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14 pages, 4002 KiB

Open AccessEditor’s ChoiceArticle

Water-Soluble Quaternary and Protonable Basic Chitotriazolans: Synthesis by Click Chemistry Conversion of Chitosan Azides and Investigation of Antibacterial Activity

by Sankar Rathinam, Romano Magdadaro, Martha Á. Hjálmarsdóttir and Már Másson

J. Funct. Biomater. 2024, 15(3), 63; https://doi.org/10.3390/jfb15030063 - 05 Mar 2024

Viewed by 974

Abstract

The azide transfer reaction and copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC) can be used to convert the amino groups in chitosan to triazole 1,2,3-moieties. The resulting polymer has been named chitotriazolan. This synthesis was performed with six different quaternary ammonium alkynes and three amine alkynes [...] Read more.

The azide transfer reaction and copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC) can be used to convert the amino groups in chitosan to triazole 1,2,3-moieties. The resulting polymer has been named chitotriazolan. This synthesis was performed with six different quaternary ammonium alkynes and three amine alkynes to obtain a series of nine water-soluble chitotriazolan derivatives. The structure and complete conversion of the azide were confirmed by FT-IR and proton NMR spectroscopy. The derivatives were investigated for antibacterial activity against S. aureus, E. faecalis, E. coli, and P. aeruginosa. The activity of the quaternized chitotriazolan derivatives varied depending on the structure of the quaternary moiety and the species of bacteria. The basic protonable derivatives were less active or inactive against the bacteria. Full article

(This article belongs to the Special Issue Biomedical Applications of Chitin and Chitosan-II)

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15 pages, 3840 KiB

Open AccessArticle

Antiseptic Chitosan-Poly(hexamethylene) Biguanide Hydrogel for the Treatment of Infectious Wounds

by Irine Rose Antony, Aathira Pradeep, Anoop Vasudevan Pillai, Riju Ramachandran Menon, Vasudevan Anil Kumar and Rangasamy Jayakumar

J. Funct. Biomater. 2023, 14(10), 528; https://doi.org/10.3390/jfb14100528 - 19 Oct 2023

Cited by 2 | Viewed by 1622

Abstract

Topical wound infections create the ideal conditions for microbial colonization and growth in terms of moisture, temperature, and nutrients. When they are not protected, numerous types of bacteria from the internal microbiota and the external environment may colonize them, creating a polymicrobial population. [...] Read more.

Topical wound infections create the ideal conditions for microbial colonization and growth in terms of moisture, temperature, and nutrients. When they are not protected, numerous types of bacteria from the internal microbiota and the external environment may colonize them, creating a polymicrobial population. Treatment of these wounds often necessitates the use of antibiotics that may have systemic harmful effects. Unlike antibiotics, topical antiseptics exhibit a wider range of activity and reduced systemic toxicity and resistance. In order to address this issue, we developed an antiseptic Chitosan-Poly (hexamethylene) Biguanide (CS-PHMB) hydrogel. The prepared hydrogel was characterized using Fourier Transform Infrared Spectroscopy (FTIR) and Scanning Electron Microscopy (SEM). SEM images showed the smooth morphology and characteristic FTIR peaks of PHMB and confirmed the incorporation of the antiseptic into the chitosan (CS) hydrogel. A Water Vapor Permeation Rate study confirms the moisture retention ability of the CS-PHMB hydrogel. Rheological studies proved the gel strength and temperature stability. The prepared hydrogel inhibited the growth of S. aureus, P. aeruginosa, E. coli, methicillin-resistant Staphylococcus aureus (MRSA), and K. pneumoniae, which confirms its antibacterial properties. It also inhibited biofilm formation for S. aureus and E. coli. CS-PHMB hydrogel is also found to be hemo- and cytocompatible in nature. Thus, the developed CS-PHMB hydrogel is a very potent candidate to be used for treating infectious topical wounds with low systemic toxicity. Full article

(This article belongs to the Special Issue Biomedical Applications of Chitin and Chitosan-II)

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28 pages, 27005 KiB

Open AccessArticle

Preparation of Self-Assembled, Curcumin-Loaded Nano-Micelles Using Quarternized Chitosan–Vanillin Imine (QCS-Vani Imine) Conjugate and Evaluation of Synergistic Anticancer Effect with Cisplatin

by Sasikarn Sripetthong, Sirinporn Nalinbenjapun, Abdul Basit, Suvimol Surassmo, Warayuth Sajomsang and Chitchamai Ovatlarnporn

J. Funct. Biomater. 2023, 14(10), 525; https://doi.org/10.3390/jfb14100525 - 18 Oct 2023

Cited by 1 | Viewed by 1799

Abstract

Nano-micelles are self-assembling colloidal dispersions applied to enhance the anticancer efficacy of chemotherapeutic agents. In this study, the conjugate of quarternized chitosan and vanillin imine (QCS-Vani imine) was synthesized using the reaction of a Schiff base characterized by proton-NMR (¹HNMR), UV-Vis [...] Read more.

Nano-micelles are self-assembling colloidal dispersions applied to enhance the anticancer efficacy of chemotherapeutic agents. In this study, the conjugate of quarternized chitosan and vanillin imine (QCS-Vani imine) was synthesized using the reaction of a Schiff base characterized by proton-NMR (¹HNMR), UV-Vis spectroscopy, and FT-IR. The critical micelle concentration (CMC), particle size, and zeta potential of the resulting product were determined. The QCS-Vani imine conjugate was used as a carrier for the development of curcumin-loaded nano-micelles, and their entrapment efficiency (%EE), drug-loading capacity (%LC) and in vitro release were investigated using HPLC analysis. Moreover, the nano-micelles containing curcumin were combined with various concentrations of cisplatin and evaluated for a possible anticancer synergistic effect. The anticancer activity was evaluated against lung cancer A549 and mouse fibroblast L929 cell lines. The percent yield (%) of the QCS-Vani imine conjugate was 93.18%. The curcumin-loaded QCS-Vani imine nano-micelles were characterized and found to have a spherical shape (by TEM) with size < 200 nm (by DLS) with high %EE up to 67.61% and %LC up to 6.15 ± 0.41%. The loaded lyophilized powder of the nano-micelles was more stable at 4 °C than at room temperature during 120 days of storage. pH-sensitive release properties were observed to have a higher curcumin release at pH 5.5 (cancer environment) than at pH 7.4 (systemic environment). Curcumin-loaded QCS-Vani imine nano-micelles showed higher cytotoxicity and selectivity toward lung cancer A549 cell lines and exhibited lower toxicity toward the normal cell (H9C2) than pure curcumin. Moreover, the curcumin-loaded QCS-Vani imine nano-micelles exhibited an enhanced property of inducing cell cycle arrest during the S-phase against A549 cells and showed prominently induced apoptosis in lung cancer cells compared to that with curcumin. The co-treatment of cisplatin with curcumin-loaded QCS-Vani imine nano-micelles presented an enhanced anticancer effect, showing 8.66 ± 0.88 μM as the IC₅₀ value, in comparison to the treatment with cisplatin alone (14.22 ± 1.01 μM). These findings suggest that the developed QCS-Vani imine nano-micelle is a potential drug delivery system and could be a promising approach for treating lung cancer in combination with cisplatin. Full article

(This article belongs to the Special Issue Biomedical Applications of Chitin and Chitosan-II)

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8 pages, 1269 KiB

Open AccessCommunication

Evaluation of the Safety and Gastrointestinal Migration of Guanidinylated Chitosan after Oral Administration to Rats

by Nowshin Farzana Khan, Hideaki Nakamura, Hironori Izawa, Shinsuke Ifuku, Daisuke Kadowaki, Masaki Otagiri and Makoto Anraku

J. Funct. Biomater. 2023, 14(7), 340; https://doi.org/10.3390/jfb14070340 - 27 Jun 2023

Cited by 1 | Viewed by 919

Abstract

Arginine-rich membrane-permeable peptides (APPs) can be delivered to cells by forming complexes with various membrane-impermeable bioactive molecules such as proteins. We recently reported on the preparation of guanidinylated chitosan (GCS) that mimics arginine peptides, using chitosan, a naturally occurring cationic polysaccharide, and confirmed [...] Read more.

Arginine-rich membrane-permeable peptides (APPs) can be delivered to cells by forming complexes with various membrane-impermeable bioactive molecules such as proteins. We recently reported on the preparation of guanidinylated chitosan (GCS) that mimics arginine peptides, using chitosan, a naturally occurring cationic polysaccharide, and confirmed that it enhances protein permeability in an in vitro cell system. However, studies on the in vivo safety of GCS are not available. To address this, we evaluated the in vivo safety of GCS and its translocation into the gastrointestinal tract in rats after a single oral administration of an excessive dose (500 mg/kg) and observed changes in body weight, major organ weights, and organ tissue sections for periods of up to 2 weeks. The results indicated that GCS causes no deleterious effects. The results of an oral administration of rhodamine-labeled chitosan and an evaluation of its migration in the gastrointestinal tract suggested that the disappearance of rhodamine-labeled GCS from the body appeared to be slower than that of the non-dose group and pre-guanidinylated chitosan due to its mucoadhesive properties. In the future, we plan to investigate the use of GCS to improve absorption using Class III and IV drugs, which are poorly water-soluble as well as poorly membrane-permeable. Full article

(This article belongs to the Special Issue Biomedical Applications of Chitin and Chitosan-II)

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14 pages, 10830 KiB

Open AccessArticle

Zinc Oxide–Incorporated Chitosan–Poly(methacrylic Acid) Polyelectrolyte Complex as a Wound Healing Material

by David Sathya Seeli, Abinash Das and Mani Prabaharan

J. Funct. Biomater. 2023, 14(4), 228; https://doi.org/10.3390/jfb14040228 - 17 Apr 2023

Cited by 4 | Viewed by 1285

Abstract

A novel type of porous films based on the ZnO-incorporated chitosan–poly(methacrylic acid) polyelectrolyte complex was developed as a wound healing material. The structure of porous films was established by Fourier-transform infrared spectroscopy (FTIR), X-ray diffraction (XRD), and energy dispersive X-ray (EDX) analysis. Scanning [...] Read more.

A novel type of porous films based on the ZnO-incorporated chitosan–poly(methacrylic acid) polyelectrolyte complex was developed as a wound healing material. The structure of porous films was established by Fourier-transform infrared spectroscopy (FTIR), X-ray diffraction (XRD), and energy dispersive X-ray (EDX) analysis. Scanning electron microscope (SEM) and porosity studies revealed that the pore size and porosity of the developed films increased with the increase in zinc oxide (ZnO) concentration. The porous films with maximum ZnO content exhibited improved water swelling degree (1400%), controlled biodegradation (12%) for 28 days, a porosity of 64%, and a tensile strength of 0.47 MPa. Moreover, these films presented antibacterial activity toward Staphylococcus aureus and Micrococcus sp. due to the existence of ZnO particles. Cytotoxicity studies demonstrated that the developed films had no cytotoxicity against the mouse mesenchymal stem (C3H10T1/2) cell line. These results reveal that ZnO-incorporated chitosan-poly(methacrylic acid) films could be used as an ideal material for wound healing application. Full article

(This article belongs to the Special Issue Biomedical Applications of Chitin and Chitosan-II)

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16 pages, 6782 KiB

Open AccessEditor’s ChoiceArticle

Microwave-Assisted Incorporation of AgNP into Chitosan–Alginate Hydrogels for Antimicrobial Applications

by Takuma Oe, Duangkamol Dechojarassri, Sachiro Kakinoki, Hideya Kawasaki, Tetsuya Furuike and Hiroshi Tamura

J. Funct. Biomater. 2023, 14(4), 199; https://doi.org/10.3390/jfb14040199 - 04 Apr 2023

Cited by 6 | Viewed by 2097

Abstract

Herein, improving the antibacterial activity of a hydrogel system of sodium alginate (SA) and basic chitosan (CS) using sodium hydrogen carbonate by adding AgNPs was investigated. SA-coated AgNPs produced by ascorbic acid or microwave heating were evaluated for their antimicrobial activity. Unlike ascorbic [...] Read more.

Herein, improving the antibacterial activity of a hydrogel system of sodium alginate (SA) and basic chitosan (CS) using sodium hydrogen carbonate by adding AgNPs was investigated. SA-coated AgNPs produced by ascorbic acid or microwave heating were evaluated for their antimicrobial activity. Unlike ascorbic acid, the microwave-assisted method produced uniform and stable SA-AgNPs with an optimal reaction time of 8 min. Transmission electron microscopy (TEM) confirmed the formation of SA-AgNPs with an average particle size of 9 ± 2 nm. Moreover, UV-vis spectroscopy confirmed the optimal conditions for SA-AgNP synthesis (0.5% SA, 50 mM AgNO₃, and pH 9 at 80 °C). Fourier transform infrared (FTIR) spectroscopy confirmed that the –COO⁻ group of SA electrostatically interacted with either the Ag⁺ or –NH₃⁺ of CS. Adding glucono-δ-lactone (GDL) to the mixture of SA-AgNPs/CS resulted in a low pH (below the pKa of CS). An SA-AgNPs/CS gel was formed successfully and retained its shape. This hydrogel exhibited 25 ± 2 mm and 21 ± 1 mm inhibition zones against E. coli and B. subtilis and showed low cytotoxicity. Additionally, the SA-AgNP/CS gel showed higher mechanical strength than SA/CS gels, possibly due to the higher crosslink density. In this work, a novel antibacterial hydrogel system was synthesized via 8 min of microwave heating. Full article

(This article belongs to the Special Issue Biomedical Applications of Chitin and Chitosan-II)

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15 pages, 3843 KiB

Open AccessEditor’s ChoiceArticle

Anti-Inflammatory Salidroside Delivery from Chitin Hydrogels for NIR-II Image-Guided Therapy of Atopic Dermatitis

by Shengnan He, Fang Xie, Wuyue Su, Haibin Luo, Deliang Chen, Jie Cai and Xuechuan Hong

J. Funct. Biomater. 2023, 14(3), 150; https://doi.org/10.3390/jfb14030150 - 08 Mar 2023

Cited by 1 | Viewed by 1980

Abstract

Atopic dermatitis (AD) is the most common heterogeneous skin disease. Currently, effective primary prevention approaches that hamper the occurrence of mild to moderate AD have not been reported. In this work, the quaternized β-chitin dextran (QCOD) hydrogel was adopted as a topical carrier [...] Read more.

Atopic dermatitis (AD) is the most common heterogeneous skin disease. Currently, effective primary prevention approaches that hamper the occurrence of mild to moderate AD have not been reported. In this work, the quaternized β-chitin dextran (QCOD) hydrogel was adopted as a topical carrier system for topical and transdermal delivery of salidroside for the first time. The cumulative release value of salidroside reached ~82% after 72 h at pH 7.4, while in vitro drug release experiments proved that QCOD@Sal (QCOD@Salidroside) has a good, sustained release effect, and the effect of QCOD@Sal on atopic dermatitis mice was further investigated. QCOD@Sal could promote skin repair or AD by modulating inflammatory factors TNF-α and IL-6 without skin irritation. The present study also evaluated NIR-II image-guided therapy (NIR-II, 1000–1700 nm) of AD using QCOD@Sal. The treatment process of AD was monitored in real-time, and the extent of skin lesions and immune factors were correlated with the NIR-II fluorescence signals. These attractive results provide a new perspective for designing NIR-II probes for NIR-II imaging and image-guided therapy with QCOD@Sal. Full article

(This article belongs to the Special Issue Biomedical Applications of Chitin and Chitosan-II)

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15 pages, 6513 KiB

Open AccessArticle

Antioxidant Stress of Transdermal Gene Delivery by Non-Viral Gene Vectors Based on Chitosan-Oligosaccharide

by Pengfei Cui, Ting Zhu, Pengju Jiang and Jianhao Wang

J. Funct. Biomater. 2022, 13(4), 299; https://doi.org/10.3390/jfb13040299 - 15 Dec 2022

Viewed by 1270

Abstract

Oxidative stress initiated by reactive oxygen species (ROS) is the cause of many acquired or congenital skin diseases. Oral antioxidants or using topical antioxidants preparations may bring the nonspecific distribution of drugs or anaphylaxis due to repeated use. In this study, a biocompatible [...] Read more.

Oxidative stress initiated by reactive oxygen species (ROS) is the cause of many acquired or congenital skin diseases. Oral antioxidants or using topical antioxidants preparations may bring the nonspecific distribution of drugs or anaphylaxis due to repeated use. In this study, a biocompatible gene vector by cross-linking of chitosan-oligosaccharide (CSO) and N,N’-cystamine-bis-acrylamide (CBA) was synthesized (CSO-CBA), which could carry therapeutic genes into the skin, express functional proteins in epidermal cells, and play an efficient antioxidant effect. Infrared and ¹H NMR spectrum data showed that CSO-CBA was successfully synthesized. Gel electrophoresis results showed that the gene could be successfully compressed by the carrier and can be released in a reducing environment. Hemolysis experiments showed that the carrier had good biocompatibility. Transdermal gene delivery experiments proved that the vector can bring genes into the skin, express functional proteins, and protect the skin from reactive oxygen species damage after 7 days of administration. Skin compatibility experiments show that our therapy is biocompatible. Our study provides a minimally invasive and painless, high-biocompatibility, and long-term effective treatment for skin damage caused by reactive oxygen species, which has a potential application. Full article

(This article belongs to the Special Issue Biomedical Applications of Chitin and Chitosan-II)

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Review

Jump to: Research

32 pages, 9799 KiB

Open AccessEditor’s ChoiceReview

Recent Advancements in Electrospun Chitin and Chitosan Nanofibers for Bone Tissue Engineering Applications

by S Shree Ganesh, Ramprasad Anushikaa, Venkadesan Sri Swetha Victoria, Krishnaraj Lavanya, Abinaya Shanmugavadivu and Nagarajan Selvamurugan

J. Funct. Biomater. 2023, 14(5), 288; https://doi.org/10.3390/jfb14050288 - 22 May 2023

Cited by 7 | Viewed by 2199

Abstract

Treatment of large segmental bone loss caused by fractures, osteomyelitis, and non-union results in expenses of around USD 300,000 per case. Moreover, the worst-case scenario results in amputation in 10% to 14.5% of cases. Biomaterials, cells, and regulatory elements are employed in bone [...] Read more.

Treatment of large segmental bone loss caused by fractures, osteomyelitis, and non-union results in expenses of around USD 300,000 per case. Moreover, the worst-case scenario results in amputation in 10% to 14.5% of cases. Biomaterials, cells, and regulatory elements are employed in bone tissue engineering (BTE) to create biosynthetic bone grafts with effective functionalization that can aid in the restoration of such fractured bones, preventing amputation and alleviating expenses. Chitin (CT) and chitosan (CS) are two of the most prevalent natural biopolymers utilized in the fields of biomaterials and BTE. To offer the structural and biochemical cues for augmenting bone formation, CT and CS can be employed alone or in combination with other biomaterials in the form of nanofibers (NFs). When compared with several fabrication methods available to produce scaffolds, electrospinning is regarded as superior since it enables the development of nanostructured scaffolds utilizing biopolymers. Electrospun nanofibers (ENFs) offer unique characteristics, including morphological resemblance to the extracellular matrix, high surface-area-to-volume ratio, permeability, porosity, and stability. This review elaborates on the recent strategies employed utilizing CT and CS ENFs and their biocomposites in BTE. We also summarize their implementation in supporting and delivering an osteogenic response to treat critical bone defects and their perspectives on rejuvenation. The CT- and CS-based ENF composite biomaterials show promise as potential constructions for bone tissue creation. Full article

(This article belongs to the Special Issue Biomedical Applications of Chitin and Chitosan-II)

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