Synthesis and characterization of a novel chitosan-N-acetyl-homocysteine thiolactone polymer using MES buffer

Ferris, Cristina; Casas, Marta; Lucero, M.J.; de-Paz, M.-Violante; Jiménez-Castellanos, M.R.

doi:10.1016/j.carbpol.2014.03.078

Cited by 25 publications

(15 citation statements)

References 27 publications

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“…Recently, much attention has been paid to chitosan (CTS) because of its advantageous biological properties such as biodegradability, biocompatibility and non-toxicity as well as its physicochemical properties [43]. Thus, CTS and its derivatives have been used as an absorption enhancer [44], drug carrier [45,46], mucoadhesive and permeation enhancing polymer in formulations for buccal/sublingual, nasal, gastrointestinal, vaginal, colonic drug delivery [47] and for gene delivery [48].…”

Section: Resultsmentioning

confidence: 99%

Nanostructured Chitosan-Based Biomaterials for Sustained and Colon-Specific Resveratrol Release

Iglesias

Galbis

Fernández

et al. 2019

IJMS

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In the present work, we demonstrate the preparation of chitosan-based composites as vehicles of the natural occurring multi-drug resveratrol (RES). Such systems are endowed with potential therapeutic effects on inflammatory bowel diseases (IBD), such as Crohn’s disease (CD) and ulcerative colitis, through the sustained colonic release of RES from long-lasting mucoadhesive drug depots. The loading of RES into nanoparticles (NPs) was optimized regarding two independent variables: RES/polymer ratio, and temperature. Twenty experiments were carried out and a Box–Behnken experimental design was used to evaluate the significance of these independent variables related to encapsulation efficiency (EE). The enhanced RES EE values were achieved in 24 h at 39 °C and at RES/polymer ratio of 0.75:1 w/w. Sizes and polydispersities of the optimized NPs were studied by dynamic light scattering (DLS). Chitosan (CTS) dispersions containing the RES-loaded NPs were ionically gelled with tricarballylic acid to yield CTS-NPs composites. Macro- and microscopic features (morphology and porosity studied by SEM and spreadability), thermal stability (studied by TGA), and release kinetics of the RES-loaded CTS-NPs were investigated. Release patterns in simulated colon conditions for 48 h displayed significant differences between the NPs (final cumulative drug release: 79–81%), and the CTS-NPs composites (29–34%).

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Section: Resultsmentioning

confidence: 99%

Nanostructured Chitosan-Based Biomaterials for Sustained and Colon-Specific Resveratrol Release

Iglesias

Galbis

Fernández

et al. 2019

IJMS

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“…FT-IR: 1700 (CvO), 1650 and 1530 NIPAAm), 1500-900 (thiolactone) cm −1 . SEC (CHCl 3 /i-PrOH/ TEA): P(MITla-co-NIPAAm) 10 : M n = 1800 g mol −1 ; Đ = 1.11; P(MITla-co-NIPAAm) 23 : M n = 3300 g mol −1 ; Đ = 1.21; P(MITla-coNIPAAm) 35 : M n = 4300 g mol −1 ; Đ = 1.31 (PS calibration).…”

Section: Methodsmentioning

confidence: 99%

Poly(thiolactone) homo- and copolymers from maleimide thiolactone: synthesis and functionalization

et al. 2015

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We describe the synthesis of a thiolactone-functionalized maleimide (MITla), and its (co)polymerization into poly(thiolactone) homo- and copolymers via controlled or free radical polymerization (CRP or FRP) techniques. Homopolymers were synthesized using FRP whereas MITla was copolymerized with styrene and N-iso-propylacrylamide (NIPAAm) via RAFT. In that way, we were able to combine the properties of a maleimide with the possibility to use the thiolactone side chain functionality in subsequent double modification reactions. Thiolactones are susceptible to nucleophilic ring-opening in the presence of primary amines, releasing a thiol moiety that can be used for conjugate addition (nucleophilic thiol-ene) reactions afterwards. We synthesized and characterized copolymers of different compositions, followed by site-specific double modification reactions with a combination of n-butylamine and methyl acrylate

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“…This thiolation consists of aminolysis of the water-soluble N-acetylhomocysteinethiolactone 2 by the ε-NH 2 groups of lysine residues [92][93][94]. Thiolation of a large variety of macromolecular biochemical systems has been reported [80,[94][95][96][97][98][99][100][101][102][103][104][105][106].…”

Section: Reactivity and Synthetic Use Of Homocysteine-γ-thiolactone Amentioning

confidence: 99%

One-Pot Double Modification of Polymers Based on Thiolactone Chemistry

Espeel

Prez

2014

Multi-Component and Sequential Reactions in Polymer Synthesis

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One-pot multistep reactions based on thiolactone chemistry have emerged as a powerful tool for modifying thiolactone-containing polymers in one-pot and in an elegant manner. In general, thiolactones can be opened by a wide variety of functional amines and the released thiol can react with thiol 'scavengers' of choice. This overview highlights the most important features of this approach, illustrated by the versatile and site-specific double postpolymerization modification of various reactive systems.

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Synthesis and characterization of a novel chitosan-N-acetyl-homocysteine thiolactone polymer using MES buffer

Cited by 25 publications

References 27 publications

Nanostructured Chitosan-Based Biomaterials for Sustained and Colon-Specific Resveratrol Release

Nanostructured Chitosan-Based Biomaterials for Sustained and Colon-Specific Resveratrol Release

Poly(thiolactone) homo- and copolymers from maleimide thiolactone: synthesis and functionalization

One-Pot Double Modification of Polymers Based on Thiolactone Chemistry

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