N-acetylcysteine side-chain functionalization of poly(globalide-co-ε-caprolactone) through thiol-ene reaction

Guindani, Camila; Dozoretz, Pablo; Araújo, Pedro Henrique Hermes de; Ferreira, Sandra R.S.; Oliveira, Débora de

doi:10.1016/j.msec.2018.09.060

Cited by 21 publications

(23 citation statements)

References 51 publications

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“…PGlCL is a biocompatible unsaturated copolyester, whose properties can be tailored by tuning its monomer ratios and/or by the functionalization of its double bonds. As reported in previous studies, PGlCL has a great potential to be used as the basis for a new biomaterials platform. The synthesis of PGlCL was carried out by enzymatic ring‐opening polymerization (e‐ROP) using supercritical carbon dioxide (scCO 2 ) as solvent, and then PGlCL NPs were produced by the solvent evaporation method.…”

Section: Introductionmentioning

confidence: 66%

Covalently Binding of Bovine Serum Albumin to Unsaturated Poly(Globalide‐Co‐ε‐Caprolactone) Nanoparticles by Thiol‐Ene Reactions

Guindani

Frey

Simon

et al. 2019

Macromolecular Bioscience

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When nanoparticles (NPs) are introduced to a biological fluid, different proteins (and other biomolecules) rapidly get adsorbed onto their surface, forming a protein corona capable of giving to the NPs a new "identity" and determine their biological fate. Protein-nanoparticle conjugation can be used in order to promote specific interactions between living systems and nanocarriers. Non-covalent conjugates are less stable and more susceptible to desorption in biological media, which makes the development of engineered nanoparticle surfaces by covalent attachment an interesting topic. In this work, the surface of poly(globalide-co-ε-caprolactone) (PGlCL) nanoparticles containing double bonds in the main polymer chain is covalently functionalized with bovine serum albumin (BSA) by thiol-ene chemistry, producing conjugates which are resistant to dissociation. The successful formation of the covalent conjugates is confirmed by flow cytometry (FC) and fluorescence correlation spectroscopy (FCS). Transmission electron microscopy (TEM) allows the visualization of the conjugate formation, and the presence of a protein layer surrounding the NPs can be observed. After conjugation with BSA, NPs present reduced cell uptake by HeLa and macrophage RAW264.7 cells, in comparison to uncoated NP. These results demonstrate that it is possible to produce stable conjugates by covalently binding BSA to PGlCL NP through thiol-ene reaction.

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Section: Introductionmentioning

confidence: 66%

Covalently Binding of Bovine Serum Albumin to Unsaturated Poly(Globalide‐Co‐ε‐Caprolactone) Nanoparticles by Thiol‐Ene Reactions

Guindani

Frey

Simon

et al. 2019

Macromolecular Bioscience

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“…While some examples of post-functionalized polyesters obtained combining ring-opening polymerization (ROP) and thiol-ene click chemistry recently appeared in literature (Darcos et al, 2012;Pelegri-O'Day et al, 2017;Guindani et al, 2019), to the best of our knowledge, this is one of the rare examples of combination of polycondensation reaction and thiol-ene click chemistry to prepare functionalized biobased degradable polyesters, and the first example employing isopropenyl moiety as reactive alkene substrate (Kolb and Meier, 2013;Trotta et al, 2019).…”

Section: Synthesis Of Functionalized Bio-polyesters 8 and 9 Using Uv-mentioning

confidence: 99%

Regioselective Photooxidation of Citronellol: A Way to Monomers for Functionalized Bio-Polyesters

et al. 2020

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Dye-sensitized photooxygenation reaction of bio-based double bond-containing substrates is proposed as sustainable functionalization of terpenes and terpenoids to transform them into polyoxygenated compounds to be employed for the synthesis of new bio-based polyesters. As proof of concept, citronellol 1 has been regioselectively converted into diol 4 using singlet oxygen (1 O 2), a traceless reagent that can be generated from air, visible light and zeolite supported-photosensitizer (Thionine-NaY). With our synthetic approach, diol 4 has been obtained in two-steps, with good regioselectivity, using green reagents such as light and air, and finally a solvent-free oxidation step. From this compound, a citronellol-based copolyester of poly(butylene succinate) (PBS) has been synthesized and fully characterized. The results obtained evidence that the proposed copolymerization of PBS with the citronellol-based building blocks allows to obtain a more flexible and functionalizable material, by exploiting a largely available natural molecule modified through a green synthetic path.

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“…[60] The most recent contribution in this field reported the functionally analogous copolymer with N-acetylcysteine through the thiol-ene click reaction and the antioxidant character from the functional moiety provides materials that could combat the cellular oxidative stress. [61] Direct UV-triggered thiol-ene has recently been reported as an in situ method to cross-link electrospun fibers from unsaturated poly(macrolactones), which have been claimed to have potential biomedical application as load-bearing scaffolds. [62] A polyester-bearing internal triple bond, suitable as a substrate in the thiol Michael reaction, can also be prepared by condensation of acetylenedicarboxylic acid and diols in the presence of p-toluenesulfonic acid.…”

Section: Postpolymerization Modification Strategies Involving Thiol Chemistrymentioning

confidence: 99%

Synthetic Approaches to Combine the Versatility of the Thiol Chemistry with the Degradability of Aliphatic Polyesters

Fuoco

Finne‐Wistrand

2019

Polymer Reviews

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Thiol chemistry is an efficient tool to manipulate the microstructure of aliphatic polyesters and open the way to different applications. Synthetic strategies that aim to synthesize thiol-functionalized aliphatic polyesters are reviewed herein. The introduction of thiol-editable groups on aliphatic polyesters can occur both at chain ends and along the chains, enabling diverse modifications of the polymeric chains and imparting new properties and functions. The use of thiol chemistry for postpolymerization modification of this class of polymers and the (co)polymerizations of monomers bearing thiol groups has also been described herein.

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N-acetylcysteine side-chain functionalization of poly(globalide-co-ε-caprolactone) through thiol-ene reaction

Cited by 21 publications

References 51 publications

Covalently Binding of Bovine Serum Albumin to Unsaturated Poly(Globalide‐Co‐ε‐Caprolactone) Nanoparticles by Thiol‐Ene Reactions

Covalently Binding of Bovine Serum Albumin to Unsaturated Poly(Globalide‐Co‐ε‐Caprolactone) Nanoparticles by Thiol‐Ene Reactions

Regioselective Photooxidation of Citronellol: A Way to Monomers for Functionalized Bio-Polyesters

Synthetic Approaches to Combine the Versatility of the Thiol Chemistry with the Degradability of Aliphatic Polyesters

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