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Published in: Colloid and Polymer Science 5/2018

17-03-2018 | Original Contribution

Polyester nanoparticles from macrolactones via miniemulsion enzymatic ring-opening polymerization

Authors: Viviane Chiaradia, André E. Polloni, Débora de Oliveira, José Vladimir de Oliveira, Pedro H. H. Araújo, Claudia Sayer

Published in: Colloid and Polymer Science | Issue 5/2018

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Abstract

Aliphatic polyesters are the most used biodegradable polymers in biomedical applications. These polymers can be synthesized by two main routes: polycondensation and ring-opening polymerization. In this work, polyester nanoparticles were synthesized by an environmentally friendly process, enzymatic ring-opening polymerization (ε-ROP) of different 16-membered macrolactones (globalide (unsaturated) and ω-pentadecalactone (saturated)), catalyzed by a biocatalyst (free Candida antarctica B lipase) in aqueous miniemulsion. Reactions were conducted varying parameters as surfactant concentration, polymerization temperature (45 and 60 °C), and co-stabilizer type (hexadecane and crodamol, a medium chain saturated triglyceride). Saturated and unsaturated poly(macrolactones) were successfully synthesized via ε-ROP in miniemulsion, and weight average molecular weights of up to 23,200 g/mol were reached. Nanoparticles showed a “lemon-shaped” morphology, and their average diameter was affected by surfactant concentration, varying from 75 to 283 nm and from 218 to 436 nm for poly(globalide) and poly(ω-pentadecalactone), respectively. Melting points of 47–49 °C (unsaturated poly(macrolactones)) and 91–92 °C (saturated poly(macrolactones)) were obtained.

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Literature
1.
go back to reference Seyednejad H, Ghassemi AH, Van Nostrum CF et al (2011) Functional aliphatic polyesters for biomedical and pharmaceutical applications. J Control Release 152:168–176CrossRef Seyednejad H, Ghassemi AH, Van Nostrum CF et al (2011) Functional aliphatic polyesters for biomedical and pharmaceutical applications. J Control Release 152:168–176CrossRef
2.
go back to reference Samanta A, Takkar S, Kulshreshtha R, Nandan B, Srivastava RK (2017) Facile fabrication of composite electrospun Nanofibrous matrices of poly(ε-caprolactone)–silica based Pickering emulsion. Langmuir 33:8062–8069CrossRef Samanta A, Takkar S, Kulshreshtha R, Nandan B, Srivastava RK (2017) Facile fabrication of composite electrospun Nanofibrous matrices of poly(ε-caprolactone)–silica based Pickering emulsion. Langmuir 33:8062–8069CrossRef
3.
go back to reference Stempfle F, Ritter BS, Mulhaupt R, Mecking S (2014) Long-chain aliphatic polyesters from plant oils for injection molding, film extrusion and electrospinning. Green Chem 16:2008–2014CrossRef Stempfle F, Ritter BS, Mulhaupt R, Mecking S (2014) Long-chain aliphatic polyesters from plant oils for injection molding, film extrusion and electrospinning. Green Chem 16:2008–2014CrossRef
4.
go back to reference Kumar A, Sawant K (2013) Encapsulation of exemestane in polycaprolactone nanoparticles: optimization, characterization, and release kinetics. Cancer Nanotechnol 4:57–71CrossRef Kumar A, Sawant K (2013) Encapsulation of exemestane in polycaprolactone nanoparticles: optimization, characterization, and release kinetics. Cancer Nanotechnol 4:57–71CrossRef
5.
go back to reference Shadi L, Karimi M, Entezami AA (2015) Preparation of electroactive nanofibers of star-shaped polycaprolactone/polyaniline blends. Colloid Polym Sci 293:481–491CrossRef Shadi L, Karimi M, Entezami AA (2015) Preparation of electroactive nanofibers of star-shaped polycaprolactone/polyaniline blends. Colloid Polym Sci 293:481–491CrossRef
6.
go back to reference Ulery BD, Nair LS, Laurencin CT (2011) Biomedical applications of biodegradable polymers. J Polym Sci Part B Polym Phys 49:832–864CrossRef Ulery BD, Nair LS, Laurencin CT (2011) Biomedical applications of biodegradable polymers. J Polym Sci Part B Polym Phys 49:832–864CrossRef
7.
go back to reference Kobayashi S (2010) Lipase-catalyzed polyester synthesis--a green polymer chemistry. Proc Jpn Acad Ser B Phys Biol Sci 86:338–365CrossRef Kobayashi S (2010) Lipase-catalyzed polyester synthesis--a green polymer chemistry. Proc Jpn Acad Ser B Phys Biol Sci 86:338–365CrossRef
8.
go back to reference Kobayashi S (1999) Enzymatic polymerization: a new method of polymer synthesis. J Polym Sci Part A Polym Chem 37:3041–3056CrossRef Kobayashi S (1999) Enzymatic polymerization: a new method of polymer synthesis. J Polym Sci Part A Polym Chem 37:3041–3056CrossRef
9.
go back to reference Kadokawa J, Kobayashi S (2010) Polymer synthesis by enzymatic catalysis. Curr Opin Chem Biol 14:145–153CrossRef Kadokawa J, Kobayashi S (2010) Polymer synthesis by enzymatic catalysis. Curr Opin Chem Biol 14:145–153CrossRef
10.
go back to reference Miletić N, Nastasović A, Loos K (2012) Immobilization of biocatalysts for enzymatic polymerizations: possibilities, advantages, applications. Bioresour Technol 115:126–135CrossRef Miletić N, Nastasović A, Loos K (2012) Immobilization of biocatalysts for enzymatic polymerizations: possibilities, advantages, applications. Bioresour Technol 115:126–135CrossRef
11.
go back to reference Albertsson A, Srivastava R (2008) Recent developments in enzyme-catalyzed ring-opening polymerization. Adv Drug Deliv Rev 60:1077–1093CrossRef Albertsson A, Srivastava R (2008) Recent developments in enzyme-catalyzed ring-opening polymerization. Adv Drug Deliv Rev 60:1077–1093CrossRef
12.
go back to reference McGinty D, Letizia CS, Api AM (2011) Fragrance material review on w-pentadecalactone. Food Chem Toxicol 49:S193–S201CrossRef McGinty D, Letizia CS, Api AM (2011) Fragrance material review on w-pentadecalactone. Food Chem Toxicol 49:S193–S201CrossRef
13.
go back to reference de Geus M, van der Meulen I, Goderis B, van Hecke K, Dorschu M, van der Werff H, Koning CE, Heise A (2010) Performance polymers from renewable monomers: high molecular weight poly(pentadecalactone) for fiber applications. Polym Chem 1:525CrossRef de Geus M, van der Meulen I, Goderis B, van Hecke K, Dorschu M, van der Werff H, Koning CE, Heise A (2010) Performance polymers from renewable monomers: high molecular weight poly(pentadecalactone) for fiber applications. Polym Chem 1:525CrossRef
14.
go back to reference Ates Z, Thornton D, Heise A (2011) Side-chain functionalisation of unsaturated polyesters from ring-opening polymerisation of macrolactones by thiol – ene click chemistry. Polym Chem 2:309–312CrossRef Ates Z, Thornton D, Heise A (2011) Side-chain functionalisation of unsaturated polyesters from ring-opening polymerisation of macrolactones by thiol – ene click chemistry. Polym Chem 2:309–312CrossRef
15.
go back to reference De Oliveira FCS, Olvera D, Sawkins MJ et al (2017) Direct UV-triggered Thiol-ene cross-linking of electrospun polyester fibers from unsaturated poly(macrolactone)s and their drug loading by solvent swelling. Biomacromolecules 18:4292–4298CrossRef De Oliveira FCS, Olvera D, Sawkins MJ et al (2017) Direct UV-triggered Thiol-ene cross-linking of electrospun polyester fibers from unsaturated poly(macrolactone)s and their drug loading by solvent swelling. Biomacromolecules 18:4292–4298CrossRef
16.
go back to reference Yang Y, Zhang J, Wu D, Xing Z, Zhou Y, Shi W, Li Q (2014) Chemoenzymatic synthesis of polymeric materials using lipases as catalysts: a review. Biotechnol Adv 32:642–651CrossRef Yang Y, Zhang J, Wu D, Xing Z, Zhou Y, Shi W, Li Q (2014) Chemoenzymatic synthesis of polymeric materials using lipases as catalysts: a review. Biotechnol Adv 32:642–651CrossRef
17.
go back to reference Zhang J, Shi H, Wu D, Xing Z, Zhang A, Yang Y, Li Q (2014) Recent developments in lipase-catalyzed synthesis of polymeric materials. Process Biochem 49:797–806CrossRef Zhang J, Shi H, Wu D, Xing Z, Zhang A, Yang Y, Li Q (2014) Recent developments in lipase-catalyzed synthesis of polymeric materials. Process Biochem 49:797–806CrossRef
18.
go back to reference Bougard F, Jeusette M, Mespouille L, Dubois P, Lazzaroni R (2007) Synthesis and Supramolecular Organization of Amphiphilic Diblock Copolymers Combining Poly (N,N -dimethylamino-2-ethyl methacrylate ) and poly ( E-caprolactone ). Langmuir 23:2339–2345CrossRef Bougard F, Jeusette M, Mespouille L, Dubois P, Lazzaroni R (2007) Synthesis and Supramolecular Organization of Amphiphilic Diblock Copolymers Combining Poly (N,N -dimethylamino-2-ethyl methacrylate ) and poly ( E-caprolactone ). Langmuir 23:2339–2345CrossRef
19.
go back to reference Vaida C, Keul H, Moeller M (2011) Tailor-made polyesters based on pentadecalactone via enzymatic catalysis. Green Chem 13:889–899CrossRef Vaida C, Keul H, Moeller M (2011) Tailor-made polyesters based on pentadecalactone via enzymatic catalysis. Green Chem 13:889–899CrossRef
20.
go back to reference Van Der Meulen I, De Geus M, Antheunis H et al (2008) Polymers from functional Macrolactones as potential Biomaterials : enzymatic ring opening polymerization , biodegradation , and biocompatibility. Biomacromolecules 9:3404–3410CrossRef Van Der Meulen I, De Geus M, Antheunis H et al (2008) Polymers from functional Macrolactones as potential Biomaterials : enzymatic ring opening polymerization , biodegradation , and biocompatibility. Biomacromolecules 9:3404–3410CrossRef
21.
go back to reference Zhou X, Hong L (2013) Controlled ring-opening polymerization of cyclic esters with phosphoric acid as catalysts. Colloid Polym Sci 291:2155–2162CrossRef Zhou X, Hong L (2013) Controlled ring-opening polymerization of cyclic esters with phosphoric acid as catalysts. Colloid Polym Sci 291:2155–2162CrossRef
22.
go back to reference Taden A, Antonietti M, Landfester K (2003) Enzymatic polymerization towards biodegradable polyester nanoparticles. Macromol Rapid Commun 24:512–516CrossRef Taden A, Antonietti M, Landfester K (2003) Enzymatic polymerization towards biodegradable polyester nanoparticles. Macromol Rapid Commun 24:512–516CrossRef
23.
24.
go back to reference Polloni AE, Veneral JG, Rebelatto EA et al (2016) Enzymatic ring opening polymerization of ω-pentadecalactone using supercritical carbon dioxide. J Supercrit Fluids 119:221–228CrossRef Polloni AE, Veneral JG, Rebelatto EA et al (2016) Enzymatic ring opening polymerization of ω-pentadecalactone using supercritical carbon dioxide. J Supercrit Fluids 119:221–228CrossRef
25.
go back to reference Gross RA, Kumar A, Kalra B (2001) Polymer synthesis by in vitro enzyme catalysis. Chem Rev 101:2097–2124CrossRef Gross RA, Kumar A, Kalra B (2001) Polymer synthesis by in vitro enzyme catalysis. Chem Rev 101:2097–2124CrossRef
26.
go back to reference Målberg S, Finne-Wistrand A, Albertsson AC (2010) The environmental influence in enzymatic polymerization of aliphatic polyesters in bulk and aqueous mini-emulsion. Polymer (Guildf) 51:5318–5322CrossRef Målberg S, Finne-Wistrand A, Albertsson AC (2010) The environmental influence in enzymatic polymerization of aliphatic polyesters in bulk and aqueous mini-emulsion. Polymer (Guildf) 51:5318–5322CrossRef
27.
go back to reference Pascual A, Leiza JR, Mecerreyes D (2013) Acid catalyzed polymerization of macrolactones in bulk and aqueous miniemulsion: ring opening vs. condensation. Eur Polym J 49:1601–1609CrossRef Pascual A, Leiza JR, Mecerreyes D (2013) Acid catalyzed polymerization of macrolactones in bulk and aqueous miniemulsion: ring opening vs. condensation. Eur Polym J 49:1601–1609CrossRef
28.
go back to reference Ates Z, Heise A (2014) Functional films from unsaturated poly(macrolactones) by thiol-ene cross-linking and functionalisation. Polym Chem 5:2936–2941CrossRef Ates Z, Heise A (2014) Functional films from unsaturated poly(macrolactones) by thiol-ene cross-linking and functionalisation. Polym Chem 5:2936–2941CrossRef
29.
go back to reference Guindani C, Dozoretz P, Veneral JG, da Silva DM, Araújo PHH, Ferreira SRS, de Oliveira D (2017) Enzymatic ring opening copolymerization of globalide and ε-caprolactone under supercritical conditions. J Supercrit Fluids 128:404–411CrossRef Guindani C, Dozoretz P, Veneral JG, da Silva DM, Araújo PHH, Ferreira SRS, de Oliveira D (2017) Enzymatic ring opening copolymerization of globalide and ε-caprolactone under supercritical conditions. J Supercrit Fluids 128:404–411CrossRef
30.
go back to reference Meulen IVD, Li Y, Deumens R et al (2011) Copolymers from unsaturated macrolactones: toward the design of cross-linked biodegradable polyesters. Biomacromolecules 12:837–843CrossRef Meulen IVD, Li Y, Deumens R et al (2011) Copolymers from unsaturated macrolactones: toward the design of cross-linked biodegradable polyesters. Biomacromolecules 12:837–843CrossRef
31.
go back to reference Chiaradia V, Soares NS, Valério A et al (2016) Immobilization of Candida antarctica lipase B on magnetic poly(urea-urethane) nanoparticles. Appl Biochem Biotechnol:1–18 Chiaradia V, Soares NS, Valério A et al (2016) Immobilization of Candida antarctica lipase B on magnetic poly(urea-urethane) nanoparticles. Appl Biochem Biotechnol:1–18
32.
go back to reference Cipolatti EP, Valério A, Nicoletti G, Theilacker E, Araújo PHH, Sayer C, Ninow JL, de Oliveira D (2014) Enzymatic immobilization of Candida antarctica lipase B on PEGylated poly ( urea-urethane ) nanoparticles by step miniemulsion polymerization. J Mol Catal B Enzym 109:116–121CrossRef Cipolatti EP, Valério A, Nicoletti G, Theilacker E, Araújo PHH, Sayer C, Ninow JL, de Oliveira D (2014) Enzymatic immobilization of Candida antarctica lipase B on PEGylated poly ( urea-urethane ) nanoparticles by step miniemulsion polymerization. J Mol Catal B Enzym 109:116–121CrossRef
33.
go back to reference Oliveira D, Feihrmann a C, Rubira a F et al (2006) Assessment of two immobilized lipases activity treated in compressed fluids. J Supercrit Fluids 38:373–382CrossRef Oliveira D, Feihrmann a C, Rubira a F et al (2006) Assessment of two immobilized lipases activity treated in compressed fluids. J Supercrit Fluids 38:373–382CrossRef
34.
go back to reference Focarete ML, Scandola M, Kumar A, R a G (2001) Physical characterization of poly (pentadecalactone ) synthesized by lipase-catalyzed ring-opening polymerization. J Polym Sci Part B Polym Phys 39:1721–1729CrossRef Focarete ML, Scandola M, Kumar A, R a G (2001) Physical characterization of poly (pentadecalactone ) synthesized by lipase-catalyzed ring-opening polymerization. J Polym Sci Part B Polym Phys 39:1721–1729CrossRef
35.
go back to reference Cai J, Liu C, Cai M, Zhu J, Zuo F, Hsiao BS, Gross RA (2010) Effects of molecular weight on poly(ω-pentadecalactone) mechanical and thermal properties. Polymer (Guildf) 51:1088–1099CrossRef Cai J, Liu C, Cai M, Zhu J, Zuo F, Hsiao BS, Gross RA (2010) Effects of molecular weight on poly(ω-pentadecalactone) mechanical and thermal properties. Polymer (Guildf) 51:1088–1099CrossRef
Metadata
Title
Polyester nanoparticles from macrolactones via miniemulsion enzymatic ring-opening polymerization
Authors
Viviane Chiaradia
André E. Polloni
Débora de Oliveira
José Vladimir de Oliveira
Pedro H. H. Araújo
Claudia Sayer
Publication date
17-03-2018
Publisher
Springer Berlin Heidelberg
Published in
Colloid and Polymer Science / Issue 5/2018
Print ISSN: 0303-402X
Electronic ISSN: 1435-1536
DOI
https://doi.org/10.1007/s00396-018-4306-y

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