Galactose-derived poly(amide-triazole)s. Degradation, deprotection and derivatization studies

Rivas, M. Verónica; Varela, Oscar; Kolender, Adriana A.

doi:10.1016/j.eurpolymj.2020.109653

Cited by 2 publications

(5 citation statements)

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“…In addition, the 1 H NMR spectrum of PAT-P-v NPs (3e) showed a main peak at 7.84 and a minor one at 7.53 ppm, respectively, assigned to 1,4- and 1,5-disubstituted triazole CH. 3 In the presence of CLZ, the main signal became less intense and the weak one at lower field (8.31 ppm) appeared more intense. The significant downfield shift for this signal suggested that, in spite of the presence of a competitive solvent as DMSO, the triazole CH was also involved in a hydrogen bonding interaction with CLZ.…”

Section: Resultsmentioning

confidence: 97%

“…In addition, the 1 H NMR spectrum of PAT-P-v NPs (3e) showed a main peak at 7.84 and a minor one at 7.53 ppm, respectively, assigned to 1,4- and 1,5-disubstituted triazole CH . In the presence of CLZ, the main signal became less intense and the weak one at lower field (8.31 ppm) appeared more intense.…”

Section: Resultsmentioning

confidence: 97%

“…This arrangement is expected not to be perturbed by the inclusion of CLZ. In addition, non-regioregular PAT chains (PAT is obtained as an amorphous material) 3 would allow conformational flexibility in a dynamic system that can either accommodate or expel the drug to reestablish the ordered arrangement. Therefore, CLZ could be released faster from PAT NPs, as experimentally observed.…”

Section: Resultsmentioning

confidence: 99%

“…PAT was obtained by click CuFAAC polymerization of N -propargyl-6-azide-6-deoxy-2,3:4,5-di- O -isopropylidene- d -galactonamide ( 2 ) as described previously. 3 A solution of monomer 2 (0.098 g, 0.29 mmol) in THF (1 mL) was heated under Ar atmosphere at 70 °C for 16 h. After solvent evaporation, the material was dissolved in dichloromethane and precipitated by addition of ethyl ether to afford PAT as a white solid (95% yield).…”

Section: Methodsmentioning

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: 97%

Section: Resultsmentioning

confidence: 97%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%