.2020.104062_b0145) 2012; 20 Brear (10.1016/j.bioorg.2020.104062_b0170) 2016; 7 Jabor Gozzi (10.1016/j.bioorg.2020.104062_b0135) 2015; 58 Niefind (10.1016/j.bioorg.2020.104062_b0215) 2017; 10 Chilin (10.1016/j.bioorg.2020.104062_b0075) 2008; 51 Johnson (10.1016/j.bioorg.2020.104062_b0230) 2018; 61 Brear (10.1016/j.bioorg.2020.104062_b0165) 2018; 26 Reddy (10.1016/j.bioorg.2020.104062_b0205) 2011; 67 Hastie (10.1016/j.bioorg.2020.104062_b0260) 2006; 1 Goud (10.1016/j.bioorg.2020.104062_b0200) 1995; 51 Golub (10.1016/j.bioorg.2020.104062_b0105) 2008; 1784 Golub (10.1016/j.bioorg.2020.104062_b0120) 2011; 356 Kufareva (10.1016/j.bioorg.2020.104062_b0185) 2019; 9 Daya-Makin (10.1016/j.bioorg.2020.104062_b0015) 1994; 54 Golub (10.1016/j.bioorg.2020.104062_b0115) 2013; 21 Battistutta (10.1016/j.bioorg.2020.104062_b0080) 2005; 12 |
| References_xml | – volume: 116 start-page: 2724 year: 2010 end-page: 2731 ident: b0055 article-title: Targeting CK2 overexpression and hyperactivation as a novel therapeutic tool in chronic lymphocytic leukemia publication-title: Blood contributor: fullname: Barata – volume: 94 start-page: 487 year: 2002 end-page: 491 ident: b0195 article-title: Enzymology of aurone biosynthesis publication-title: J. Biosci. Bioeng. contributor: fullname: Nakayama – volume: 18 start-page: 167 year: 2004 end-page: 173 ident: b0255 article-title: VEGA – an open platform to develop chemo-bio-informatics applications, using plug-in architecture and script programming publication-title: J. Comput. Aided Mol. Des. contributor: fullname: Vistoli – volume: 12 start-page: 1211 year: 2005 end-page: 1219 ident: b0080 article-title: Inspecting the structure-activity relationship of protein kinase CK2 inhibitors derived from tetrabromo-benzimidazole publication-title: Chem. Biol. contributor: fullname: Pinna – volume: 10 year: 2017 ident: b0125 article-title: Unexpected binding mode of a potent indeno[1,2-b]indole-type inhibitor of protein kinase CK2 revealed by complex structures with the catalytic subunit CK2α and its paralog CK2α’ publication-title: Pharmaceuticals contributor: fullname: Niefind – volume: 275 start-page: 434 year: 2000 end-page: 439 ident: b0070 article-title: Biochemical characterization of casein kinase II as a protein kinase responsible for stimulation of HIV-1 protease in vitro publication-title: Biochem. Biophys. Res. Commun. contributor: fullname: Ohtsuki – volume: 10 start-page: 8 year: 2017 ident: b0130 article-title: Development of pharmacophore model for indeno[1,2-b]indoles as human protein kinase CK2 inhibitors and database mining publication-title: Pharmaceuticals contributor: fullname: Jose – volume: 1 start-page: 968 year: 2006 end-page: 971 ident: b0260 article-title: Assay of protein kinases using radiolabeled ATP: a protocol publication-title: Nat. Protoc. contributor: fullname: Cohen – volume: 115 start-page: 182 year: 2005 end-page: 190 ident: b0065 article-title: Spinal CK2 regulates nociceptive signaling in models of inflammatory pain publication-title: Pain contributor: fullname: Clark – volume: 30 start-page: 2785 year: 2009 end-page: 2791 ident: b0250 article-title: Software news and updates AutoDock4 and AutoDockTools4: automated docking with selective receptor flexibility publication-title: J. Comput. Chem. contributor: fullname: Olson – volume: 21 start-page: 6681 year: 2013 end-page: 6689 ident: b0115 article-title: Discovery and characterization of synthetic 4′-hydroxyflavones—New CK2 inhibitors from flavone family publication-title: Bioorg. Med. Chem. contributor: fullname: Yarmoluk – volume: 51 start-page: 752 year: 2008 end-page: 759 ident: b0075 article-title: Coumarin as attractive Casein Kinase 2 (CK2) inhibitor scaffold: an integrate approach to elucidate the putative binding motif and explain structure-activity relationships publication-title: J. Med. Chem. contributor: fullname: Moro – volume: 177 start-page: 382 year: 2012 end-page: 391 ident: b0085 article-title: Structural and functional analysis of the flexible regions of the catalytic α-subunit of protein kinase CK2 publication-title: J. Struct. Biol. contributor: fullname: Battistutta – volume: 54 start-page: 2262 year: 1994 end-page: 2268 ident: b0015 article-title: Activation of a tumor-associated protein kinase (p40TAK) and casein kinase 2 in human squamous cell carcinomas and adenocarcinomas of the lung publication-title: Cancer Res. contributor: fullname: Pelech – volume: 5 start-page: 113 year: 2013 end-page: 115 ident: b0240 article-title: Lipophilic efficiency: the most important efficiency metric in medicinal chemistry publication-title: Future Med. Chem. contributor: fullname: Johnson – volume: 19 start-page: 4406 year: 2009 end-page: 4409 ident: b0235 article-title: Rapid assessment of a novel series of selective CB2 agonists using parallel synthesis protocols: a Lipophilic Efficiency (LipE) analysis publication-title: Bioorganic Med. Chem. Lett. contributor: fullname: Young – volume: 26 start-page: 3016 year: 2018 end-page: 3020 ident: b0165 article-title: Novel non-ATP competitive small molecules targeting the CK2 α/β interface publication-title: Bioorg. Med. Chem. contributor: fullname: Spring – volume: 25 start-page: 3471 year: 2017 end-page: 3482 ident: b0175 article-title: A fragment-based approach leading to the discovery of a novel binding site and the selective CK2 inhibitor CAM4066 publication-title: Bioorg. Med. Chem. contributor: fullname: Spring – volume: 10 start-page: 1654 year: 2015 end-page: 1660 ident: b0225 article-title: A note of caution on the role of halogen bonds for protein kinase/inhibitor recognition suggested by high- and low-salt CK2α complex structures publication-title: ACS Chem. Biol. contributor: fullname: Niefind – volume: 2010 start-page: 499 year: 1804 end-page: 504 ident: b0010 article-title: Addiction to protein kinase CK2: A common denominator of diverse cancer cells? publication-title: Biochim. Biophys. Acta – Proteins Proteomics contributor: fullname: Pinna – volume: 67 year: 2011 ident: b0205 article-title: (Z)-2-(4-Nitrobenzylidene)-1-benzofuran-3(2H)-one publication-title: Acta Crystallogr. Sect. E Struct. Reports Online contributor: fullname: Solomon – volume: 356 start-page: 107 year: 2011 end-page: 115 ident: b0120 article-title: Structure-based discovery of novel flavonol inhibitors of human protein kinase CK2 publication-title: Mol. Cell. Biochem. contributor: fullname: Yarmoluk – volume: 9 start-page: 15893 year: 2019 ident: b0185 article-title: Discovery of holoenzyme-disrupting chemicals as substrate-selective CK2 inhibitors publication-title: Sci. Rep. contributor: fullname: Abagyan – volume: 118 start-page: 3762 year: 2008 end-page: 3774 ident: b0050 article-title: PTEN posttranslational inactivation and hyperactivation of the PI3K/Akt pathway sustain primary T cell leukemia viability publication-title: J. Clin. Invest. contributor: fullname: Barata – volume: 58 start-page: 265 year: 2015 end-page: 277 ident: b0135 article-title: Converting potent indeno[1,2- b ]indole inhibitors of protein kinase CK2 into selective inhibitors of the breast cancer resistance protein ABCG2 publication-title: J. Med. Chem. contributor: fullname: Di Pietro – volume: 46 start-page: 870 year: 2011 end-page: 876 ident: b0095 article-title: Synthesis and biological evaluation of substituted (thieno[2,3-d]pyrimidin- 4-ylthio)carboxylic acids as inhibitors of human protein kinase CK2 publication-title: Eur. J. Med. Chem. contributor: fullname: Yarmoluk – volume: 9 start-page: 3041 year: 2018 end-page: 3049 ident: b0180 article-title: Second-generation CK2α inhibitors targeting the αD pocket publication-title: Chem. Sci. contributor: fullname: Spring – volume: 1 start-page: 25 year: 2015 end-page: 31 ident: b0220 article-title: The synthesis of combinatorial row of aurone derivatives as potential inhibitors of protein kinase CK2 publication-title: Ukr. Bioorg. Acta contributor: fullname: Yarmoluk – volume: 374 start-page: 639 year: 2003 end-page: 646 ident: b0090 article-title: Biochemical and three-dimensional-structural study of the specific inhibition of protein kinase CK2 by [5-oxo-5,6-dihydroindolo-(1,2-a)quinazolin-7-yl]acetic acid (IQA) publication-title: Biochem. J. contributor: fullname: Pinna – volume: 115 start-page: 148 year: 2016 end-page: 160 ident: b0100 article-title: Design and synthesis of novel protein kinase CK2 inhibitors on the base of 4-aminothieno[2,3-d]pyrimidines publication-title: Eur. J. Med. Chem. contributor: fullname: Yarmoluk – volume: 202 start-page: 141 year: 1994 end-page: 147 ident: b0020 article-title: Asymmetric expression of protein kinase CK2 subunits in human kidney tumors publication-title: Biochem. Biophys. Res. Commun. contributor: fullname: Issinger – volume: 62 start-page: 1803 year: 2019 end-page: 1816 ident: b0160 article-title: 2-aminothiazole derivatives as selective allosteric modulators of the protein kinase CK2. 1. Identification of an allosteric binding site publication-title: J. Med. Chem. contributor: fullname: Lomberget – volume: 51 start-page: 265 year: 1995 end-page: 267 ident: b0200 article-title: 4,6-Dimethyl-2-(4-nitrobenzylidene)-3(2H)-benzofuranone publication-title: Acta Crystallogr. Sect. C Cryst. Struct. Commun. contributor: fullname: Desiraju – volume: 13 start-page: 1019 year: 2007 end-page: 1028 ident: b0045 article-title: Protein kinase CK2α as an unfavorable prognostic marker and novel therapeutic target in acute myeloid leukemia publication-title: Clin. Cancer Res. contributor: fullname: Yoo – volume: 108 start-page: 1698 year: 2006 end-page: 1707 ident: b0040 article-title: Multiple myeloma cell survival relies on high activity of protein kinase CK2 publication-title: Blood contributor: fullname: Semenzato – volume: 96 start-page: 396 year: 2015 end-page: 404 ident: b0190 article-title: Identification of protein kinase CK2 inhibitors using solvent dipole ordering virtual screening publication-title: Eur. J. Med. Chem. contributor: fullname: Kitaura – volume: 86 start-page: 887 year: 2008 end-page: 897 ident: b0060 article-title: Protein kinase CK2, an important regulator of the inflammatory response? publication-title: J. Mol. Med. contributor: fullname: Ramji – volume: 12 start-page: 885 year: 2017 end-page: 896 ident: b0245 article-title: Lipophilicity and biomimetic properties to support drug discovery publication-title: Expert Opin. Drug Discov. contributor: fullname: Tsantili-Kakoulidou – volume: 7 start-page: 6839 year: 2016 end-page: 6845 ident: b0170 article-title: Specific inhibition of CK2α from an anchor outside the active site publication-title: Chem. Sci. contributor: fullname: Hyvönen – volume: 50 start-page: 8478 year: 2011 end-page: 8488 ident: b0155 article-title: Unprecedented selectivity and structural determinants of a new class of protein kinase CK2 inhibitors in clinical trials for the treatment of cancer publication-title: Biochemistry contributor: fullname: Pinna – volume: 20 start-page: 2282 year: 2012 end-page: 2289 ident: b0145 article-title: Indeno[1,2-b]indole derivatives as a novel class of potent human protein kinase CK2 inhibitors publication-title: Bioorg. Med. Chem. contributor: fullname: Jose – volume: 24 start-page: 11 year: 1994 end-page: 16 ident: b0030 article-title: Nuclear casein kinase 2 (CK-2) activity in human normal, benign hyperplastic, and cancerous prostate publication-title: Prostate contributor: fullname: Ahmed – volume: 67 year: 2011 ident: b0210 article-title: (Z)-2-(2-Hydroxy-4-methoxybenzylidene)-1-benzofuran-3(2 H)-one publication-title: Acta Crystallogr. Sect. E Struct. Reports Online contributor: fullname: Anand Solomon – volume: 1784 start-page: 143 year: 2008 end-page: 149 ident: b0105 article-title: Evaluation of 4,5,6,7-tetrahalogeno-1H-isoindole-1,3(2H)-diones as inhibitors of human protein kinase CK2 publication-title: Biochim. Biophys. Acta – Proteins Proteomics contributor: fullname: Yarmoluk – volume: 585 start-page: 104 year: 2011 end-page: 110 ident: b0150 article-title: Structural basis of CX-4945 binding to human protein kinase CK2 publication-title: FEBS Lett. contributor: fullname: Le – volume: 51 start-page: 6097 year: 2012 end-page: 6107 ident: b0110 article-title: Inhibition of protein kinase CK2 by flavonoids and tyrphostins. A structural insight publication-title: Biochemistry contributor: fullname: Pinna – volume: 10 year: 2017 ident: b0215 article-title: Structural hypervariability of the two human protein kinase CK2 catalytic subunit paralogs revealed by complex structures with a flavonoland a thieno[2,3-d]pyrimidine-based inhibitor publication-title: Pharmaceuticals contributor: fullname: Yarmoluk – volume: 17 start-page: 349 year: 2003 end-page: 368 ident: b0005 article-title: One-thousand-and-one substrates of protein kinase CK2? publication-title: FASEB J. contributor: fullname: Pinna – volume: 20 start-page: 3247 year: 2001 end-page: 3257 ident: b0035 article-title: Protein kinase CK2 in mammary gland tumorigenesis publication-title: Oncogene contributor: fullname: Seldin – volume: 22 start-page: 341 year: 2000 end-page: 346 ident: b0025 article-title: Antisense oligonucleotides against protein kinase CK2-α inhibit growth of squamous cell carcinoma of the head and neck in vitro publication-title: Head Neck contributor: fullname: Ahmed – volume: 61 start-page: 6401 year: 2018 end-page: 6420 ident: b0230 article-title: Lipophilic efficiency as an important metric in drug design publication-title: J. Med. Chem. contributor: fullname: Edwards – volume: 8 start-page: 279 year: 2015 end-page: 302 ident: b0140 article-title: Synthesis, biological evaluation and molecular modeling of substituted indeno[1,2-b]indoles as inhibitors of human protein kinase CK2 publication-title: Pharmaceuticals contributor: fullname: Borgne – volume: 118 start-page: 3762 year: 2008 ident: 10.1016/j.bioorg.2020.104062_b0050 article-title: PTEN posttranslational inactivation and hyperactivation of the PI3K/Akt pathway sustain primary T cell leukemia viability publication-title: J. Clin. Invest. doi: 10.1172/JCI34616 contributor: fullname: Silva – volume: 275 start-page: 434 year: 2000 ident: 10.1016/j.bioorg.2020.104062_b0070 article-title: Biochemical characterization of casein kinase II as a protein kinase responsible for stimulation of HIV-1 protease in vitro publication-title: Biochem. Biophys. Res. Commun. doi: 10.1006/bbrc.2000.3319 contributor: fullname: Haneda – volume: 21 start-page: 6681 issue: 21 year: 2013 ident: 10.1016/j.bioorg.2020.104062_b0115 article-title: Discovery and characterization of synthetic 4′-hydroxyflavones—New CK2 inhibitors from flavone family publication-title: Bioorg. Med. Chem. doi: 10.1016/j.bmc.2013.08.013 contributor: fullname: Golub – volume: 12 start-page: 1211 year: 2005 ident: 10.1016/j.bioorg.2020.104062_b0080 article-title: Inspecting the structure-activity relationship of protein kinase CK2 inhibitors derived from tetrabromo-benzimidazole publication-title: Chem. Biol. doi: 10.1016/j.chembiol.2005.08.015 contributor: fullname: Battistutta – volume: 58 start-page: 265 year: 2015 ident: 10.1016/j.bioorg.2020.104062_b0135 article-title: Converting potent indeno[1,2- b ]indole inhibitors of protein kinase CK2 into selective inhibitors of the breast cancer resistance protein ABCG2 publication-title: J. Med. Chem. doi: 10.1021/jm500943z contributor: fullname: Jabor Gozzi – volume: 2010 start-page: 499 year: 1804 ident: 10.1016/j.bioorg.2020.104062_b0010 article-title: Addiction to protein kinase CK2: A common denominator of diverse cancer cells? publication-title: Biochim. Biophys. Acta – Proteins Proteomics contributor: fullname: Ruzzene – volume: 7 start-page: 6839 year: 2016 ident: 10.1016/j.bioorg.2020.104062_b0170 article-title: Specific inhibition of CK2α from an anchor outside the active site publication-title: Chem. Sci. doi: 10.1039/C6SC02335E contributor: fullname: Brear – volume: 10 start-page: 1654 year: 2015 ident: 10.1016/j.bioorg.2020.104062_b0225 article-title: A note of caution on the role of halogen bonds for protein kinase/inhibitor recognition suggested by high- and low-salt CK2α complex structures publication-title: ACS Chem. Biol. doi: 10.1021/acschembio.5b00235 contributor: fullname: Guerra – volume: 20 start-page: 2282 year: 2012 ident: 10.1016/j.bioorg.2020.104062_b0145 article-title: Indeno[1,2-b]indole derivatives as a novel class of potent human protein kinase CK2 inhibitors publication-title: Bioorg. Med. Chem. doi: 10.1016/j.bmc.2012.02.017 contributor: fullname: Hundsdörfer – volume: 374 start-page: 639 year: 2003 ident: 10.1016/j.bioorg.2020.104062_b0090 article-title: Biochemical and three-dimensional-structural study of the specific inhibition of protein kinase CK2 by [5-oxo-5,6-dihydroindolo-(1,2-a)quinazolin-7-yl]acetic acid (IQA) publication-title: Biochem. J. doi: 10.1042/bj20030674 contributor: fullname: Sarno – volume: 1 start-page: 25 year: 2015 ident: 10.1016/j.bioorg.2020.104062_b0220 article-title: The synthesis of combinatorial row of aurone derivatives as potential inhibitors of protein kinase CK2 publication-title: Ukr. Bioorg. Acta contributor: fullname: Vdovin – volume: 18 start-page: 167 year: 2004 ident: 10.1016/j.bioorg.2020.104062_b0255 article-title: VEGA – an open platform to develop chemo-bio-informatics applications, using plug-in architecture and script programming publication-title: J. Comput. Aided Mol. Des. doi: 10.1023/B:JCAM.0000035186.90683.f2 contributor: fullname: Pedretti – volume: 51 start-page: 752 year: 2008 ident: 10.1016/j.bioorg.2020.104062_b0075 article-title: Coumarin as attractive Casein Kinase 2 (CK2) inhibitor scaffold: an integrate approach to elucidate the putative binding motif and explain structure-activity relationships publication-title: J. Med. Chem. doi: 10.1021/jm070909t contributor: fullname: Chilin – volume: 1 start-page: 968 year: 2006 ident: 10.1016/j.bioorg.2020.104062_b0260 article-title: Assay of protein kinases using radiolabeled ATP: a protocol publication-title: Nat. Protoc. doi: 10.1038/nprot.2006.149 contributor: fullname: Hastie – volume: 13 start-page: 1019 year: 2007 ident: 10.1016/j.bioorg.2020.104062_b0045 article-title: Protein kinase CK2α as an unfavorable prognostic marker and novel therapeutic target in acute myeloid leukemia publication-title: Clin. Cancer Res. doi: 10.1158/1078-0432.CCR-06-1602 contributor: fullname: Jin – volume: 20 start-page: 3247 year: 2001 ident: 10.1016/j.bioorg.2020.104062_b0035 article-title: Protein kinase CK2 in mammary gland tumorigenesis publication-title: Oncogene doi: 10.1038/sj.onc.1204411 contributor: fullname: Landesman-Bollag – volume: 62 start-page: 1803 year: 2019 ident: 10.1016/j.bioorg.2020.104062_b0160 article-title: 2-aminothiazole derivatives as selective allosteric modulators of the protein kinase CK2. 1. Identification of an allosteric binding site publication-title: J. Med. Chem. doi: 10.1021/acs.jmedchem.8b01766 contributor: fullname: Bestgen – volume: 9 start-page: 15893 year: 2019 ident: 10.1016/j.bioorg.2020.104062_b0185 article-title: Discovery of holoenzyme-disrupting chemicals as substrate-selective CK2 inhibitors publication-title: Sci. Rep. doi: 10.1038/s41598-019-52141-5 contributor: fullname: Kufareva – volume: 30 start-page: 2785 year: 2009 ident: 10.1016/j.bioorg.2020.104062_b0250 article-title: Software news and updates AutoDock4 and AutoDockTools4: automated docking with selective receptor flexibility publication-title: J. Comput. Chem. doi: 10.1002/jcc.21256 contributor: fullname: Morris – volume: 177 start-page: 382 year: 2012 ident: 10.1016/j.bioorg.2020.104062_b0085 article-title: Structural and functional analysis of the flexible regions of the catalytic α-subunit of protein kinase CK2 publication-title: J. Struct. Biol. doi: 10.1016/j.jsb.2011.12.007 contributor: fullname: Papinutto – volume: 9 start-page: 3041 year: 2018 ident: 10.1016/j.bioorg.2020.104062_b0180 article-title: Second-generation CK2α inhibitors targeting the αD pocket publication-title: Chem. Sci. doi: 10.1039/C7SC05122K contributor: fullname: Iegre – volume: 115 start-page: 148 year: 2016 ident: 10.1016/j.bioorg.2020.104062_b0100 article-title: Design and synthesis of novel protein kinase CK2 inhibitors on the base of 4-aminothieno[2,3-d]pyrimidines publication-title: Eur. J. Med. Chem. doi: 10.1016/j.ejmech.2016.03.004 contributor: fullname: Ostrynska – volume: 202 start-page: 141 year: 1994 ident: 10.1016/j.bioorg.2020.104062_b0020 article-title: Asymmetric expression of protein kinase CK2 subunits in human kidney tumors publication-title: Biochem. Biophys. Res. Commun. doi: 10.1006/bbrc.1994.1904 contributor: fullname: Stalter – volume: 115 start-page: 182 year: 2005 ident: 10.1016/j.bioorg.2020.104062_b0065 article-title: Spinal CK2 regulates nociceptive signaling in models of inflammatory pain publication-title: Pain doi: 10.1016/j.pain.2005.02.025 contributor: fullname: Li – volume: 17 start-page: 349 year: 2003 ident: 10.1016/j.bioorg.2020.104062_b0005 article-title: One-thousand-and-one substrates of protein kinase CK2? publication-title: FASEB J. doi: 10.1096/fj.02-0473rev contributor: fullname: Meggio – volume: 96 start-page: 396 year: 2015 ident: 10.1016/j.bioorg.2020.104062_b0190 article-title: Identification of protein kinase CK2 inhibitors using solvent dipole ordering virtual screening publication-title: Eur. J. Med. Chem. doi: 10.1016/j.ejmech.2015.04.032 contributor: fullname: Nakanishi – volume: 86 start-page: 887 year: 2008 ident: 10.1016/j.bioorg.2020.104062_b0060 article-title: Protein kinase CK2, an important regulator of the inflammatory response? publication-title: J. Mol. Med. doi: 10.1007/s00109-008-0352-0 contributor: fullname: Singh – volume: 12 start-page: 885 year: 2017 ident: 10.1016/j.bioorg.2020.104062_b0245 article-title: Lipophilicity and biomimetic properties to support drug discovery publication-title: Expert Opin. Drug Discov. doi: 10.1080/17460441.2017.1344210 contributor: fullname: Tsopelas – volume: 8 start-page: 279 year: 2015 ident: 10.1016/j.bioorg.2020.104062_b0140 article-title: Synthesis, biological evaluation and molecular modeling of substituted indeno[1,2-b]indoles as inhibitors of human protein kinase CK2 publication-title: Pharmaceuticals doi: 10.3390/ph8020279 contributor: fullname: Alchab – volume: 356 start-page: 107 year: 2011 ident: 10.1016/j.bioorg.2020.104062_b0120 article-title: Structure-based discovery of novel flavonol inhibitors of human protein kinase CK2 publication-title: Mol. Cell. Biochem. doi: 10.1007/s11010-011-0945-8 contributor: fullname: Golub – volume: 54 start-page: 2262 year: 1994 ident: 10.1016/j.bioorg.2020.104062_b0015 article-title: Activation of a tumor-associated protein kinase (p40TAK) and casein kinase 2 in human squamous cell carcinomas and adenocarcinomas of the lung publication-title: Cancer Res. contributor: fullname: Daya-Makin – volume: 116 start-page: 2724 year: 2010 ident: 10.1016/j.bioorg.2020.104062_b0055 article-title: Targeting CK2 overexpression and hyperactivation as a novel therapeutic tool in chronic lymphocytic leukemia publication-title: Blood doi: 10.1182/blood-2010-04-277947 contributor: fullname: Martins – volume: 10 year: 2017 ident: 10.1016/j.bioorg.2020.104062_b0215 article-title: Structural hypervariability of the two human protein kinase CK2 catalytic subunit paralogs revealed by complex structures with a flavonoland a thieno[2,3-d]pyrimidine-based inhibitor publication-title: Pharmaceuticals doi: 10.3390/ph10010009 contributor: fullname: Niefind – volume: 61 start-page: 6401 year: 2018 ident: 10.1016/j.bioorg.2020.104062_b0230 article-title: Lipophilic efficiency as an important metric in drug design publication-title: J. Med. Chem. doi: 10.1021/acs.jmedchem.8b00077 contributor: fullname: Johnson – volume: 5 start-page: 113 year: 2013 ident: 10.1016/j.bioorg.2020.104062_b0240 article-title: Lipophilic efficiency: the most important efficiency metric in medicinal chemistry publication-title: Future Med. Chem. doi: 10.4155/fmc.12.208 contributor: fullname: Freeman-Cook – volume: 51 start-page: 265 year: 1995 ident: 10.1016/j.bioorg.2020.104062_b0200 article-title: 4,6-Dimethyl-2-(4-nitrobenzylidene)-3(2H)-benzofuranone publication-title: Acta Crystallogr. Sect. C Cryst. Struct. Commun. doi: 10.1107/S0108270194007973 contributor: fullname: Goud – volume: 26 start-page: 3016 year: 2018 ident: 10.1016/j.bioorg.2020.104062_b0165 article-title: Novel non-ATP competitive small molecules targeting the CK2 α/β interface publication-title: Bioorg. Med. Chem. doi: 10.1016/j.bmc.2018.05.011 contributor: fullname: Brear – volume: 94 start-page: 487 year: 2002 ident: 10.1016/j.bioorg.2020.104062_b0195 article-title: Enzymology of aurone biosynthesis publication-title: J. Biosci. Bioeng. doi: 10.1016/S1389-1723(02)80184-0 contributor: fullname: Nakayama – volume: 50 start-page: 8478 year: 2011 ident: 10.1016/j.bioorg.2020.104062_b0155 article-title: Unprecedented selectivity and structural determinants of a new class of protein kinase CK2 inhibitors in clinical trials for the treatment of cancer publication-title: Biochemistry doi: 10.1021/bi2008382 contributor: fullname: Battistutta – volume: 585 start-page: 104 year: 2011 ident: 10.1016/j.bioorg.2020.104062_b0150 article-title: Structural basis of CX-4945 binding to human protein kinase CK2 publication-title: FEBS Lett. doi: 10.1016/j.febslet.2010.11.019 contributor: fullname: Ferguson – volume: 19 start-page: 4406 year: 2009 ident: 10.1016/j.bioorg.2020.104062_b0235 article-title: Rapid assessment of a novel series of selective CB2 agonists using parallel synthesis protocols: a Lipophilic Efficiency (LipE) analysis publication-title: Bioorganic Med. Chem. Lett. doi: 10.1016/j.bmcl.2009.05.062 contributor: fullname: Ryckmans – volume: 10 year: 2017 ident: 10.1016/j.bioorg.2020.104062_b0125 article-title: Unexpected binding mode of a potent indeno[1,2-b]indole-type inhibitor of protein kinase CK2 revealed by complex structures with the catalytic subunit CK2α and its paralog CK2α’ publication-title: Pharmaceuticals doi: 10.3390/ph10040098 contributor: fullname: Hochscherf – volume: 10 start-page: 8 year: 2017 ident: 10.1016/j.bioorg.2020.104062_b0130 article-title: Development of pharmacophore model for indeno[1,2-b]indoles as human protein kinase CK2 inhibitors and database mining publication-title: Pharmaceuticals doi: 10.3390/ph10010008 contributor: fullname: Haidar – volume: 1784 start-page: 143 year: 2008 ident: 10.1016/j.bioorg.2020.104062_b0105 article-title: Evaluation of 4,5,6,7-tetrahalogeno-1H-isoindole-1,3(2H)-diones as inhibitors of human protein kinase CK2 publication-title: Biochim. Biophys. Acta – Proteins Proteomics doi: 10.1016/j.bbapap.2007.10.009 contributor: fullname: Golub – volume: 67 year: 2011 ident: 10.1016/j.bioorg.2020.104062_b0205 article-title: (Z)-2-(4-Nitrobenzylidene)-1-benzofuran-3(2H)-one publication-title: Acta Crystallogr. Sect. E Struct. Reports Online doi: 10.1107/S1600536811041869 contributor: fullname: Reddy – volume: 46 start-page: 870 year: 2011 ident: 10.1016/j.bioorg.2020.104062_b0095 article-title: Synthesis and biological evaluation of substituted (thieno[2,3-d]pyrimidin- 4-ylthio)carboxylic acids as inhibitors of human protein kinase CK2 publication-title: Eur. J. Med. Chem. doi: 10.1016/j.ejmech.2010.12.025 contributor: fullname: Golub – volume: 51 start-page: 6097 year: 2012 ident: 10.1016/j.bioorg.2020.104062_b0110 article-title: Inhibition of protein kinase CK2 by flavonoids and tyrphostins. A structural insight publication-title: Biochemistry doi: 10.1021/bi300531c contributor: fullname: Lolli – volume: 25 start-page: 3471 year: 2017 ident: 10.1016/j.bioorg.2020.104062_b0175 article-title: A fragment-based approach leading to the discovery of a novel binding site and the selective CK2 inhibitor CAM4066 publication-title: Bioorg. Med. Chem. doi: 10.1016/j.bmc.2017.04.037 contributor: fullname: De Fusco – volume: 108 start-page: 1698 year: 2006 ident: 10.1016/j.bioorg.2020.104062_b0040 article-title: Multiple myeloma cell survival relies on high activity of protein kinase CK2 publication-title: Blood doi: 10.1182/blood-2005-11-013672 contributor: fullname: Piazza – volume: 22 start-page: 341 year: 2000 ident: 10.1016/j.bioorg.2020.104062_b0025 article-title: Antisense oligonucleotides against protein kinase CK2-α inhibit growth of squamous cell carcinoma of the head and neck in vitro publication-title: Head Neck doi: 10.1002/1097-0347(200007)22:4<341::AID-HED5>3.0.CO;2-3 contributor: fullname: Faust – volume: 67 year: 2011 ident: 10.1016/j.bioorg.2020.104062_b0210 article-title: (Z)-2-(2-Hydroxy-4-methoxybenzylidene)-1-benzofuran-3(2 H)-one publication-title: Acta Crystallogr. Sect. E Struct. Reports Online doi: 10.1107/S1600536811016217 contributor: fullname: Satyanarayana Reddy – volume: 24 start-page: 11 year: 1994 ident: 10.1016/j.bioorg.2020.104062_b0030 article-title: Nuclear casein kinase 2 (CK-2) activity in human normal, benign hyperplastic, and cancerous prostate publication-title: Prostate doi: 10.1002/pros.2990240105 contributor: fullname: Yenice |
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•New substituted benzylidenebenzofuran-3(2H)-ones were synthesized.•41 aurones inhibited CK2 with IC50 in nanomolar range of values.•The most... In this work, we describe the design, synthesis and SAR studies of 2-benzylidenebenzofuran-3-ones (aurones), a new family of potent inhibitors of CK2. A series... |
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| StartPage | 104062 |
| SubjectTerms | 2-benzylidenebenzofuran-3-ones Aurone Benzofurans - pharmacology Benzofurans - therapeutic use Casein Kinase II - chemistry Flavones - pharmacology Flavones - therapeutic use Humans In vitro biochemical assay Molecular docking Molecular Docking Simulation - methods Protein kinase CK2 inhibitor Structure-Activity Relationship Virtual screening |
| Title | Flavone inspired discovery of benzylidenebenzofuran-3(2H)-ones (aurones) as potent inhibitors of human protein kinase CK2 |
| URI | https://dx.doi.org/10.1016/j.bioorg.2020.104062 https://www.ncbi.nlm.nih.gov/pubmed/32683178 https://search.proquest.com/docview/2425590017 |
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