Synthesis, characterization and potential application of hydrophobically modified carrageenan derivatives as pharmaceutical excipients

Toumi, Selma; Yahoum, Madiha Melha; Lefnaoui, Sonia; Hadjsadok, Abdelkader

doi:10.1016/j.carbpol.2020.116997

Cited by 21 publications

(26 citation statements)

References 52 publications

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“…This contributes to the unfolding of the chains by expelling anionic polar groups in an aqueous medium, and therefore, the electrostatic repulsion becomes preponderant, which will result in a decreased viscosity by the disentanglement of the polymeric network. These results are not totally in agreement with previous works related to the hydrophobic modification of xanthan by Sara et al [ 26 ] and Toumi et al [ 27 , 29 ] for kappa-carrageenan. This may be because, in these works, the length of the hydrophobic octyl moieties is more important than that of benzyl groups, which resulted in stronger associative forces that increased with increased DS.…”

Section: Resultscontrasting

confidence: 80%

“…All of the characteristic peaks of native XG were observed, in particular at 1022.36 cm −1 for the ether function, 1248.13 cm −1 for the acetal function, 1407 cm −1 for the carboxyl function, and 1602.13 cm −1 for the carbonyls, as well as the peak at 1718.53 cm −1 for the CH 2 OCOCH 3 ester function of the acetyl group. The peaks at 2800 and 3315 cm −1 correspond, respectively, to the -CH 2 [ 26 , 27 ], and -OH bonds [ 6 ].…”

Section: Resultsmentioning

confidence: 99%

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Experimental Analysis and Neural Network Modeling of the Rheological Behavior of Xanthan Gum and Its Derivatives

et al. 2023

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The main objective of this study was to create a mathematical tool that could be used with experimental data to predict the rheological flow behavior of functionalized xanthan gum according to the types of chemical groups grafted onto its backbone. Different rheological and physicochemical analyses were applied to assess six derivatives synthesized via the etherification of xanthan gum by hydrophobic benzylation with benzyl chloride and carboxymethylation with monochloroacetic acid at three (regent/polymer) ratios R equal to 2.4 and 6. Results from the FTIR study verified that xanthan gum had been modified. The degree of substitution (DS) values varying between 0.2 and 2.9 for carboxymethylxanthan gum derivatives were found to be higher than that of hydrophobically modified benzyl xanthan gum for which the DS ranged from 0.5 to 1. The molecular weights of all the derivatives were found to be less than that of xanthan gum for the two types of derivatives, decreasing further as the degree of substitution (DS) increased. However, the benzyl xanthan gum derivatives presented higher molecular weights varying between 1,373,146 (g/mol) and 1,262,227 (g/mol) than carboxymethylxanthan gum derivatives (1,326,722–1,015,544) (g/mol). A shear-thinning behavior was observed in the derivatives, and the derivatives’ viscosity was found to decrease with increasing DS. The second objective of this research was to create an ANN model to predict one of the rheological properties (the apparent viscosity). The significance of the ANN model (R2 = 0.99998 and MSE = 5.95 × 10−3) was validated by comparing experimental results with the predicted ones. The results showed that the model was an efficient tool for predicting rheological flow behavior.

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Section: Resultscontrasting

confidence: 80%

Section: Resultsmentioning

confidence: 99%

Experimental Analysis and Neural Network Modeling of the Rheological Behavior of Xanthan Gum and Its Derivatives

et al. 2023

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“…The appearance of the main characteristic peaks of MTH and XG on the spectrum of the mixture (MTH/XG) was noticed ( Figure 1 ), with the observation of the N–H stretching of the primary amine group of metformin in the range of 3400 to 3100 cm −1 , along with the presence of two bands at 1038 cm −1 and 1166 cm −1 [ 38 ] ascribed to C–N stretching, as well as the N–H deformation at 1602.34 cm −1 [ 12 , 16 ]. Characteristic absorption bands of XG were also observed at 1015.55 cm −1 , 1407.66 cm −1 and 1732.13 cm −1 , corresponding, respectively, to the elongation of the ether COC function, the CH bonds of the methyl groups [ 39 ] and the asymmetric vibrations of COO–, as well as the elongation of the acetyl group [ 34 , 35 , 36 , 37 ]. The FTIR spectra of the formulated microspheres, depicted in Figure 2 , also demonstrate the absence of interactions between XG and MTH.…”

Section: Resultsmentioning

confidence: 99%

Formulation and Evaluation of Xanthan Gum Microspheres for the Sustained Release of Metformin Hydrochloride

et al. 2023

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This work aimed to formulate xanthan gum microspheres for the encapsulation of metformin hydrochloride, according to the process of ionotropic gelation. The obtained microparticles, based on various fractions of xanthan gum (0.5–1.25), were subjected to different physico-chemical tests and a drug release study. Microspheres with an average size varying between 110.96 μm and 208.27 μm were obtained. Encapsulation efficiency reached 93.11% at a 1.25% biopolymer concentration. The swelling study showed a swelling rate reaching 29.8% in the gastric medium (pH 1.2) and 360% in the intestinal medium (pH 6.8). The drug release studies showed complete metformin hydrochloride release from the beads, especially those prepared from xanthan gum at the concentration of 1.25%, in intestinal medium at 90.00% after 6 h. However, limited and insignificant drug release was observed within the gastric medium (32.50%). The dissolution profiles showed sustained release kinetics.

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“…Among these disadvantages, the most commonly cited are inappropriate mechanical properties, unstable viscosity, and low shear strength, making them unsuitable for many applications such as emulsification [9]. They have several resources such as algae, like carrageenans [10], plants such as cellulose, or micro-organisms such as dextran and xanthan gum [11].…”

Section: Introductionmentioning

confidence: 99%

Evaluation of Physicochemical and Amphiphilic Properties of New Xanthan Gum Hydrophobically Functionalized Derivatives

et al. 2023

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This research aimed to develop new hydrophobic and potentially amphiphilic benzyl xanthan gum (BXG) derivatives using a Williamson synthesis. This modification consists of an etherification reaction between xanthan gum (XG) and benzyl chloride (BC) under microwave heating. The effects of the molar ratio (R = XG/CLB, with R equal to 2 or 4) on the amphiphilic character and the degree of substitution (DS) were studied. The two benzyl xanthan gum derivatives (BXG1 and BXG2) were subsequently subjected to various physicochemical and rheological characterization techniques. The obtained results of FTIR and H1-NMR spectroscopy showed the effectiveness of the grafting of aromatic moieties onto the XG molecule with DS values of 0.59 for BXG1 and 0.7 for BXG2. The XRD analysis revealed slight modifications in the xanthan crystallinity after etherification, where the degree of crystallinity (DOC) values were 8.46%, 10.18%, and 14.67% for XG, BXG1, and BXG2, respectively. Additionally, conductivity measurements showed that the BXG derivatives exhibit higher values than native XG, due to the inter- and intra-molecular associations following the grafting of aromatic groups. Moreover, the critical aggregation concentration (CAC) was detected at 0.32% for BXG1 and 0.28% for BXG2. The rheological study confirmed that XG and its BXG derivatives exhibited a shear-thinning pseudoplastic behavior and that the viscosity increases when the DS increases. The emulsifying power test of the BXGs compared to the native XG confirmed the amphiphilic properties of the new benzylated derivatives, where the stabilizing capacity increases with increased DS.

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Synthesis, characterization and potential application of hydrophobically modified carrageenan derivatives as pharmaceutical excipients

Cited by 21 publications

References 52 publications

Experimental Analysis and Neural Network Modeling of the Rheological Behavior of Xanthan Gum and Its Derivatives

Experimental Analysis and Neural Network Modeling of the Rheological Behavior of Xanthan Gum and Its Derivatives

Formulation and Evaluation of Xanthan Gum Microspheres for the Sustained Release of Metformin Hydrochloride

Evaluation of Physicochemical and Amphiphilic Properties of New Xanthan Gum Hydrophobically Functionalized Derivatives

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