Synthesis and Characterization of New Thiolated Chitosan Nanoparticles Obtained by Ionic Gelation Method

Esquivel, Reynaldo; Juárez, Josué; Almada, Mario; Ibarra, Jaime; Váldez, Miguel A.

doi:10.1155/2015/502058

Cited by 69 publications

(46 citation statements)

References 39 publications

(39 reference statements)

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“…The pCNP has a greater utilization than CNP in all measured data, due to the utilization of amine groups through the conjugation of -NHS palmitic acid to the amine groups of chitosan. The study of Esquivel et al reported a synthesis of thiol-modified chitosan with a utilization of 11% of amine groups in chitosan which is similar to our study that has utilized around 15% of free amine in chitosan following –NHS palmitic acid conjugation [ 54 ]. Besides that, the literature described by Mohammed et al also proposed that chemical modifications of chitosan such as amphiphilic chitosan, carboxylated chitosan, and lactose-modified chitosan were achieved through the reaction between amine groups of chitosan and the modifying agents [ 41 ].…”

Section: Resultssupporting

confidence: 75%

Increased Cytotoxic Efficacy of Protocatechuic Acid in A549 Human Lung Cancer Delivered via Hydrophobically Modified-Chitosan Nanoparticles As an Anticancer Modality

et al. 2020

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The growing incidence of global lung cancer cases against successful treatment modalities has increased the demand for the development of innovative strategies to complement conventional chemotherapy, radiation, and surgery. The substitution of chemotherapeutics by naturally occurring phenolic compounds has been touted as a promising research endeavor, as they sideline the side effects of current chemotherapy drugs. However, the therapeutic efficacy of these compounds is conventionally lower than that of chemotherapeutic agents due to their lower solubility and consequently poor intracellular uptake. Therefore, we report herein a hydrophobically modified chitosan nanoparticle (pCNP) system for the encapsulation of protocatechuic acid (PCA), a naturally occurring but poorly soluble phenolic compound, for increased efficacy and improved intracellular uptake in A549 lung cancer cells. The pCNP system was modified by the inclusion of a palmitoyl group and physico-chemically characterized to assess its particle size, Polydispersity Index (PDI) value, amine group quantification, functional group profiling, and morphological properties. The inclusion of hydrophobic palmitoyl in pCNP-PCA was found to increase the encapsulation of PCA by 54.5% compared to unmodified CNP-PCA samples whilst it only conferred a 23.4% larger particle size. The single-spherical like particles with uniformed dispersity pCNP-PCA exhibited IR bands, suggesting the successful incorporation of PCA within its core, and a hydrophobic layer was elucidated via electron micrographs. The cytotoxic efficacy was then assessed by using an MTT cytotoxicity assay towards A549 human lung cancer cell line and was compared with traditional chitosan nanoparticle system. Fascinatingly, a controlled release delivery and enhanced therapeutic efficacy were observed in pCNP-PCA compared to CNP, which is ascribed to lower IC50 values in the 72-h treatment in the pCNP system. Using the hydrophobic system, efficacy of PCA was significantly increased in 24-, 48-, and 72-h treatments compared to a single administration of the compound, and via the unmodified CNP system. Findings arising from this study exhibit the potential of using such modified nanoparticulate systems in increasing the efficacy of natural phenolic compounds by augmenting their delivery potential for better anti-cancer responses.

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Section: Resultssupporting

confidence: 75%

Increased Cytotoxic Efficacy of Protocatechuic Acid in A549 Human Lung Cancer Delivered via Hydrophobically Modified-Chitosan Nanoparticles As an Anticancer Modality

et al. 2020

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“…While, when chitosan molecular weights are low such as below 148kDa, chitosan will form a rod shape structure. Similarly, when the chitosan crossing linking reaction occurred through the addition of gum arabic, aggregated particulates were formed as noted by [24]. Higher hydrogen ion concentration favours rearrangement of protonated chitosan free chains, leading to formation of semi spherical shapes and homogeneous population of nanoparticles.…”

Section: Morphology Characterisationmentioning

confidence: 78%

“…Mechanical properties of a scaffold used for tissue engineering are very important due to the need for the structural stability to oppose the various stresses incurred during culture, in-vitro or implantation, in-vivo [24]. Bone tissues undergo compression and due to that compression test was used for evaluation.…”

Section: Mechanical Propertiesmentioning

confidence: 99%

Synthesis and Characterization of Chitosan/Gum Arabic Nanoparticles for Bone Regeneration

Ibekwe¹,

Oyatogun²,

Esan³

et al. 2017

AJMSE

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Chitosan /gum arabic nanoparticles (C/G)have been prepared by ionic gelation method. This was with a view to enhance the mechanical properties and its application as bone graft scaffold. The cowry shells were washed, dried, pulverized and subsequently sieved with mesh No. 60, size 250 µm. It was deproteinized, Chitin was isolated from the synthesis by demineralising in 0.5 M Hydrochloric acid, and subsequently deacetylated by the addition of 40% (W/V) of Sodium hydroxide to synthesize chitosan. The raw chitosan was purified using 2% (v/v) acetic acid solution. The synthesized chitosan and gum arabic, a product of Acacia tree, were used to prepare chitosan/gum arabic nanoparticles by ionic gelation method. Mechanical characterization was carried out on the synthesized material using universal testing machine. Analysis of the chemical composition was carried out using Fourier transform infrared spectrometer (FTIR) and X-Ray fluorescence, (XRF). Furthermore, the morphology of the materials were studied using scanning electron microscopy, SEM and the dimension of the nanoparticles were characterized using transmission electron microscopy (TEM). Finally, an attempt was made to ascertain its suitability for bone regeneration. The FTIR spectra result confirmed that the nanoparticle was actually a derivative of chitosan by the observed shift in the peak 3462 to 3404cm- -1 and 712 cm -1 on C/G nanoparticles spectrum were similar to the native chitosan spectrum which shows that there was no change in the main backbone of chitosan structure. The scanning electron microscopy (SEM) study revealed chitosan as polymeric rods, while the chitosan /gum arabic nanoparticles in aggregate. The TEM was to confirm nanoparticles of average size of 200nm. The ultimate compressive strength was found to have increased by 78.21%, the Young Modulus by 54.4 % and percentage elongation by 7%. In overall assessment, mechanical properties of the chitosan/gum arabic nanoparticles were better than native chitosan. The study concluded that crosslinking of chitosan with gum arabic to form its nanoparticles derivative improved the mechanical properties of chitosan and consequently its application as a bone graft substitute for bone regeneration.

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“…The existence of mercaptans is confirmed by the presence of the peaks at 751 cm −1 SS disulfide bond and 1,243 cm −1 CSH stretching in thiolated chitosan since such peaks are not seen in unmodified chitosan spectra. [ 36 ] Thus, the analysis exhibited successful modification of chitosan with thiol ligand.…”

Section: Resultsmentioning

confidence: 99%

Molecular docking, synthesis, and characterization of chitosan‐graft‐2‐mercaptobenzoic acid derivative as potential drug carrier

Marwaha¹,

Madgulkar²,

Bhalekar³

et al. 2020

J of Applied Polymer Sci

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Chitosan is a hydrophilic polymer with prominent mucoadhesive properties. However, it forms weak hydrogen bonds with mucin thus limiting its mucoadhesion and exhibit reduced bioavailability due to its short retention time in the body. The aim of the present study was to synthesize and characterize novel thiolated chitosan with improved functional property. A unique approach of using molecular docking to select ligand to chemically modify chitosan has been employed in the present research. A set of ligands were screened virtually using docking analysis and 2‐mercapto benzoic acid showed the lowest glide score of −4.31 Kcal/Mol thus displayed better binding interaction with chitosan. Based on the docking results, the best‐fit ligand was selected for wet lab synthesis. 2‐Mercapto benzoic acid was covalently attached to chitosan via formation of an amide bond and the reaction was mediated by carbodiimide and N‐hydroxysuccinimide. The synthesized polymer was in turn evaluated for zeta potential, Fourier transformed infrared, differential scanning calorimetry, molecular weight that confirmed conjugation of chitosan with the thiol ligand. The prepared thiomer was further subjected to mucoadhesion studies and displayed better mucoadhesion properties as compared to unmodified chitosan. Thus, the potential of the novel thiomer can be further explored as an excipient for drug delivery system with an emphasis on mucoadhesion.

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Synthesis and Characterization of New Thiolated Chitosan Nanoparticles Obtained by Ionic Gelation Method

Cited by 69 publications

References 39 publications

Increased Cytotoxic Efficacy of Protocatechuic Acid in A549 Human Lung Cancer Delivered via Hydrophobically Modified-Chitosan Nanoparticles As an Anticancer Modality

Increased Cytotoxic Efficacy of Protocatechuic Acid in A549 Human Lung Cancer Delivered via Hydrophobically Modified-Chitosan Nanoparticles As an Anticancer Modality

Synthesis and Characterization of Chitosan/Gum Arabic Nanoparticles for Bone Regeneration

Molecular docking, synthesis, and characterization of chitosan‐graft‐2‐mercaptobenzoic acid derivative as potential drug carrier

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