Thiol-ene miniemulsion polymerization of a biobased monomer for biomedical applications

• Published in: Colloids and surfaces, B, Biointerfaces B, Biointerfaces, 2017-11, Vol.159, p.509-517
• Main Authors: Machado, Thiago O., Cardoso, Priscilla B., Feuser, Paulo Emilio, Sayer, Claudia, Araújo, Pedro H.H.
• Format: Article
• Language: English
• Subjects: Biobased monomer; Biocompatibility; Cellular uptake; Miniemulsion; Nanoparticle; Thiol-ene polymerization
• ISSN: 0927-7765; 1873-4367
• DOI: 10.1016/j.colsurfb.2017.07.043

[Display omitted] •Synthesis of a biobased diene monomer derived from castor oil and isosorbide.•Waterborne poly(thioether-ester) nanoparticles.•In-situ encapsulation by thiol-ene miniemulsion polymerization.•Nanoparticles presented biocompatibility in L929 and HeLa cells.•Cellular uptake of dye-labeled polymeric nanoparticles by HeLa cells. Herein, we present the synthesis and characterization of poly(thioether-ester) nanoparticles via thiol-ene miniemulsion polymerization using a biobased α,ω-diene diester monomer, namely dianhydro-d-glucityl diundec-10-enoate (DGU), synthesized from 10-undecenoic acid (derived from castor oil) and isosorbide (derived from starch). DGU was copolymerized with 1,4-butanedithiol by thiol-ene miniemulsion polymerization resulting in waterborne poly(thioether-ester) particles with diameter around 200nm. Polymers with number average molecular weight up to 11kDa were obtained via miniemulsion polymerization. DSC and XRD analyses indicated a semi-crystalline polymer with a degree of crystallinity of at least 20% and Tm around 68°C. In addition, Coumarin 6 was encapsulated in the polymer particles with efficiency up to 98%. Nanoparticles presented biocompatibility in murine fibroblast (L929) and uterine colon cancer (HeLa) cells. The substantial cellular uptake of poly(thioether-ester) nanoparticles by HeLa cells suggests a potential use in uterine colon cancer treatment.