One-Pot Photo-Induced Sequential CuAAC and Thiol–Ene Click Strategy for Bioactive Macromolecular Synthesis

Abstract

Conceptually new one-pot photoinduced sequential click reactions were implemented to yield novel block copolymers with the ability for cell adhesion. Poly(e-caprolcatone) possessing clickable functional groups at the chain ends, namely α-alkynyl-ω-alkenyl-poly(e-caprolactone) (A-PCL-MA), was prepared by ring-opening polymerization of e-caprolactone using propargyl alcohol in the presence of stannous octoate at 110 °C followed by esterification with methacrylic acid. Azide-functional poly(methyl methacrylate) (PMMA-N3) was prepared independently by atom transfer radical polymerization (ATRP) followed by an azidation process using sodium azide. Finally, A-PCL-MA was reacted with PMMA-N3 and N-acetyl-l-cysteine (NAC) in a one-pot process through photoinduced sequential click reactions to furnish desired bioactive block copolymer (PMMA-b-PCL-NAC). A matrix for cell adhesion was then prepared from the yielded block copolymer PMMA-b-PCL-NAC and cell proliferation on the matrix was measured. Cells from the Vero ...