Synthesis, characterization and chemical degradation of poly(ester-triazole)s derived from <scp>d</scp>-galactose

Rivas, M. Verónica; Petroselli, Gabriela; Erra‐Balsells, Rosa; Varela, Oscar; Kolender, Adriana A.

doi:10.1039/c9ra00398c

Cited by 11 publications

(12 citation statements)

References 35 publications

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“…Thus, PET is a regioregular polymer carrying ester groups that can only act as H-bond acceptors; while PAT is non-regioregular and the amide function can behave as donor and acceptor of H-bonding. The increase in the size of PET NPs upon inclusion of CLZ could arise from an alteration of the ordered disposition of the regioregular PET chains (PET is obtained in a semicrystalline state with T m 204 °C in the first heating cycle of DSC) . The disruption of the ordered arrangement to accommodate CLZ gives rise to an increase of the diameter.…”

Section: Resultsmentioning

confidence: 99%

“…The use of different protecting strategies on the carbohydrate hydroxyl groups allows the modulation of the hydrophilicity of the repeating units as well as the intra- and intermolecular interactions. 1 Previously, we have described the synthesis and properties of poly(ester-triazole)s 2 (PET) and poly(amide-triazole)s 3 (PAT) derived from d -galactose ( Scheme 1 ). Their precursors were α-azido-ω-alkyne monomers with the secondary hydroxyl groups protected as 1,2-di- O -isopropylidene derivatives.…”

Section: Introductionmentioning

confidence: 99%

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Carbohydrate-Derived Polytriazole Nanoparticles Enhance the Anti-Inflammatory Activity of Cilostazol

et al. 2022

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Poly(amide-triazole) and poly(ester-triazole) synthesized from d-galactose as a renewable resource were applied for the synthesis of nanoparticles (NPs) by the emulsification/solvent evaporation method. The NPs were characterized as stable, spherical particles, and none of their components, including the stabilizer poly(vinyl alcohol), were cytotoxic for normal rat kidney cells. These NPs proved to be useful for the efficient encapsulation of cilostazol (CLZ), an antiplatelet and vasodilator drug currently used for the treatment of intermittent claudication, which is associated with undesired side-effects. In this context, the nanoencapsulation of CLZ was expected to improve its therapeutic administration. The carbohydrate-derived polymeric NPs were designed taking into account that the triazole rings of the polymer backbone could have attractive interactions with the tetrazole ring of CLZ. The activity of the nanoencapsulated CLZ was measured using a matrix metalloproteinase model in a lipopolysaccharide-induced inflammation system. Interestingly, the encapsulated drug exhibited enhanced anti-inflammatory activity in comparison with the free drug. The results are very promising since the stable, noncytotoxic NP systems efficiently reduced the inflammation response at low CLZ doses. In summary, the NPs were obtained through an innovative methodology that combines a carbohydrate-derived synthetic polymer, designed to interact with the drug, ease of preparation, adequate biological performance, and environmentally friendly production.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Carbohydrate-Derived Polytriazole Nanoparticles Enhance the Anti-Inflammatory Activity of Cilostazol

et al. 2022

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“…Then the catalytic solution was added immediately into the reaction mixture and the reaction condition was maintained at 30 °C for 3 h. After completion of the reaction, the polymer-grafted surfaces (Polymer-NC 2) were removed and washed with 20 mL of water and toluene repeatedly. Finally, the polymer-grafted nitrocellulose (Polymer-NC 2) surfaces were dried at 65 °C for 6 h …”

Section: Methodsmentioning

confidence: 99%

Functionalization of Nitrocellulose Film by AB-Type Click Polymerization: Methods and Property Enhancements

Ramar

Samanta

2022

ACS Appl. Polym. Mater.

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Nitrocellulose (NC), predominantly used in propellants and purifying membranes, has further gained attention recently because of its application potential in flexible solar cells, molecular electronic devices, biochemical processes, and leather coatings. For the diversification of application areas of nitrocellulose-based materials, some of the inherent properties like flexibility, transparency, hydrophobicity, stability, heat of denitration, etc., require improvements. As presented in this paper, most of those properties were found to be substantially enhanced after the functionalization of nitrocellulose surfaces by a unique AB-type click polymerization, attributed to changes in chemical functionality, crystallinity, morphology, etc., as observed from X-ray diffraction (XRD), field-emission scanning electron microscopy, atomic force microscopy (AFM), and small-angle X-ray scattering (SAXS) analyses. Unlike conventional AABB-type click polymerization, herein, both azide and alkyne functional groups have been incorporated in the same monomer for better efficacy, where AB-type click polymerization took place in the presence of azide-functionalized nitrocellulose. This is a typical graft-through approach, where polymerization took place both in solution as well as on surfaces, providing flexibility of characterization in both states for the clear-cut evidence of the success of this typical polymerization as well as immobilization, as studied by solution-state as well as solid-state nuclear magnetic resonance (NMR), X-ray photoelectron spectroscopy (XPS), and attenuated total reflectance Fourier transform infrared (ATR-FTIR) spectroscopy. The material was used as a hydrophobic/superhydrophobic coating for leather surfaces.

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“…Recently, Kolender et al designed the synthesis of α-azide-ω-alkynyl ester monomers to generate the hydrolytically degradable poly(ester triazoles) by using the α-azido-ω-alkyne ester 463 as a monomer . The synthesis of monomer began with the bromination of d -galactone-1,4-lactone 460 , which was treated with sodium azide followed by alkaline hydrolysis and produced O -isopropylidene protected galactonic acid 462 .…”

Section: Cuaac Click Chemistry Mediated Synthesis Of Diverse Glycocon...mentioning

confidence: 99%

“…Click polymerization of monomer 463 in bulk yielded mainly poly(ester triazole) 464 , whereas cyclic products (i.e., 466 – 468 ) prevailed when the reaction was carried out with diluted solution of monomers (Scheme ). Finally, the poly(ester triazole) 465 was developed without admitting copper as a catalyst. Cu-catalyzed click polymerization produced 1,4-regioselective triazolyl product, while under metal-free polymerization random distributions of triazole rings were noticed in the polymer backbone.…”

Section: Cuaac Click Chemistry Mediated Synthesis Of Diverse Glycocon...mentioning

confidence: 99%

Cu(I)-Catalyzed Click Chemistry in Glycoscience and Their Diverse Applications

et al. 2021

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Copper(I)-catalyzed 1,3-dipolar cycloaddition between organic azides and terminal alkynes, commonly known as CuAAC or click chemistry, has been identified as one of the most successful, versatile, reliable, and modular strategies for the rapid and regioselective construction of 1,4-disubstituted 1,2,3-triazoles as diversely functionalized molecules. Carbohydrates, an integral part of living cells, have several fascinating features, including their structural diversity, biocompatibility, bioavailability, hydrophilicity, and superior ADME properties with minimal toxicity, which support increased demand to explore them as versatile scaffolds for easy access to diverse glycohybrids and well-defined glycoconjugates for complete chemical, biochemical, and pharmacological investigations. This review highlights the successful development of CuAAC or click chemistry in emerging areas of glycoscience, including the synthesis of triazole appended carbohydrate-containing molecular architectures (mainly glycohybrids, glycoconjugates, glycopolymers, glycopeptides, glycoproteins, glycolipids, glycoclusters, and glycodendrimers through regioselective triazole forming modular and bio-orthogonal coupling protocols). It discusses the widespread applications of these glycoproducts as enzyme inhibitors in drug discovery and development, sensing, gelation, chelation, glycosylation, and catalysis. This review also covers the impact of click chemistry and provides future perspectives on its role in various emerging disciplines of science and technology.

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Synthesis, characterization and chemical degradation of poly(ester-triazole)s derived from d-galactose

Abstract: Carbohydrate-derived poly(ester-triazoles), soluble in organic solvents and degradable in aqueous media, have been synthesized by CuAAC or thermal polymerization.

Cited by 11 publications

References 35 publications

Carbohydrate-Derived Polytriazole Nanoparticles Enhance the Anti-Inflammatory Activity of Cilostazol

Carbohydrate-Derived Polytriazole Nanoparticles Enhance the Anti-Inflammatory Activity of Cilostazol

Functionalization of Nitrocellulose Film by AB-Type Click Polymerization: Methods and Property Enhancements

Cu(I)-Catalyzed Click Chemistry in Glycoscience and Their Diverse Applications

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