Impact of Crystalline Structural Differences Between α- and β-Chitosan on Their Nanoparticle Formation Via Ionic Gelation and Superoxide Radical Scavenging Activities

Jampafuang, Yattra; Tongta, Anan; Waiprib, Yaowapha

doi:10.3390/polym11122010

Cited by 69 publications

(39 citation statements)

References 41 publications

(109 reference statements)

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“… 17 , 56 , 57 The peak at 2θ ≈ 9–11° corresponds to amide I (−N–CO–CH 3 ), while the peak at 2θ ≈ 19–20° corresponds to amide II (−NH 2 ). 58 Regarding the results obtained with DES, it is evident that all of the systems present an identical spectrum to chitin, which was expected considering the results attained with FTIR. Additionally, these samples presented a crystallinity index identical to or higher than that of chitin.…”

Section: Resultssupporting

confidence: 65%

Chitin Deacetylation Using Deep Eutectic Solvents: Ab Initio-Supported Process Optimization

Vicente

Huš

Likozar

et al. 2021

ACS Sustainable Chem. Eng.

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Chitin is the most abundant marine biopolymer, being recovered during the shell biorefining of crustacean shell waste. In its native form, chitin displays a poor reactivity and solubility in most solvents due to its extensive hydrogen bonding. This can be overcome by deacetylation. However, this process requires a high concentration of acids or bases at high temperatures, forming large amounts of toxic waste. Herein, we report on the first deacetylation with deep eutectic solvents (DESs) as an environmentally friendly alternative, requiring only mild reaction conditions. Biocompatible DESs are efficient in disturbing the native hydrogen-bonding network of chitin, readily dissolving it. First, quantum chemical calculations have been performed to evaluate the feasibility of different DESs to perform chitin deacetylation by studying their mechanism. Comparing these with the calculated barriers for garden-variety alkaline/acidic hydrolysis, which are known to proceed, prospective DESs were identified with barriers around 25 kcal·mol –1 or lower. Based on density functional theory results, an experimental screening of 10 distinct DESs for chitin deacetylation followed. The most promising DESs were identified as K 2 CO 3 :glycerol (K 2 CO 3 :G), choline chloride:acetic acid ([Ch]Cl:AA), and choline chloride:malic acid ([Ch]Cl:MA) and were subjected to further optimization with respect to the water content, process duration, and temperature. Ultimately, [Ch]Cl:MA showed the best results, yielding a degree of deacetylation (DDA) of 40% after 24 h of reaction at 120 °C, which falls slightly behind the threshold value (50%) for chitin to be considered chitosan. Further quantum chemical calculations were performed to elucidate the mechanism. Upon the removal of 40% N -acetyl groups from the chitin structure, its reactivity was considerably improved.

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Section: Resultssupporting

confidence: 65%

Chitin Deacetylation Using Deep Eutectic Solvents: Ab Initio-Supported Process Optimization

Vicente

Huš

Likozar

et al. 2021

ACS Sustainable Chem. Eng.

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“…Regarding the inhibitory effect on P. ultimum, it was observed that CC maintained the oomycete in the lag stage for a more extended period than the UC. The above was attributed to the availability of the acetyl groups, attributed to a lower Icr and M W of CC than UC [51,52]. This effect is related to a higher number of protonated groups available to interact with the microbial cells [42,53].…”

Section: Discussionmentioning

confidence: 99%

Structural and Physicochemical Characterization of Chitosan Obtained by UAE and Its Effect on the Growth Inhibition of Pythium ultimum

Martín-López¹,

Pech-Cohuo²,

Herrera-Pool³

et al. 2020

Agriculture

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The objective of this work was the recovery of chitosan by ultrasound-assisted extraction (UAE) from white shrimp (Litopenaeus vannamei) chitin, and the physicochemical and structural characterization of the obtained biopolymer, as well as its antimicrobial effect on Pythium ultimum growth. A 23 factorial design was used to evaluate chitosan extraction conditions. Instrumental analysis techniques for chitosan characterization and radial growth inhibition, as an antifungal activity test, were performed. The ultrasonically extracted chitosan (UC) reached a yield of 86.96% with 100% solubility, a degree of deacetylation (DDA) >78%, molecular weight (MW) of 3.928 × 105 g mol−1, and a crystallinity index (Icr) of 87%, calculated through nuclear magnetic resonance (1H NMR) and Fourier transform infrared spectroscopy (FTIR), size exclusion chromatography (SEC), and X-ray diffraction (XRD), respectively. The inhibitory activity of the chitosan was evaluated against the oomycete Pythium ultimum, observing a 93% radial inhibition over 24 h. UAE proved to be an excellent alternative to the conventional deacetylation, reducing reaction time and obtaining a UC with higher MW and (Icr) than the commercial one, which could potentiate its applications.

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“…It has been shown that α-chitosan has a higher crystallinity index as compared to β-chitin. However, the crystallinity index for both forms is lower than the raw chitosan [21]. The crystallinity index will increase when the degree of deacetylation of chitosan increases [16].…”

Section: Crystalline Structurementioning

confidence: 91%

“…β-chitin has a parallel structure, which leads to the formation of the intramolecular hydrogen bond. γ-chitin consists of both antiparallel and parallel structure, as it is the combination of α-chitin and β-chitin [21].…”

Section: Crystalline Structurementioning

confidence: 99%

See 1 more Smart Citation

Chitosan-Based Oral Drug Delivery System for Peptide, Protein and Vaccine Delivery

Zainuddin¹,

Hamid²

2021

Chitin and Chitosan - Physicochemical Properties and Industrial Applications [Working Title]

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Oral delivery is the most common and preferred route of drug administration due to its convenience and ease of administration. However, various factors such as poor solubility, low dissolution rate, stability, and bioavailability of many drugs remain an ongoing challenge in achieving desired therapeutic levels. The delivery of drugs must overcome various obstacles, including the acidic gastric environment, the presence of the intestinal efflux and influx transporters and the continuous secretion of mucus that protects the gastrointestinal tract (GIT). As the number and chemical diversity of drugs has increased, various strategies are required to develop orally active therapeutics. One of the approaches is to use chitosan as a carrier for oral delivery of peptides, proteins as well as vaccines delivery. Chitosan, a non-toxic N-deacetylated derivative of chitin appears to be under intensive progress during the last years towards the development of safe and efficient chitosan-based drug delivery systems. This polymer has been recognised as a versatile biomaterial because of its biodegradability, biocompatibility, and non-toxicity. This chapter reviews the physicochemical characteristics of chitosan and the strategies that have been successfully applied to improve oral proteins, peptides, and vaccines bioavailability, primarily through various formulation strategies.

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Impact of Crystalline Structural Differences Between α- and β-Chitosan on Their Nanoparticle Formation Via Ionic Gelation and Superoxide Radical Scavenging Activities

Cited by 69 publications

References 41 publications

Chitin Deacetylation Using Deep Eutectic Solvents: Ab Initio-Supported Process Optimization

Chitin Deacetylation Using Deep Eutectic Solvents: Ab Initio-Supported Process Optimization

Structural and Physicochemical Characterization of Chitosan Obtained by UAE and Its Effect on the Growth Inhibition of Pythium ultimum

Chitosan-Based Oral Drug Delivery System for Peptide, Protein and Vaccine Delivery

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