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2017-10-20 - Colloque/Présentation - communication orale - Anglais - 20 page(s)

Baroni Alexandra , Blankert Bertrand , Mespouille Laetitia , "TAD click-chemistry onto Aliphatic PolyCarbonates - A promising platform for tailor-made drug delivery" in GEMO 2017, Gand, Belgique, 2017

  • Codes CREF : Chimie macromoléculaire (DI1315), Chimie des polymères de synthèse (DI131C), Chimie pharmaceutique (DI3413)
  • Unités de recherche UMONS : Matériaux Polymères et Composites (S816), Analyse pharmaceutique (M130)
  • Instituts UMONS : Institut des Sciences et Technologies de la Santé (Santé)
  • Centres UMONS : Centre d’Innovation et de Recherche en Matériaux Polymères (CIRMAP)

Abstract(s) :

(Anglais) The concept of click chemistry was introduced by Sharpless, Kolb and Finn in 20011 and provides the base of a valuable toolbox for many scientific research areas and applications. This powerful chemistry relies on specific and orthogonal reactions enabling the effective formation of covalent bond under mild conditions. Among the click member family, triazoline dione (TAD) compounds can be used as a dienophile in a Diels-Alder type reaction respecting the features of the click chemistry concept2. Moreover, this fast reaction process occurs without any catalyst, making it very suitable for biomedical applications purposes. Finally, the transition from deep red colour arising from TAD to colourless solution provides a visual feedback of the advance of the reaction. Its applicability in polymer science for post-modification of functional polymers open the doors to new options in the tailoring of biomaterials for “on demand” applications. Herein, simple and ultrafast macromolecular functionalization under mild conditions using TAD click chemistry is introduced. Aliphatic polycarbonates (APCs) are chosen as macromolecular platform since this family of polymers present all the prerequisites to be used as biomaterials (biocompatibility and biodegradability)3,4. Those “clickable” copolymers are synthetized by ring-opening polymerization (ROP) of cyclocarbonate carrying diene dangling functions. According to biomedical prerequisites, they were produced using metal-free and non-toxic catalyst5. Post-modification with various TAD based compounds were carried out in optimised conditions and the effectiveness of the reaction was assessed with the traditional characterisation tools. Impacts on final thermal properties were evidenced by DSC where shift of the glass transition temperature was observed. A degradability study in different storage conditions also demonstrates the impact of the nature of the lateral function on the shelf-stability of the resulting polymer. This study provides the proof of concept of the APCs functionalization using TAD click-chemistry and constitutes a key step in the macromolecular design of well-tailored biomaterials. (1) Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Click Chemistry: Diverse Chemical Function from a Few Good Reactions. Angew. Chemie Int. Ed. 2001, 40 (11), 2004–2021 DOI: 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.3.CO;2-X. (2) Billiet, S.; Bruycker, K. De; Driessen, F. Triazolinediones Enable Ultrafast and Reversible Click Chemistry for the Design of Dynamic Polymer Systems. Nat. Chem. 2014, No. August, 1–7 DOI: 10.1038/nchem.2023. (3) Tempelaar, S.; Mespouille, L.; Coulembier, O.; Dubois, P.; Dove, A. P. Synthesis and Post-Polymerisation Modifications of Aliphatic Poly(carbonate)s Prepared by Ring-Opening Polymerisation. Chem. Soc. Rev. 2013, 42 (3), 1312–1336 DOI: 10.1039/C2CS35268K. (4) Mespouille, L.; Coulembier, O.; Kawalec, M.; Dove, A. P.; Dubois, P. Implementation of Metal-Free Ring-Opening Polymerization in the Preparation of Aliphatic Polycarbonate Materials. Prog. Polym. Sci. 2014, 39 (6), 1144–1164 DOI: 10.1016/j.progpolymsci.2014.02.003. (5) Nachtergael, A.; Coulembier, O.; Dubois, P.; Helvenstein, M.; Duez, P.; Blankert, B.; Mespouille, L. Organocatalysis Paradigm Revisited: Are Metal-Free Catalysts Really Harmless? Biomacromolecules 2015, 16 (2), 507–514 DOI: 10.1021/bm5015443.