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A semisynthetic fusicoccane stabilizes a protein-protein interaction and enhances the expression of K+ channels at the cell surface.

Anders C, Higuchi Y, Koschinsky K, Bartel M, Schumacher B, Thiel P, Nitta H, Preisig-Müller R, Schlichthörl G, Renigunta V, Ohkanda J, Daut J, Kato N, Ottmann C
Chem Biol 20 583-93 (2013)
Related entries: 3p1n, 3p1p, 3p1q, 3p1r, 3p1s, 3smk, 3sml, 3smm, 3smn, 3smo, 3sp5, 3spr, 3ux0, 4fr3

Cited: 52 times
EuropePMC logo PMID: 23601647

Abstract

Small-molecule stabilization of protein-protein interactions is an emerging field in chemical biology. We show how fusicoccanes, originally identified as fungal toxins acting on plants, promote the interaction of 14-3-3 proteins with the human potassium channel TASK-3 and present a semisynthetic fusicoccane derivative (FC-THF) that targets the 14-3-3 recognition motif (mode 3) in TASK-3. In the presence of FC-THF, the binding of 14-3-3 proteins to TASK-3 was increased 19-fold and protein crystallography provided the atomic details of the effects of FC-THF on this interaction. We also tested the functional effects of FC-THF on TASK channels heterologously expressed in Xenopus oocytes. Incubation with 10 μM FC-THF was found to promote the transport of TASK channels to the cell membrane, leading to a significantly higher density of channels at the surface membrane and increased potassium current.

Reviews - 3p1o mentioned but not cited (1)

  1. Protein-protein interfaces in molecular glue-induced ternary complexes: classification, characterization, and prediction. Rui H, Ashton KS, Min J, Wang C, Potts PR. RSC Chem Biol 4 192-215 (2023)


Reviews citing this publication (17)

  1. Modulators of 14-3-3 Protein-Protein Interactions. Stevers LM, Sijbesma E, Botta M, MacKintosh C, Obsil T, Landrieu I, Cau Y, Wilson AJ, Karawajczyk A, Eickhoff J, Davis J, Hann M, O'Mahony G, Doveston RG, Brunsveld L, Ottmann C. J Med Chem 61 3755-3778 (2018)
  2. Stabilization of protein-protein interactions in drug discovery. Andrei SA, Sijbesma E, Hann M, Davis J, O'Mahony G, Perry MWD, Karawajczyk A, Eickhoff J, Brunsveld L, Doveston RG, Milroy LG, Ottmann C. Expert Opin Drug Discov 12 925-940 (2017)
  3. Stabilization of protein-protein interaction complexes through small molecules. Zarzycka B, Kuenemann MA, Miteva MA, Nicolaes GAF, Vriend G, Sperandio O. Drug Discov Today 21 48-57 (2016)
  4. Stabilization of protein-protein interactions by small molecules. Giordanetto F, Schäfer A, Ottmann C. Drug Discov Today 19 1812-1821 (2014)
  5. 14-3-3: A Case Study in PPI Modulation. Ballone A, Centorrino F, Ottmann C. Molecules 23 E1386 (2018)
  6. Molecular insight into specific 14-3-3 modulators: Inhibitors and stabilisers of protein-protein interactions of 14-3-3. Hartman AM, Hirsch AKH. Eur J Med Chem 136 573-584 (2017)
  7. The Surprising Story of Fusicoccin: A Wilt-Inducing Phytotoxin, a Tool in Plant Physiology and a 14-3-3-Targeted Drug. Marra M, Camoni L, Visconti S, Fiorillo A, Evidente A. Biomolecules 11 1393 (2021)
  8. 14-3-3 Proteins: Novel Pharmacological Targets in Neurodegenerative Diseases. Pair FS, Yacoubian TA. Trends Pharmacol Sci 42 226-238 (2021)
  9. The role of protein-protein interactions in the intracellular traffic of the potassium channels TASK-1 and TASK-3. Kilisch M, Lytovchenko O, Schwappach B, Renigunta V, Daut J. Pflugers Arch 467 1105-1120 (2015)
  10. Emerging modes-of-action in drug discovery. Valeur E, Narjes F, Ottmann C, Plowright AT. Medchemcomm 10 1550-1568 (2019)
  11. Small molecules, peptides and natural products: getting a grip on 14-3-3 protein-protein modulation. Bartel M, Schäfer A, Stevers LM, Ottmann C. Future Med Chem 6 903-921 (2014)
  12. 14-3-3σ and Its Modulators in Cancer. Aljabal G, Yap BK. Pharmaceuticals (Basel) 13 E441 (2020)
  13. From plant physiology to pharmacology: fusicoccin leaves the leaves. Camoni L, Visconti S, Aducci P, Marra M. Planta 249 49-57 (2019)
  14. Pathways to Parkinson's disease: a spotlight on 14-3-3 proteins. Giusto E, Yacoubian TA, Greggio E, Civiero L. NPJ Parkinsons Dis 7 85 (2021)
  15. Computational approaches for the design of modulators targeting protein-protein interactions. Rehman AU, Khurshid B, Ali Y, Rasheed S, Wadood A, Ng HL, Chen HF, Wei Z, Luo R, Zhang J. Expert Opin Drug Discov 18 315-333 (2023)
  16. Targeting 14-3-3 adaptor protein-protein interactions to stimulate central nervous system repair. Kaplan A, Fournier AE. Neural Regen Res 12 1040-1043 (2017)
  17. Small molecules targeting protein-protein interactions for cancer therapy. Wu D, Li Y, Zheng L, Xiao H, Ouyang L, Wang G, Sun Q. Acta Pharm Sin B 13 4060-4088 (2023)

Articles citing this publication (34)

  1. Small-Molecule Stabilization of 14-3-3 Protein-Protein Interactions Stimulates Axon Regeneration. Kaplan A, Morquette B, Kroner A, Leong S, Madwar C, Sanz R, Banerjee SL, Antel J, Bisson N, David S, Fournier AE. Neuron 93 1082-1093.e5 (2017)
  2. Involvement of 14-3-3 in tubulin instability and impaired axon development is mediated by Tau. Joo Y, Schumacher B, Landrieu I, Bartel M, Smet-Nocca C, Jang A, Choi HS, Jeon NL, Chang KA, Kim HS, Ottmann C, Suh YH. FASEB J 29 4133-4144 (2015)
  3. Small-Molecule Stabilization of the 14-3-3/Gab2 Protein-Protein Interaction (PPI) Interface. Bier D, Bartel M, Sies K, Halbach S, Higuchi Y, Haranosono Y, Brummer T, Kato N, Ottmann C. ChemMedChem 11 911-918 (2016)
  4. Stabilizer-Guided Inhibition of Protein-Protein Interactions. Milroy LG, Bartel M, Henen MA, Leysen S, Adriaans JM, Brunsveld L, Landrieu I, Ottmann C. Angew Chem Int Ed Engl 54 15720-15724 (2015)
  5. The Molecular Tweezer CLR01 Stabilizes a Disordered Protein-Protein Interface. Bier D, Mittal S, Bravo-Rodriguez K, Sowislok A, Guillory X, Briels J, Heid C, Bartel M, Wettig B, Brunsveld L, Sanchez-Garcia E, Schrader T, Ottmann C. J Am Chem Soc 139 16256-16263 (2017)
  6. Cooperativity basis for small-molecule stabilization of protein-protein interactions. de Vink PJ, Andrei SA, Higuchi Y, Ottmann C, Milroy LG, Brunsveld L. Chem Sci 10 2869-2874 (2019)
  7. Rationally Designed Semisynthetic Natural Product Analogues for Stabilization of 14-3-3 Protein-Protein Interactions. Andrei SA, de Vink P, Sijbesma E, Han L, Brunsveld L, Kato N, Ottmann C, Higuchi Y. Angew Chem Int Ed Engl 57 13470-13474 (2018)
  8. Fusicoccin Activates KAT1 Channels by Stabilizing Their Interaction with 14-3-3 Proteins. Saponaro A, Porro A, Chaves-Sanjuan A, Nardini M, Rauh O, Thiel G, Moroni A, Moroni A. Plant Cell 29 2570-2580 (2017)
  9. Selectivity via Cooperativity: Preferential Stabilization of the p65/14-3-3 Interaction with Semisynthetic Natural Products. Wolter M, de Vink P, Neves JF, Srdanović S, Higuchi Y, Kato N, Wilson A, Landrieu I, Brunsveld L, Ottmann C. J Am Chem Soc 142 11772-11783 (2020)
  10. Virtual screening and experimental validation reveal novel small-molecule inhibitors of 14-3-3 protein-protein interactions. Thiel P, Röglin L, Meissner N, Hennig S, Kohlbacher O, Ottmann C. Chem Commun (Camb) 49 8468-8470 (2013)
  11. Identification of Two Secondary Ligand Binding Sites in 14-3-3 Proteins Using Fragment Screening. Sijbesma E, Skora L, Leysen S, Brunsveld L, Koch U, Nussbaumer P, Jahnke W, Ottmann C. Biochemistry 56 3972-3982 (2017)
  12. Letter Biophysical and structural insight into the USP8/14-3-3 interaction. Centorrino F, Ballone A, Wolter M, Ottmann C. FEBS Lett 592 1211-1220 (2018)
  13. A dual phosphorylation switch controls 14-3-3-dependent cell surface expression of TASK-1. Kilisch M, Lytovchenko O, Arakel EC, Bertinetti D, Schwappach B. J Cell Sci 129 831-842 (2016)
  14. Fragment-based Differential Targeting of PPI Stabilizer Interfaces. Guillory X, Wolter M, Leysen S, Neves JF, Kuusk A, Genet S, Somsen B, Morrow JK, Rivers E, van Beek L, Patel J, Goodnow R, Schoenherr H, Fuller N, Cao Q, Doveston RG, Brunsveld L, Arkin MR, Castaldi P, Boyd H, Landrieu I, Chen H, Ottmann C. J Med Chem 63 6694-6707 (2020)
  15. Inhibition of 14-3-3/Tau by Hybrid Small-Molecule Peptides Operating via Two Different Binding Modes. Andrei SA, Meijer FA, Neves JF, Brunsveld L, Landrieu I, Ottmann C, Milroy LG. ACS Chem Neurosci 9 2639-2654 (2018)
  16. The phytotoxin fusicoccin differently regulates 14-3-3 proteins association to mode III targets. Paiardini A, Aducci P, Cervoni L, Cutruzzolà F, Di Lucente C, Janson G, Pascarella S, Rinaldo S, Visconti S, Camoni L. IUBMB Life 66 52-62 (2014)
  17. Discovery of 14-3-3 protein-protein interaction inhibitors that sensitize multidrug-resistant cancer cells to doxorubicin and the Akt inhibitor GSK690693. Mori M, Vignaroli G, Cau Y, Dinić J, Hill R, Rossi M, Colecchia D, Pešić M, Link W, Chiariello M, Ottmann C, Botta M. ChemMedChem 9 973-983 (2014)
  18. 14-3-3 proteins inactivate DAPK2 by promoting its dimerization and protecting key regulatory phosphosites. Horvath M, Petrvalska O, Herman P, Obsilova V, Obsil T. Commun Biol 4 986 (2021)
  19. Discovery of Small-Molecule Stabilizers of 14-3-3 Protein-Protein Interactions via Dynamic Combinatorial Chemistry. Hartman AM, Elgaher WAM, Hertrich N, Andrei SA, Ottmann C, Hirsch AKH. ACS Med Chem Lett 11 1041-1046 (2020)
  20. Henipavirus W Proteins Interact with 14-3-3 To Modulate Host Gene Expression. Edwards MR, Hoad M, Tsimbalyuk S, Menicucci AR, Messaoudi I, Forwood JK, Basler CF. J Virol 94 e00373-20 (2020)
  21. Rational Design, Binding Studies, and Crystal-Structure Evaluation of the First Ligand Targeting the Dimerization Interface of the 14-3-3ζ Adapter Protein. Ehlers M, Grad JN, Mittal S, Bier D, Mertel M, Ohl L, Bartel M, Briels J, Heimann M, Ottmann C, Sanchez-Garcia E, Hoffmann D, Schmuck C, Schmuck C. Chembiochem 19 591-595 (2018)
  22. Molecular Dynamics Investigations Suggest a Non-specific Recognition Strategy of 14-3-3σ Protein by Tweezer: Implication for the Inhibition Mechanism. Shi M, Xu D. Front Chem 7 237 (2019)
  23. Identification and X-ray co-crystal structure of a small-molecule activator of LFA-1-ICAM-1 binding. Hintersteiner M, Kallen J, Schmied M, Graf C, Jung T, Mudd G, Shave S, Gstach H, Auer M. Angew Chem Int Ed Engl 53 4322-4326 (2014)
  24. A new class of supramolecular ligands stabilizes 14-3-3 protein-protein interactions by up to two orders of magnitude. Gigante A, Grad JN, Briels J, Bartel M, Hoffmann D, Ottmann C, Schmuck C. Chem Commun (Camb) 55 111-114 (2018)
  25. Analysis of Interactions Stabilized by Fusicoccin A Reveals an Expanded Suite of Potential 14-3-3 Binding Partners. Sengupta A, Liriano J, Miller BG, Frederich JH. ACS Chem Biol 15 305-310 (2020)
  26. Probing the 14-3-3 Isoform-Specificity Profile of Protein-Protein Interactions Stabilized by Fusicoccin A. Sengupta A, Liriano J, Bienkiewicz EA, Miller BG, Frederich JH. ACS Omega 5 25029-25035 (2020)
  27. Structural Effects of Fusicoccin upon Upregulation of 14-3-3-Phospholigand Interaction and Cytotoxic Activity. Ohkanda J, Kusumoto A, Punzalan L, Masuda R, Wang C, Parvatkar P, Akase D, Aida M, Uesugi M, Higuchi Y, Kato N. Chemistry 24 16066-16071 (2018)
  28. Fragment-based exploration of the 14-3-3/Amot-p130 interface. Centorrino F, Andlovic B, Cossar P, Brunsveld L, Ottmann C. Curr Res Struct Biol 4 21-28 (2022)
  29. Mono- and Bivalent 14-3-3 Inhibitors for Characterizing Supramolecular "Lysine Wrapping" of Oligoethylene Glycol (OEG) Moieties in Proteins. Yilmaz E, Bier D, Guillory X, Briels J, Ruiz-Blanco YB, Sanchez-Garcia E, Ottmann C, Kaiser M. Chemistry 24 13807-13814 (2018)
  30. A new soaking procedure for X-ray crystallographic structural determination of protein-peptide complexes. Ballone A, Lau RA, Zweipfenning FPA, Ottmann C. Acta Crystallogr F Struct Biol Commun 76 501-507 (2020)
  31. Straightforward model construction and analysis of multicomponent biomolecular systems in equilibrium. Geertjens NHJ, de Vink PJ, Wezeman T, Markvoort AJ, Brunsveld L. RSC Chem Biol 4 252-260 (2023)
  32. Designing Selective Drug-like Molecular Glues for the Glucocorticoid Receptor/14-3-3 Protein-Protein Interaction. Pallesen JS, Munier CC, Bosica F, Andrei SA, Edman K, Gunnarsson A, La Sala G, Putra OD, Srdanović S, Wilson AJ, Wissler L, Ottmann C, Perry MWD, O'Mahony G. J Med Chem 65 16818-16828 (2022)
  33. In Silico Studies on GCP-Lys-OMe as a Potential 14-3-3σ Homodimer Stabilizer. Aljabal G, Yap BK. Pharmaceuticals (Basel) 15 1290 (2022)
  34. Lenalidomide Stabilizes Protein-Protein Complexes by Turning Labile Intermolecular H-Bonds into Robust Interactions. Miñarro-Lleonar M, Bertran-Mostazo A, Duro J, Barril X, Juárez-Jiménez J. J Med Chem 66 6037-6046 (2023)


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