Adhesion of Preosteoblasts and Fibroblasts onto Poly(pentafluorostyrene)‐Based Glycopolymeric Films and their Biocompatibility

Abstract

An efficient and metal-catalyst free method of glycopolymer synthesis via thiol/para-fluorine "click" reaction was used to graft acetylated 1-thio-β-D-glucopyranose and 1-thio-β-D-galactopyranose onto a homopolymer of pentafluorostyrene (PFS) as well as onto a block copolymer of styrene and PFS. Subsequent deprotection of the carbohydrate moieties yielded well-defined, sugar-modified polymers (PDI < 1.2). The prepared polymers were not cytotoxic against 3T3 fibroblasts and MC3T3-E1 preosteoblasts. Furthermore, the water-insoluble copolymers were drop-cast and examined as synthetic biocompatible coatings on poly(propylene) substrates for culturing the investigated cell types. Both fibro- and preosteoblasts showed stable adhesion and proliferation on the glycopolymer-coated surfaces.

Heterofunctionalized Multiarm Star Polymers via Sequential Thiol-para-Fluoro and Thiol-Ene Double “Click” Reactions

“…Moreover, it is well known that the labile para ‐fluorine substituents of pentafluorophenyl groups can undergo nucleophilic substitution reactions particularly with thiol‐based nucleophiles even at room temperature . Recently, Schubert and co‐workers employed thiol‐ para‐ fluoro “click” reaction to obtain glycopolymers at low temperature to prevent degradation of sugar units . Although it is mainly a nucleophilic substitution reaction, the versatility and efficiency of thiol substitution of the para ‐fluoro group has been demonstrated by Schubert et al to follow with most of the‘‘click” chemistry requirements …”

Synthesis of Glycopolymer Architectures by Reversible-Deactivation Radical Polymerization

“…Materials covered with a suitable glycopolymer have improved biocompatibility [97,99] and, in the case of nanoparticles, can be targeted to a specific organ [10,247,248]. Examples have already emerged of glycopolymer decorated quantum dots [221], and superparamagnetic iron oxide nanoparticles which may be used for in vivo imaging and hyperthermia treatment [249].…”

“…The obtained glycopolymers were then deprotected with sodium methoxide in DMF and purified by precipitation in cold EtOH. The same method was later applied to the synthesis of β-thiogalactoside-functionalized homo and block copolymers [97]. The deprotected block copolymers were used to coat polypropylene microtiter plates and glass slides.…”

Functional‐Polymer Library through Post‐Polymerization Modification of Copolymers Having Oleate and Pentafluorophenyl Pendants

“…Nucleophilic aromatic substitution of the labile para ‐fluoro substituent of the pentafluorophenyl group ( para ‐fluoro‐thiol reaction: PFTR) by nucleophiles such as amines, thiols, and alcohols have been widely used in organic chemistry to modify pentafluorophenyl porphyrins . Recently, this PFTR technique has been employed for near‐quantitative post‐polymerization functionalization of polymers . The pentafluorophenyl group is unreactive during (radical) polymerization and radical post‐polymerization modification processes, but it undergoes selective nucleophilic aromatic substitution reactions with thiols in the para and, in a few cases, meta positions under basic conditions .…”