Multi-Facial, Non-Peptidic α-Helix Mimetics

Overview

Journal Biology (Basel)

Publisher MDPI

Specialty Biology

Date 2015 Sep 26

PMID 26404384

Citations 2

Authors

Maryanna E Lanning

Steven Fletcher

Affiliations

Soon will be listed here.

Abstract

α-Helices often recognize their target proteins at protein-protein interfaces through more than one recognition face. This review describes the state-of-the-art in the design of non-peptidic α-helix mimetics that reproduce functionality from multiple faces of an α-helix.

Citing Articles

Using Peptidomimetics and Constrained Peptides as Valuable Tools for Inhibiting Protein⁻Protein Interactions.

Robertson N, Spring D Molecules. 2018; 23(4).

PMID: 29671834 PMC: 6017787. DOI: 10.3390/molecules23040959.

Structural Re-engineering of the α-Helix Mimetic JY-1-106 into Small Molecules: Disruption of the Mcl-1-Bak-BH3 Protein-Protein Interaction with 2,6-Di-Substituted Nicotinates.

Drennen B, Scheenstra J, Yap J, Chen L, Lanning M, Roth B ChemMedChem. 2016; 11(8):827-33.

PMID: 26844930 PMC: 4838500. DOI: 10.1002/cmdc.201500461.

References

Orner B, Ernst J, Hamilton A . Toward proteomimetics: terphenyl derivatives as structural and functional mimics of extended regions of an alpha-helix. J Am Chem Soc. 2001; 123(22):5382-3. DOI: 10.1021/ja0025548. View

Kutzki O, Park H, Ernst J, Orner B, Yin H, Hamilton A . Development of a potent Bcl-x(L) antagonist based on alpha-helix mimicry. J Am Chem Soc. 2002; 124(40):11838-9. DOI: 10.1021/ja026861k. View

Ernst J, Becerril J, Park H, Yin H, Hamilton A . Design and application of an alpha-helix-mimetic scaffold based on an oligoamide-foldamer strategy: antagonism of the Bak BH3/Bcl-xL complex. Angew Chem Int Ed Engl. 2003; 42(5):535-9. DOI: 10.1002/anie.200390154. View

Spivey A, McKendrick J, Srikaran R, Helm B . Solid-phase synthesis of an A-B loop mimetic of the Cepsilon3 domain of human IgE: macrocyclization by Sonogashira coupling. J Org Chem. 2003; 68(5):1843-51. DOI: 10.1021/jo026693e. View

Yin H, Hamilton A . Terephthalamide derivatives as mimetics of the helical region of Bak peptide target Bcl-xL protein. Bioorg Med Chem Lett. 2004; 14(6):1375-9. DOI: 10.1016/j.bmcl.2003.09.096. View

Arkin M, Wells J . Small-molecule inhibitors of protein-protein interactions: progressing towards the dream. Nat Rev Drug Discov. 2004; 3(4):301-17. DOI: 10.1038/nrd1343. View

Kritzer J, Lear J, Hodsdon M, Schepartz A . Helical beta-peptide inhibitors of the p53-hDM2 interaction. J Am Chem Soc. 2004; 126(31):9468-9. DOI: 10.1021/ja031625a. View

Knight J, Miranker A . Phospholipid catalysis of diabetic amyloid assembly. J Mol Biol. 2004; 341(5):1175-87. DOI: 10.1016/j.jmb.2004.06.086. View

Walensky L, Kung A, Escher I, Malia T, Barbuto S, Wright R . Activation of apoptosis in vivo by a hydrocarbon-stapled BH3 helix. Science. 2004; 305(5689):1466-70. PMC: 1360987. DOI: 10.1126/science.1099191. View

10.

Chapman R, Dimartino G, Arora P . A highly stable short alpha-helix constrained by a main-chain hydrogen-bond surrogate. J Am Chem Soc. 2004; 126(39):12252-3. DOI: 10.1021/ja0466659. View

11.

Bouvier M, Taylor J . Probing the functional conformation of neuropeptide Y through the design and study of cyclic analogues. J Med Chem. 1992; 35(6):1145-55. DOI: 10.1021/jm00084a021. View

12.

Yin H, Lee G, Sedey K, Kutzki O, Park H, Orner B . Terphenyl-Based Bak BH3 alpha-helical proteomimetics as low-molecular-weight antagonists of Bcl-xL. J Am Chem Soc. 2005; 127(29):10191-6. DOI: 10.1021/ja050122x. View

13.

Fletcher S, Hamilton A . Protein surface recognition and proteomimetics: mimics of protein surface structure and function. Curr Opin Chem Biol. 2005; 9(6):632-8. DOI: 10.1016/j.cbpa.2005.10.006. View

14.

Davis J, Truong A, Hamilton A . Synthesis of a 2,3';6',3''-terpyridine scaffold as an alpha-helix mimetic. Org Lett. 2005; 7(24):5405-8. DOI: 10.1021/ol0521228. View

15.

Cummings M, Schubert C, Parks D, Calvo R, LaFrance L, Lattanze J . Substituted 1,4-benzodiazepine-2,5-diones as alpha-helix mimetic antagonists of the HDM2-p53 protein-protein interaction. Chem Biol Drug Des. 2006; 67(3):201-5. DOI: 10.1111/j.1747-0285.2006.00365.x. View

16.

Kim I, Hamilton A . Diphenylindane-based proteomimetics reproduce the projection of the i, i+3, i+4, and i+7 residues on an alpha-helix. Org Lett. 2006; 8(9):1751-4. DOI: 10.1021/ol052956q. View

17.

Davis J, Tsou L, Hamilton A . Synthetic non-peptide mimetics of alpha-helices. Chem Soc Rev. 2007; 36(2):326-34. DOI: 10.1039/b608043j. View

18.

Becerril J, Hamilton A . Helix mimetics as inhibitors of the interaction of the estrogen receptor with coactivator peptides. Angew Chem Int Ed Engl. 2007; 46(24):4471-3. DOI: 10.1002/anie.200700657. View

19.

Al-Quobaili F, Montenarh M . Pancreatic duodenal homeobox factor-1 and diabetes mellitus type 2 (review). Int J Mol Med. 2008; 21(4):399-404. View

20.

Blazer L, Neubig R . Small molecule protein-protein interaction inhibitors as CNS therapeutic agents: current progress and future hurdles. Neuropsychopharmacology. 2008; 34(1):126-41. DOI: 10.1038/npp.2008.151. View