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Glycochemistry for Life Science and Polymer Science


Project Leader in Glycochemistry – CNRS Researcher

Our research is in the field of carbohydrate chemistry at the Interface between chemical biology and physical-chemistry.

The importance of carbohydrates in biological and biophysical processes is now well established. They are involved, and in particular glycoconjugates (glycoproteins, glycolipids, etc.) in a plethora of biological processes ranging from cell-cell recognition and response (e.g. bacterial and viral infection, immune response, cancer metastasis, inflammation etc.), to the cellular membrane organization.

 

We are particularly interested in chemical synthesis, e.g. the development of synthetic methodology, allowing the direct access to various precisely modified carbohydrates from protecting-group free strategies. These developments enable the preparation of biologically important (neo)glycoconjugates, or mimics of polysaccharides as binders or as regenerative matrix, or glyco-amphiphiles (glycolipids, block copolymers, grafted glycopolymers) with self-assembled properties in solution or in solid state (nanostructured materials, liquid crystals, supramolecular fibers). The applications are found in biomedical, electronic, biosensor, composites, soft matter, etc.  And we are continually attempting to develop more versatile or efficient chemoselective methods, for example by the use of novel chemical platforms.


Journal articles36 documents

  • Bárbara Sthéfani Caldas, Danielle Lazarin-Bidóia, Celso Vataru Nakamura, Sami Halila, Redouane Borsali, et al.. Drug carrier systems made from self-assembled glyco-nanoparticles of maltoheptaose-b-polyisoprene enhanced the distribution and activity of curcumin against cancer cells. Journal of Molecular Liquids, Elsevier, 2020, 309, pp.113022. ⟨10.1016/j.molliq.2020.113022⟩. ⟨hal-02954391⟩
  • Marie Gestranius, Issei Otsuka, Sami Halila, Daniel Hermida‐merino, Eduardo Solano, et al.. High‐Resolution Patterned Biobased Thin Films via Self‐Assembled Carbohydrate Block Copolymers and Nanocellulose. Advanced Materials Interfaces, Wiley, 2020, 7 (7), pp.1901737. ⟨10.1002/admi.201901737⟩. ⟨hal-02998234⟩
  • Hua Zhang, Penggang Ren, Hua Wei, Sami Halila, Amarachi Rosemary Osi, et al.. Reinforced macromolecular micelle-crosslinked hyaluronate gels induced by water/DMSO binary solvent. Soft Matter, Royal Society of Chemistry, 2020, ⟨10.1039/d0sm01099e⟩. ⟨hal-02948762⟩
  • Bárbara Sthéfani Caldas, Danielle Lazarin-Bidóia, Celso Vataru Nakamura, Sami Halila, Redouane Borsali, et al.. Drug carrier systems made from self-assembled glyco-nanoparticles of maltoheptaose-b-polyisoprene enhanced the distribution and activity of curcumin against cancer cells. Journal of Molecular Liquids, Elsevier, 2020, 309, pp.113022. ⟨10.1016/j.molliq.2020.113022⟩. ⟨hal-02948775⟩
  • Teemu Myllymäki, Aynur Guliyeva, Antti Korpi, Mauri Kostiainen, Ville Hynninen, et al.. Lyotropic liquid crystals and linear supramolecular polymers of end-functionalized oligosaccharides. Chemical Communications, Royal Society of Chemistry, 2019, 55 (78), pp.11739-11742. ⟨10.1039/C9CC04715H⟩. ⟨hal-02998259⟩
  • François Portier, Anne Imberty, Sami Halila. Expeditious Synthesis of C -Glycosyl Barbiturate Ligands of Bacterial Lectins: From Monomer Design to Glycoclusters and Glycopolymers. Bioconjugate Chemistry, American Chemical Society, 2019, 30 (3), pp.647-656. ⟨10.1021/acs.bioconjchem.8b00847⟩. ⟨hal-02322076⟩
  • François Portier, Justine Solier, Sami Halila. N , N′ -Disubstituted Barbituric Acid: A Versatile and Modular Multifunctional Platform for Obtaining β- C -Glycoconjugates from Unprotected Carbohydrates in Water. European Journal of Organic Chemistry, Wiley-VCH Verlag, 2019, 2019 (36), pp.6158-6162. ⟨10.1002/ejoc.201901251⟩. ⟨hal-02322037⟩
  • Yingjie Liao, Laurent Goujon, Eric Reynaud, Sami Halila, Alain Gibaud, et al.. Self-assembly of copper-free maltoheptaose-block-polystyrene nanostructured thin films in real and reciprocal space. Carbohydrate Polymers, Elsevier, 2019, 212, pp.222-228. ⟨10.1016/j.carbpol.2019.02.014⟩. ⟨hal-02954596⟩
  • Nívia Do N. Marques, Rosangela de C. Balaban, Sami Halila, Redouane Borsali. Synthesis and characterization of carboxymethylcellulose grafted with thermoresponsive side chains of high LCST: The high temperature and high salinity self-assembly dependence. Carbohydrate Polymers, Elsevier, 2018, 184, pp.108-117. ⟨10.1016/j.carbpol.2017.12.053⟩. ⟨hal-02954624⟩
  • Nívia Do N. Marques, Rosangela de C. Balaban, Sami Halila, Redouane Borsali. Synthesis and characterization of carboxymethylcellulose grafted with thermoresponsive side chains of high LCST: The high temperature and high salinity self-assembly dependence. Carbohydrate Polymers, Elsevier, 2018, 184, pp.108-117. ⟨10.1016/j.carbpol.2017.12.053⟩. ⟨hal-02322152⟩
  • Yoko Sakai-Otsuka, Soraia Zaioncz, Issei Otsuka, Sami Halila, Patrice Rannou, et al.. Self-Assembly of Carbohydrate- block -Poly(3-hexylthiophene) Diblock Copolymers into Sub-10 nm Scale Lamellar Structures. Macromolecules, American Chemical Society, 2017, 50 (8), pp.3365-3376. ⟨10.1021/acs.macromol.7b00118⟩. ⟨hal-02114456⟩
  • Chih-Chien Hung, Yu-Cheng Chiu, Hung-Chin Hung, Chien Lu, Cécile Bouilhac, et al.. Conception of Stretchable Resistive Memory Devices Based on Nanostructure-Controlled Carbohydrate- block -Polyisoprene Block Copolymers. Advanced Functional Materials, Wiley, 2017, 27 (13), pp.1606161. ⟨10.1002/adfm.201606161⟩. ⟨hal-02114459⟩
  • Jing Chen, Christophe Travelet, Redouane Borsali, Sami Halila. Hemicellulosic Polysaccharides Mimics: Synthesis of Tailored Bottlebrush-Like Xyloglucan Oligosaccharide Glycopolymers as Binders of Nanocrystalline Cellulose. Biomacromolecules, American Chemical Society, 2017, 18 (10), pp.3410-3417. ⟨10.1021/acs.biomac.7b01056⟩. ⟨hal-02322175⟩
  • Antoine Petrelli, Eric Samain, Stéphanie Pradeau, Sami Halila, Sébastien Fort. Efficient Conjugation of Oligosaccharides to Polymer Particles through Furan/Maleimide Diels-Alder Reaction: Application to the Capture of Carbohydrate-Binding Proteins. ChemBioChem, Wiley-VCH Verlag, 2017, 18 (2), pp.206-212. ⟨10.1002/cbic.201600509⟩. ⟨hal-02115628⟩
  • Tatiane Popiolski, Issei Otsuka, Sami Halila, Edvani Muniz, Valdir Soldi, et al.. Preparation of Polymeric Micelles of Poly(Ethylene Oxide-b-Lactic Acid) and their Encapsulation With Lavender Oil. Materials Research, Associação Brasileira de Metalurgia e Materiais (ABM); Associação Brasileira de Cerâmica (ABC); Associação Brasileira de Polímeros (ABPol), 2016, 19 (6), pp.1356-1365. ⟨10.1590/1980-5373-MR-2016-0430⟩. ⟨hal-02114462⟩
  • Antoine Petrelli, Redouane Borsali, Sébastien Fort, Sami Halila. Redox tunable delivery systems: sweet block copolymer micelles via thiol–(bromo)maleimide conjugation. Chemical Communications, Royal Society of Chemistry, 2016, 52 (82), pp.12202-12205. ⟨10.1039/C6CC07136H⟩. ⟨hal-02119204⟩
  • Leticia Mazzarino, Gecioni Loch-Neckel, Lorena dos Santos Bubniak, Fabiana Ourique, Issei Otsuka, et al.. Nanoparticles Made From Xyloglucan-Block-Polycaprolactone Copolymers: Safety Assessment for Drug Delivery. Toxicological Sciences, Oxford University Press (OUP), 2015, 147 (1), pp.104-115. ⟨10.1093/toxsci/kfv114⟩. ⟨hal-02114476⟩
  • Takuya Isono, Issei Otsuka, Sami Halila, Redouane Borsali, Toyoji Kakuchi, et al.. Sub-20 nm Microphase-Separated Structures in Hybrid Block Copolymers Consisting of Polycaprolactone and Maltoheptaose. Journal of Photopolymer Science and Technology, Technical Assoc of Photopolymers Japan, 2015, 28 (5), pp.635-642. ⟨10.2494/photopolymer.28.635⟩. ⟨hal-02114485⟩
  • Carole Urbach, Sami Halila, Catherine Guerreiro, Hugues Driguez, Laurence Mulard, et al.. CGTase-Catalysed cis -Glucosylation of L -Rhamnosides for the Preparation of Shigella flexneri 2a and 3a Haptens. ChemBioChem, Wiley-VCH Verlag, 2014, 15 (2), pp.293-300. ⟨10.1002/cbic.201300597⟩. ⟨pasteur-02043361⟩
  • Yu-Cheng Chiu, Issei Otsuka, Sami Halila, Redouane Borsali, Wen-Chang Chen. High-Performance Nonvolatile Transistor Memories of Pentacence Using the Green Electrets of Sugar-based Block Copolymers and Their Supramolecules. Advanced Functional Materials, Wiley, 2014, 24 (27), pp.4240-4249. ⟨10.1002/adfm.201304297⟩. ⟨hal-02114565⟩
  • Leticia Mazzarino, Issei Otsuka, Sami Halila, Lorena dos Santos Bubniak, Suelen Mazzucco, et al.. Xyloglucan- block -Poly(ϵ-Caprolactone) Copolymer Nanoparticles Coated with Chitosan as Biocompatible Mucoadhesive Drug Delivery System. Macromolecular Bioscience, Wiley-VCH Verlag, 2014, 14 (5), pp.709-719. ⟨10.1002/mabi.201300465⟩. ⟨hal-02114567⟩
  • Alexandre Guerry, Sylvain Cottaz, Etienne Fleury, Julien Bernard, Sami Halila. Redox-stimuli responsive micelles from DOX-encapsulating polycaprolactone-g-chitosan oligosaccharide. Carbohydrate Polymers, Elsevier, 2014, 112, pp.746-752. ⟨10.1016/j.carbpol.2014.06.052⟩. ⟨hal-01089690⟩
  • Takuya Isono, Issei Otsuka, Yohei Kondo, Sami Halila, Sébastien Fort, et al.. Sub-10 nm Nano-Organization in AB 2 - and AB 3 -Type Miktoarm Star Copolymers Consisting of Maltoheptaose and Polycaprolactone. Macromolecules, American Chemical Society, 2013, 46 (4), pp.1461-1469. ⟨10.1021/ma3026578⟩. ⟨hal-02114582⟩
  • Salomé Tallegas, Thierry Baron, Guillaume Gay, Claire Aggrafeil, Billel Salhi, et al.. Block copolymer technology applied to nanoelectronics. physica status solidi (c), Wiley, 2013, 10 (9), pp.1195-1206. ⟨10.1002/pssc.201300002⟩. ⟨hal-02114577⟩
  • Issei Otsuka, Salomé Tallegas, Yoko Sakai, Cyrille Rochas, Sami Halila, et al.. Control of 10 nm scale cylinder orientation in self-organized sugar-based block copolymer thin films. Nanoscale, Royal Society of Chemistry, 2013, 5 (7), pp.2637. ⟨10.1039/c3nr00332a⟩. ⟨hal-02114580⟩
  • Alexandre Guerry, Julien Bernard, Eric Samain, Etienne Fleury, Sylvain Cottaz, et al.. Aniline-Catalyzed Reductive Amination as a Powerful Method for the Preparation of Reducing End-"Clickable" Chitooligosaccharides. Bioconjugate Chemistry, American Chemical Society, 2013, 24, pp.544-549. ⟨10.1021/bc3003716⟩. ⟨hal-00862391⟩
  • Issei Otsuka, Christophe Travelet, Sami Halila, Sébastien Fort, Isabelle Pignot-Paintrand, et al.. Thermoresponsive Self-Assemblies of Cyclic and Branched Oligosaccharide- block -poly( N -isopropylacrylamide) Diblock Copolymers into Nanoparticles. Biomacromolecules, American Chemical Society, 2012, 13 (5), pp.1458-1465. ⟨10.1021/bm300167e⟩. ⟨hal-02114597⟩
  • Samuel de Medeiros Modolon, Issei Otsuka, Sébastien Fort, Edson Minatti, Redouane Borsali, et al.. Sweet Block Copolymer Nanoparticles: Preparation and Self-Assembly of Fully Oligosaccharide-Based Amphiphile. Biomacromolecules, American Chemical Society, 2012, 13 (4), pp.1129-1135. ⟨10.1021/bm3000138⟩. ⟨hal-02114600⟩
  • Issei Otsuka, Takuya Isono, Cyrille Rochas, Sami Halila, Sébastien Fort, et al.. 10 nm Scale Cylinder–Cubic Phase Transition Induced by Caramelization in Sugar-Based Block Copolymers. ACS Macro Letters, Washington, D.C : American Chemical Society, 2012, 1 (12), pp.1379-1382. ⟨10.1021/mz300543u⟩. ⟨hal-02114585⟩
  • Julia Cushen, Issei Otsuka, Christopher Bates, Sami Halila, Sébastien Fort, et al.. Oligosaccharide/Silicon-Containing Block Copolymers with 5 nm Features for Lithographic Applications. ACS Nano, American Chemical Society, 2012, 6 (4), pp.3424-3433. ⟨10.1021/nn300459r⟩. ⟨hal-02114592⟩
  • Karim Aissou, Issei Otsuka, Cyrille Rochas, Sébastien Fort, Sami Halila, et al.. Nano-Organization of Amylose- b -Polystyrene Block Copolymer Films Doped with Bipyridine. Langmuir, American Chemical Society, 2011, 27 (7), pp.4098-4103. ⟨10.1021/la104936k⟩. ⟨hal-02114617⟩
  • Karim Aissou, Issei Otsuka, Cyrille Rochas, Sébastien Fort, Sami Halila, et al.. Nano-Organization of Amylose-b-Polystyrene Block Copolymer Films Doped with Bipyridine. Langmuir, American Chemical Society, 2011, 27 (7), pp.4098-4103. ⟨10.1021/la104936k⟩. ⟨hal-00951650⟩
  • Issei Otsuka, Keita Fuchise, Sami Halila, Sébastien Fort, Karim Aissou, et al.. Thermoresponsive Vesicular Morphologies Obtained by Self-Assemblies of Hybrid Oligosaccharide- block -poly( N -isopropylacrylamide) Copolymer Systems. Langmuir, American Chemical Society, 2010, 26 (4), pp.2325-2332. ⟨10.1021/la902743y⟩. ⟨hal-02114632⟩
  • Issei Otsuka, Keita Fuchise, Sami Halila, Sébastien Fort, Karim Aissou, et al.. Thermoresponsive Vesicular Morphologies Obtained by Self-Assemblies of Hybrid Oligosaccharide-block-poly(N-isopropylacrylamide) Copolymer Systems. Langmuir, American Chemical Society, 2010, 26 (4), pp.2325-2332. ⟨10.1021/la902743y⟩. ⟨hal-00950666⟩
  • S. Berson, D. Viet, Sami Halila, H. Driguez, Etienne Fleury, et al.. Synthesis of new cellobiose-based glycopolysiloxanes and their use as polymer stabilizers in miniemulsion polymerisation. Macromolecular Chemistry and Physics, Wiley-VCH Verlag, 2008, pp.1814-1825. ⟨hal-00320164⟩
  • Sami Halila, Maggy Manguian, Sébastien Fort, Sylvain Cottaz, Thierry Hamaide, et al.. Syntheses of well-defined glyco-polyorganosiloxanes by "click" chemistry and their surfactant properties. Macromolecular Chemistry and Physics, Wiley-VCH Verlag, 2008, 209 (12), pp.1282-1290. ⟨hal-00373953⟩

Conference papers8 documents

  • Gestranius Marie, Issei Otsuka, Sami Halila, Redouane Borsali, Tekla Tammelin. High resolution self-​assembled patterns on flexible nanocellulose film. 257th ACS National Meeting & Exposition, Mar 2019, Orlando, FL, United States. ⟨hal-02308460⟩
  • Gino Mangiante, Morgan Tizzotti, Alexandre Guerry, Sylvain Cottaz, Michel Petit-Conil, et al.. Alkyne-functionalized Cellulose: Toward Green Tailored Biohybrid Conception. Workshop AXELERA-ARDI, May 2014, Grenoble, France. ⟨hal-00996264⟩
  • M. Tizzoti, C. Creuzet, M.P. Labeau, Thierry Hamaide, Eric Drockenmuller, et al.. Click chemistry: an efficient tool for polysaccharide modifications. Workshop International, Jun 2009, Marrakech, Morocco. ⟨hal-00379042⟩
  • Sami Halila, Maggy Manguian, Thierry Hamaide, Etienne Fleury, Hugues Driguez. Syntheses of well-Designed glyco-polyorganosiloxanes and their surface active properties. Second Chemical Workshop France Lyon- China- Xiamen, Oct 2007, Xiamen, China. ⟨hal-00380012⟩
  • Thierry Hamaide, S. Berson, Etienne Fleury, Sami Halila, Hugues Driguez. Synthèses et applications de glyco polysiloxanes à propriétés tensioactives. Vers de nouvelles voies de synthèses par click chemistry. 37ème Colloque Annuel du Groupe Français des Polymères (GFP), Nov 2007, Strasbourg, France. ⟨hal-00381730⟩
  • Sami Halila, Sébastien Fort, Sylvain Cottaz, Etienne Fleury, Thierry Hamaide, et al.. Well-defined glyco-polyorganosiloxane by click chemistry. ISPO 07, 5th International Workshop of Silicon-based Polymers, Jun 2007, Montpellier, France. ⟨hal-00380010⟩
  • Sami Halila, Maggy Manguian, Thierry Hamaide, Etienne Fleury, Hugues Driguez. Syntheses of well-designed glyco-polyorganosiloxanes and their surface active properties. Second Chemical Workshop France Lyon- China- Xiamen, Oct 2007, Xiamen, China. ⟨hal-00378937⟩
  • Sami Halila, Hugues Driguez, Sylvain Cottaz, Thierry Hamaide, Etienne Fleury. Nouveaux glyco-polyorganosiloxanes. Meeting of ADEME/AGRICE, May 2007, Paris, France. ⟨hal-00381728⟩