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20 pages, 3643 KiB

Open AccessArticle

Chitosan Soft Matter Vesicles Loaded with Acetaminophen as Promising Systems for Modified Drug Release

by Loredana Nicoleta Hilițanu, Liliana Mititelu-Tarțău, Eliza Grațiela Popa, Beatrice Rozalina Bucă, Irina Luciana Gurzu, Paula Alina Fotache, Ana-Maria Pelin, Daniela Angelica Pricop and Liliana Lăcrămioara Pavel

Molecules 2024, 29(1), 57; https://doi.org/10.3390/molecules29010057 - 21 Dec 2023

Cited by 1 | Viewed by 1229

Abstract

Our study was designed to acquire, characterize and evaluate the biocompatibility of novel lipid vesicles loaded with acetaminophen (APAP) and coated with chitosan (CS). We investigated the in vitro and in vivo drug release kinetics from these systems, and we conducted assessments for [...] Read more.

Our study was designed to acquire, characterize and evaluate the biocompatibility of novel lipid vesicles loaded with acetaminophen (APAP) and coated with chitosan (CS). We investigated the in vitro and in vivo drug release kinetics from these systems, and we conducted assessments for both in vitro hemocompatibility and in vivo biocompatibility. For the in vivo biocompatibility evaluation, the mice were randomly divided into four groups of six animals and were treated orally as follows: control group: 0.1 mL/10 g body weight of double-distilled water; CS group: 0.1 mL/10 g body weight 1% CS solution; APAP group: 150 mg/kg body weight APAP; APAP-v group: 150 mg/kg body weight APAP-loaded lipid vesicles. The impact of APAP-v on various hematological, biochemical, and immune parameters in mice were assessed, and the harvested tissues were subjected to histopathological examination. The innovative formulations effectively encapsulating APAP within soft vesicles exhibited reasonable stability in solution and prolonged drug release in both in vitro and in vivo studies. The in vitro hemolysis test involving APAP-loaded vesicles revealed no signs of damage to red blood cells. The mice treated with APAP-v showed neither significant variances in hematological, biochemical, and immune parameters, nor structural changes in the examined organ samples, compared to the control group. APAP-v administration led to prolonged drug release. We can conclude that the APAP-v are innovative carrier systems for modifying drug release, making them promising candidates for biomedical applications. Full article

(This article belongs to the Special Issue Chitosan, Chitosan Derivatives and Their Applications)

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18 pages, 2466 KiB

Open AccessArticle

Cytotoxicity Enhancement of α-Mangostin with Folate-Conjugated Chitosan Nanoparticles in MCF-7 Breast Cancer Cells

by Yedi Herdiana, Nasrul Wathoni, Shaharum Shamsuddin and Muchtaridi Muchtaridi

Molecules 2023, 28(22), 7585; https://doi.org/10.3390/molecules28227585 - 14 Nov 2023

Cited by 1 | Viewed by 1530

Abstract

α-mangostin (AM) is a promising natural anticancer agent that can be used in cancer research. However, its effectiveness can be limited by poor solubility and bioavailability. To address this issue, chitosan-based nanoparticles (CSNPs) have been investigated as a potential delivery system to enhance [...] Read more.

α-mangostin (AM) is a promising natural anticancer agent that can be used in cancer research. However, its effectiveness can be limited by poor solubility and bioavailability. To address this issue, chitosan-based nanoparticles (CSNPs) have been investigated as a potential delivery system to enhance the cytotoxicity to cancer cells and improve selectivity against normal cells. In this study, we developed folate-conjugated chitosan nanoparticles (F-CS-NPs) using a carbodiimide-based conjugation method to attach folate to chitosan (CS), which have different molecular weights. The NPs were crosslinked using tripolyphosphate (TPP) via ionic gelation. To characterize the F-CS-NPs, we utilized various analytical techniques, including transmission electron microscopy (TEM) to evaluate the particle size and morphology, Fourier-transform infrared spectroscopy (FTIR) to confirm the presence of functional groups, and ultraviolet-visible spectroscopy (UV-Vis) to measure the absorption spectrum and confirm the presence of folate. The particle size of AM-F-CS-NPs ranged from 180 nm to 250 nm, with many having favorable charges ranging from +40.33 ± 3.4 to 10.69 ± 1.3 mV. All NPs exhibited the same spherical morphology. The use of F-CS-NPs increased drug release, followed by a sustained release pattern. We evaluated the cytotoxicity of AM, AM-F-CS-HMW, and AM-F-CS-LMW NPs against MCF-7 cells and found IC₅₀ values of 8.47 ± 0.49, 5.3 ± 0.01, and 4.70 ± 0.11 µg/mL, respectively. These results confirm the improved cytotoxicity of AM in MCF-7 cells when delivered via F-CS-NPs. Overall, our in vitro study demonstrated that the properties of F-CS-NPs greatly influence the cytotoxicity of AM in MCF-7 breast cancer cells (significantly different (p < 0.05)). The use of F-CS-NPs as a drug-delivery system for AM may have the potential to develop novel therapies for breast cancer. Full article

(This article belongs to the Special Issue Chitosan, Chitosan Derivatives and Their Applications)

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13 pages, 1173 KiB

Open AccessArticle

Chitosan–Glycolic Acid Gel Modification of Chloride Ion Transport in Mammalian Skin: An In Vitro Study

by Olga Zavyalova, Dominika Dąbrowska-Wisłocka, Konrad Misiura and Iga Hołyńska-Iwan

Molecules 2023, 28(18), 6581; https://doi.org/10.3390/molecules28186581 - 12 Sep 2023

Viewed by 1083

Abstract

Chitosan, a polyaminosaccharide with high medical and cosmetic potential, can be combined with the beneficial properties of glycolic acid to form a gel that not only moisturizes the skin, but also has a regenerative effect. Its involvement in the activation of biochemical processes [...] Read more.

Chitosan, a polyaminosaccharide with high medical and cosmetic potential, can be combined with the beneficial properties of glycolic acid to form a gel that not only moisturizes the skin, but also has a regenerative effect. Its involvement in the activation of biochemical processes may be associated with the activity of skin ion channels. Therefore, the aim of the research was to evaluate the immediate (15 s) and long-term (24 h) effect of chitosan–glycolic acid gel (CGG) on the transepithelial electric potential and the transepithelial electric resistance (R) of skin specimens tested in vitro. Stimulation during immediate and prolonged application of CGG to skin specimens resulted in a significant decrease in the measured minimal transepithelial electric potential (PDmin). The absence of any change in the R after the CGG application indicates that it does not affect the skin transmission, or cause distortion, microdamage or changes in ion permeability. However, the reduction in potential may be due to the increased transport of chloride ions, and thus water, from outside the cell into the cell interior. Increased secretion of chloride ions is achieved by stimulating the action of the CFTR (cystic fibrosis transmembrane conductance). It can be assumed that chitosan gently stimulates the secretion of chlorides, while maintaining a tendency to reduce the transport of sodium ions, without causing deformation or tissue damage. Full article

(This article belongs to the Special Issue Chitosan, Chitosan Derivatives and Their Applications)

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15 pages, 2717 KiB

Open AccessArticle

Multi-Functional Chitosan Nanovesicles Loaded with Bioactive Manganese for Potential Wound Healing Applications

by Edwin Davidson, Jorge Pereira, Giuliana Gan Giannelli, Zachary Murphy, Vasileios Anagnostopoulos and Swadeshmukul Santra

Molecules 2023, 28(16), 6098; https://doi.org/10.3390/molecules28166098 - 17 Aug 2023

Cited by 7 | Viewed by 1684

Abstract

Chronic skin wound is a chronic illness that possesses a risk of infection and sepsis. In particular, infections associated with antibiotic-resistant bacterial strains are challenging to treat. To combat this challenge, a suitable alternative that is complementary to antibiotics is desired for wound [...] Read more.

Chronic skin wound is a chronic illness that possesses a risk of infection and sepsis. In particular, infections associated with antibiotic-resistant bacterial strains are challenging to treat. To combat this challenge, a suitable alternative that is complementary to antibiotics is desired for wound healing. In this work, we report multi-functional nanoscale chitosan vesicles loaded with manganese (Chi-Mn) that has potential to serve as a new tool to augment traditional antibiotic treatment for skin wound healing. Chi-Mn showed antioxidant activity increase over time as well as antimicrobial activity against E. coli and P. aeruginosa PA01. The modified motility assay that mimicked a skin wound before bacterial colonization showed inhibition of bacterial growth with Chi-Mn treatment at a low area density of 0.04 µg of Mn per cm². Furthermore, this study demonstrated the compatibility of Chi-Mn with a commercial antibiotic showing no loss of antimicrobial potency. In vitro cytotoxicity of Chi-Mn was assessed with macrophages and dermal cell lines (J774A.1 and HDF) elucidating biocompatibility at a wide range (2 ppm–256 ppm). A scratch wound assay involving human dermal fibroblast (HDF) cells was performed to assess any negative effect of Chi-Mn on cell migration. Confocal microscopy study confirmed that Chi-Mn tested at the MIC (16 ppm Mn) has no effect on cell migration with respect to control. Overall, this study demonstrated the potential of Chi-Mn nanovesicles for wound healing applications. Full article

(This article belongs to the Special Issue Chitosan, Chitosan Derivatives and Their Applications)

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13 pages, 5352 KiB

Open AccessArticle

Chitosan and Its Carboxymethyl-Based Membranes Produced by Crosslinking with Magnesium Phytate

by Adam Zając, Wojciech Sąsiadek, Lucyna Dymińska, Paulina Ropuszyńska-Robak, Jerzy Hanuza, Maciej Ptak, Szymon Smółka, Radosław Lisiecki and Katarzyna Skrzypczak

Molecules 2023, 28(16), 5987; https://doi.org/10.3390/molecules28165987 - 10 Aug 2023

Cited by 2 | Viewed by 1679

Abstract

Membranes produced by crosslinking chitosan with magnesium phytate were prepared using highly deacetylated chitosan and its N-carboxymethyl, O-carboxymethyl and N,O-carboxymethyl derivatives. The conditions of the membrane production were described. IR, Raman, electron absorption and emission spectra were measured [...] Read more.

Membranes produced by crosslinking chitosan with magnesium phytate were prepared using highly deacetylated chitosan and its N-carboxymethyl, O-carboxymethyl and N,O-carboxymethyl derivatives. The conditions of the membrane production were described. IR, Raman, electron absorption and emission spectra were measured and analyzed for all the substrates. It was found that O-carboxymethyl chitosan derivative is the most effectively crosslinked by magnesium phytate, and the films formed on this substrate exhibit good mechanical parameters of strength, resistance and stability. Strong O–H···O hydrogen bonds proved to be responsible for an effective crosslinking process. Newly discovered membrane types produced from chitosan and magnesium phytate were characterized as morphologically homogenous and uniform by scanning electron microscopy (SEM) and IR measurements. Due to their good covering properties, they do not have pores or channels and are proposed as packaging materials. Full article

(This article belongs to the Special Issue Chitosan, Chitosan Derivatives and Their Applications)

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13 pages, 2814 KiB

Open AccessArticle

Impact of UV Irradiation on the Chitosan Bioactivity for Biopesticide Applications

by Solène Meynaud, Gaël Huet, Daphnée Brulé, Christian Gardrat, Benoit Poinssot and Véronique Coma

Molecules 2023, 28(13), 4954; https://doi.org/10.3390/molecules28134954 - 23 Jun 2023

Cited by 3 | Viewed by 1548

Abstract

Chitosan is known for its antimicrobial and antifungal properties that make it a promising candidate for plant protection. However, when sprayed in open fields, the bioactivity of chitosan significantly diminishes, suggesting a possible influence of sunlight on chitosan structure. This study aimed to [...] Read more.

Chitosan is known for its antimicrobial and antifungal properties that make it a promising candidate for plant protection. However, when sprayed in open fields, the bioactivity of chitosan significantly diminishes, suggesting a possible influence of sunlight on chitosan structure. This study aimed to investigate the effects of UV radiation, by using artificial UV sources simulating sunlight, on the stability of chitosan. A powdered chitosan with a low polymerization degree was selected and analyzed using various physicochemical methods, both before and after irradiation. Some minor differences appeared. UV spectra analysis revealed the disappearance of initially present chromophores and the emergence of a new band around 340 nm, potentially indicating the formation of carbonyl compounds. However, elemental analysis, MALDI-TOF spectra, polymerization degree, and infrared spectra did not exhibit any clear structural modifications of chitosan. Interestingly, irradiated powdered chitosan samples maintained their bioactivity, including their eliciting and antifungal properties. In the case of grapevine, irradiated chitosan demonstrated effectiveness in controlling grapevine diseases such as downy mildew, contradicting the assumption that sunlight is responsible for the decreased effectiveness of chitosan in open field conditions. Full article

(This article belongs to the Special Issue Chitosan, Chitosan Derivatives and Their Applications)

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13 pages, 3674 KiB

Open AccessArticle

Development of Chitosan Green Composites Reinforced with Hemp Fibers: Study of Mechanical and Barrier Properties for Packaging Application

by Rim Gheribi, Yassine Taleb, Louise Perrin, Cesar Segovia, Nicolas Brosse and Stephane Desobry

Molecules 2023, 28(11), 4488; https://doi.org/10.3390/molecules28114488 - 1 Jun 2023

Cited by 4 | Viewed by 1543

Abstract

The use of bioresourced packaging materials is an interesting solution for ecological issues. This work aimed to develop novel chitosan-based packaging materials reinforced with hemp fibers (HF). For this purpose, chitosan (CH) films were filled with 15%, 30%, and 50% (w/ [...] Read more.

The use of bioresourced packaging materials is an interesting solution for ecological issues. This work aimed to develop novel chitosan-based packaging materials reinforced with hemp fibers (HF). For this purpose, chitosan (CH) films were filled with 15%, 30%, and 50% (w/w) of two kinds of HF: Untreated fibers cut to 1 mm (UHF) and steam exploded fibers (SEHF). The effect of HF addition and HF treatments on chitosan composites was studied in terms of mechanical properties (tensile strength (TS), elongation at break (EB), and Young’s modulus (YM)), barrier properties (water vapor (WVP) and oxygen permeabilities), and thermal properties (glass transition (T_g) and melting temperatures (T_m)). The addition of HF, whether untreated or steam exploded, increased the TS of chitosan composites by 34–65%. WVP was significantly reduced by the addition of HF but no significant change was observed for O₂ barrier property, which was in the range between 0.44 and 0.68 cm³·mm/m²·d. T_m of the composite films increased from 133 °C for CH films to 171 °C for films filled with 15% SEHF. However, no significant modification was observed for T_g (105–107 °C). The present study showed that the developed biocomposites had improved properties, mainly the mechanical resistance. Their use in food packaging will help industrials the move toward a sustainable development and circular economy. Full article

(This article belongs to the Special Issue Chitosan, Chitosan Derivatives and Their Applications)

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14 pages, 3600 KiB

Open AccessArticle

A Simple Method for Synthesis of Chitosan Nanoparticles with Ionic Gelation and Homogenization

by Nicolas Van Bavel, Travis Issler, Liping Pang, Max Anikovskiy and Elmar J. Prenner

Molecules 2023, 28(11), 4328; https://doi.org/10.3390/molecules28114328 - 25 May 2023

Cited by 18 | Viewed by 10439

Abstract

Chitosan nanoparticles (CNPs) are known to have great utility in many fields (pharmaceutical, agricultural, food industry, wastewater treatment, etc.). In this study we aimed to synthesize sub-100 nm CNPs as a precursor of new biopolymer-based virus surrogates for water applications. We present a [...] Read more.

Chitosan nanoparticles (CNPs) are known to have great utility in many fields (pharmaceutical, agricultural, food industry, wastewater treatment, etc.). In this study we aimed to synthesize sub-100 nm CNPs as a precursor of new biopolymer-based virus surrogates for water applications. We present a simple yet efficient synthesis procedure for obtaining high yield, monodisperse CNPs with size 68–77 nm. The CNPs were synthesized by ionic gelation using low molecular weight chitosan (deacetylation 75–85%) and tripolyphosphate as crosslinker, under rigorous homogenization to decrease size and increase uniformity, and purified by passing through 0.1 μm polyethersulfone syringe filters. The CNPs were characterized using dynamic light scattering, tunable resistive pulse sensing, and scanning electron microscopy. We demonstrate reproducibility of this method at two separate facilities. The effects of pH, ionic strength and three different purification methods on the size and polydispersity of CNP formation were examined. Larger CNPs (95–219) were produced under ionic strength and pH controls, and when purified using ultracentrifugation or size exclusion chromatography. Smaller CNPs (68–77 nm) were formulated using homogenization and filtration, and could readily interact with negatively charge proteins and DNA, making them an ideal precursor for the development of DNA-labelled, protein-coated virus surrogates for environmental water applications. Full article

(This article belongs to the Special Issue Chitosan, Chitosan Derivatives and Their Applications)

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13 pages, 2889 KiB

Open AccessArticle

Flexible and Wearable Strain–Temperature Sensors Based on Chitosan/Ink Sponges

by Xiaoying Lin, Feng Wu, Yunqing He and Mingxian Liu

Molecules 2023, 28(10), 4083; https://doi.org/10.3390/molecules28104083 - 14 May 2023

Cited by 5 | Viewed by 1985

Abstract

A simple and economic strategy to construct a chitosan-ink carbon nanoparticle sponge sensor was proposed by freeze-drying of chitosan and Chinese ink mixture solution. The microstructure and physical properties of the composite sponges with different ratios are characterized. The interfacial compatibility of chitosan [...] Read more.

A simple and economic strategy to construct a chitosan-ink carbon nanoparticle sponge sensor was proposed by freeze-drying of chitosan and Chinese ink mixture solution. The microstructure and physical properties of the composite sponges with different ratios are characterized. The interfacial compatibility of chitosan and carbon nanoparticles in ink is satisfied, and the mechanical property and porosity of chitosan was increased by the incorporation of carbon nanoparticles. Due to excellent conductivity and good photothermal conversion effect of the carbon nanoparticles in ink, the constructed flexible sponge sensor has satisfactory strain and temperature sensing performance and high sensitivity (133.05 ms). In addition, these sensors can be successfully applied to monitor the large joint movement of the human body and the movement of muscle groups near the esophagus. Dual functionally integrated sponge sensors show great potential for strain and temperature detection in real time. The prepared chitosan-ink carbon nanoparticle composite shows promising applications in wearable smart sensors. Full article

(This article belongs to the Special Issue Chitosan, Chitosan Derivatives and Their Applications)

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14 pages, 657 KiB

Open AccessArticle

Chitosan Modulates Volatile Organic Compound Emission from the Biocontrol Fungus Pochonia chlamydosporia

by Jorge Mestre-Tomás, David Esgueva-Vilà, Alba Fuster-Alonso, Federico Lopez-Moya and Luis V. Lopez-Llorca

Molecules 2023, 28(10), 4053; https://doi.org/10.3390/molecules28104053 - 12 May 2023

Cited by 1 | Viewed by 2583

Abstract

Fungal volatile organic compounds (VOCs) are responsible for fungal odor and play a key role in biological processes and ecological interactions. VOCs represent a promising area of research to find natural metabolites for human exploitation. Pochonia chlamydosporia is a chitosan-resistant nematophagous fungus used [...] Read more.

Fungal volatile organic compounds (VOCs) are responsible for fungal odor and play a key role in biological processes and ecological interactions. VOCs represent a promising area of research to find natural metabolites for human exploitation. Pochonia chlamydosporia is a chitosan-resistant nematophagous fungus used in agriculture to control plant pathogens and widely studied in combination with chitosan. The effect of chitosan on the production of VOCs from P. chlamydosporia was analyzed using gas chromatography–mass spectrometry (GC-MS). Several growth stages in rice culture medium and different times of exposure to chitosan in modified Czapek–Dox broth cultures were analyzed. GC-MS analysis resulted in the tentative identification of 25 VOCs in the rice experiment and 19 VOCs in the Czapek–Dox broth cultures. The presence of chitosan in at least one of the experimental conditions resulted in the de novo production of 3-methylbutanoic acid and methyl 2,4-dimethylhexanoate, and oct-1-en-3-ol and tetradec-1-ene in the rice and Czapek–Dox experiments, respectively. Other VOCs changed their abundance because of the effect of chitosan and fungal age. Our findings suggest that chitosan can be used as a modulator of the production of VOCs in P. chlamydosporia and that there is also an effect of fungal age and exposure time. Full article

(This article belongs to the Special Issue Chitosan, Chitosan Derivatives and Their Applications)

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31 pages, 5692 KiB

Open AccessArticle

Preparation and Surface Characterization of Chitosan-Based Coatings for PET Materials

by Klaudia Szafran, Małgorzata Jurak, Robert Mroczka and Agnieszka Ewa Wiącek

Molecules 2023, 28(5), 2375; https://doi.org/10.3390/molecules28052375 - 4 Mar 2023

Cited by 4 | Viewed by 2811

Abstract

Poly(ethylene terephthalate)—PET—is one of the most frequently used polymers in biomedical applications. Due to chemical inertness, PET surface modification is necessary to gain specific properties, making the polymer biocompatible. The aim of this paper is to characterize the multi-component films containing chitosan (Ch), [...] Read more.

Poly(ethylene terephthalate)—PET—is one of the most frequently used polymers in biomedical applications. Due to chemical inertness, PET surface modification is necessary to gain specific properties, making the polymer biocompatible. The aim of this paper is to characterize the multi-component films containing chitosan (Ch), phospholipid 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC), immunosuppressant cyclosporine A (CsA) and/or antioxidant lauryl gallate (LG) which can be utilized as a very attractive material for developing the PET coatings. Chitosan was employed owing to its antibacterial activity and also its ability to promote cell adhesion and proliferation favorable for tissue engineering and regeneration purposes. Moreover, the Ch film can be additionally modified with other substances of biological importance (DOPC, CsA and LG). The layers of varying compositions were prepared using the Langmuir—Blodgett (LB) technique on the air plasma-activated PET support. Then their nanostructure, molecular distribution, surface chemistry and wettability were determined by atomic force microscopy (AFM), time-of-flight secondary ion mass spectrometry (TOF-SIMS), X-ray photoelectron spectroscopy (XPS), contact angle (CA) measurements and the surface free energy and its components’ determination, respectively. The obtained results show clearly the dependence of the surface properties of the films on the molar ratio of components and allow for a better understanding of the coating organization and mechanisms of interactions at the molecular level both inside the films and between the films and the polar/apolar liquids imitating the environment of different properties. The organized layers of this type can be helpful in gaining control over the surface properties of the biomaterial, thus getting rid of the limitations in favor of increased biocompatibility. This is a good basis for further investigations on the correlation of the immune system response to the presence of biomaterial and its physicochemical properties. Full article

(This article belongs to the Special Issue Chitosan, Chitosan Derivatives and Their Applications)

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23 pages, 6784 KiB

Open AccessArticle

Characteristics of Hybrid Bioglass-Chitosan Coatings on the Plasma Activated PEEK Polymer

by Kacper Przykaza, Małgorzata Jurak, Grzegorz Kalisz, Robert Mroczka and Agnieszka Ewa Wiącek

Molecules 2023, 28(4), 1729; https://doi.org/10.3390/molecules28041729 - 11 Feb 2023

Cited by 11 | Viewed by 2787

Abstract

Polyetheretherketone (PEEK) is a biocompatible, chemically and physically stable radiolucent polymer that exhibits a similar elastic modulus to the normal human bone, making it an attractive orthopedic implant material. However, PEEK is biologically inert, preventing strong enough bonding with the surrounding bone tissue [...] Read more.

Polyetheretherketone (PEEK) is a biocompatible, chemically and physically stable radiolucent polymer that exhibits a similar elastic modulus to the normal human bone, making it an attractive orthopedic implant material. However, PEEK is biologically inert, preventing strong enough bonding with the surrounding bone tissue when implanted in vivo. Surface modification and composite preparation are the two main strategies for the improvement of the bioactivity of PEEK. In this study, the plasma activated PEEK surfaces with the embedded bioglass, chitosan, and bioglass-chitosan mixed layers applying from the solution dip-coating technique were investigated. The most prominent factors affecting the coating biocompatibility are strictly connected with the composition of its outer surface (its charge and functional groups), hydrophilic-hydrophobic character, wettability and surface free energy, and topography (size of pores/substructures, roughness, stiffness), as well as the personal characteristics of the patient. The obtained surfaces were examined in terms of wettability and surface-free energy changes. Additionally, FTIR (Fourier Transformation Infrared Spectrometry) and SIMS (Secondary Ion Mass Spectrometry) were applied to establish and control the coating composition. Simultaneously the structure of coatings was visualized with the aid of SEM (Scanning Electron Microscopy). Finally, the obtained systems were incubated in SBF (Simulated Body Fluid) to verify the modifications’ influence on the bioactivity/biocompatibility of the PEEK surface. Different structures with variable compositions, as well as changes of the wettability, were observed depending on the applied modification. In addition, the incubation in SBF suggested that the bioglass-chitosan ratio influenced the formation of apatite-like structures on the modified PEEK surfaces. Full article

(This article belongs to the Special Issue Chitosan, Chitosan Derivatives and Their Applications)

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13 pages, 1316 KiB

Open AccessArticle

Effects of Chitosan Molecular Weight and Degree of Deacetylation on Chitosan−Cellulose Nanocrystal Complexes and Their Formation

by Hezhong Wang and Maren Roman

Molecules 2023, 28(3), 1361; https://doi.org/10.3390/molecules28031361 - 31 Jan 2023

Cited by 10 | Viewed by 3056

Abstract

This study was conducted to determine the effects of chitosan molecular weight and degree of deacetylation (DD) on chitosan–cellulose nanocrystal (CNC) polyelectrolyte–macroion complexes (PMCs) and their formation. Chitosan samples with three different molecular weights (81, 3 · 10³, 6 · 10 [...] Read more.

This study was conducted to determine the effects of chitosan molecular weight and degree of deacetylation (DD) on chitosan–cellulose nanocrystal (CNC) polyelectrolyte–macroion complexes (PMCs) and their formation. Chitosan samples with three different molecular weights (81, 3 · 10³, 6 · 10³ kDa) and four different DDs (77, 80, 85, 89%) were used. The effects on PMC formation were determined by turbidimetric titration. An effect of the molecular weight of chitosan was not observed in turbidimetric titrations. Turbidity levels were higher for CNCs with lower sulfate group density and larger hydrodynamic diameter than for CNCs with higher sulfate group density and smaller hydrodynamic diameter. Conversely, turbidity levels were higher for chitosans with higher DD (higher charge density) than for chitosans with lower DD (lower charge density). PMC particles from chitosans with different molecular weights were characterized by scanning electron microscopy, laser Doppler electrophoresis, and dynamic light scattering. PMCs from high-molecular-weight chitosan were more spherical and those from medium-molecular-weight chitosan had a slightly larger hydrodynamic diameter than PMCs from the respective other two chitosans. The molecular weight of the chitosan was concluded to have no effect on the formation of chitosan–CNC PMC particles and only a minor effect on the shape and size of the particles. The higher turbidity levels for CNCs with lower sulfate group density and larger hydrodynamic diameter and for chitosans with higher DD were attributed to a larger number of CNCs being required for charge compensation. Full article

(This article belongs to the Special Issue Chitosan, Chitosan Derivatives and Their Applications)

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19 pages, 4424 KiB

Open AccessArticle

Fabrication of PEGylated Chitosan Nanoparticles Containing Tenofovir Alafenamide: Synthesis and Characterization

by Muhammad Zaman, Muhammad Hammad Butt, Waqar Siddique, Muhammad Omer Iqbal, Naveed Nisar, Asma Mumtaz, Hafiza Yusra Nazeer, Abdulrahman Alshammari and Muhammad Shahid Riaz

Molecules 2022, 27(23), 8401; https://doi.org/10.3390/molecules27238401 - 1 Dec 2022

Cited by 13 | Viewed by 3124

Abstract

Tenofovir alafenamide (TAF) is an antiretroviral (ARV) drug that is used for the management and prevention of human immunodeficiency virus (HIV). The clinical availability of ARV delivery systems that provide long-lasting protection against HIV transmission is lacking. There is a dire need to [...] Read more.

Tenofovir alafenamide (TAF) is an antiretroviral (ARV) drug that is used for the management and prevention of human immunodeficiency virus (HIV). The clinical availability of ARV delivery systems that provide long-lasting protection against HIV transmission is lacking. There is a dire need to formulate nanocarrier systems that can help in revolutionizing the way to fight against HIV/AIDS. Here, we aimed to synthesize a polymer using chitosan and polyethylene glycol (PEG) by the PEGylation of chitosan at the hydroxyl group. After successful modification and confirmation by FTIR, XRD, and SEM, TAF-loaded PEGylated chitosan nanoparticles were prepared and analyzed for their particle size, zeta potential, morphology, crystallinity, chemical interactions, entrapment efficacy, drug loading, in vitro drug release, and release kinetic modeling. The fabricated nanoparticles were found to be in a nanosized range (219.6 nm), with ~90% entrapment efficacy, ~14% drug loading, and a spherical uniform distribution. The FTIR analysis confirmed the successful synthesis of PEGylated chitosan and nanoparticles. The in vitro analysis showed ~60% of the drug was released from the PEGylated polymeric reservoir system within 48 h at pH 7.4. The drug release kinetics were depicted by the Korsmeyer–Peppas release model with thermodynamically nonspontaneous drug release. Conclusively, PEGylated chitosan has the potential to deliver TAF from a nanocarrier system, and in the future, cytotoxicity and in vivo studies can be performed to further authenticate the synthesized polymer. Full article

(This article belongs to the Special Issue Chitosan, Chitosan Derivatives and Their Applications)

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12 pages, 1783 KiB

Open AccessCommunication

Novel Chitosan-Based Schiff Base Compounds: Chemical Characterization and Antimicrobial Activity

by Riccardo Fontana, Peggy Carla Raffaella Marconi, Antonella Caputo and Vasak B. Gavalyan

Molecules 2022, 27(9), 2740; https://doi.org/10.3390/molecules27092740 - 24 Apr 2022

Cited by 19 | Viewed by 2667

Abstract

Chitosan (CS) and its derivatives are receiving considerable attention for their great biocompatibility and broad-spectrum activities in many fields. In this work, we aimed to characterize the antimicrobial activity of novel chitosan Schiff bases (CSSB). CS was synthesized by double deacetylation of chitin [...] Read more.

Chitosan (CS) and its derivatives are receiving considerable attention for their great biocompatibility and broad-spectrum activities in many fields. In this work, we aimed to characterize the antimicrobial activity of novel chitosan Schiff bases (CSSB). CS was synthesized by double deacetylation of chitin (Cn) after its extraction from the armors of crustaceans Astacus leptodactylus, and CSSB-1 and CSSB-2 were synthesized by interaction of CS with 4-(2-chloroethyl) benzaldehyde (aldehyde-1) and 4-(bromoethyl) benzaldehyde (aldehyde-2), respectively, at room temperature. The synthesized compounds were characterized by elemental analysis, gel permeation chromatography (GPC), infrared spectroscopy (FTIR), thermogravimetry (TG), and differential scanning calorimetry (DSC). The antimicrobial activity against Gram-positive (Staphylococcus aureus) and Gram-negative (Pseudomonas aeruginosa) bacteria and against yeasts (Candida albicans) was significantly increased due to their higher solubility as compared to unmodified CS opening perspectives for the use of these compounds for antimicrobial prevention in different fields as, for example, food industry, cosmetics, or restoration. Full article

(This article belongs to the Special Issue Chitosan, Chitosan Derivatives and Their Applications)

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11 pages, 1184 KiB

Open AccessArticle

Impact of Chitosan on the Mechanical Stability of Soils

by Agnieszka Adamczuk and Grzegorz Jozefaciuk

Molecules 2022, 27(7), 2273; https://doi.org/10.3390/molecules27072273 - 31 Mar 2022

Cited by 18 | Viewed by 2727

Abstract

Chitosan is becoming increasingly applied in agriculture, mostly as a powder, however little is known about its effect on soil mechanical properties. Uniaxial compression test was performed for cylindrical soil aggregates prepared from four soils of various properties (very acidic Podzol, acidic Arenosol, [...] Read more.

Chitosan is becoming increasingly applied in agriculture, mostly as a powder, however little is known about its effect on soil mechanical properties. Uniaxial compression test was performed for cylindrical soil aggregates prepared from four soils of various properties (very acidic Podzol, acidic Arenosol, neutral Fluvisol and alkaline Umbrisol) containing different proportions of two kinds of chitosan (CS1 of higher molecular mass and lower deacetylation degree, and CS2 of lower molecular mass and higher deacetylation degree), pretreated with 1 and 10 wetting–drying cycles. In most cases increasing chitosan rates successively decreased the mechanical stability of soils that was accompanied by a tendential increase in soil porosity. In one case (Fluvisol treated with CS2) the porosity decreased and mechanical stability increased with increasing chitosan dose. The behavior of acidic soils (Podzol and Arenosol) treated with CS2, differed from the other soils: after an initial decrease, the strength of aggregates increased with increasing chitosan amendment, despite the porosity consequently decreasing. After 10 wetting–drying cycles, the strength of the aggregates of acidic soils appeared to increase while it decreased for neutral and alkaline soils. Possible mechanisms of soil–chitosan interactions affecting mechanical strength are discussed and linked with soil water stability and wettability. Full article

(This article belongs to the Special Issue Chitosan, Chitosan Derivatives and Their Applications)

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30 pages, 5472 KiB

Open AccessArticle

The Influence of Polysaccharides/TiO₂ on the Model Membranes of Dipalmitoylphosphatidylglycerol and Bacterial Lipids

by Agata Ładniak, Małgorzata Jurak, Marta Palusińska-Szysz and Agnieszka Ewa Wiącek

Molecules 2022, 27(2), 343; https://doi.org/10.3390/molecules27020343 - 6 Jan 2022

Cited by 7 | Viewed by 2205

Abstract

The aim of the study was to determine the bactericidal properties of popular medical, pharmaceutical, and cosmetic ingredients, namely chitosan (Ch), hyaluronic acid (HA), and titanium dioxide (TiO₂). The characteristics presented in this paper are based on the Langmuir monolayer studies [...] Read more.

The aim of the study was to determine the bactericidal properties of popular medical, pharmaceutical, and cosmetic ingredients, namely chitosan (Ch), hyaluronic acid (HA), and titanium dioxide (TiO₂). The characteristics presented in this paper are based on the Langmuir monolayer studies of the model biological membranes formed on subphases with these compounds or their mixtures. To prepare the Langmuir film, 1,2-dipalmitoyl-sn-glycero-3-phospho-rac-(1-glycerol) (DPPG) phospholipid, which is the component of most bacterial membranes, as well as biological material-lipids isolated from bacteria Escherichia coli and Staphylococcus aureus were used. The analysis of the surface pressure-mean molecular area (π-A) isotherms, compression modulus as a function of surface pressure, C_S⁻¹ = f(π), relative surface pressure as a function of time, π/π₀ = f(t), hysteresis loops, as well as structure visualized using a Brewster angle microscope (BAM) shows clearly that Ch, HA, and TiO₂ have antibacterial properties. Ch and TiO₂ mostly affect S. aureus monolayer structure during compression. They can enhance the permeability of biological membranes leading to the bacteria cell death. In turn, HA has a greater impact on the thickness of E. coli film. Full article

(This article belongs to the Special Issue Chitosan, Chitosan Derivatives and Their Applications)

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Review

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39 pages, 4795 KiB

Open AccessReview

Strategies for the Preparation of Chitosan Derivatives for Antimicrobial, Drug Delivery, and Agricultural Applications: A Review

by Rajeev Shrestha, Anusree Thenissery, Rahul Khupse and Gireesh Rajashekara

Molecules 2023, 28(22), 7659; https://doi.org/10.3390/molecules28227659 - 18 Nov 2023

Cited by 10 | Viewed by 2583

Abstract

Chitosan has received much attention for its role in designing and developing novel derivatives as well as its applications across a broad spectrum of biological and physiological activities, owing to its desirable characteristics such as being biodegradable, being a biopolymer, and its overall [...] Read more.

Chitosan has received much attention for its role in designing and developing novel derivatives as well as its applications across a broad spectrum of biological and physiological activities, owing to its desirable characteristics such as being biodegradable, being a biopolymer, and its overall eco-friendliness. The main objective of this review is to explore the recent chemical modifications of chitosan that have been achieved through various synthetic methods. These chitosan derivatives are categorized based on their synthetic pathways or the presence of common functional groups, which include alkylated, acylated, Schiff base, quaternary ammonia, guanidine, and heterocyclic rings. We have also described the recent applications of chitosan and its derivatives, along with nanomaterials, their mechanisms, and prospective challenges, especially in areas such as antimicrobial activities, targeted drug delivery for various diseases, and plant agricultural domains. The accumulation of these recent findings has the potential to offer insight not only into innovative approaches for the preparation of chitosan derivatives but also into their diverse applications. These insights may spark novel ideas for drug development or drug carriers, particularly in the antimicrobial, medicinal, and plant agricultural fields. Full article

(This article belongs to the Special Issue Chitosan, Chitosan Derivatives and Their Applications)

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18 pages, 1882 KiB

Open AccessReview

Green-Chemical Strategies for Production of Tailor-Made Chitooligosaccharides with Enhanced Biological Activities

by Reeba Thomas, Tamo Fukamizo and Wipa Suginta

Molecules 2023, 28(18), 6591; https://doi.org/10.3390/molecules28186591 - 13 Sep 2023

Cited by 4 | Viewed by 1376

Abstract

Chitooligosaccharides (COSs) are b-1,4-linked homo-oligosaccharides of N-acetylglucosamine (GlcNAc) or glucosamine (GlcN), and also include hetero-oligosaccharides composed of GlcNAc and GlcN. These sugars are of practical importance because of their various biological activities, such as antimicrobial, anti-inflammatory, antioxidant and antitumor activities, as well [...] Read more.

Chitooligosaccharides (COSs) are b-1,4-linked homo-oligosaccharides of N-acetylglucosamine (GlcNAc) or glucosamine (GlcN), and also include hetero-oligosaccharides composed of GlcNAc and GlcN. These sugars are of practical importance because of their various biological activities, such as antimicrobial, anti-inflammatory, antioxidant and antitumor activities, as well as triggering the innate immunity in plants. The reported data on bioactivities of COSs used to contain some uncertainties or contradictions, because the experiments were conducted with poorly characterized COS mixtures. Recently, COSs have been satisfactorily characterized with respect to their structures, especially the degree of polymerization (DP) and degree of N-acetylation (DA); thus, the structure–bioactivity relationship of COSs has become more unambiguous. To date, various green-chemical strategies involving enzymatic synthesis of COSs with designed sequences and desired biological activities have been developed. The enzymatic strategies could involve transglycosylation or glycosynthase reactions using reducing end-activated sugars as the donor substrates and chitinase/chitosanase and their mutants as the biocatalysts. Site-specific chitin deacetylases were also proposed to be applicable for this purpose. Furthermore, to improve the yields of the COS products, metabolic engineering techniques could be applied. The above-mentioned approaches will provide the opportunity to produce tailor-made COSs, leading to the enhanced utilization of chitin biomass. Full article

(This article belongs to the Special Issue Chitosan, Chitosan Derivatives and Their Applications)

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17 pages, 967 KiB

Open AccessReview

Biomaterials Based on Chitosan and Its Derivatives and Their Potential in Tissue Engineering and Other Biomedical Applications—A Review

by Marta Szulc and Katarzyna Lewandowska

Molecules 2023, 28(1), 247; https://doi.org/10.3390/molecules28010247 - 28 Dec 2022

Cited by 25 | Viewed by 3223

Abstract

In the times of dynamically developing regenerative medicine, more and more attention is focused on the use of natural polymers. This is due to their high biocompatibility and biodegradability without the production of toxic compounds, which means that they do not hurt humans [...] Read more.

In the times of dynamically developing regenerative medicine, more and more attention is focused on the use of natural polymers. This is due to their high biocompatibility and biodegradability without the production of toxic compounds, which means that they do not hurt humans and the natural environment. Chitosan and its derivatives are polymers made most often from the shells of crustaceans and are biodegradable and biocompatible. Some of them have antibacterial or metal-chelating properties. This review article presents the development of biomaterials based on chitosan and its derivatives used in regenerative medicine, such as a dressing or graft of soft tissues or bones. Various examples of preparations based on chitosan and its derivatives in the form of gels, films, and 3D structures and crosslinking products with another polymer are discussed herein. This article summarizes the latest advances in medicine with the use of biomaterials based on chitosan and its derivatives and provides perspectives on future research activities. Full article

(This article belongs to the Special Issue Chitosan, Chitosan Derivatives and Their Applications)

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17 pages, 821 KiB

Open AccessReview

Protective, Biostimulating, and Eliciting Effects of Chitosan and Its Derivatives on Crop Plants

by Maria Stasińska-Jakubas and Barbara Hawrylak-Nowak

Molecules 2022, 27(9), 2801; https://doi.org/10.3390/molecules27092801 - 28 Apr 2022

Cited by 63 | Viewed by 6601

Abstract

Chitosan is a biodegradable and biocompatible polysaccharide obtained by partial deacetylation of chitin. This polymer has been gaining increasing popularity due to its natural origin, favorable physicochemical properties, and multidirectional bioactivity. In agriculture, the greatest hopes are raised by the possibility of using [...] Read more.

Chitosan is a biodegradable and biocompatible polysaccharide obtained by partial deacetylation of chitin. This polymer has been gaining increasing popularity due to its natural origin, favorable physicochemical properties, and multidirectional bioactivity. In agriculture, the greatest hopes are raised by the possibility of using chitosan as a biostimulant, a plant protection product, an elicitor, or an agent to increase the storage stability of plant raw materials. The most important properties of chitosan include induction of plant defense mechanisms and regulation of metabolic processes. Additionally, it has antifungal, antibacterial, antiviral, and antioxidant activity. The effectiveness of chitosan interactions is determined by its origin, deacetylation degree and acetylation pattern, molecular weight, type of chemical modifications, pH, concentration, and solubility. There is a need to conduct research on alternative sources of chitosan, extraction methods, optimization of physicochemical properties, and commercial implementation of scientific progress outcomes in this field. Moreover, studies are necessary to assess the bioactivity and toxicity of chitosan nanoparticles and chitosan conjugates with other substances and to evaluate the consequences of the large-scale use thereof. This review presents the unique properties of chitosan and its derivatives that have the greatest importance for plant production and yield quality as well as the benefits and limitations of their application. Full article

(This article belongs to the Special Issue Chitosan, Chitosan Derivatives and Their Applications)

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