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In Vitro Degradation and Cytotoxicity Response of Biobased Nanoparticles Prepared by Thiol-ene Polymerization in Miniemulsion

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Abstract

Biodegradability is a key feature for the application of polymeric devices in medicine. This study reports an experimental and theoretical study of the degradation of poly(thioether-ester) (PTEe) nanoparticles in aqueous media. The α,ω-diene diester derived from vegetable oil, 1,3-propylene diundeca-10-polenoate (Pd10e), was used as monomer in the solvent-free synthesis of Pd10e-based nanoparticles (A-PTEe nanoparticles) via thiol-ene miniemulsion polymerization. The theoretical partition coefficients of A-PTEe and a PTEe based on dianhydro-d-glucityl diundec-10-enoate (DGU) (B-PTEe nanoparticles) were calculated using density functional theory (DFT), in order to compare their degradation behavior. The results showed that A-PTEe is more hydrophilic than B-PTEe, thus indicating the possible faster degradation of the former. The experimental degradation studies showed that, in fact, A-PTEe nanoparticles are faster degraded than B-PTEe, presenting substantial molecular weight decrease, which confirms the theoretical results. The effects of degradation could be observed in the chemical composition and thermal properties of the polymer. Considering its applicability potential as a biomaterial due to its fast degradation behavior, the cytotoxicity of A-PTEe nanoparticles and its degradation products were evaluated. In vitro assays confirmed the biocompatibility of A-PTEe nanoparticles and its degradation products when exposed on fibroblasts and red blood cells. These results suggest A-PTEe nanoparticles can be promising candidates as biobased nanocarriers for biomedical applications.

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Acknowledgments

We gratefully acknowledge CAPES (Coordenação de Aperfeiçoamento de Pessoal de Nível Superior), especially to CAPES-PRINT Program (Project number 88887.310560/2018-00), and CNPq (Conselho Nacional de Desenvolvimento Científico e Tecnológico) for the financial support. G. Candiotto and C. Guindani gratefully acknowledge FAPERJ (Fundação Carlos Chagas Filho de Amparo à Pesquisa do Estado do Rio de Janeiro), process numbers E-26/200.008/2020 and E-26/201.911/2020, for the financial support. G. Candiotto also thanks the support of Núcleo Avançado de Computação de Alto Desempenho (NACAD/COPPE/UFRJ) and Sistema Nacional de Processamento de Alto Desempenho (SINAPAD).

Funding

CAPES (Coordenação de Aperfeiçoamento de Pessoal de Nível Superior), CAPES-PRINT Program (Project number 88887.310560/2018-00); CNPq (Conselho Nacional de Desenvolvimento Científico e Tecnológico) and FAPERJ (Fundação Carlos Chagas Filho de Amparo à Pesquisa do Estado do Rio de Janeiro) Process E-26/201.911/2020 and Process E-26/200.008/2020.

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Authors and Affiliations

  1. Department of Chemical Engineering and Food Engineering, EQA/UFSC, Federal University of Santa Catarina, C.P. 476, Florianópolis, SC, CEP 88040-900, Brazil

    Fernanda Hoelscher, Priscilla B. Cardoso, Camila Guindani, Paulo Feuser, Pedro H. H. Araújo & Claudia Sayer

  2. Institute of Chemistry, IQ/UFRJ, Federal University of Rio de Janeiro, Rio de Janeiro, RJ, CEP 21941-909, Brazil

    Graziâni Candiotto

  3. Chemical Engineering Program, COPPE, PEQ/COPPE/UFRJ, Federal University of Rio de Janeiro, Rio de Janeiro, RJ, CEP 21941-972, Brazil

    Camila Guindani

Authors
  1. Fernanda Hoelscher
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  2. Priscilla B. Cardoso
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  3. Graziâni Candiotto
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  4. Camila Guindani
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  5. Paulo Feuser
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  6. Pedro H. H. Araújo
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  7. Claudia Sayer
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Contributions

FH: Investigation, methodology, writing—original draft, writing—review & editing. PBC: Investigation, concept development, writing—original draft. GC: Formal analysis, investigation, methodology, writing—original draft, writing—review & editing. CG: Formal analysis, concept development, methodology, writing—original draft, writing—review & editing. PF: Investigation—biological assays, methodology, writing—original draft. PHHA: Formal analysis, conceptualization, project administration, supervision, writing—review & editing. CS: Conceptualization, writing—review & editing, project administration, funding acquisition, supervision.

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Correspondence to Claudia Sayer.

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Hoelscher, F., Cardoso, P.B., Candiotto, G. et al. In Vitro Degradation and Cytotoxicity Response of Biobased Nanoparticles Prepared by Thiol-ene Polymerization in Miniemulsion. J Polym Environ 29, 3668–3678 (2021). https://doi.org/10.1007/s10924-021-02139-w

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