Article
Chemistry, Multidisciplinary
Jose Garcia-Calvo, Javier Lopez-Andarias, Naomi Sakai, Stefan Matile
Summary: This study elaborates on the role of sulfoximines in fluorescent flipper probes and demonstrates the advantages of sulfoximine flippers in imaging membrane tension.
HELVETICA CHIMICA ACTA
(2022)
Article
Chemistry, Multidisciplinary
Jose Garcia-Calvo, Javier Lopez-Andarias, Jimmy Maillard, Vincent Mercier, Chloe Roffay, Aurelien Roux, Alexandre Fuerstenberg, Naomi Sakai, Stefan Matile
Summary: HydroFlippers are fluorescent membrane tension probes that report on both membrane compression and hydration. Different cellular membranes show varied responses to tension-induced decompression and hydration. The mechanical compression is independent of the nature of the membrane of interest (MOI), while the response to hydration depends on the intrinsic order of the MOI.
Article
Biochemistry & Molecular Biology
Lea Assies, Vincent Mercier, Javier Lopez-Andarias, Aurelien Roux, Naomi Sakai, Stefan Matile
Summary: This study reveals that primary ammonium cations with higher pK(a) efficiently label early endosomes and Golgi networks. Guanidinium cations with higher pK(a) selectively label the plasma membrane in endocytosis. It is also found that guanidinium cations can self-assemble into micelles and penetrate mitochondria unidirectionally.
Article
Chemistry, Multidisciplinary
Quentin Laurent, Naomi Sakai, Stefan Matile
Summary: A model system is introduced as a tool for orthogonal templation of dynamic covalent ring-opening polymerization. The tool shows high templation efficiency at the level of short model oligomers and promises to be useful for intractable or unknown cyclic dynamic covalent monomers.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Biochemistry & Molecular Biology
S. Matile
Summary: By using flipper probes with cationic acids, researchers have elucidated the mechanics of endocytosis and revealed universal rules for unidirectional penetration along pH gradients.
Article
Chemistry, Multidisciplinary
Naomi Sakai, Lea Assies, Stefan Matile
Summary: This paper investigates the planarization of fluorescent flippers on DNA architectures through chemical interactions. Compared to fluorescence in water, planarization on DNA architectures results in a red shift and an increase in fluorescence intensity. The planarization occurs on the water-accessible surface, and different DNA structures can be used for the planarization of flippers. These findings have significant implications for expanding the applications of planarizable push-pull flipper probes.
HELVETICA CHIMICA ACTA
(2022)
Article
Chemistry, Multidisciplinary
Inga Shybeka, John R. J. Maynard, Saidbakhrom Saidjalolov, Dimitri Moreau, Naomi Sakai, Stefan Matile
Summary: Chalcogen-centered cascade exchange chemistry plays a significant role in thiol-mediated uptake. Reversible Michael acceptors are found to both enable and inhibit thiol-mediated uptake, including the cytosolic delivery of proteins. These findings expand the understanding of thiol-mediated uptake and suggest the existence of a universal exchange network for matter entry into cells.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Multidisciplinary
Xiao-Xiao Chen, Felix Bayard, Nerea Gonzalez-Sanchis, Khurnia Krisna Puji Pamungkas, Naomi Sakai, Stefan Matile
Summary: Flipper probes have been introduced as small molecule fluorophores for imaging physical forces in living systems. The article describes their evolution in design and synthesis as well as their spectroscopic properties. Mechanosensitivity to image membrane tension in living cells is identified as their ideal origin. A variety of flippers have been developed for specific delivery and release in subcellular membranes, enabling super-resolution imaging and dual-sensing of membrane compression and hydration. The availability and broad use of flipper probes validate their power in translational supramolecular chemistry.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Jules Bouffard, Filipe Coelho, Naomi Sakai, Stefan Matile
Summary: In this study, phosphorus is introduced as an exchange center for dynamic covalent chemistry. The cascade exchange of phosphorotri- and -tetrathioates with thiolates is demonstrated in different systems. The exchange rates are influenced by factors such as pH value, electrophilicity of the exchange center, and nucleophilicity of the exchangers. The dynamic phosphorotri- and -tetrathioates are non-toxic and participate in thiol-mediated uptake into living cells.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Mei-Ling Tan, M. Angeles Gutierrez Lopez, Naomi Sakai, Stefan Matile
Summary: This article introduces the principles and applications of anion-pi catalysis and anion-(pi)(n)-pi catalysis. The self-assembly of micelles is utilized to achieve anion-(pi)(n)-pi catalytic reactions in water, with high reaction rates and autocatalytic behavior.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Nina Declas, John R. J. Maynard, Laure Menin, Natalia Gasilova, Sebastian Goetze, Jakob L. Sprague, Pierre Stallforth, Stefan Matile, Jerome Waser
Summary: The study presents a novel tyrosine bioconjugation methodology that introduces hypervalent iodine onto biomolecules under physiological conditions, providing a powerful tool for late-stage peptide and protein functionalization. This approach not only successfully applied to peptides and proteins but also enabled the modification of bioactive natural products and streptavidin.
Article
Chemistry, Multidisciplinary
Hao Chen, Tian-Ren Li, Naomi Sakai, Celine Besnard, Laure Guenee, Marion Pupier, Jasmine Viger-Gravel, Konrad Tiefenbacher, Stefan Matile
Summary: This research introduces cascade cyclizations of diepoxides as a new tool for characterizing supramolecular catalysis. By decoding product fingerprints, the chemical selectivity, diastereo- and enantioselectivity, mechanism, and autocatalysis of substrate stereoisomers can be studied. The application of this tool to various supramolecular systems reveals interesting findings, such as pnictogen-bonding catalysis breaking the Baldwin rules and converting substrate diastereomers into completely different products.
Article
Chemistry, Multidisciplinary
Bumhee Lim, Takehiro Kato, Celine Besnard, Amalia I. Poblador Bahamonde, Naomi Sakai, Stefan Matile
Summary: This study expands the dynamic covalent chalcogen exchange cascades by inserting pnictogen relays and identifies privileged scaffolds for inhibiting cellular entry and viral infection.
Article
Chemistry, Multidisciplinary
Takehiro Kato, Bumhee Lim, Yangyang Cheng, Anh-Tuan Pham, John Maynard, Dimitri Moreau, Amalia Poblador-Bahamonde, Naomi Sakai, Stefan Matile
Summary: Thiol-mediated uptake is an effective method for cell penetration, and cyclic oligochalcogenides (COCs) have been found to be a useful tool in enabling and inhibiting this process. This study focuses on the unexplored COCs of higher oxidation levels and demonstrates their potential in enhancing cell uptake and inhibiting the entry of SARS-CoV-2 lentivectors. The results suggest that COCs with hydrophobic directing groups exhibit selective and synergistic exchange in hydrophobic pockets, making them promising candidates for cytosolic delivery and the evolution of dynamic covalent networks.
Article
Chemistry, Multidisciplinary
Javier Lopez-Andarias, Krikor Eblighatian, Quentin T. L. Pasquer, Lea Assies, Naomi Sakai, Sascha Hoogendoorn, Stefan Matile
Summary: Researchers have introduced photocleavable flipper probes that can release and label the most ordered regions of membranes upon irradiation. These probes provide spatiotemporal control for observing dynamic changes in membranes without chemical or physical interference, making them useful tools for biological research.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Faiza Diaba, Gisela Trenchs
Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed
Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Hyunjin Oh, Ikyon Kim
Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst
Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar
Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Review
Chemistry, Organic
Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan
Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
