Hend Khalifa, Ahmed K. ElHady, Ting Liu, Walid A.M. Elgaher, Odile Filhol, Claude Cochet, Ashraf H. Abadi, Mostafa M. Hamed, Mohammad Abdel-Halim, Matthias Engel
{"title":"发现具有不寻常基本支架的新型选择性 CK2 抑制剂类别","authors":"Hend Khalifa, Ahmed K. ElHady, Ting Liu, Walid A.M. Elgaher, Odile Filhol, Claude Cochet, Ashraf H. Abadi, Mostafa M. Hamed, Mohammad Abdel-Halim, Matthias Engel","doi":"10.1016/j.ejmech.2024.117048","DOIUrl":null,"url":null,"abstract":"CK2 is a Ser/Thr-protein kinase playing a crucial role in promoting cell growth and survival, hence it is considered a promising target for anti-cancer drugs. However, many previously reported CK2 inhibitors lack selectivity. In search of novel scaffolds for selective CK2 inhibition, we identified a dihydropyrido-thieno[2,3-<em>d</em>]pyrimidine derivative displaying submicromolar inhibitory activity against CK2α. This scaffold captured our interest because of the basic secondary amine, a rather unusual motif for CK2 inhibitors. Our optimization strategy comprised the incorporation of a 4-piperazinyl moiety as a linker group and introduction of varying substituents on the pendant phenyl ring. All resulting compounds exhibited potent CK2α inhibition, with IC<sub>50</sub> values in the nanomolar range. Compound <strong>10b</strong> demonstrated the most balanced activity profile with a cell-free IC<sub>50</sub> value of 36.7 nM and a notable cellular activity with a GI<sub>50</sub> of 7.3 μM and 7.5 μM against 786-O renal cell carcinoma and U937 lymphoma cells, respectively. <strong>10b</strong> displayed excellent selectivity when screened against a challenging kinase selectivity profiling panel. Moreover, <strong>10b</strong> inhibited CK2 in the cells, albeit less potently than CX-4945, but induced cell death more strongly than CX-4945. Altogether, we have identified a novel CK2 inhibitory scaffold with drug-like physicochemical properties in a favorable basic pKa range.","PeriodicalId":314,"journal":{"name":"European Journal of Medicinal Chemistry","volume":"33 1","pages":""},"PeriodicalIF":6.0000,"publicationDate":"2024-11-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Discovery of a novel, selective CK2 inhibitor class with an unusual basic scaffold\",\"authors\":\"Hend Khalifa, Ahmed K. ElHady, Ting Liu, Walid A.M. Elgaher, Odile Filhol, Claude Cochet, Ashraf H. Abadi, Mostafa M. Hamed, Mohammad Abdel-Halim, Matthias Engel\",\"doi\":\"10.1016/j.ejmech.2024.117048\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"CK2 is a Ser/Thr-protein kinase playing a crucial role in promoting cell growth and survival, hence it is considered a promising target for anti-cancer drugs. However, many previously reported CK2 inhibitors lack selectivity. In search of novel scaffolds for selective CK2 inhibition, we identified a dihydropyrido-thieno[2,3-<em>d</em>]pyrimidine derivative displaying submicromolar inhibitory activity against CK2α. This scaffold captured our interest because of the basic secondary amine, a rather unusual motif for CK2 inhibitors. Our optimization strategy comprised the incorporation of a 4-piperazinyl moiety as a linker group and introduction of varying substituents on the pendant phenyl ring. All resulting compounds exhibited potent CK2α inhibition, with IC<sub>50</sub> values in the nanomolar range. Compound <strong>10b</strong> demonstrated the most balanced activity profile with a cell-free IC<sub>50</sub> value of 36.7 nM and a notable cellular activity with a GI<sub>50</sub> of 7.3 μM and 7.5 μM against 786-O renal cell carcinoma and U937 lymphoma cells, respectively. <strong>10b</strong> displayed excellent selectivity when screened against a challenging kinase selectivity profiling panel. Moreover, <strong>10b</strong> inhibited CK2 in the cells, albeit less potently than CX-4945, but induced cell death more strongly than CX-4945. 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Discovery of a novel, selective CK2 inhibitor class with an unusual basic scaffold
CK2 is a Ser/Thr-protein kinase playing a crucial role in promoting cell growth and survival, hence it is considered a promising target for anti-cancer drugs. However, many previously reported CK2 inhibitors lack selectivity. In search of novel scaffolds for selective CK2 inhibition, we identified a dihydropyrido-thieno[2,3-d]pyrimidine derivative displaying submicromolar inhibitory activity against CK2α. This scaffold captured our interest because of the basic secondary amine, a rather unusual motif for CK2 inhibitors. Our optimization strategy comprised the incorporation of a 4-piperazinyl moiety as a linker group and introduction of varying substituents on the pendant phenyl ring. All resulting compounds exhibited potent CK2α inhibition, with IC50 values in the nanomolar range. Compound 10b demonstrated the most balanced activity profile with a cell-free IC50 value of 36.7 nM and a notable cellular activity with a GI50 of 7.3 μM and 7.5 μM against 786-O renal cell carcinoma and U937 lymphoma cells, respectively. 10b displayed excellent selectivity when screened against a challenging kinase selectivity profiling panel. Moreover, 10b inhibited CK2 in the cells, albeit less potently than CX-4945, but induced cell death more strongly than CX-4945. Altogether, we have identified a novel CK2 inhibitory scaffold with drug-like physicochemical properties in a favorable basic pKa range.
期刊介绍:
The European Journal of Medicinal Chemistry is a global journal that publishes studies on all aspects of medicinal chemistry. It provides a medium for publication of original papers and also welcomes critical review papers.
A typical paper would report on the organic synthesis, characterization and pharmacological evaluation of compounds. Other topics of interest are drug design, QSAR, molecular modeling, drug-receptor interactions, molecular aspects of drug metabolism, prodrug synthesis and drug targeting. The journal expects manuscripts to present the rational for a study, provide insight into the design of compounds or understanding of mechanism, or clarify the targets.