Biocompatible Polymeric Nanoparticles From Castor Oil Derivatives via Thiol‐Ene Miniemulsion Polymerization

Abstract

Biocompatible polymeric nanoparticles are obtained via thiol-ene polymerization of a biobased monomer in miniemulsion. The α,ω-diene-diester monomer is synthesized through esterification reaction of a glycerol derivative, namely 1,3-propanediol, with 10-undecenoic acid, a long-chain diene carboxylic acid. In order to investigate how different monomeric structures behave toward thiolene polymerization in miniemulsion, two types of thiols are investigated: 1,4-butanedithiol and 2-mercaptoethyl ether. Poly(thioether-ester)s with weight average molecular weight up to 15 kDa (M n ) are obtained, depending on initiator concentration and types of surfactant and dithiol employed. Finally, biobased poly(thioether-ester) nanoparticles are submitted to cytotoxicity and hemolysis analyses. High cell viability and no significant changes in cell morphology are observed after the incubation on murine fibroblast (L929) and human cervical cancer cells (HeLa). Last, hemolysis assays revealed blood compatibility and therefore polymeric nanoparticles have been shown to be a potential alternative drug delivery vector for intravenous administration. Practical Applications: There is a great demand for polymeric systems that fulfill a number of requirements, such as biodegradability and biocompatibility, for biomedical applications. In this context, biobased polymers obtained from vegetable oils are a very attractive sustainable alternative to fossil-derived polymeric materials, presenting potential biodegradability and low toxicity. By thiol-ene reactions, polymeric materials containing ester groups in the main chain -which can undergo hydrolysis-can be prepared in miniemulsion, enabling their degradation in physiological environment and, therefore, being interesting for biomedical applications and material disposal. Such novel materials could be used in temporary implants, tissue engineering, and drug delivery systems.

Renewable Poly(Thioether‐Ester)s from Fatty Acid Derivatives via Thiol‐Ene Photopolymerization

“…Repetition with 1.0 wt.% DMPA and otherwise similar conditions proceeded quantitatively in 5 min. These results agreed with previous studies that indicated photoreactions are dramatically accelerated when PI are employed (Alagi et al, ; Cardoso et al, ; Claudino et al, ; Northrop and Coffey, ; Samuelsson et al, ; Unverferth and Meier, ). Consequently, all ensuing photochemical reactions were conducted with 1.0 wt.% DMPA.…”

“…Subsequent treatment with isocyanate gave a polyurethane (Lluch et al, ). Polyesters were also prepared via reaction of alkyl 10‐undecenoates with various thiols (Cardoso et al, ; Turunc and Meier, ), and polyamides were synthesized from a thiolactone derivative of UDA (Goethals et al, ).…”

Self-Assembled chitosan/phospholipid nanoparticles: from fundamentals to preparation for advanced drug delivery

“…The biocompatibility and bioactivity of SACPNs are typically investigated by MTT assay and hemolysis test in vitro. Moreover, intraperitoneally administration into mouse is used to investigate the acute toxicity in vivo and biodistribution test is also applied to identify whether it has good biocompatibility and bioactivity (Cardoso et al, 2018;Nosrati et al, 2018;Yuan et al, 2018). Among all these techniques, MTT assay is the primary one that is typically used as the first test to investigate the biocompatibility and bioactivity of SACPNs.…”

Superparamagnetic biobased poly(thioether‐ester) via thiol‐ene polymerization in miniemulsion for hyperthermia

“…[24][25][26][27][28] Thiol-ene polymerization in miniemulsion has only been reported after 2014 in works describing the synthesis of nanoparticles comprised of linear polymers. 22,29,30 The synthesis of nanoparticles via thiol-ene miniemulsion polymerization allows the development of different kinds of material that could not be straightforwardly produced through other polymerization techniques, such as waterborne polyesters, some works were able to synthesize high molecular poly(thioetherester) (PTEE) via thiol-ene polymerization in miniemulsion 22,30 ; in addition, thiol-ene polymerization is a versatile technique that can be applied to the polymerization of biobased monomers from vegetable oils containing double bonds that are less reactive toward traditional free radical polymerization. 31,32 Also, in the past few years this click chemistry reaction has drawn attention to its use in the production of biomaterials, especially PTEE which is biodegradable 33,34 and no cytotoxic.…”

“…31,32 Also, in the past few years this click chemistry reaction has drawn attention to its use in the production of biomaterials, especially PTEE which is biodegradable 33,34 and no cytotoxic. 30 Therefore, this work aims to synthesize nanocomposites suitable to biomedical applications by encapsulating MNPs in situ via thiol-ene polymerization in miniemulsion and to utilize the PTEE/MNPs-oleic acid (OA) hybrid nanoparticles for hyperthermia treatment of tumors.…”