Furfuryl‐ and Maleimido Polysaccharides: Synthetic Strategies Toward Functional Biomaterials

Abstract

In context with facile and efficient syntheses of functional polymeric materials, the combination of polysaccharides and functional moieties based on renewable resources is a sustainable and valuable approach. This review presents alternatives to prominent click reactions utilizing biopolymer derivatives with furfuryl and maleimide groups. On the one hand, the cross‐linking by Diels–Alder reaction of these polymers enables the synthesis of novel materials in the fields of self‐healing polymers, tissue engineering, and drug delivery. On the other hand, thiol‐ene click reactions allow their conjugation to complex (bio)molecules. Different synthetic strategies are reviewed and the applicability of functional materials is evaluated.

Diels-Alder-Chitosan based dissociative covalent adaptable networks

“…Hannaa, * , 2005) , (Kaya et al, 2018) Crosslinked chitosan films are generally obtained by reaction with glutaraldehyde, diepoxides, dianhydride, genipin and tripolyphosphate (Divya Nataraj, Seema Sakkara, 2018) , (Jin et al, 2004) , (Singh, Kuldeep Rajat Suri & Rana, 2012) , (Tiwary & Rana, 2010) , (Kavianinia et al, 2014) and few literature is provided on Diels-Alder based hydrogels for chitosan but not in view of film forming. (Matsumoto et al, 2016) , (Montiel-Herrera et al, 2015) , , (Elschner et al, 2018) In 2015, Montiel-Herrera et al (Montiel-Herrera et al, 2015) synthesized Diels-Alder chitosan microparticles. They functionalized chitosan with furan chitosan by a two-step reductive amidation (Erreur !…”

Solvent-Free Synthesis of Amidated Carboxymethyl Cellulose Derivatives: Effect on the Thermal Properties

“…In the current context of sustainable development, the increased demand for greener alternatives to conventional materials and procedures is attracting a renovated interest towards the study of novel approaches for the design of bio-sourced products [1,2,3,4]. In this regard, cellulose, the most abundant polymer on earth [5], and its derivatives represent a promising source of raw materials, thanks to their high availability, low environmental impact, non-toxicity and presence of reactive groups.…”

Switching of Cell Proliferation/Differentiation in Thiol–Maleimide Clickable Microcapsules Triggered by in Situ Conjugation of Biomimetic Peptides

“…Bioorthogonal click reactions , are expected to be a promising chemical tool for immobilizing new components to scaffolds. Examples include the Diels–Alder reaction, tetrazine ligation, azide–alkyne cycloaddition, and thiol–ene reactions. − Because the click reactions proceed under physiological conditions even in the presence of cells, in situ cross-linkable hydrogels produced via click reactions were developed for tissue engineering applications. − Due to their excellent biocompatibility, it is expected that bioorthogonal click reactions will become an ideal chemical tool for achieving “ in situ conjugation” of functional molecules to scaffolds, which can change the extracellular environment to stimulate cultured cells/tissues. Among several click reactions, the thiol–maleimide reaction , is one of the candidates for in situ conjugation due to its performance and safety in recent clinical applications of antibody–drug conjugates …”

“…26−30 Due to their excellent biocompatibility, it is expected that bioorthogonal click reactions will become an ideal chemical tool for achieving "in situ conjugation" of functional molecules to scaffolds, which can change the extracellular environment to stimulate cultured cells/tissues. Among several click reactions, the thiol−maleimide reaction 24,29 is one of the candidates for in situ conjugation due to its performance and safety in recent clinical applications of antibody−drug conjugates. 25 In demonstrating the potential of in situ conjugation, rapid diffusion is also an important factor.…”