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16 pages, 3278 KiB

Open AccessArticle

The Kinetics of Chitosan Degradation in Organic Acid Solutions

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Dominik Sikorski

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Karolina Gzyra-Jagieła

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Zbigniew Draczyński

Mar. Drugs 2021, 19(5), 236; https://doi.org/10.3390/md19050236 - 22 Apr 2021

Cited by 17 | Viewed by 3434

Abstract

This paper presents a comparative study on chitosan degradation in organic acid solutions according to their different dissociation characteristics. More precisely, the aim of the study was to determine the kinetics of the degradation process depending on the different acid dissociation constants (pKa [...] Read more.

This paper presents a comparative study on chitosan degradation in organic acid solutions according to their different dissociation characteristics. More precisely, the aim of the study was to determine the kinetics of the degradation process depending on the different acid dissociation constants (pKa values). The scientists involved in chitosan to date have focused mainly on acetic acid solutions. Solutions of lactic, acetic, malic, and formic acids in concentrations of 3% wt. were used in this research. The progress of degradation was determined based on the intrinsic viscosity measurement, GPC/SEC chromatographic analysis, and their correlation. Changes in the viscosity parameters were performed at a temperature of 20 °C ± 1 °C and a timeframe of up to 168 h (7 days). The chemical structure and DDA of the initial chitosan were analyzed using 1H-NMR spectroscopy analysis. The results of this study can be considered of high importance for the purpose of electrospinning, production of micro- and nano-capsules for drug delivery, and other types of processing. Understanding the influence of the dissociation constant of the solvent on the kinetics of chitosan degradation will allow the selection of an appropriate medium, ensuring an effective and stable spinning process, in which the occurrence of polymer degradation is unfavorable. Full article

(This article belongs to the Special Issue Application of Marine Chitin and Chitosan)

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12 pages, 3965 KiB

Open AccessArticle

A Study of Combining Elastin in the Chitosan Electrospinning to Increase the Mechanical Strength and Bioactivity

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Hengjie Su

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Tomoko Fujiwara

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Joel D. Bumgardner

Mar. Drugs 2021, 19(3), 169; https://doi.org/10.3390/md19030169 - 22 Mar 2021

Cited by 13 | Viewed by 2154

Abstract

While electrospun chitosan membranes modified to retain nanofibrous morphology have shown promise for use in guided bone regeneration applications in in vitro and in vivo studies, their mechanical tear strengths are lower than commercial collagen membranes. Elastin, a natural component of the extracellular [...] Read more.

While electrospun chitosan membranes modified to retain nanofibrous morphology have shown promise for use in guided bone regeneration applications in in vitro and in vivo studies, their mechanical tear strengths are lower than commercial collagen membranes. Elastin, a natural component of the extracellular matrix, is a protein with extensive elastic property. This work examined the incorporation of elastin into electrospun chitosan membranes to improve their mechanical tear strengths and to further mimic the native extracellular composition for guided bone regeneration (GBR) applications. In this work, hydrolyzed elastin (ES12, Elastin Products Company, USA) was added to a chitosan spinning solution from 0 to 4 wt% of chitosan. The chitosan–elastin (CE) membranes were examined for fiber morphology using SEM, hydrophobicity using water contact angle measurements, the mechanical tear strength under simulated surgical tacking, and compositions using Fourier-transform infrared spectroscopy (FTIR) and post-spinning protein extraction. In vitro experiments were conducted to evaluate the degradation in a lysozyme solution based on the mass loss and growth of fibroblastic cells. Chitosan membranes with elastin showed significantly thicker fiber diameters, lower water contact angles, up to 33% faster degradation rates, and up to seven times higher mechanical strengths than the chitosan membrane. The FTIR spectra showed stronger amide peaks at 1535 cm⁻¹ and 1655 cm⁻¹ in membranes with higher concentrated elastin, indicating the incorporation of elastin into electrospun fibers. The bicinchoninic acid (BCA) assay demonstrated an increase in protein concentration in proportion to the amount of elastin added to the CE membranes. In addition, all the CE membranes showed in vitro biocompatibility with the fibroblasts. Full article

(This article belongs to the Special Issue Application of Marine Chitin and Chitosan)

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18 pages, 2670 KiB

Open AccessArticle

Chitosan Activated with Genipin: A Nontoxic Natural Carrier for Tannase Immobilization and Its Application in Enhancing Biological Activities of Tea Extract

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Mar. Drugs 2021, 19(3), 166; https://doi.org/10.3390/md19030166 - 19 Mar 2021

Cited by 10 | Viewed by 2564

Abstract

In this work, a non-toxic chitosan-based carrier was constructed via genipin activation and applied for the immobilization of tannase. The immobilization carriers and immobilized tannase were characterized using Fourier transform infrared spectroscopy and thermogravimetric analysis. Activation conditions (genipin concentration, activation temperature, activation pH [...] Read more.

In this work, a non-toxic chitosan-based carrier was constructed via genipin activation and applied for the immobilization of tannase. The immobilization carriers and immobilized tannase were characterized using Fourier transform infrared spectroscopy and thermogravimetric analysis. Activation conditions (genipin concentration, activation temperature, activation pH and activation time) and immobilizations conditions (enzyme amount, immobilization time, immobilization temperature, immobilization pH, and shaking speed) were optimized. The activity and activity recovery rate of the immobilized tannase prepared using optimal activation and immobilization conditions reached 29.2 U/g and 53.6%, respectively. The immobilized tannase exhibited better environmental adaptability and stability. The immobilized tannase retained 20.1% of the initial activity after 12 cycles and retained 81.12% of residual activity after 30 days storage. The catechins composition analysis of tea extract indicated that the concentration of non-ester-type catechins, EGC and EC, were increased by 1758% and 807% after enzymatic treatment. Biological activity studies of tea extract revealed that tea extract treated with the immobilized tannase possessed higher antioxidant activity, higher inhibitory effect on α-amylase, and lower inhibitory effect on α-glucosidase. Our results demonstrate that chitosan activated with genipin could be an effective non-toxic carrier for tannase immobilization and enhancing biological activities of tea extract. Full article

(This article belongs to the Special Issue Application of Marine Chitin and Chitosan)

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15 pages, 3623 KiB

Open AccessArticle

Physicochemical and Antimicrobial Properties of Thermosensitive Chitosan Hydrogel Loaded with Fosfomycin

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Luke J. Tucker

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Christine S. Grant

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Malley A. Gautreaux

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Dhanush L. Amarasekara

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Nicholas C. Fitzkee

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Amol V. Janorkar

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Anandavalli Varadarajan

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Santanu Kundu

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Lauren B. Priddy

Mar. Drugs 2021, 19(3), 144; https://doi.org/10.3390/md19030144 - 06 Mar 2021

Cited by 7 | Viewed by 3274

Abstract

Thermosensitive chitosan hydrogels—renewable, biocompatible materials—have many applications as injectable biomaterials for localized drug delivery in the treatment of a variety of diseases. To combat infections such as Staphylococcus aureus osteomyelitis, localized antibiotic delivery would allow for higher doses at the site of infection [...] Read more.

Thermosensitive chitosan hydrogels—renewable, biocompatible materials—have many applications as injectable biomaterials for localized drug delivery in the treatment of a variety of diseases. To combat infections such as Staphylococcus aureus osteomyelitis, localized antibiotic delivery would allow for higher doses at the site of infection without the risks associated with traditional antibiotic regimens. Fosfomycin, a small antibiotic in its own class, was loaded into a chitosan hydrogel system with varied beta-glycerol phosphate (β-GP) and fosfomycin (FOS) concentrations. The purpose of this study was to elucidate the interactions between FOS and chitosan hydrogel. The Kirby Bauer assay revealed an unexpected concentration-dependent inhibition of S. aureus, with reduced efficacy at the high FOS concentration but only at the low β-GP concentration. No effect of FOS concentration was observed for the planktonic assay. Rheological testing revealed that increasing β-GP concentration increased the storage modulus while decreasing gelation temperature. NMR showed that FOS was removed from the liquid portion of the hydrogel by reaction over 12 h. SEM and FTIR confirmed gels degraded and released organophosphates over 5 days. This work provides insight into the physicochemical interactions between fosfomycin and chitosan hydrogel systems and informs selection of biomaterial components for improving infection treatment. Full article

(This article belongs to the Special Issue Application of Marine Chitin and Chitosan)

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13 pages, 23169 KiB

Open AccessArticle

A Comparative Study on the Flocculation of Silica and China Clay with Chitosan and Synthetic Polyelectrolytes

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Konstantin B. L. Borchert

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Christine Steinbach

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Simona Schwarz

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Dana Schwarz

Mar. Drugs 2021, 19(2), 102; https://doi.org/10.3390/md19020102 - 10 Feb 2021

Cited by 6 | Viewed by 2202

Abstract

Flocculation is still one of the most important and efficient processes for water treatment. However, most industrial processes, such as in water treatment plants, still use huge amounts of synthetic polyelectrolytes for the flocculation process. Here we compare the flocculation of two different [...] Read more.

Flocculation is still one of the most important and efficient processes for water treatment. However, most industrial processes, such as in water treatment plants, still use huge amounts of synthetic polyelectrolytes for the flocculation process. Here we compare the flocculation of two different suspended particles, i.e., silica particles and china clay, with the biopolymer chitosan and two common strong synthetic polyelectrolytes. As a flocculant, chitosan featured a minimum uptake rate of 0.05 mg/g for silica and 1.8 mg/g for china clay. Polydiallyldimethylammonium chloride (PDADMAC) for comparison possessed a minimum uptake rate of 0.05 mg/g for silica and 2.2 mg/g for china clay. Chitosan as an environmentally friendly biopolymer competes with the synthetic polyelectrolytes and thus represents a beneficial economic alternative to synthetic flocculants. Full article

(This article belongs to the Special Issue Application of Marine Chitin and Chitosan)

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18 pages, 4274 KiB

Open AccessArticle

Preliminary Evaluation of 3D Printed Chitosan/Pectin Constructs for Biomedical Applications

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Dimitrios N. Bikiaris

Mar. Drugs 2021, 19(1), 36; https://doi.org/10.3390/md19010036 - 15 Jan 2021

Cited by 23 | Viewed by 3726

Abstract

In the present study, chitosan (CS) and pectin (PEC) were utilized for the preparation of 3D printable inks through pneumatic extrusion for biomedical applications. CS is a polysaccharide with beneficial properties; however, its printing behavior is not satisfying, rendering the addition of a [...] Read more.

In the present study, chitosan (CS) and pectin (PEC) were utilized for the preparation of 3D printable inks through pneumatic extrusion for biomedical applications. CS is a polysaccharide with beneficial properties; however, its printing behavior is not satisfying, rendering the addition of a thickening agent necessary, i.e., PEC. The influence of PEC in the prepared inks was assessed through rheological measurements, altering the viscosity of the inks to be suitable for 3D printing. 3D printing conditions were optimized and the effect of different drying procedures, along with the presence or absence of a gelating agent on the CS-PEC printed scaffolds were assessed. The mean pore size along with the average filament diameter were measured through SEM micrographs. Interactions among the characteristic groups of the two polymers were evident through FTIR spectra. Swelling and hydrolysis measurements confirmed the influence of gelation and drying procedure on the subsequent behavior of the scaffolds. Ascribed to the beneficial pore size and swelling behavior, fibroblasts were able to survive upon exposure to the ungelated scaffolds. Full article

(This article belongs to the Special Issue Application of Marine Chitin and Chitosan)

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18 pages, 6718 KiB

Open AccessArticle

Physicochemical and Antifungal Properties of Clotrimazole in Combination with High-Molecular Weight Chitosan as a Multifunctional Excipient

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Mar. Drugs 2020, 18(12), 591; https://doi.org/10.3390/md18120591 - 26 Nov 2020

Cited by 14 | Viewed by 2080

Abstract

Chitosans represent a group of multifunctional drug excipients. Here, we aimed to estimate the impact of high-molecular weight chitosan on the physicochemical properties of clotrimazole–chitosan solid mixtures (CL–CH), prepared by grinding and kneading methods. We characterised these formulas by infrared spectroscopy, differential scanning [...] Read more.

Chitosans represent a group of multifunctional drug excipients. Here, we aimed to estimate the impact of high-molecular weight chitosan on the physicochemical properties of clotrimazole–chitosan solid mixtures (CL–CH), prepared by grinding and kneading methods. We characterised these formulas by infrared spectroscopy, differential scanning calorimetry, and powder X-ray diffractometry, and performed in vitro clotrimazole dissolution tests. Additionally, we examined the antifungal activity of clotrimazole–chitosan mixtures against clinical Candida isolates under neutral and acid conditions. The synergistic effect of clotrimazole and chitosan S combinations was observed in tests carried out at pH 4 on Candida glabrata strains. The inhibition of C. glabrata growth reached at least 90%, regardless of the drug/excipient weight ratio, and even at half of the minimal inhibitory concentrations of clotrimazole. Our results demonstrate that clotrimazole and high-molecular weight chitosan could be an effective combination in a topical antifungal formulation, as chitosan acts synergistically with clotrimazole against non-albicans candida strains. Full article

(This article belongs to the Special Issue Application of Marine Chitin and Chitosan)

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11 pages, 1012 KiB

Open AccessArticle

Chitosan Inhibits Helicobacter pylori Growth and Urease Production and Prevents Its Infection of Human Gastric Carcinoma Cells

by

Shun-Hsien Chang

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Pei-Ling Hsieh

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Guo-Jane Tsai

Mar. Drugs 2020, 18(11), 542; https://doi.org/10.3390/md18110542 - 29 Oct 2020

Cited by 3 | Viewed by 2174

Abstract

This study investigated the effects of shrimp chitosan with 95% degree of deacetylation (DD95) in combination with clinical antibiotics on the growth and urease production of Helicobacter pylori. The inhibitory effect of DD95 on the adherence of H. pylori to the human [...] Read more.

This study investigated the effects of shrimp chitosan with 95% degree of deacetylation (DD95) in combination with clinical antibiotics on the growth and urease production of Helicobacter pylori. The inhibitory effect of DD95 on the adherence of H. pylori to the human intestinal carcinoma cells (TSGH9201) was also investigated. Five strains of H. pylori, including three standard strains and two strains of clinical isolates were used as the test strains. The inhibitory effects of DD95 on growth and urease production of various strains of H. pylori increased with increasing DD95 concentration and decreasing pH values from pH 6.0 to pH 2.0. Urease activity of H. pylori at pH 2.0 in the presence of 4000 μg/mL of DD95 decreased by 37.86% to 46.53%. In the presence of 50 μg/mL antibiotics of amoxicillin, tetracycline, or metronidazole at pH 6.0 and pH 2.0, H. pylori counts were decreased by 1.51–3.19, and 1.47–2.82 Log CFU/mL, respectively. Following the addition of 4000 μg/mL DD95 into the 50 μg/mL antibiotic-containing culture medium with pH 6.0 and pH 2.0, overall H. pylori counts were strongly decreased by 3.67–7.61 and 6.61–6.70 Log CFU/mL, respectively. Further, DD95 could inhibit the adherence of H. pylori on TSGH 9201 cells, as evidenced by fluorescent microscopy and thus may potentially protect against H. pylori infection. Full article

(This article belongs to the Special Issue Application of Marine Chitin and Chitosan)

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10 pages, 1700 KiB

Open AccessCommunication

Effects of Chitosan Oligosaccharide on Plasma and Hepatic Lipid Metabolism and Liver Histomorphology in Normal Sprague-Dawley Rats

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Shing-Hwa Liu

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Rui-Yi Chen

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Meng-Tsan Chiang

Mar. Drugs 2020, 18(8), 408; https://doi.org/10.3390/md18080408 - 02 Aug 2020

Cited by 14 | Viewed by 2322

Abstract

Chitosan oligosaccharide is known to ameliorate hypercholesterolemia and diabetes. However, some studies found that chitosan oligosaccharide might induce mild to moderate hepatic damage in high-fat (HF) diet-induced obese rats or diabetic rats. Chitosan oligosaccharide can be as a dietary supplement, functional food, or [...] Read more.

Chitosan oligosaccharide is known to ameliorate hypercholesterolemia and diabetes. However, some studies found that chitosan oligosaccharide might induce mild to moderate hepatic damage in high-fat (HF) diet-induced obese rats or diabetic rats. Chitosan oligosaccharide can be as a dietary supplement, functional food, or drug. Its possible toxic effects to normal subjects need to be clarified. This study is designed to investigate the effects of chitosan oligosaccharide on plasma and hepatic lipid metabolism and liver histomorphology in normal Sprague-Dawley rats. Diets supplemented with 5% chitosan oligosaccharide have been found to induce liver damage in HF diet-fed rats. We therefore selected 5% chitosan oligosaccharide as an experimental object. Rats were divided into: a normal control diet group and a normal control diet +5% chitosan oligosaccharide group. The experimental period was 12 weeks. The results showed that supplementation of 5% chitosan oligosaccharide did not significantly change the body weight, food intake, liver/adipose tissue weights, plasma lipids, hepatic lipids, plasma levels of AST, ALT, and TNF-α/IL-6, hepatic lipid peroxidation and anti-oxidative enzyme activities, fecal lipids, and liver histomorphology in normal rats. These findings suggest that supplementation of 5% chitosan oligosaccharide for 12 weeks may not induce lipid metabolism disorder and liver toxicity in normal rats. Full article

(This article belongs to the Special Issue Application of Marine Chitin and Chitosan)

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13 pages, 2715 KiB

Open AccessArticle

Chitosan Coated Microparticles Enhance Simvastatin Colon Targeting and Pro-Apoptotic Activity

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Muhammed A. Bakhrebah

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Mar. Drugs 2020, 18(4), 226; https://doi.org/10.3390/md18040226 - 24 Apr 2020

Cited by 21 | Viewed by 3240

Abstract

This work aimed at improving the targeting and cytotoxicity of simvastatin (SMV) against colon cancer cells. SMV was encapsulated in chitosan polymers, followed by eudragit S100 microparticles. The release of SMV double coated microparticles was dependent on time and pH. At pH 7.4 [...] Read more.

This work aimed at improving the targeting and cytotoxicity of simvastatin (SMV) against colon cancer cells. SMV was encapsulated in chitosan polymers, followed by eudragit S100 microparticles. The release of SMV double coated microparticles was dependent on time and pH. At pH 7.4 maximum release was observed for 6 h. The efficiency of the double coat to target colonic tissues was confirmed using real-time X-ray radiography of iohexol dye. Entrapment efficiency and particle size were used in the characterization of the formula. Cytotoxicity of SMV microparticles against HCT-116 colon cancer cells was significantly improved as compared to raw SMV. Cell cycle analysis by flow cytomeric technique indicated enhanced accumulation of colon cancer cells in the G2/M phase. Additionally, a significantly higher cell fraction was observed in the pre-G phase, which highlighted enhancement of the proapoptotic activity of SMV prepared in the double coat formula. Assessment of annexin V staining was used for confirmation. Cell fraction in early, late and total cell death were significantly elevated. This was accompanied by a significant elevation of cellular caspase 3 activity. In conclusion, SMV-loaded chitosan coated with eudragit S100 formula exhibited improved colon targeting and enhanced cytotoxicity and proapoptotic activity against HCT-116 colon cancer cells. Full article

(This article belongs to the Special Issue Application of Marine Chitin and Chitosan)

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17 pages, 3952 KiB

Open AccessArticle

In Situ Gel Loaded with Chitosan-Coated Simvastatin Nanoparticles: Promising Delivery for Effective Anti-Proliferative Activity against Tongue Carcinoma

by

Mallesh Kurakula

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N. Raghavendra Naveen

Mar. Drugs 2020, 18(4), 201; https://doi.org/10.3390/md18040201 - 09 Apr 2020

Cited by 41 | Viewed by 3379

Abstract

The goal of this study is to develop optimized chitosan-coated Simvastatin (SIM) nanoparticles (NPs) loaded in an in situ gel (ISG) formulation via a face-centered central composite design (FCCCD). Coated SIM-NPs were doped with Quercetin (QRC) using a modified nanoprecipitation method. The concentrations [...] Read more.

The goal of this study is to develop optimized chitosan-coated Simvastatin (SIM) nanoparticles (NPs) loaded in an in situ gel (ISG) formulation via a face-centered central composite design (FCCCD). Coated SIM-NPs were doped with Quercetin (QRC) using a modified nanoprecipitation method. The concentrations of poloxamer 188 (A) and chitosan (B) at five different levels, plus/minus alpha (+1.414 and −1.414: axial points), plus/minus 1 (factorial points) and the center point were optimized for particle size (PS-Y1), entrapment efficacy (EE-Y2) and stability index (SI-Y3). Based on the desirability approach, a formulation containing poloxamer 188 0.24% and chitosan 0.43% renders the prerequisites of optimum formulation for preparing SIM–QRC NP-loaded ISG. Scanning microscopy showed spherical SIM-NPs, indicating monodispersity in the range of 0.50 ± 0.04 nm with a charge of +32.42 mV. The optimized formulation indicated the highest EE 79.67% and better stability at 4 °C. Drug release from SIM–QRC NP-loaded ISG was slower to plateau by up to 96 h and, at the end of 168 h, only 65.12% of SIM was released in a more controlled manner in comparison to SIM–QRC NPs and plain SIM. ISG formulation showed a considerable increase in apoptosis occurrence through caspase-3 mediation and it also enhanced the tumor suppressor protein levels. Enhanced biological activity of SIM was observed due to QRC enabling promising drug and polymer synergistic interaction. The proposed formulation can provide a breakthrough in localized therapy, overcoming the potential drawbacks of systemic chemotherapy for tongue carcinoma. Full article

(This article belongs to the Special Issue Application of Marine Chitin and Chitosan)

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15 pages, 2504 KiB

Open AccessArticle

Application of Gelatin Decorated with Allura Red as Resonance Rayleigh Scattering Sensor to Detect Chito-Oligosaccharides

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Mar. Drugs 2020, 18(3), 146; https://doi.org/10.3390/md18030146 - 29 Feb 2020

Viewed by 1902

Abstract

A convenient and sensitive triple-wavelength overlapping resonance Rayleigh scattering (TWO-RRS) method for the detection of chito-oligosaccharides (COS) was proposed based on enhancing the rigid surface of porous reticular spatial structure of gelatin and COS by introducing allura red AC (AR). The interaction and [...] Read more.

A convenient and sensitive triple-wavelength overlapping resonance Rayleigh scattering (TWO-RRS) method for the detection of chito-oligosaccharides (COS) was proposed based on enhancing the rigid surface of porous reticular spatial structure of gelatin and COS by introducing allura red AC (AR). The interaction and resultant porous reticular spatial structure were characterized with transmission electron microscopy (TEM), RRS, and UV-Vis spectroscopy. The results indicated that gelatin and COS formed porous reticular spatial structure with an average diameter of 1.5–2.0 μm, and the RRS value of COS-AR-gelatin ternary system with gelatin participation was significantly higher than that of COS-AR binary system. Under the optimal conditions, the enhanced TWO-RRS intensity of the system was linearly proportional to COS concentration in the range of 0.30–2.50 μg/mL, and the regression equation was ΔI = 4933.2c − 446.21 with R² = 0.9980. The limit of detection was 0.0478 μg/mL. So, a new method for the detection of COS was established and verified in the health products with satisfactory results. Full article

(This article belongs to the Special Issue Application of Marine Chitin and Chitosan)

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Review

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23 pages, 8329 KiB

Open AccessReview

Chitin Synthesis and Degradation in Crustaceans: A Genomic View and Application

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Mar. Drugs 2021, 19(3), 153; https://doi.org/10.3390/md19030153 - 15 Mar 2021

Cited by 31 | Viewed by 4143

Abstract

Chitin is among the most important components of the crustacean cuticular exoskeleton and intestinal peritrophic matrix. With the progress of genomics and sequencing technology, a large number of gene sequences related to chitin metabolism have been deposited in the GenBank database in recent [...] Read more.

Chitin is among the most important components of the crustacean cuticular exoskeleton and intestinal peritrophic matrix. With the progress of genomics and sequencing technology, a large number of gene sequences related to chitin metabolism have been deposited in the GenBank database in recent years. Here, we summarized the genes and pathways associated with the biosynthesis and degradation of chitins in crustaceans based on genomic analyses. We found that chitin biosynthesis genes typically occur in single or two copies, whereas chitin degradation genes are all multiple copies. Moreover, the chitinase genes are significantly expanded in most crustacean genomes. The gene structure and expression pattern of these genes are similar to those of insects, albeit with some specific characteristics. Additionally, the potential applications of the chitin metabolism genes in molting regulation and immune defense, as well as industrial chitin degradation and production, are also summarized in this review. Full article

(This article belongs to the Special Issue Application of Marine Chitin and Chitosan)

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