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Development of cyclic peptomer inhibitors targeting the polo-box domain of polo-like kinase 1.

Murugan RN, Park JE, Lim D, Ahn M, Cheong C, Kwon T, Nam KY, Choi SH, Kim BY, Yoon DY, Yaffe MB, Yu DY, Lee KS, Bang JK
Bioorg Med Chem 21 2623-34 (2013)
Cited: 26 times
EuropePMC logo PMID: 23498919

Abstract

The polo-box domain (PBD) of polo-like kinase 1 (Plk1) is essentially required for the function of Plk1 in cell proliferation. The availability of the phosphopeptide-binding pocket on PBD provides a unique opportunity to develop novel protein-protein interaction inhibitors. Recent identification of a minimal 5-residue-long phosphopeptide, PLHSpT, as a Plk1 PBD-specific ligand has led to the development of several peptide-based inhibitors, but none of them is cyclic peptide. Through the combination of single-peptoid mimics and thio-ether bridged cyclization, we successfully demonstrated for the first time two cyclic peptomers, PL-116 and PL-120, dramatically improved the binding affinity without losing mono-specificity against Plk1 PBD in comparison with the linear parental peptide, PLHSpT. These cyclic peptomers could serve as promising templates for future drug designs to inhibit Plk1 PBD.

Articles - 4hy2 mentioned but not cited (2)

  1. Exploring the binding nature of pyrrolidine pocket-dependent interactions in the polo-box domain of polo-like kinase 1. Murugan RN, Ahn M, Lee WC, Kim HY, Song JH, Cheong C, Hwang E, Seo JH, Shin SY, Choi SH, Park JE, Bang JK. PLoS ONE 8 e80043 (2013)
  2. Dynamic and multi-pharmacophore modeling for designing polo-box domain inhibitors. Sakkiah S, Senese S, Yang Q, Lee KW, Torres JZ. PLoS ONE 9 e101405 (2014)


Reviews citing this publication (7)

  1. Modulating protein-protein interactions: the potential of peptides. Nevola L, Giralt E. Chem. Commun. (Camb.) 51 3302-3315 (2015)
  2. Recent Advances and New Strategies in Targeting Plk1 for Anticancer Therapy. Lee KS, Burke TR, Park JE, Bang JK, Lee E. Trends Pharmacol. Sci. 36 858-877 (2015)
  3. Targeting kinase signaling pathways with constrained peptide scaffolds. Hanold LE, Fulton MD, Kennedy EJ. Pharmacol. Ther. 173 159-170 (2017)
  4. Current progress and future perspectives in the development of anti-polo-like kinase 1 therapeutic agents. Park JE, Hymel D, Burke TR, Lee KS. F1000Res 6 1024 (2017)
  5. Inhibitors of the Polo-Box Domain of Polo-Like Kinase 1. Berg A, Berg T. Chembiochem 17 650-656 (2016)
  6. Putting a bit into the polo-box domain of polo-like kinase 1. Park JE, Kim TS, Meng L, Bang JK, Kim BY, Lee KS. J Anal Sci Technol 6 27 (2015)
  7. Recent Trends in Cyclic Peptides as Therapeutic Agents and Biochemical Tools. Choi JS, Joo SH. Biomol Ther (Seoul) 28 18-24 (2020)

Articles citing this publication (17)

  1. Design and synthesis of a cell-permeable, drug-like small molecule inhibitor targeting the polo-box domain of polo-like kinase 1. Srinivasrao G, Park JE, Kim S, Ahn M, Cheong C, Nam KY, Gunasekaran P, Hwang E, Kim NH, Shin SY, Lee KS, Ryu E, Bang JK. PLoS ONE 9 e107432 (2014)
  2. An easy-to-detect nona-arginine peptide for epidermal targeting. Clède S, Delsuc N, Laugel C, Lambert F, Sandt C, Baillet-Guffroy A, Policar C. Chem. Commun. (Camb.) 51 2687-2689 (2015)
  3. Neighbor-directed histidine N (τ)-alkylation: A route to imidazolium-containing phosphopeptide macrocycles. Qian WJ, Park JE, Grant R, Lai CC, Kelley JA, Yaffe MB, Lee KS, Burke TR. Biopolymers 104 663-673 (2015)
  4. Application of oxime-diversification to optimize ligand interactions within a cryptic pocket of the polo-like kinase 1 polo-box domain. Zhao XZ, Hymel D, Burke TR. Bioorg. Med. Chem. Lett. 26 5009-5012 (2016)
  5. Structural basis for recognition of Emi2 by Polo-like kinase 1 and development of peptidomimetics blocking oocyte maturation and fertilization. Jia JL, Han YH, Kim HC, Ahn M, Kwon JW, Luo Y, Gunasekaran P, Lee SJ, Lee KS, Kyu Bang J, Kim NH, Namgoong S. Sci Rep 5 14626 (2015)
  6. Structural features of peptoid-peptide hybrids in lipid-water interfaces. Uggerhøj LE, Munk JK, Hansen PR, Güntert P, Wimmer R. FEBS Lett. 588 3291-3297 (2014)
  7. Conformational preferences of peptide-peptoid hybrid oligomers. Butterfoss GL, Drew K, Renfrew PD, Kirshenbaum K, Bonneau R. Biopolymers 102 369-378 (2014)
  8. Design, synthesis, and evaluation of non-ATP-competitive small-molecule Polo-like kinase 1 (Plk1) inhibitors. Chen DX, Huang J, Liu M, Xu YG, Jiang C. Arch. Pharm. (Weinheim) 348 2-9 (2015)
  9. Structural analysis of the polo-box domain of human Polo-like kinase 2. Kim JH, Ku B, Lee KS, Kim SJ. Proteins 83 1201-1208 (2015)
  10. A Rapid and Efficient Building Block Approach for Click Cyclization of Peptoids. Samarasimhareddy M, Shamir M, Shalev DE, Hurevich M, Friedler A. Front Chem 8 405 (2020)
  11. Histidine N(τ)-cyclized macrocycles as a new genre of polo-like kinase 1 polo-box domain-binding inhibitors. Hymel D, Grant RA, Tsuji K, Yaffe MB, Burke TR. Bioorg. Med. Chem. Lett. 28 3202-3205 (2018)
  12. Identification of indole-3-carboxylic acids as non-ATP-competitive Polo-like kinase 1 (Plk1) inhibitors. Liu M, Huang J, Chen DX, Jiang C. Bioorg. Med. Chem. Lett. 25 431-434 (2015)
  13. Novel Macrocyclic Peptidomimetics Targeting the Polo-Box Domain of Polo-Like Kinase 1. Ryu S, Park JE, Ham YJ, Lim DC, Kwiatkowski NP, Kim DH, Bhunia D, Kim ND, Yaffe MB, Son W, Kim N, Choi TI, Swain P, Kim CH, Lee JY, Gray NS, Lee KS, Sim T. J Med Chem 65 1915-1932 (2022)
  14. Pyrrole-Based Macrocyclic Small-Molecule Inhibitors That Target Oocyte Maturation. Gunasekaran P, Lee SR, Jeong SM, Kwon JW, Takei T, Asahina Y, Bang G, Kim S, Ahn M, Ryu EK, Kim HN, Nam KY, Shin SY, Hojo H, Namgoong S, Kim NH, Bang JK. ChemMedChem 12 580-589 (2017)
  15. Synthesis of the natural product descurainolide and cyclic peptides from lignin-derived aromatics. Ojo OS, Nardone B, Musolino SF, Neal AR, Wilson L, Lebl T, Slawin AMZ, Cordes DB, Taylor JE, Naismith JH, Smith AD, Westwood NJ. Org. Biomol. Chem. 16 266-273 (2018)
  16. DNA Three Way Junction Core Decorated with Amino Acids-Like Residues-Synthesis and Characterization. Addamiano C, Gerland B, Payrastre C, Escudier JM. Molecules 21 (2016)
  17. Macrocyclization enhances affinity of chemokine-binding peptoids. Brahm K, Wack JS, Eckes S, Engemann V, Schmitz K. Biopolymers 110 e23244 (2019)


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