Green, Solid-State Synthesis of Maleated Chitosan and Ionotropic Gelation with Chitosan

Ravishankar, K.; Shelly, K. M.; Desingh, Raj Preeth; Rajalakshmi, S.; Narayanan, Abathodharanan; Dhamodharan, R.

doi:10.1021/acssuschemeng.8b03648

Cited by 35 publications

(13 citation statements)

References 49 publications

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“…Unmodified chitosan (Figure 7a) shows major peaks at 3280/3360, 2860-2930, 1660, 1593, 1423, 1377, and 1000-1150 cm −1 , corresponding to ν(OH/NH), ν(CH), ν(C=O), δ(NH 2 ), two δ(COH), and mixed ν(C-O-C/C-OH) vibrations, respectively [42]. After maleation and cross-linking (Figure 7b), the chitosan peaks of δ(NH 2 ) and ν(C=O) at 1593 and 1660 cm −1 are shifted to spectral regions of lower energy at 1555 and 1633 cm −1 , respectively, which agrees with the data described in [43] wherein 22-36-cm −1 shifts of these bands were also observed. A peak from remaining acetamide group of chitosan ν(C=O) is present at 1656 cm −1 .…”

Section: Ft-ir Spectrasupporting

confidence: 87%

Imaging-Guided Delivery of a Hydrophilic Drug to Eukaryotic Cells Based on Its Hydrophobic Ion Pairing with Poly(hexamethylene guanidine) in a Maleated Chitosan Carrier

Zakharenkova

Lebedeva

et al. 2021

Molecules

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Imaging-guided delivery is developed for hydrophobic drugs, and to a much lesser extent, hydrophilic ones. In this work we have designed a novel strategy for real-time monitoring of hydrophilic drug delivery. Traditionally, the drug and the dye are covalently attached to a nanocarrier or are electrostatically adsorbed. Recently, we found an efficient way to bind the drug by ion-paring with an appropriate counter-ion to form the aggregate that embeds a hydrophobic dye with a considerable fluorescence enhancement. We synthesized a series of carbocyanine dyes of hydrophobicity sufficient for solubilization in hydrophobic ion pairs, which restores their emission in the near-infrared (NIR) region upon the formation of the ternary aggregates. To avoid using toxic surfactants, we applied an amphiphilic polymer-oligomer poly(hexamethylene guanidine) (PHMG) as a counter-ion. Сeftriaxone was used as a model hydrophilic drug ensuring the highest fluorescent signal. The so-formed drug–counter-ion–dye aggregates were encapsulated into a cross-linked maleated chitosan carrier. Confocal laser scanning microscopy (CLSM) studies have demonstrated internalization of the encapsulated model drug by breast adenocarcinoma cells at 40 min after treatment. These results suggest the potential application of hydrophobic ion pairs containing an NIR dye in imaging-guided delivery of hydrophilic compounds.

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Section: Ft-ir Spectrasupporting

confidence: 87%

Imaging-Guided Delivery of a Hydrophilic Drug to Eukaryotic Cells Based on Its Hydrophobic Ion Pairing with Poly(hexamethylene guanidine) in a Maleated Chitosan Carrier

Zakharenkova

Lebedeva

et al. 2021

Molecules

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“…For comparison purpose, the same characterization was also given for CSP. For both CSM and CSP, the characteristic diffraction peaks ascribed to CS can be clearly observed at about 2q ¼ 10 and 20 , 24 indicating the single phase composition of the two samples and no other phases apparently appeared aer the CS membranes forming (Fig. 1a).…”

Section: Characterizationmentioning

confidence: 97%

Facile synthesis of chitosan membranes for visible-light-driven photocatalytic degradation of tetracycline hydrochloride

Liang

Chen

et al. 2020

RSC Adv.

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“…Chitosan and control samples (CH, CHUR, CHTA, and TAUR) were also tested under identical conditions (Figure S6). It was clear from these studies that CHTAUR, as well as chitosan-based control samples, clearly exhibited a cell viability of 80% over 48 h. 41 Thus, purified CHTAUR is similar to CH in being nontoxic to cell growth.…”

Section: ■ Results and Discussionmentioning

confidence: 83%

Tough Gels and Macroporous Foams Based on Chitosan through Hydrothermal Synthesis of Chitosan, Tartaric Acid, and Urea

Sangeetha

Sharma

Narayanan

et al. 2022

ACS Appl. Polym. Mater.

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Tough gels and foams (CHTAUR) based on chitosan were prepared by the hydrothermal reaction of a mixture of chitosan (CH), tartaric acid (TA), and urea (UR). The structure of purified CHTAUR in the solid state was analyzed by Fourier-transform infrared spectroscopy, cross-polarization magic angle spinning 13C-nuclear magnetic resonance spectroscopy, powder X-ray diffraction, and thermogravimetric analysis. CHTAUR is observed to be predominantly chitosan although a minor extent of TAUR salt is present as physical cross-links. The morphology of CHTAUR, as assessed by SEM, suggests the formation of macroporous structures with pore sizes in the range of 90 μm to 1.5 mm. X-ray CT analysis, on the other hand, suggests that the as-prepared CHTAUR foam exhibited open pores of cellular structures with a porosity of around 75% and the average pore size could be in the range of hundreds of μm to few mm. Under conditions of excess water usage, the foams turn into tough gels through water absorption. The suitability of CHTAUR for different applications was examined. Tough gels formed by using a higher extent of water were found to be suitable for compressive loading. The water absorption of the foam was around 25 g/g. A compressive strength study of foams enabled the estimation of the Young’s moduli of CHTAUR foams to be 44.28, 43.80, and 9.96 kPa for foams prepared with CH/H2O weight ratios of 1:5, 1:6, and 1:7.5, respectively. Cytotoxicity studies carried out using the NIH-3T3 cell line showed that CHTAUR, after purification through solvent extraction, supported cell growth and was not toxic to the cell growth, a feature that is also shown by CH. CHTAUR, consisting predominantly of CH, could find use as a biodegradable packaging material and also as a scaffold for tissue engineering applications.

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Green, Solid-State Synthesis of Maleated Chitosan and Ionotropic Gelation with Chitosan

Cited by 35 publications

References 49 publications

Imaging-Guided Delivery of a Hydrophilic Drug to Eukaryotic Cells Based on Its Hydrophobic Ion Pairing with Poly(hexamethylene guanidine) in a Maleated Chitosan Carrier

Imaging-Guided Delivery of a Hydrophilic Drug to Eukaryotic Cells Based on Its Hydrophobic Ion Pairing with Poly(hexamethylene guanidine) in a Maleated Chitosan Carrier

Facile synthesis of chitosan membranes for visible-light-driven photocatalytic degradation of tetracycline hydrochloride

Tough Gels and Macroporous Foams Based on Chitosan through Hydrothermal Synthesis of Chitosan, Tartaric Acid, and Urea

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