Design and synthesis of a cell-permeable, drug-like small molecule inhibitor targeting the polo-box domain of polo-like kinase 1

PLoS ONE

Volumn 9, Issue 9, 2014, Pages

  Srinivasrao, Ganipisetti ^a   Park, Jung Eun ^b   Kim, Sungmin ^a   Ahn, Mija ^a   Cheong, Chaejoon ^a   Nam, Ky Youb ^c   Gunasekaran, Pethaiah ^d   Hwang, Eunha ^a   Kim, Nam Hyung ^d   Shin, Song Yub ^e   Lee, Kyung S ^b   Ryu, Eunkyung ^a   Bang, Jeong Kyu ^a  

^a Korea Basic Science Institute (KBSI)   (South Korea)

^b NATIONAL CANCER INSTITUTE   (United States)

^c Asan Medical Center   (South Korea)

^d Chungbuk National University   (South Korea)

^e Chosun University College of Medicine   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

1 (4 METHOXYBENZYL) 2 (4 PHENYLBUTYL) 1H BENZO[D]IMIDAZOLE 5 CARBOXYLIC ACID; 1 (4 PHENYLBUTYL) 1H BENZO[D]IMIDAZOLE 5 CARBOXYLATE; 1 PHENETHYL 2 (4 PHENYLBUTYL) 1H BENZO[D]IMIDAZOLE 5 CARBOXYLIC ACID; 2 (4 METHOXYPHENYL) 1 (4 PHENYLBUTYL) 1H BENZO[D]IMIDAZOLE 5 CARBOXYLIC ACID; ANTINEOPLASTIC AGENT; BG 34; DIBENZYL [1 PHENETHYL 2 (4 PHENYLBUTYL) 1H BENZO[D]IMIDAZOL 5 YL]METHYL PHOSPHATE; METHYL 1 (4 METHOXYBENZYL) 2 (4PHENYLBUTYL) 1H BENZO[D]IMIDAZOLE 5 CARBOXYLATE; METHYL 1 (4 PHENYLBUTYL) 1H BENZO[D]IMIDAZOLE 5 CARBOXYLATE; METHYL 1 PHENETHYL 2 (4 PHENYLBUTYL) 1H BENZO[D]IMIDAZOLE 5 CARBOXYLATE; METHYL 2 (4 METHOXYPHENYL) 1 (4 PHENYLBUTYL) 1H BENZO[D]IMIDAZOLE 5 CARBOXYLATE; METHYL 2 (4 METHOXYPHENYL) 1H BENZO[D]IMIDAZOLE 5 CARBOXYLATE; N (4 METHOXYBENZYL) 5 PHENYLPENTANAMIDE; N PHENETHYL 5 PHENYLPENTANAMIDE; POLO LIKE KINASE 1; UNCLASSIFIED DRUG; [1 (4 METHOXYBENZYL) 2 (4 PHENYLBUTYL) 1H BENZO[D]IMIDAZOL 5 YL]METHANOL; [1 BENZYL 2 (4 PHENYLBUTYL) 1H BENZO[D]IMIDAZOL 5 YL]METHYL DIHYDROGEN PHOSPHATE; [1 PHENETHYL 2 (4 PHENYLBUTYL) 1H BENZO[D]IMIDAZOL 5 YL]METHYL DIHYDROGEN PHOSPHATE; [2 (4 CYCLOHEXYLBUTYL) 1 PHENETHYL 1H BENZO[D]IMIDAZOL 5 YL]METHYL DIHYDROGEN PHOSPHATE; [2 HEPTYL 1 (4 PHENYLBUTYL) 1 PHENETHYL 1H BENZO[D]IMIDAZOL 5 YL]METHYL DIHYDROGEN PHOSPHATE;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; BINDING AFFINITY; CELL MEMBRANE PERMEABILITY; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG PROTEIN BINDING; ENZYME INHIBITION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; MOLECULAR MODEL; PROTEIN BINDING; PROTEIN FUNCTION; PROTEIN INTERACTION; PROTEIN STABILITY; PROTEIN STRUCTURE; PROTEIN SYNTHESIS; PROTEIN TRANSPORT; THIN LAYER CHROMATOGRAPHY;

EID: 84957727850     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0107432     Document Type: Article

References (36)

1. Barr FA, Sillje HH, Nigg EA (2004) Polo-like kinases and the orchestration of cell division. Nat Rev Mol Cell Biol 5: 429-40.
2. Van Vugt MA, Medema RH (2005) Getting in and out of mitosis with Polo-like kinase-1. Oncogene 24: 2844-59.
3. Nigg EA (1998) Polo-like kinases: positive regulators of cell division from start to finish. Curr Opin Cell Biol 10(6): 776-83.
4. Glover DM, Ohkura H, Tavares A (1996) Polo kinase: the choreographer of the mitotic stage. J Cell Biol 135: 1681-4.
5. Glover DM, Hagan IM, Tavares AA (1998) Polo-like kinases: a team that plays throughout mitosis. Genes Dev 12: 3777-87.
6. Donaldson MM, Tavares AA, Hagan IM, Nigg EA, Glover DM (2001) The mitotic roles of Polo-like kinase. J Cell Sci 114: 2357-8.
7. Strebhardt K, Ullrich A (2006) Targeting polo-like kinase 1 for cancer therapy. Nat Rev Cancer 6: 321.
8. Eckerdt F, Yuan J, Strebhardt K (2005) Polo-like kinases and oncogenesis. Oncogene 24: 267-276.
9. Takai N, Hamanaka R, Yoshimatsu J, Miyakawa I (2005) Polo-like kinases (Plks) and cancer. Oncogene 24: 287-291.
10. Burns TF, Fei P, Scata KA, Dicker DT, El-Deiry WS (2003) Silencing of the novel p53 target gene Snk/Plk2 leads to mitotic catastrophe in paclitaxel (taxol)- exposed cells. Mol Cell Biol 23: 5556-5571.
11. Xie S, Xie B, Lee MY, Dai W (2005) Regulation of cell cycle checkpoints by polo-like kinases. Oncogene 24: 277-286.
12. Elia AEH, Cantley LC, Yaffe MB (2003) Proteomic screen finds pSer/pThrbinding domain localizing Plk1 to mitotic substrates. Science 299: 1228-123.
13. Elia AEH, Rellos P, Haire LF, Chao JW, Lvins FJ, et al. (2003) The molecular basis for phosphodependent substrate targeting and regulation of Plks by the polo-box domain. Cell 15: 83-95.
14. Cheng KY, Lowe ED, Sinclair J, Nigg EA, Johnson LN (2003) The crystal structure of the human polo-like kinase-1 polo box domain and its phosphopeptide complex. EMBO J 22: 5757-5768.
15. Reindl W, Yuan J, Kramer A, Strebhardt K, Berg T (2008) Inhibition of pololike kinase 1 by blocking polobox domain-dependent protein-protein interactions. Chem Biol 15: 459-466.
16. Yun SM, Moulaei T, Lim D, Bang JK, Park JE, et al. (2009) Structural and functional analyses of minimal phosphopeptides targeting the polo-box domain of polo-like kinase 1. Nat Struct Mol Biol 16: 876-882.
17. Watanabe N, Sekine T, Takagi M, Iwasaki J, Imamoto N, et al. (2009) Deficiency in chromosome congression by the inhibition of Plk1 polo box domain-dependent recognition. J Biol Chem 284: 2344-2353.
18. Park JE, Soung NK, Johmura Y, Kang YH, Liao C, et al. (2010) Polo-box domain: a versatile mediator of polo-like kinase function. Cell Mol Life Sci 67: 1957-1970.
19. Murugan RN, Park JE, Kim EH, Shin SY, Cheong C, et al. (2011) Plk1-targeted small molecule inhibitors: molecular basis for their potency and specificity. Mol Cells 32: 209-220.
20. Kang YH, Park JE, Yu LR, Soung KK, Yun SM, et al. (2006) Self-regulated Plk1 recruitment to kinetochores by the Plk1-PBIP1 interaction is critical for proper chromosome segregation. Mol Cell 24: 409-422.
21. Sledz P, Stubbs CJ, Lang S, Yang YQ, McKenzie GJ, et al. (2011) From crystal packing to molecular recognition: prediction and discovery of a binding site on the surface of polo-like kinase 1. Angew Chem Int Ed Engl 50: 4003-4006.
22. Liu F, Park JE, Qian WJ, Lim D, Garber M, et al. (2011) Serendipitous alkylation of a Plk1 ligand uncovers a new binding channel. Nat Chem Biol 7: 595-601.
23. McInnes C, Estes K, Baxter M, Yang Z, Farag DB, et al. (2012) Targeting subcellular localization through the polo-box domain: non- ATP competitive inhibitors recapitulate a PLK1 phenotype. Mol Cancer Ther 11: 1683-1692.
24. Liu F, Park JE, Qian WJ, Lim D, Scharow A, et al. (2012) Identification of high affinity polo-like kinase 1 (Plk1) polo-box domain binding peptides using oximebased diversification. ACS Chem Biol 7: 805-810.
25. Liu F, Park JE, Qian WJ, Lim D, Scharow A, et al. (2012) Peptoid-peptide hybrid ligands targeting the polo box domain of polo-like kinase 1. Chembiochem 13: 1291-1296.
26. Qian WJ, Park JE, Lee KS, Burke TR Jr (2012)Non-proteinogenic amino acids in the pThr-2 position of a pentamer peptide that confer high binding affinity for the polobox domain (PBD) of polo-like kinase 1 (Plk1). Bioorg Med Chem Lett 15: 7306-08.
27. ͆ledź P, Lang S, Stubbs CJ, Abell C (2012) High-throughput interrogation of ligand binding mode using a fluorescence-based assay. Angew Chem Int Ed 51: 7680-7683.
28. Qian W, Park JE, Liu F, Lee KS, Burke TR Jr (2013) Effects on pololike kinase 1 polo-box domain binding affinities of peptides incurred by structural variation at the phosphoamino acid position. Bioorg Med Chem 21: 3996-4003.
29. Murugan RN, Park JE, Lim D, Ahn M, Cheong C, et al. (2013) Development of cyclic peptomer inhibitors targeting the polo-box domain of polo-like kinase 1. Bioorg Med Chem 21: 2623-2634.
30. Murugan RN, Ahn M, Lee WC, Kim HY, Song JH, et al. (2013) Exploring the Binding Nature of Pyrrolidine Pocket-Dependent Interactions in the Polo-Box Domain of Polo-Like Kinase 1. PLoS One 8: e80043.
31. Liao C, Park JE, Bang JK, Nicklaus MC, Lee KS (2010) Probing Binding Modes of Small Molecule Inhibitors to the Polo-Box Domain of Human Polo-like Kinase 1. ACS Med Chem Lett 1: 110-114.
32. Garciá-Alvarez B, de CG, Ibanez S, Bragado-Nilsson E, Montoya G (2007) Molecular and structural basis of polo-like kinase 1 substrate recognition: implications in centrosomal localization. Proc Natl Acad Sci USA 104: 3107-3112.
33. Horton DA, Bourne GT, Smythe ML (2003) The Combinatorial Synthesis of Bicyclic Privileged Structures or Privileged Substructures. Chem Rev 103: 893-930.
34. Alonso J, Halland N, Nazaré M, R'kyek O, Urmann M, et al. (2011) A Direct, Regioselective Palladium-Catalyzed Synthesis of N-Substituted Benzimidazoles and Imidazopyridines. Eur J Org Chem: 234-237.
35. Bang JK, Yamaguchi H, Durell SR, Appella E, Appella DH (2008) A Small Molecular Scaffold for Selective Inhibition of Wip1 Phosphatase. ChemMed- Chem 3: 230-232.
36. Xiangming H, Huiqiang M, Yulu W (2007) p-TsOH Catalyzed synthesis of 2- arylsubstituted benzimidazoles. Arkivoc 13: 150-154.