The Microstructure, Antibacterial and Antitumor Activities of Chitosan Oligosaccharides and Derivatives

Chitosan obtained from abundant marine resources has been proven to have a variety of biological activities. However, due to its poor water solubility, chitosan application is limited, and the degradation products of chitosan oligosaccharides are better than chitosan regarding performance. Chitosan oligosaccharides have two kinds of active groups, amino and hydroxyl groups, which can form a variety of derivatives, and the properties of these derivatives can be further improved. In this review, the key structures of chitosan oligosaccharides and recent studies on chitosan oligosaccharide derivatives, including their synthesis methods, are described. Finally, the antimicrobial and antitumor applications of chitosan oligosaccharides and their derivatives are discussed.

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Competitive Biological Activities of Chitosan and Its Derivatives: Antimicrobial, Antioxidant, Anticancer, and Anti-Inflammatory Activities

International Journal of Polymer Science ◽

10.1155/2018/1708172 ◽

2018 ◽

Vol 2018 ◽

pp. 1-13 ◽

Cited By ~ 30

Author(s):

Suyeon Kim

Keyword(s):

Water Solubility ◽

Biological Activities ◽

Biological Properties ◽

Biomedical Science ◽

Amino Groups ◽

Chitosan Oligosaccharides ◽

Primary Amino ◽

Anti Inflammatory ◽

Key Functional Groups ◽

Application Fields

Chitosan is obtained from alkaline deacetylation of chitin, and acetamide groups are transformed into primary amino groups during the deacetylation. The diverse biological activities of chitosan and its derivatives are extensively studied that allows to widening the application fields in various sectors especially in biomedical science. The biological properties of chitosan are strongly depending on the solubility in water and other solvents. Deacetylation degree (DDA) and molecular weight (MW) are the most decisive parameters on the bioactivities since the primary amino groups are the key functional groups of chitosan where permits to interact with other molecules. Higher DDA and lower MW of chitosan and chitosan derivatives demonstrated higher antimicrobial, antioxidant, and anticancer capacities. Therefore, the chitosan oligosaccharides (COS) with a low polymerization degree are receiving a great attention in medical and pharmaceutical applications as they have higher water solubility and lower viscosity than chitosan. In this review articles, the antimicrobial, antioxidant, anticancer, anti-inflammatory activities of chitosan and its derivatives are highlighted. The influences of physicochemical parameters of chitosan like DDA and MW on bioactivities are also described.

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Synthesis and Evaluation of a Chitosan Oligosaccharide-Streptomycin Conjugate against Pseudomonas aeruginosa Biofilms

Marine Drugs ◽

10.3390/md17010043 ◽

2019 ◽

Vol 17 (1) ◽

pp. 43 ◽

Cited By ~ 7

Author(s):

Ruilian Li ◽

Xianghua Yuan ◽

Jinhua Wei ◽

Xiafei Zhang ◽

Gong Cheng ◽

...

Keyword(s):

Pseudomonas Aeruginosa ◽

Water Solubility ◽

Efflux Pump ◽

Degree Of Polymerization ◽

Water Soluble ◽

Chitosan Oligosaccharide ◽

Gram Positive ◽

Pump System ◽

Gram Positive Bacteria ◽

Chitosan Oligosaccharides

Microbial biofilms are considerably more resistant to antibiotics than planktonic cells. It has been reported that chitosan coupling with the aminoglycoside antibiotic streptomycin dramatically disrupted biofilms of several Gram-positive bacteria. This finding suggested the application of the covalent conjugate of antimicrobial natural polysaccharides and antibiotics on anti-infection therapy. However, the underlying molecular mechanism of the chitosan-streptomycin conjugate (CS-Strep) remains unclear and the poor water-solubility of the conjugate might restrict its applications for anti-infection therapy. In this study, we conjugated streptomycin with water-soluble chitosan oligosaccharides (COS). Unlike CS-Strep, the COS-streptomycin conjugate (COS-Strep) barely affected biofilms of tested Gram-positive bacteria. However, COS-Strep efficiently eradicated established biofilms of the Gram-negative pathogen Pseudomonas aeruginosa. This activity of COS-Strep was influenced by the degree of polymerization of chitosan oligosaccharide. The increased susceptibility of P. aeruginosa biofilms to antibiotics after conjugating might be related to the following: Suppression of the activation of MexX-MexY drug efflux pump system induced by streptomycin treatment; and down-regulation of the biosynthesis of biofilm exopolysaccharides. Thus, this work indicated that covalently linking antibiotics to chitosan oligosaccharides was a possible approach for the development of antimicrobial drugs against biofilm-related infections.

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Physicochemical Characterization and Antinociceptive Effect of β-cyclodextrin/Lippia pedunculosa Essential Oil in Mice

Current Topics in Medicinal Chemistry ◽

10.2174/1568026618666180607081742 ◽

2018 ◽

Vol 18 (9) ◽

pp. 797-807 ◽

Cited By ~ 1

Author(s):

Paula dos Passos Menezes ◽

Francielly de Oliveira Araujo ◽

Tatianny Araujo Andrade ◽

Igor Araujo Santos Trindade ◽

Heitor Gomes de Araujo-Filho ◽

...

Keyword(s):

Essential Oil ◽

Physicochemical Properties ◽

Water Solubility ◽

Therapeutic Potential ◽

Biological Activities ◽

Antinociceptive Effect ◽

Physicochemical Characterization ◽

Good Tool ◽

Main Challenge ◽

Higher Temperature

Background: Some research studies have shown that Lippia pedunculosa essential oil (EOLP) has interesting biological activities. However, its low water solubility is the main challenge to achieve its therapeutic potential. In this context, Cyclodextrins (CDs) have been widely used in order to overcome this problem due to your capability to improve the physicochemical properties of drugs. Objective: In this perspective, the main goal of this study was to investigate how the improvement of the physicochemical properties of inclusion complexes (EOLP and β-CD) enhance the antinociceptive effect in mice. Methods: To achieve that, we prepared samples by Physical Mixture (PM), Paste Complexation (PC) and Slurry Complexation (SC) methods, followed by their physicochemical characterization. In addition, it was evaluated if the use of β-CD enhances the antinociceptive effect of EOLP in mice. Results: The analysis showed that rotundifolone (72.02%) was the major compound of EOLP and we found out based on DSC results that β-CD protected it from oxidation. In addition, TG techniques demonstrated that the best inclusion methods were PC and SC, due to their greater weight loss (10.8 and 11.6%, respectively) in the second stage (171-312°C), indicating that more complexed oil was released at the higher temperature than oil free. Other characteristics, such as changes in the typical crystalline form, and reduced particle size were observed by SEM and laser diffraction, respectively. The SC was the most effective complexation method, once the presence of rotundifolone was detected by FTIR. Based on that, SC method was used in all mice tests. In this regard, the number of paw licks was reduced for both compounds (all doses), but EOLP was more effective in reducing the nociceptive behavior. Conclusion: Therefore, CDs seem not to be a good tool to enhance the pharmacological properties of EOs rich in peroxide compounds such as rotundifolone.

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Anticancer Active Heterocyclic Chalcones: Recent Developments

Anti-Cancer Agents in Medicinal Chemistry ◽

10.2174/1871520620666200705215722 ◽

2020 ◽

Vol 20 ◽

Author(s):

Prasad Dandawate ◽

Khursheed Ahmed ◽

Subhash Padhye ◽

Aamir Ahmad ◽

Bernhard Biersack

Keyword(s):

Histone Deacetylases ◽

Biological Activities ◽

Synthetic Methods ◽

Antitumor Activities ◽

Web Based ◽

Chemical Structures ◽

Recent Developments ◽

Number Of Publications ◽

Tubulin Polymerization Inhibitors ◽

Dna Binding Properties

Background: Chalcones are structurally simple compounds that are easily accessible by synthetic methods. Heterocyclic chalcones have gained the interest among scientists due to their diverse biological activities. The anti-tumor activities of heterocyclic chalcones are especially remarkable and the growing number of publications dealing with this topic warrants an up-to-date compilation. Methods: Search for antitumor active heterocyclic chalcones was carried out using Pubmed and Scifinder as common web-based literature searching tools. Pertinent and current literature is covered from 2015/2016 to 2019. Chemical structures, biological activities and modes of action of anti-tumor active heterocyclic chalcones are summarized. Results: Simply prepared chalcones have emerged over the last years with promising antitumor activities. Among them is a considerable number of tubulin polymerization inhibitors. But there are also new chalcones targeting special enzymes such as histone deacetylases or with DNA-binding properties. Conclusion: This review provides a summary of recent heterocyclic chalcone derivatives with distinct anti-tumor activities.

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Hydrolytic Modification of SiO2 Microspheres with Na2SiO3 and the Performance of Supported Nano-TiO2 Composite Photocatalyst

Materials ◽

10.3390/ma14102553 ◽

2021 ◽

Vol 14 (10) ◽

pp. 2553

Author(s):

Yu Tu ◽

Weihua Ao ◽

Chunhong Wang ◽

Tianyu Ren ◽

Lijuan Zhang ◽

...

Keyword(s):

Sol Gel ◽

Active Surface ◽

Hydroxyl Groups ◽

Nano Tio2 ◽

Amorphous Sio2 ◽

Composite Photocatalyst ◽

Sio2 Shell ◽

Functional Efficiency ◽

Sio2 Microspheres ◽

Better Than

Modified microspheres (SiO2-M) were obtained by the hydrolytic modification of silicon dioxide (SiO2) microspheres with Na2SiO3, and then, SiO2-M was used as a carrier to prepare a composite photocatalyst (SiO2-M/TiO2) using the sol-gel method; i.e., nano-TiO2 was loaded on the surface of SiO2-M. The structure, morphology, and photocatalytic properties of SiO2-M/TiO2 were investigated. Besides, the mechanism of the effect of SiO2-M was also explored. The results show that the hydrolytic modification of Na2SiO3 coated the surface of SiO2 microspheres with an amorphous SiO2 shell layer and increased the quantity of hydroxyl groups. The photocatalytic performance of the composite photocatalyst was slightly better than that of pure nano-TiO2 and significantly better than that of the composite photocatalyst supported by unmodified SiO2. Thus, increasing the loading capacity of nano-TiO2, improving the dispersion of TiO2, and increasing the active surface sites are essential factors for improving the functional efficiency of nano-TiO2. This work provides a new concept for the design of composite photocatalysts by optimizing the performance of the carrier.

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Nanoformulations for Delivery of Pentacyclic Triterpenoids in Anticancer Therapies

Molecules ◽

10.3390/molecules26061764 ◽

2021 ◽

Vol 26 (6) ◽

pp. 1764

Author(s):

Anna Kaps ◽

Paweł Gwiazdoń ◽

Ewa Chodurek

Keyword(s):

Water Solubility ◽

Biological Activities ◽

Premature Mortality ◽

Delivery Systems ◽

Pentacyclic Triterpenoids ◽

Anticancer Properties ◽

Oncological Patients ◽

Antitumor Potential ◽

Ring Structures

The search for safe and effective anticancer therapies is one of the major challenges of the 21st century. The ineffective treatment of cancers, classified as civilization diseases, contributes to a decreased quality of life, health loss, and premature mortality in oncological patients. Many natural phytochemicals have anticancer potential. Pentacyclic triterpenoids, characterized by six- and five-membered ring structures, are one of the largest class of natural metabolites sourced from the plant kingdom. Among the known natural triterpenoids, we can distinguish lupane-, oleanane-, and ursane-types. Pentacyclic triterpenoids are known to have many biological activities, e.g., anti-inflammatory, antibacterial, hepatoprotective, immunomodulatory, antioxidant, and anticancer properties. Unfortunately, they are also characterized by poor water solubility and, hence, low bioavailability. These pharmacological properties may be improved by both introducing some modifications to their native structures and developing novel delivery systems based on the latest nanotechnological achievements. The development of nanocarrier-delivery systems is aimed at increasing the transport capacity of bioactive compounds by enhancing their solubility, bioavailability, stability in vivo and ensuring tumor-targeting while their toxicity and risk of side effects are significantly reduced. Nanocarriers may vary in sizes, constituents, shapes, and surface properties, all of which affect the ultimate efficacy and safety of a given anticancer therapy, as presented in this review. The presented results demonstrate the high antitumor potential of systems for delivery of pentacyclic triterpenoids.

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Recent Findings in Azaphilone Pigments

Journal of Fungi ◽

10.3390/jof7070541 ◽

2021 ◽

Vol 7 (7) ◽

pp. 541

Author(s):

Lúcia P. S. Pimenta ◽

Dhionne C. Gomes ◽

Patrícia G. Cardoso ◽

Jacqueline A. Takahashi

Keyword(s):

Water Solubility ◽

Biological Activities ◽

Low Cost ◽

Scale Up ◽

Structural Diversity ◽

Downstream Processing ◽

Global Market ◽

Yield Improvement ◽

Potential Applications ◽

New Compounds

Filamentous fungi are known to biosynthesize an extraordinary range of azaphilones pigments with structural diversity and advantages over vegetal-derived colored natural products such agile and simple cultivation in the lab, acceptance of low-cost substrates, speed yield improvement, and ease of downstream processing. Modern genetic engineering allows industrial production, providing pigments with higher thermostability, water-solubility, and promising bioactivities combined with ecological functions. This review, covering the literature from 2020 onwards, focuses on the state-of-the-art of azaphilone dyes, the global market scenario, new compounds isolated in the period with respective biological activities, and biosynthetic pathways. Furthermore, we discussed the innovations of azaphilone cultivation and extraction techniques, as well as in yield improvement and scale-up. Potential applications in the food, cosmetic, pharmaceutical, and textile industries were also explored.

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Pre-Harvest Treatment of Chitosan Oligosaccharides Improved Strawberry Fruit Quality

International Journal of Molecular Sciences ◽

10.3390/ijms19082194 ◽

2018 ◽

Vol 19 (8) ◽

pp. 2194 ◽

Cited By ~ 12

Author(s):

Yanqiu He ◽

Santosh Bose ◽

Wenxia Wang ◽

Xiaochen Jia ◽

Hang Lu ◽

...

Keyword(s):

Cell Wall ◽

Plant Immunity ◽

Titratable Acidity ◽

Growth Stages ◽

Chitosan Oligosaccharide ◽

Uniform Size ◽

Chitosan Oligosaccharides ◽

Soluble Solid ◽

Regulated Gene Expression

Chitosan oligosaccharide (COS), derived through hydrolysis of chitosan, has been proved to be an effective plant immunity elicitor, eco-friendly, and easily soluble in water, and influenced several secondary metabolites content to improve fruit qualities. COS are widely used in agriculture to improve the defense response in plants. The purpose of this study was to investigate the pre-harvest treatment effect of COS on the quality of strawberry (Fragaria × ananassa cv.qingxiang). COS was dissolved in distilled water at a concentration of 50 mg·L−1 and sprayed at four different growth stages of strawberry plants, namely seedling stage, before flowering, fruit coloring (the stage of fruit from white to red) and full bloom. Uniform size, shape, color, without any visible damage, and disease-free fruits were harvested for determining the quality. The results showed that the fruit firmness, viscosity, lignin, sugars, protein, total soluble solid, and titratable acidity content increased in COS-treated fruits compared to control. In addition, COS pre-harvest treatment had a positive effect on anthocyanin, total phenol, flavonoid, vitamin C content and DPPH(2,2-diphenyl-1-picrylhydrazyl) scavenging activity of strawberry. Moreover, COS also increased the cell wall composition and regulated gene expression of some important enzymes involved in ethylene compound biosynthesis and cell wall degradation. The finding of this study suggests that pre-harvest application of COS is very useful for improving quality and antioxidant capacity of strawberry.

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Chitosan Oligosaccharides Stimulate the Efficacy of Somatic Embryogenesis in Different Genotypes of the Liriodendron Hybrid

Forests ◽

10.3390/f12050557 ◽

2021 ◽

Vol 12 (5) ◽

pp. 557

Author(s):

Asif Ali ◽

Jiaji Zhang ◽

Minmin Zhou ◽

Tingting Chen ◽

Liaqat Shah ◽

...

Keyword(s):

Somatic Embryogenesis ◽

Antagonistic Effect ◽

Growth Speed ◽

Chitosan Oligosaccharide ◽

Chitosan Oligosaccharides ◽

Germination Ability ◽

Auxin Synthesis ◽

Branch Development ◽

The Impact ◽

Seed Setting Rate

Liriodendron hybrid (L. chinense × L. tulipifera), an essential medium-sized tree generally famous for its timber, is also used as an ornamental and greenery tool in many places around the world. The Liriodendron hybrid (L. hybrid) tree goes through many hurdles to achieve its maximum strength and vigor, such as loss of habitat, vast genetic variation, and low seed setting rate. The establishment of an effective and well-organized somatic embryogenesis (S.E.) system could be used to overcome these obstacles, rather than the old-fashioned seed culture and organogenesis. This study is based on the impact of chitosan oligosaccharide (COS) and its role in the induction of S.E. on the callus of four genotypes of the L. hybrid. The optimal concentration of COS could enhance the momentum and effectiveness in S.E.’s mechanism, which further improves the growth rate of the L. hybrid tree’s plantlets. This study shows that COS has a prominent role in endogenous hormones like indole acetic acid (IAA), zeatin (Z.T.), and gibberellic acid (GA3). Furthermore, COS improves the growth development, growth speed, as well as the development situation of plant germination ability. COS can also regulate branch development and root growth, which could be linked to the antagonistic effect on growth factors to some extent or by affecting auxin synthesis and polar transport.

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Study on the Preparation and Performance of Carboxymethyl Chitosan Calcium and Carboxymethyl Chitosan Zinc Composite Materials

Materials Science Forum ◽

10.4028/www.scientific.net/msf.852.1319 ◽

2016 ◽

Vol 852 ◽

pp. 1319-1324 ◽

Cited By ~ 1

Author(s):

Jing Li ◽

Chang Ping Wei ◽

Feng Ming Wang ◽

Li Dan Dong ◽

Shuang Sun ◽

...

Keyword(s):

Chloride Solution ◽

Water Solubility ◽

Chloroacetic Acid ◽

Sem Analysis ◽

Carboxymethyl Chitosan ◽

X Ray Diffraction ◽

Test Study ◽

Alkaline Conditions ◽

And Performance ◽

Better Than

In this paper,under alkaline conditions,with chloroacetic acid to modify chitosan,obtained carboxymethyl chitosan. At pH<7 conditions,the obtained carboxymethy chitosan respectively were reacted with calcium chloride solution,zinc chloride solution,after fully reacted,obtained carboxymethyl chitosan calcium and carboxymethyl chitosan zinc .Through infrared spectrum,X-ray diffraction and scanning electron microscopy (sem) analysis means,the structure of the products were characterized.Through the cutting of mice tail hemostasia test ,study the performance of the product.The results showed that the water solubility of carboxymethyl chitosan is better than that of chitosan and with excellent performance,and the performance of carboxymethyl chitosan calcium and carboxymethyl chitosan zinc was better than that of carboxymethyl chitosan.

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