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

Publications

M. Paraja, X. Hao, S. Matile “Polyether Natural Product Inspired Cascade Cyclizations: Autocatalysis on π-Acidic Aromatic Surfaces“ Angew. Chem. Int. Ed. 2020. [DOI]
J. López-Andarias, J. Saarbach, D. Moreau, Y. Cheng, E. Derivery, Q. Laurent, M. González-Gaitán, N. Winssinger, N. Sakai, S. Matile “Cell-Penetrating Streptavidin: A General Tool for Bifunctional Delivery with Spatiotemporal Control, Mediated by Transport Systems Such as Adaptive Benzopolysulfane Networks“ J. Am. Chem. Soc. 2020. [DOI]
M. Paraja, S. Matile “Primary Anion–π Catalysis of Epoxide-Opening Ether Cyclization into Rings of Different Sizes: Access to New Reactivity“ Angew. Chem. Int. Ed. 2020. [DOI]
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. Matile, M. Fussenegger, T. 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. Ward, S. 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. Matile, W. Meier, C. 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. Reddy, W. Meier, C. G. Palivan, K. Gademann, T. R. Ward, S. Matile “Interfacing Functional Systems“ Chimia 2016, 6:418. [DOI]
W. Kelton, T. Pesch, S. Matile, S. 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. Ward, S. 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]