Helix mimetics: Recent developments

Progress in Biophysics and Molecular Biology

Volumn 119, Issue 1, 2015, Pages 33-40

  Wilson, Andrew J ^a  

^a UNIVERSITY OF LEEDS   (United Kingdom)

Author keywords

Chemical biology; Inhibitors; Protein protein interactions; Helix; Helix mimetic

Indexed keywords

BIOMIMETIC MATERIAL;

ANIMAL; CHEMISTRY; DRUG DEVELOPMENT; DRUG EFFECTS; PROCEDURES; PROTEIN PROTEIN INTERACTION; PROTEIN SECONDARY STRUCTURE;

ANIMALS; BIOMIMETIC MATERIALS; DRUG DISCOVERY; PROTEIN INTERACTION MAPS; PROTEIN STRUCTURE, SECONDARY;

EID: 84940893619     PISSN: 00796107     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.pbiomolbio.2015.05.001     Document Type: Review

References (65)

1. Azzarito V., Prabhakaran P., Bartlett A.I., Murphy N.S., Hardie M.J., Kilner C.A., Edwards T.A., Warriner S.L., Wilson A.J. 2-O-Alkylated para-benzamide α-Helix mimetics: the role of scaffold curvature. Org. Biomol. Chem. 2012, 10:6469-6472.
2. Azzarito V., Long K., Murphy N.S., Wilson A.J. Inhibition of α-helix-mediated protein-protein interactions using designed molecules. Nat. Chem. 2013, 5:161-173.
3. Azzarito V., Miles J.A., Fisher J., Edwards T.A., Warriner S., Wilson A. Stereocontrolled protein surface recognition using Chiral oligoamide proteomimetic foldamers. Chem. Sci. 2015, 6:2434-2443.
4. Barnard A., Long K., Martin H.L., Miles J.A., Edwards T.A., Tomlinson D.C., Macdonald A., Wilson A.J. Selective and potent proteomimetic inhibitors of intracellular protein-protein interactions. Angew. Chem. Int. Ed. 2015, 54:2960-2965.
5. Becerril J., Hamilton A.D. Helix mimetics as inhibitors of the interaction of the estrogen receptor with coactivator peptides. Angew. Chem. Int. Ed. 2007, 46:4471-4473.
6. Bergey C.M., Watkins A.M., Arora P.S. HippDB: a database of readily targeted helical protein-protein interactions. Bioinformatics 2013.
7. Bird G.H., Gavathiotis E., LaBelle J.L., Katz S.G., Walensky L.D. Distinct BimBH3 (BimSAHB) stapled peptides for structural and cellular studies. ACS Chem. Biol. 2013, 9:831-837.
8. Boersma M.D., Haase H.S., Peterson-Kaufman K.J., Lee E.F., Clarke O.B., Colman P.M., Smith B.J., Horne W.S., Fairlie W.D., Gellman S.H. Evaluation of diverse α/β-backbone patterns for functional α-Helix mimicry: analogues of the Bim BH3 domain. J. Am. Chem. Soc. 2011, 134:315-323.
9. Brown Z.Z., Akula K., Arzumanyan A., Alleva J., Jackson M., Bichenkov E., Sheffield J.B., Feitelson M.A., Schafmeister C.E.A. Spiroligomer α-Helix mimic that binds HDM2, penetrates human cells and stabilizes HDM2 in cell culture. PLoS ONE 2012, 7:e45948.
10. Burslem G.M., Kyle H.F., Breeze A.L., Edwards T.A., Nelson A., Warriner S.L., Wilson A.J. Small-molecule proteomimetic inhibitors of the HIF-1α-p300 protein-protein interaction. ChemBioChem 2014, 15:1083-1087.
11. Campbell F., Plante J.P., Edwards T.A., Warriner S.L., Wilson A.J. N-alkylated oligoamide α-helical proteomimetics. Org. Biomol. Chem. 2010, 8:2344-2351.
12. Cao X., Yap J., Newell-Rogers M., Peddaboina C., Jiang W., Papaconstantinou H., Jupitor D., Rai A., Jung K.-Y., Tubin R., Yu W., Vanommeslaeghe K., Wilder P., MacKerell A., Fletcher S., Smythe R. The novel BH3 alpha-helix mimetic JY-1-106 induces apoptosis in a subset of cancer cells (lung cancer, colon cancer and mesothelioma) by disrupting Bcl-xL and Mcl-1 protein-protein interactions with Bak. Mol. Cancer 2013, 12:42.
13. Chang Y.S., Graves B., Guerlavais V., Tovar C., Packman K., To K.-H., Olson K.A., Kesavan K., Gangurde P., Mukherjee A., Baker T., Darlak K., Elkin C., Filipovic Z., Qureshi F.Z., Cai H., Berry P., Feyfant E., Shi X.E., Horstick J., Annis D.A., Manning A.M., Fotouhi N., Nash H., Vassilev L.T., Sawyer T.K. Stapled α-helical peptide drug development: a potent dual inhibitor of MDM2 and MDMX for p53-dependent cancer therapy. Proc. Natl. Acad. Sci. U. S. A. 2013, 110:E3445-E3454.
14. Cummings C.G., Hamilton A.D. Disrupting protein-protein interactions with non-peptidic, small molecule α-Helix mimetics. Curr. Opin. Chem. Biol. 2010, 14:341-346.
15. Czabotar P.E., Lessene G., Strasser A., Adams J.M. Control of apoptosis by the BCL-2 protein family: implications for physiology and therapy. Nat. Rev. Mol. Cell. Biol. 2014, 15:49-63.
16. Edwards T., Wilson A. Helix-mediated protein-protein interactions as targets for intervention using foldamers. Amino Acids 2011, 41:743-754.
17. Edwards A.M., Isserlin R., Bader G.D., Frye S.V., Willson T.M., Yu F.H. Too many roads not taken. Nature 2011, 470:163-165.
18. Fedorov O., Marsden B., Pogacic V., Rellos P., Müller S., Bullock A.N., Schwaller J., Sundström M., Knapp S. A systematic interaction map of validated kinase inhibitors with Ser/Thr kinases. Proc. Natl. Acad. Sci. 2007, 104:20523-20528.
19. Frye S.V. The art of the chemical probe. Nat. Chem. Biol. 2010, 6:159-161.
20. Gavathiotis E., Suzuki M., Davis M.L., Pitter K., Bird G.H., Katz S.G., Tu H.-C., Kim H., Cheng E.H.Y., Tjandra N., Walensky L.D. BAX activation is initiated at a novel interaction site. Nature 2008, 455. 1076-U1076.
21. Hebda J.A., Saraogi I., Magzoub M., Hamilton A.D., Miranker A.D.A. Peptidomimetic approach to targeting pre-amyloidogenic States in type II diabetes. Chem. Biol. 2009, 16:943-950.
22. Hoe K.K., Verma C.S., Lane D.P. Drugging the p53 pathway: understanding the route to clinical efficacy. Nat. Rev. Drug Discov. 2014, 13:217-236.
23. Jung K.-Y., Vanommeslaeghe K., Lanning M.E., Yap J.L., Gordon C., Wilder P.T., MacKerell A.D., Fletcher S. Amphipathic α-Helix mimetics based on a 1,2-Diphenylacetylene scaffold. Org. Lett. 2013, 15:3234-3237.
24. Jung K.-Y., Wang H., Teriete P., Yap J.L., Chen L., Lanning M.E., Hu A., Lambert L.J., Holien T., Sudan A., Cosford N.D.P., Prochownik E.V., Fletcher S. Perturbation of the c-Myc-Max protein-protein interaction via synthetic α-Helix mimetics. J. Med. Chem. 2015.
25. L, Bcl-2, and MCL-1 protein-protein interactions with Bax, Bak, Bad, or Bim and induces apoptosis in a Bax- and Bim-dependent manner. J. Biol. Chem. 2011, 286:9382-9392.
26. Ko E., Liu J., Perez L.M., Lu G., Schaefer A., Burgess K. Universal peptidomimetics. J. Am. Chem. Soc. 2010, 133:462-477.
27. Ko E., Raghuraman A., Perez L.M., Ioerger T.R., Burgess K. Exploring key orientations at Protein-Protein interfaces with small molecule probes. J. Am. Chem. Soc. 2012, 135:167-173.
28. Kodadek T. Rethinking screening. Nat. Chem. Biol. 2010, 6:162-165.
29. Kussie P.H., Gorina S., Marechal V., Elenbaas B., Moreau J., Levine A.J., Pavletich N.P. Structure of the MDM2 oncoprotein bound to the p53 tumor Suppressor transactivation domain. Science 1996, 274:948-953.
30. Lao B.B., Drew K., Guarracino D.A., Brewer T.F., Heindel D.W., Bonneau R., Arora P.S. Rational design of topographical Helix mimics as potent inhibitors of protein-protein interactions. J. Am. Chem. Soc. 2014, 136:7877-7888.
31. Lao B.B., Grishagin I., Mesallati H., Brewer T.F., Olenyuk B.Z., Arora P.S. In vivo modulation of hypoxia-inducible signaling by topographical helix mimetics. Proc. Natl. Acad. Sci. U. S. A. 2014, 111:7531-7536.
32. Lee T.-K., Ahn J.-M. Solid-phase synthesis of tris-benzamides as α-Helix mimetics. ACS Comb. Sci. 2010, 13:107-111.
33. L. Angew. Chem. Int. Ed. 2009, 48:4318-4322.
34. Lee J.H., Zhang Q., Jo S., Chai S.C., Oh M., Im W., Lu H., Lim H.-S. Novel pyrrolopyrimidine-based α-Helix mimetics: cell-permeable inhibitors of Protein-Protein interactions. J. Am. Chem. Soc. 2010, 133:676-679.
35. Lee G.M., Shahian T., Baharuddin A., Gable J.E., Craik C.S. Enzyme inhibition by allosteric capture of an inactive conformation. J. Mol. Biol. 2011, 411:999-1016.
36. Lim Z., Duggan P.J., Meyer A.G., Tuck K.L. An iterative in silico and modular synthetic approach to aqueous soluble tercyclic [small alpha]-helix mimetics. Org. Biomol. Chem. 2014, 12:4432-4444.
37. Long K., Edwards T.A., Wilson A.J. Microwave assisted solid phase synthesis of highly functionalized N-alkylated oligobenzamide α-helix mimetics. Bioorg. Med. Chem. 2013, 21:4034-4040.
38. Lu F., Chi S.-W., Kim D.-H., Han K.-H., Kuntz I.D., Guy R.K. Proteomimetic libraries: design, synthesis, and evaluation of p53-MDM2 interaction inhibitors. J. Comb. Chem. 2006, 8:315-325.
39. Marimganti S., Cheemala M.N., Ahn J.-M. Novel amphiphilic α-helix mimetics based on a bis-benzamide scaffold. Org. Lett. 2009, 11:4418-4421.
40. Martucci W.E., Rodriguez J.M., Vargo M.A., Marr M., Hamilton A.D., Anderson K.S. Exploring novel strategies for AIDS protozoal pathogens: [small alpha]-helix mimetics targeting a key allosteric protein-protein interaction in C. hominis thymidylate synthase-dihydrofolate reductase (TS-DHFR). MedChemComm 2013, 4:1247-1256.
41. Moon H., Lim H.-S. Synthesis and screening of small-molecule α-helix mimetic libraries targeting protein-protein interactions. Curr. Opin. Chem. Biol. 2015, 24:38-47.
42. Moon H., Lee W.S., Oh M., Lee H., Lee J.H., Im W., Lim H.-S. Design, solid-phase synthesis, and evaluation of a phenyl-piperazine-triazine scaffold as α-Helix mimetics. ACS Comb. Sci. 2014, 16:695-701.
43. Morelli X., Hupp T. Searching for the holy Grail; protein-protein interaction analysis and modulation. EMBO Rep. 2012, 13:877-879.
44. Murphy N.S., Prabhakaran P., Azzarito V., Plante J.P., Hardie M.J., Kilner C.A., Warriner S.L., Wilson A.J. Solid-phase methodology for synthesis of O-alkylated aromatic oligoamide inhibitors of alpha-helix-mediated protein-protein interactions. Chem. Eur. J. 2013, 19:5546-5550.
45. Nolan W.P., Ratcliffe G.S., Rees D.C. The synthesis of 1,6-Disubstituted indanes which mimic the orientation of amino acid side-chains in a protein Alpha-Helix motif. Tetrahedron Lett. 1992, 33:6879-6882.
46. Oh M., Lee J.H., Wang W., Lee H.S., Lee W.S., Burlak C., Im W., Hoang Q.Q., Lim H.-S. Potential pharmacological chaperones targeting cancer-associated MCL-1 and Parkinson disease-associated α-synuclein. Proc. Natl. Acad. Sci. U. S. A. 2014, 111:11007-11012.
47. Orner B.P., Ernst J.T., Hamilton A.D. Toward proteomimetics: terphenyl derivatives as structural and functional mimics of extended regions of an α-Helix. J. Am. Chem. Soc. 2001, 123:5382-5383.
48. Plante J., Campbell F., Malkova B., Kilner C., Warriner S.L., Wilson A.J. Synthesis of functionalised aromatic oligamide rods. Org. Biomol. Chem. 2008, 6:138-146.
49. Prabhakaran P., Azzarito V., Jacobs T., Hardie M.J., Kilner C.A., Edwards T.A., Warriner S.L., Wilson A.J. Conformational properties of O-alkylated benzamides. Tetrahedron 2012, 68:4485-4491.
50. Raghuraman A., Ko E., Perez L.M., Ioerger T.R., Burgess K. Pyrrolinone-Pyrrolidine oligomers as universal peptidomimetics. J. Am. Chem. Soc. 2011, 133:12350-12353.
51. Ravindranathan P., Lee T.-K., Yang L., Centenera M.M., Butler L., Tilley W.D., Hsieh J.-T., Ahn J.-M., Raj G.V. Peptidomimetic targeting of critical androgen receptor-coregulator interactions in prostate cancer. Nat. Commun. 2013, 4:1923.
52. L-Bak peptide complex: recognition between regulators of apoptosis. Science 1997, 275:983-986.
53. Schäfer G., Milić J., Eldahshan A., Götz F., Zühlke K., Schillinger C., Kreuchwig A., Elkins J.M., Abdul Azeez K.R., Oder A., Moutty M.C., Masada N., Beerbaum M., Schlegel B., Niquet S., Schmieder P., Krause G., von Kries J.P., Cooper D.M.F., Knapp S., Rademann J., Rosenthal W., Klussmann E. Highly functionalized terpyridines as competitive inhibitors of AKAP-PKA interactions. Angew. Chem. Int. Ed. 2013, 52:12187-12191.
54. Shaginian A., Whitby L., Hong S., Hwang I., Farooqi B., Searcey M., Chen J., Vogt P., Boger D. Design, synthesis, and evaluation of an alpha-helix mimetic library targeting protein-protein interactions. J. Am. Chem. Soc. 2009, 131:5564-5572.
55. Smith B.J., Lee E.F., Checco J.W., Evangelista M., Gellman S.H., Fairlie W.D. Structure-guided rational design of α/β-peptide foldamers with high affinity for BCL-2 family prosurvival proteins. ChemBioChem 2013, 14:1564-1572.
56. Surade S., Blundell T.L. Structural biology and drug discovery of difficult targets: the limits of ligandability. Chem. Biol. 2012, 19:42-50.
57. Tošovská P., Arora P.S. Oligooxopiperazines as nonpeptidic α-Helix mimetics. Org. Lett. 2010, 12:1588-1591.
58. Vu B., Wovkulich P., Pizzolato G., Lovey A., Ding Q., Jiang N., Liu J.-J., Zhao C., Glenn K., Wen Y., Tovar C., Packman K., Vassilev L., Graves B. Discovery of RG7112: a small-molecule MDM2 inhibitor in clinical development. ACS Med. Chem. Lett. 2013, 4:466-469.
59. Walensky L.D., Bird G.H. Hydrocarbon-stapled peptides: principles, practice, and progress. J. Med. Chem. 2014, 57:6275-6288.
60. Whitby L.R., Boyle K.E., Cai L., Yu X., Gochin M., Boger D.L. Discovery of HIV fusion inhibitors targeting gp41 using a comprehensive α-helix mimetic library. Bioorg. Med. Chem. Lett. 2012, 22:2861-2865.
61. Xin D., Ko E., Perez L.M., Ioerger T.R., Burgess K. Evaluating minimalist mimics by exploring key orientations on secondary structures (EKOS). Org. Biomol. Chem. 2013, 11:7789-7801.
62. Xin D., Holzenburg A., Burgess K. Small molecule probes that perturb a protein-protein interface in antithrombin. Chem. Sci. 2014, 5:4914-4921.
63. Yin H., Lee G.-i., Sedey K.A., Rodriguez J.M., Wang H.-G., Sebti S.M., Hamilton A.D. Terephthalamide derivatives as mimetics of helical Peptides: disruption of the Bcl-xL/Bak interaction. J. Am. Chem. Soc. 2005, 127:5463-5468.
64. L. J. Am. Chem. Soc. 2005, 127:10191-10196.
65. Yin H., Lee G.-I., Park H.S., Payne G.A., Rodriguez J.M., Sebti S.M., Hamilton A.D. Terphenyl-based helical mimetics that disrupt the p53/HDM2 interaction. Angew. Chem. Int. Ed. 2005, 44:2704-2707.