Literature DB >> 23763721

Amphipathic α-helix mimetics based on a 1,2-diphenylacetylene scaffold.

Kwan-Young Jung1, Kenno Vanommeslaeghe, Maryanna E Lanning, Jeremy L Yap, Caryn Gordon, Paul T Wilder, Alexander D MacKerell, Steven Fletcher.   

Abstract

In order to mimic amphipathic α-helices, a novel scaffold based on a 1,2-diphenylacetylene was designed. NMR and computational modeling confirmed that an intramolecular hydrogen bond favors conformations of the 1,2-diphenylacetylene that allow for accurate mimicry of the i, i + 7 and i + 2, i + 5 side chains found on opposing faces of an α-helix.

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Year:  2013        PMID： 23763721     DOI： 10.1021/ol401197n

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  14 in total

1.  Synthetic, structural mimetics of the β-hairpin flap of HIV-1 protease inhibit enzyme function.

Authors:  Jay Chauhan; Shen-En Chen; Katherine J Fenstermacher; Aurash Naser-Tavakolian; Tali Reingewertz; Rosene Salmo; Christian Lee; Emori Williams; Mithun Raje; Eric Sundberg; Jeffrey J DeStefano; Ernesto Freire; Steven Fletcher
Journal:  Bioorg Med Chem       Date:  2015-09-07       Impact factor: 3.641

2.  Potential pharmacological chaperones targeting cancer-associated MCL-1 and Parkinson disease-associated α-synuclein.

Authors:  Misook Oh; Ji Hoon Lee; Wei Wang; Hui Sun Lee; Woo Sirl Lee; Christopher Burlak; Wonpil Im; Quyen Q Hoang; Hyun-Suk Lim
Journal:  Proc Natl Acad Sci U S A       Date:  2014-07-14       Impact factor: 11.205

3.  Structure-based design of N-substituted 1-hydroxy-4-sulfamoyl-2-naphthoates as selective inhibitors of the Mcl-1 oncoprotein.

Authors:  Maryanna E Lanning; Wenbo Yu; Jeremy L Yap; Jay Chauhan; Lijia Chen; Ellis Whiting; Lakshmi S Pidugu; Tyler Atkinson; Hala Bailey; Willy Li; Braden M Roth; Lauren Hynicka; Kirsty Chesko; Eric A Toth; Paul Shapiro; Alexander D MacKerell; Paul T Wilder; Steven Fletcher
Journal:  Eur J Med Chem       Date:  2016-02-04       Impact factor: 6.514

4.  Perturbation of the c-Myc-Max protein-protein interaction via synthetic α-helix mimetics.

Authors:  Kwan-Young Jung; Huabo Wang; Peter Teriete; Jeremy L Yap; Lijia Chen; Maryanna E Lanning; Angela Hu; Lester J Lambert; Toril Holien; Anders Sundan; Nicholas D P Cosford; Edward V Prochownik; Steven Fletcher
Journal:  J Med Chem       Date:  2015-03-30       Impact factor: 7.446

5.  Targeting the Side-Chain Convergence of Hydrophobic α-Helical Hot Spots To Design Small-Molecule Mimetics: Key Binding Features for i, i + 3, and i + 7.

Authors:  Zhen Wang; Haitao Ji
Journal:  J Med Chem       Date:  2019-10-22       Impact factor: 7.446

6.  Towards more drug-like proteomimetics: two-faced, synthetic α-helix mimetics based on a purine scaffold.

Authors:  M E Lanning; P T Wilder; H Bailey; B Drennen; M Cavalier; L Chen; J L Yap; M Raje; S Fletcher
Journal:  Org Biomol Chem       Date:  2015-07-24       Impact factor: 3.876

Review 7.  Recent applications of covalent chemistries in protein-protein interaction inhibitors.

Authors:  Alexandria M Chan; Christopher C Goodis; Elie G Pommier; Steven Fletcher
Journal:  RSC Med Chem       Date:  2022-06-03

8.  Scaffold hopping from indoles to indazoles yields dual MCL-1/BCL-2 inhibitors from MCL-1 selective leads.

Authors:  Brandon Drennen; Christopher C Goodis; Nathan Bowen; Wenbo Yu; Gregory Vickers; Paul T Wilder; Alexander D MacKerell; Steven Fletcher
Journal:  RSC Med Chem       Date:  2022-06-03

9.  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.

Authors:  Brandon Drennen; Jacob A Scheenstra; Jeremy L Yap; Lijia Chen; Maryanna E Lanning; Braden M Roth; Paul T Wilder; Steven Fletcher
Journal:  ChemMedChem       Date:  2016-02-04       Impact factor: 3.466

Review 10.  Multi-Facial, Non-Peptidic α-Helix Mimetics.

Authors:  Maryanna E Lanning; Steven Fletcher
Journal:  Biology (Basel)       Date:  2015-08-31
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