Stefan Matile - NCCR MSE

Stefan Matile

School of Chemistry and Biochemistry, University of Geneva

Work Package Leader WP1: Top-Down Fabrication of Molecular Factories

Project Leader


L. Oberhauser, S. Granziera, A. Colom, A. Goujon, V. Lavallard, S. Matile, A. Roux, T. Brun, P. Maechler “Palmitate and oleate modify membrane fluidity and kinase activities of INS-1E β-cells alongside altered metabolism-secretion coupling“ Biochim. Biophys. Acta, Mol. Cell Res. 2019. [DOI]
X. Zhang, N. Sakai, S. Matile “Methyl Scanning for Mechanochemical Chalcogen-Bonding Cascade Switches“ ChemistryOpen 2019. [DOI]
K. Strakova, A. I. Poblador-Bahamonde, N. Sakai, S. Matile “Fluorescent Flipper Probes: Comprehensive Twist Coverage“ Chem. Eur. J. 2019. [DOI]
Q. Laurent, M. Berthet, Y. Cheng, N. Sakai, S. Barluenga, N. Winssinger, S. Matile “Probing for Thiol-Mediated Uptake into Bacteria“ ChemBioChem 2019. [DOI]
A. Bornhof, M. Vázquez-Nakagawa, L. Rodríguez-Pérez, M. Ángeles Herranz, N. Sakai, N. Martín, S. Matile, J. López-Andarias “Anion–π Catalysis on Carbon Nanotubes“ Angew. Chem. Int. Ed. 2019. [DOI]
M. Macchione, A. Goujon, K. Strakova, H. V. Humeniuk, G. Licari, E. Tajkhorshid, N. Sakai, S. Matile “A Chalcogen-Bonding Cascade Switch for Planarizable Push–Pull Probes“ Angew. Chem. Int. Ed. 2019. [DOI]
K. Strakova, L. Assies, A. Goujon, F. Piazzolla, H. V. Humeniuk, S. Matile “Dithienothiophenes at Work: Access to Mechanosensitive Fluorescent Probes, Chalcogen-Bonding Catalysis, and Beyond“ Chem. Rev. 2019. [DOI]
M. Tsemperouli, E. Amstad, N. Sakai, S. Matile, K. Sugihara “Black Lipid Membranes: Challenges in Simultaneous Quantitative Characterization by Electrophysiology and Fluorescence Microscopy“ Langmuir 2019. [DOI]
Y. Cheng, L. Zong, J. López-Andarias, E. Bartolami, Y. Okamoto, T. R. Ward, N. Sakai, S. Matile “Cell-Penetrating Dynamic-Covalent Benzopolysulfane Networks“ Angew. Chem. Int. Ed. 2019. [DOI]
R. Martinent, Q. Laurent, N. Sakai, S. Matile “Cellular Uptake Mediated by Cyclic Oligochalcogenides“ Chimia 2019. [DOI]
G. S. Pulcu, N. S. Galenkamp, Y. Qing, G. Gasparini, E. Mikhailova, S. Matile, H. Bayley “Single-Molecule Kinetics of Growth and Degradation of Cell-Penetrating Poly(disulfide)s“ J. Am. Chem. Soc. 2019. [DOI]
E. Bartolami, D. Basagiannis, L. Zong, R. Martinent, Y. Okamoto, Q. Laurent, T. R. Ward, M. Gonzalez-Gaitan, N. Sakai, S. Matile “Diselenolane-Mediated Cellular Uptake: Efficient Cytosolic Delivery of Probes, Peptides, Proteins, Artificial Metalloenzymes and Protein-Coated Quantum Dots“ Chem. Eur. J. 2019. [DOI]
A. Goujon, A. Colom, K. Straková, V. Mercier, D. Mahecic, S. Manley, N. Sakai, A. Roux, S. Matile “Mechanosensitive Fluorescent Probes to Image Membrane Tension in Mitochondria, Endoplasmic Reticulum, and Lysosomes“ J. Am. Chem. Soc. 2019. [DOI]
Q. Laurent, N. Sakai, S. Matile “The Opening of 1,2-Dithiolanes and 1,2-Diselenolanes: Regioselectivity, Rearrangements, and Consequences for Poly(disulfide)s, Cellular Uptake and Pyruvate Dehydrogenase Complexes“ Helv. Chim. Acta 2019. [DOI]
L. M. Lee, M. Tsemperouli, A. I. Poblador-Bahamonde, S. Benz, N. Sakai, K. Sugihara, S. Matile “Anion Transport with Pnictogen Bonds in Direct Comparison with Chalcogen and Halogen Bonds“ J. Am. Chem. Soc. 2019. [DOI]
X. Zhang, X. Hao, L. Liu, A. Pham, J. López-Andarias, A. Frontera, N. Sakai, S. Matile “Primary Anion−π Catalysis and Autocatalysis“ J. Am. Chem. Soc. 2018, 140(51):17867-17871. [DOI]
A. Goujon, K. Straková, N. Sakai, S. Matile “Streptavidin interfacing as a general strategy to localize fluorescent membrane tension probes in cells“ Chem. Sci. 2018. [DOI]
Y. Zhao, Y. Cotelle, L. Liu, J. López-Andarias, A. Bornhof, M. Akamatsu, N. Sakai, S. Matile “The Emergence of Anion−π Catalysis“ Acc. Chem. Res. 2018, 51(9):2255-2263. [DOI]
N. Sakai, S. Matile “Conjugated Polyimine Dynamers as Phase-Sensitive Membrane Probes“ J. Am. Chem. Soc. 2018. [DOI]
A. Colom, E. Derivery, S. Soleimanpour, C. Tomba, M. D. Molin, N. Sakai, M. González-Gaitán, S. Matile, A. Roux “A fluorescent membrane tension probe“ Nat. Chem. 2018. [DOI]
S. Matile “Chalcogen-Bonding Catalysis: From Neutral to Cationic Benzodiselenazole Scaffolds“ 2018. [DOI]
H. V. Humeniuk, A. Rosspeintner, G. Licari, V. Kilin, L. Bonacina, E. Vauthey, N. Sakai, S. Matile “White‐Fluorescent Dual‐Emission Mechanosensitive Membrane Probes that Function by Bending Rather than Twisting“ Angew. Chem. Int. Ed. 2018. [DOI]
J. López‐Andarias, A. Bauzá, N. Sakai, A. Frontera, S. Matile “Remote Control of Anion–π Catalysis on Fullerene‐Centered Catalytic Triads“ Angewandte Chemie International Edition 2018. [DOI]
Y. Okamoto, R. Kojima, F. Schwizer, E. Bartolami, T. Heinisch, S. MatileM. FusseneggerT. R. Ward “A cell-penetrating artificial metalloenzyme regulates a gene switch in a designer mammalian cell“ Nat. Commun. 2018. [DOI]
K. Strakova, S. Soleimanpour, M. Diez-Castellnou, N. Sakai, S. Matile “Ganglioside‐Selective Mechanosensitive Fluorescent Membrane Probes“ Helv. Chim. Acta 2018. [DOI]
M. Macchione, M. Tsemperouli, A. Goujon, A. R. Mallia, N. Sakai, K. Sugihara, S. Matile “Mechanosensitive Oligodithienothiophenes: Transmembrane Anion Transport Along Chalcogen‐Bonding Cascades“ 2018. [DOI]
A. Bornhof, A. Bauzá, A. Aster, M. Pupier, A. Frontera, E. Vauthey, N. Sakai, S. Matile “Synergistic Anion–(π)n–π Catalysis on π-Stacked Foldamers“ J. Am. Chem. Soc. 2018. [DOI]
G. Licari, J. S. Beckwith, S. Soleimanpour, S. Matile, E. Vauthey “Detecting Order and Lateral Pressure at Biomimetic Interfaces Using a Mechanosensitive Second-Harmonic-Generation Probe“ Phys. Chem. Chem. Phys. 2018. [DOI]
X. Zhang, L. Liu, J. López-Andarias, C. Wang, N. Sakai, S. Matile “Anion-π Catalysis: Focus on Nonadjacent Stereocenters“ Helv. Chim. Acta 2018. [DOI]
P. Morelli, E. Bartolami, N. Sakai, S. Matile “Glycosylated Cell-Penetrating Poly(disulfide)s: Multifunctional Cellular Uptake at High Solubility“ Helv. Chim. Acta 2018, 101(1):e1700266. [DOI]
N. Chuard, A. I. Poblador-Bahamonde, L. Zong, E. Bartolami, J. Hildebrandt, W. Weigand, N. Sakai, S. Matile “Diselenolane-mediated cellular uptake“ 2018. [DOI]
M. M. Pellizzoni, F. Schwizer, C. W. Wood, V. Sabatino, Y. Cotelle, S. Matile, D. N. Woolfson, T. R. Ward “Chimeric Streptavidins as Host Proteins for Artificial Metalloenzymes“ ACS Catal. 2018. [DOI]
S. Benz, J. Mareda, C. Besnard, N. Sakai, S. Matile “Catalysis with chalcogen bonds: neutral benzodiselenazole scaffolds with high-precision selenium donors of variable strength“ Chem. Sci. 2017. [DOI]
J. López-Andarias, A. Frontera, S. Matile “Anion−π Catalysis on Fullerenes“ J. Am. Chem. Soc. 2017
L. Liu, Y. Cotelle, A. Bornhof, C. Besnard, N. Sakai, S. Matile “Anion–π Catalysis of Diels–Alder Reactions“ Angew. Chem. Int. Ed. 2017. [DOI]
C. Wang, S. Matile “Anion-π Catalysts with Axial Chirality“ Chem. Eur. J. 2017. [DOI]
E. Derivery, E. Bartolami, S. Matile, M. Gonzalez-Gaitan “Efficient Delivery of Quantum Dots into the Cytosol of Cells Using Cell-Penetrating Poly(disulfide)s“ J. Am. Chem. Soc. 2017. [DOI]
M. Akamatsu, N. Sakai, S. Matile “Electric-Field-Assisted Anion−π Catalysis“ J. Am. Chem. Soc. 2017, 139:6558-61. [DOI]
L. Liu, Y. Cotelle, J. Klehr, N. Sakai, T. R. WardS. Matile “Anion-π catalysis: bicyclic products with four contiguous stereogenic centers from otherwise elusive diastereospecific domino reactions on π-acidic surfaces“ Chem. Sci. 2017, 8:3770-74. [DOI]
S. MatileW. MeierC. G. Palivan “Strain-Promoted Thiol-Mediated Cellular Uptake of Giant Substrates: Liposomes and Polymersomes“ Angew. Chem. Int. Ed. 2017, 56:2947-50. [DOI]
P. Morelli, S. Matile “Sidechain Engineering in Cell-Penetrating Poly(disulfide)s“ Helv. Chim. Acta 2017, 100. [DOI]
M. Macchione, N. Chuard, N. Sakai, S. Matile “Planarizable Push–Pull Probes: Overtwisted Flipper Mechanophores“ ChemPlusChem 2017. [DOI]
Q. Verolet, M. Dal Molin, A. Colom, A. Roux, L. Guénée, N. Sakai, S. Matile “Twisted Push‐Pull Probes with Turn‐On Sulfide Donors“ Helv. Chim. Acta 2017, 100:e1600328. [DOI]
S. Soleimanpour, A. Colom, E. Derivery, M. Gonzalez-Gaitan, A. Roux, N. Sakai, S. Matile “Headgroup engineering in mechanosensitive membrane probes“ Chem. Commun. 2016, 52:14450-53. [DOI]
C. Wang, F. N. Miros, J. Mareda, N. Sakai, S. Matile “Asymmetric Anion–π Catalysis on Perylenediimides“ Angew. Chem. Int. Ed. 2016, 55:14422-26. [DOI]
N. Chuard, K. Fujisawa, P. Morelli, J. Saarbach, N. Winssinger, P. Metrangolo, G. Resnati, N. Sakai, S. Matile “Activation of Cell-Penetrating Peptides with Ionpair−π Interactions and Fluorophiles“ J. Am. Chem. Soc. 2016, 138:11264-71. [DOI]
S. Benz, M. Macchione, Q. Verolet, J. Mareda, N. Sakai, S. Matile “Anion Transport with Chalcogen Bonds“ J. Am. Chem. Soc. 2016, 138:9093-96. [DOI]
Y. Cotelle, N. Chuard, S. Lascano, V. Lebrun, R. Wehlauch, N. Bohni, S. Lörcher, V. Postupalenko, S. ReddyW. MeierC. G. Palivan, K. Gademann, T. R. WardS. Matile “Interfacing Functional Systems“ Chimia 2016, 6:418. [DOI]
W. Kelton, T. PeschS. MatileS. Reddy “Surveying the Delivery Methods of CRISPR/Cas9 for ex vivo Mammalian Cell Engineering“ Chimia 2016, 6:439. [DOI]
L. Liu, Y. Cotelle, A. Avestro, N. Sakai, S. Matile “Asymmetric Anion−π Catalysis of Iminium/Nitroaldol Cascades To Form Cyclohexane Rings with Five Stereogenic Centers Directly on π-Acidic Surfaces“ J. Am. Chem. Soc. 2016, 138:7876-79. [DOI]
A. Bolag, N. Sakai, S. Matile “Dipolar Photosystems: Engineering Oriented Push–Pull Components into Double- and Triple-Channel Surface Architectures“ Chem. Eur. J. 2016, 22:9006-14. [DOI]
L. Liu, S. Matile “Anion-π transaminase mimics“ Supramol. Chem. 2016:1-5. [DOI]
P. Morelli, X. Martin-Benlloch, R. Tessier, J. Waser, N. Sakai, S. Matile “Ethynyl benziodoxolones: functional terminators for cell-penetrating poly(disulfide)s“ Polym. Chem. 2016, 7:3465-70. [DOI]
Y. Cotelle, V. Lebrun, N. Sakai, T. R. WardS. Matile “Anion‑π Enzymes“ ACS Cent. Sci. 2016:DOI: 10.1021/acscentsci.6b00097. [DOI] [More Information]
S. Lascano, K. Zhang, R. Wehlauch, K. Gademann, N. Sakaiab, S. Matile “The third orthogonal dynamic covalent bond“ Chem. Sci. 2016, 7:4720. [DOI]
M. Akamatsu, S. Matile “Expanded Chiral Surfaces for Asymmetric Anion–π Catalysis“ Synlett 2016, 27:1041-46. [DOI]
Y. Zhao, Y. Cotelle, N. Sakai, S. Matile “Unorthodox Interactions at Work“ J. Am. Chem. Soc. 2016, 138:4270-77. [DOI]
Y. Cotelle, S. Benz, A. Avestro, T. R. Ward, N. Sakai, S. Matile “Anion-π Catalysis of Enolate Chemistry: Rigidified Leonard Turns as a General Motif to Run Reactions on Aromatic Surfaces“ Angew. Chem. Int. Ed. 2016, 55:4275. [DOI]
F. N. Miros, Y. Zhao, G. Sargsyan, M. Pupier, C. Besnard, C. Beuchat, J. Mareda, N. Sakai, S. Matile “Enolate Stabilization by Anion–π Interactions: Deuterium Exchange in Malonate Dilactones on π-Acidic Surfaces“ Chem. Eur. J. 2016, 22:2648-57. [DOI]
S. Benz, J. López‐Andarias, J. Mareda, N. Sakai, S. Matile “Catalysis with Chalcogen Bonds“ Angew. Chem. Int. Ed. 2016, 56:812-15. [DOI]
Q. Verolet, A. Rosspeintner, S. Soleimanpour, N. Sakai, E. Vauthey, S. Matile “Turn-On Sulfide π Donors: An Ultrafast Push for Twisted Mechanophores“ J. Am. Chem. Soc. 2015, 137:15644-47. [DOI]
G. Gasparini, S. Matile “Protein delivery with cell-penetrating poly(disulfide)s“ Chem. Commun. 2015, 51:17160-62. [DOI]
Y. Zhao, Y. Cotelle, A. J. Avestro, N. Sakai, S. Matile “Asymmetric Anion-π Catalysis: Enamine Addition to Nitroolefins on pi-Acidic Surfaces“ J. Am. Chem. Soc. 2015, 137:11582-85. [DOI]
K. Fujisawa, M. Humbert-Droz, R. Letrun, E. Vauthey, T. A. Wesolowski, N. Sakai, S. Matile “Ion Pair-π Interactions“ J. Am. Chem. Soc. 2015, 137:11047-56. [DOI]
K. D. Zhang, N. Sakai, S. Matile “Colorful surface architectures with three different types of dynamic covalent bonds: integration of anthocyanins, tritylium ions and flavins“ Org. Biomol. Chem. 2015, 13:8687-94. [DOI]
K. D. Zhang, S. Matile “Complex Functional Systems with Three Different Types of Dynamic Covalent Bonds“ Angew. Chem. Int. Ed. 2015, 54:8980-83. [DOI]
G. Gasparini, E. K. Bang, J. Montenegro, S. Matile “Cellular uptake: lessons from supramolecular organic chemistry“ Chem. Commun. 2015, 51:10389-402. [DOI]
G. Gasparini, G. Sargsyan, E. Bang, N. Sakai, S. Matile “Ring Tension Applied to Thiol‐Mediated Cellular Uptake“ Angew. Chem. Int. Ed. 2015, 54:7328-31. [DOI]
O. Yushchenko, G. Licari, S. Mosquera-Vazquez, N. Sakai, S. Matile, E. Vauthey “Ultrafast Intersystem-Crossing Dynamics and Breakdown of the Kasha-Vavilov's Rule of Naphthalenediimides“ J. Phys. Chem. Lett. 2015, 6:2096-100. [DOI]
Q. Verolet, S. Soleimanpour, K. Fujisawa, M. Dal Molin, N. Sakai, S. Matile “Design and Synthesis of Mixed Oligomers with Thiophenes, Dithienothiophene S, S‐Dioxides, Thieno [3, 4] pyrazines and 2, 1, 3‐Benzothiadiazoles: Flipper Screening for Mechanosensitive Systems“ ChemistryOpen 2015, 4:264-67. [DOI]
O. Yushchenko, D. Villamaina, N. Sakai, S. Matile, E. Vauthey “Comparison of Charge-Transfer Dynamics of Naphthalenediimide Triads in Solution and π-Stack Architectures on Solid Surfaces“ J. Phys. Chem. B 2015, 119:14999-15008. [DOI]
Y. Zhao, S. Benz, N. Sakai, S. Matile “Selective acceleration of disfavored enolate addition reactions by anion–π interactions“ Chem. Sci. 2015, 6:6219-23. [DOI]
J. Lopez-Andarias, A. Bolag, C. Nancoz, E. Vauthey, C. Atienza, N. Sakai, N. Martin, S. Matile “Electron-deficient fullerenes in triple-channel photosystems“ Chem. Commun. 2015, 51:7543-45. [DOI]
M. Dal Molin, Q. Verolet, S. Soleimanpour, S. Matile “Mechanosensitive membrane probes“ Chem. Eur. J. 2015, 21:6012-21. [DOI]
Y. Zhao, G. Huang, C. Besnard, J. Mareda, N. Sakai, S. Matile “Big, Strong, Neutral, Twisted, and Chiral π Acids“ Chem. Eur. J. 2015, 21:6202-07. [DOI]
N. Chuard, G. Gasparini, A. Roux, N. Sakai, S. Matile “Cell-penetrating poly(disulfide)s: the dependence of activity, depolymerization kinetics and intracellular localization on their length“ Org. Biomol. Chem. 2015, 13:64-7. [DOI]
K. Fujisawa, C. Beuchat, M. Humbert-Droz, A. Wilson, T. A. Wesolowski, J. Mareda, N. Sakai, S. Matile “Anion-π and cation-π interactions on the same surface“ Angew. Chem. Int. Ed. 2014, 53:11266-9. [DOI]
F. N. Miros, G. Huang, Y. Zhao, N. Sakai, S. Matile “Coumarin synthesis on π-acidic surfaces“ Supramol. Chem. 2014, 27:303-09. [DOI]
H. Hayashi, A. Sobczuk, A. Bolag, N. Sakai, S. Matile “Antiparallel three-component gradients in double-channel surface architectures“ Chem. Sci. 2014, 5:4610-14. [DOI]
A. V. Jentzsch, S. Matile “Anion transport with halogen bonds“ Halogen Bonding I 2014:205-39. [DOI]