Carbohydrate Research最新文献

{"title":"Bile acid conjugated chitosan nanoparticles promote the proliferation and epithelial-mesenchymal transition of hepatocellular carcinoma by regulating the PI3K/Akt/mTOR pathway","authors":"Ziyu Jiang ,&nbsp;Yi Xu ,&nbsp;Liu Yang ,&nbsp;Xing Huang ,&nbsp;Jun Bao","doi":"10.1016/j.carres.2024.109296","DOIUrl":"10.1016/j.carres.2024.109296","url":null,"abstract":"<div><div>Bile acids have been known to play significant roles at certain physiological levels in gastrointestinal metabolism. Yet, they are known to be carcinogenic and aid in tumor progression in most cases, although the roles remain uncertain. Hence, we tested the cytotoxic potential of cholic acid (CA) loaded chitosan nanoparticles (CNPs) on Hep3B cells. The physicochemical properties of the CNPs synthesized with CA load (CA-CNPs) were determined using standard techniques such as ultraviolet–visible spectrophotometry (UV–Vis), fourier-transform infrared spectroscopy (FTIR), X-ray diffraction (XRD), dynamic light scattering (DLS) and transmission electron microscopy (TEM). The characteristic peak for chitosan nanoparticles were observed for plain CNPs (pCNPs) and CA-CNPs at around 300 nm as per UV–Vis analysis. FTIR analysis indicated the possible trapping of CA onto CNPs as certain peaks were retained and some peaks were shifted. XRD analysis determined that the peaks representing CA and pCNPs were collectively obtained in CA-CNPs. As per DLS analysis, the particle size, PDI and ζ-potential of the CA-CNPs were 259 nm, 0.284 and 30.4 mV. Further, the CA-CNPs were non-cytotoxic on Hep3B cells at the maximum tested concentration of 500 μg/mL. The viability at 500 μg/mL of CA-CNPs was two-fold higher than 500 μg/mL of pCNPs. Also, the pCNPs were not hemolytic and therefore could not have played a role in the increase of viability after treatment with CA-CNPs, which indicates that CA posed a major role in increased viability of Hep3B cells. As per quantitative PCR (qPCR), the upregulated gene expressions of PI3K, Akt, mTORC2, cMyc, Fibronectin, hVPS34, Slug and ZEB1 and the downregulated expression of the tumor suppressor PTEN indicates that PI3K/Akt/mTOR pathway mediated the induction of epithelial-to-mesenchymal transition (EMT) in response to CA-CNPs treatment on Hep3B cells.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"545 ","pages":"Article 109296"},"PeriodicalIF":2.4,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142543870","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Chitosan-curcumin conjugate prepared by one-step free radical grafting: Characterization, and functional evaluation","authors":"Xuerong Luo ,&nbsp;Lingyu Zhao ,&nbsp;Imran Mahmood Khan ,&nbsp;Lin Yue ,&nbsp;Yin Zhang ,&nbsp;Zhouping Wang","doi":"10.1016/j.carres.2024.109297","DOIUrl":"10.1016/j.carres.2024.109297","url":null,"abstract":"<div><div>Curcumin (Cur) is a naturally hydrophobic polyphenol, and it has a wide range of physiological functions. But the practical application of Cur is constrained by its low water solubility and poor stability. To improve these deficiencies of Cur, a novel Cur derivative (CS-Cur) was prepared by grafting chitosan (CS) with Cur through a one-step reaction of a free radical-mediated redox system. A series of characterizations provided evidence that the grafting of CS with Cur was successful. The obtained CS-Cur showed lower crystallinity and thermal properties than CS and Cur. After grafting, the water solubility of CS-Cur was found to be 9.76 ± 2.45 g/L and greatly improved. Meanwhile, the CS-Cur showed good photothermal stability, antioxidant activity, and photodynamic antibacterial activity in an aqueous solution, and it had good <em>in vitro</em> biosafety. This provides an idea for the design and synthesis of novel highly water-soluble Cur derivatives and also improves the practical application of Cur in aqueous systems.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"545 ","pages":"Article 109297"},"PeriodicalIF":2.4,"publicationDate":"2024-10-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142521075","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Exploring the therapeutic potential of polysaccharide from Portulaca oleracea L.: A review of phytochemistry and immunomodulatory effect","authors":"Hai-Xin Liu ,&nbsp;Ling-Ling Ding ,&nbsp;Yan-Yan Chen ,&nbsp;Shi-Yuan Wen","doi":"10.1016/j.carres.2024.109298","DOIUrl":"10.1016/j.carres.2024.109298","url":null,"abstract":"<div><div><em>Portulaca oleracea</em> L., a plant with both edible and medicinal properties, is traditionally valued for its diuretic, antipyretic, antiseptic, antispasmodic, and anthelmintic functions in folk medicine. <em>P</em>. <em>oleracea</em> polysaccharide (POP), a pivotal bioactive component, has various biological activities. Notably, their immunomodulatory capabilities have emerged as a significant area of research. The extraction, purification, monosaccharide composition, structure characterization, and biological activity of POP have been extensively investigated to identify the active components and to clarify their pharmacological actions and underlying molecular mechanisms. It aims to delineate the pharmacological mechanisms and molecular pathways associated with these polysaccharides, thereby underscoring their therapeutic promise and nutritional significance. Furthermore, the review critically examines the current research landscape of POP, identifying gaps and proposing innovative perspectives to enrich the scientific discourse surrounding these bioactive compounds.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"545 ","pages":"Article 109298"},"PeriodicalIF":2.4,"publicationDate":"2024-10-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142532063","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Synthesis of the pentasaccharide repeating unit with a conjugation-ready linker corresponding to the O-antigenic polysaccharide of Acinetobacter junii strain 65","authors":"Aniket Majhi,&nbsp;Samim Sahaji,&nbsp;Anup Kumar Misra","doi":"10.1016/j.carres.2024.109295","DOIUrl":"10.1016/j.carres.2024.109295","url":null,"abstract":"<div><div>A straightforward synthesis of the pentasaccharide with a readily available linker arm corresponding to the <em>O</em>-antigenic polysaccharide of <em>Acinetobacter junii</em> strain 65 has been achieved in good yield. The synthesis has been carried out using thioglycosides as glycosyl donor in the presence of a combination of <em>N</em>-iodosuccinimide (NIS) and trifluoromethanesulfonic acid (TfOH) as thiophilic activator. The yields of the glycosylation steps were very good with satisfactory stereochemistry at the glycosidic linkages. The pentasaccharide derivative has also been obtained using a one-pot iterative glycosylation strategy.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"545 ","pages":"Article 109295"},"PeriodicalIF":2.4,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142495632","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Trehalulose: Exploring its benefits, biosynthesis, and enhanced production techniques","authors":"Yogaletchumy Seevanathan ,&nbsp;Norhasnida Zawawi ,&nbsp;Abu Bakar Salleh ,&nbsp;Siti Nurbaya Oslan ,&nbsp;Nur Suhanawati Ashaari ,&nbsp;Amir Syahir Amir Hamzah ,&nbsp;Suriana Sabri","doi":"10.1016/j.carres.2024.109293","DOIUrl":"10.1016/j.carres.2024.109293","url":null,"abstract":"<div><div>The increasing concern over sugar-related health issues has sparked research interest in seeking alternatives to sucrose. Trehalulose, a beneficial structural isomer of sucrose, is a non-cariogenic sugar with a low glycemic and insulinemic index. Besides its potential as a sugar substitute, trehalulose exhibits high antioxidant properties, making it attractive for various industrial applications. Despite its numerous advantages and potential application in various sectors, the industrial adoption of trehalulose has yet to be established due to lack of studies on its characteristics and practical uses. This review aims to provide a comprehensive overview of the properties of trehalulose, emphasizing its health benefits. The industrial prospects of trehalulose as sweetener and reducing agent, particularly in food and beverages pharmaceutical, and cosmeceutical sectors, are explored. Additionally, the review delves into the sources of trehalulose and the diverse organisms capable of producing trehalulose. The biosynthesis of this sugar primarily involves an enzyme-mediated process. Thus, these enzymes' properties, mechanisms, and the heterologous expression of genes associated with trehalulose production are explored. The strategies discussed in this review can be improved and applied to establish trehalulose bio-factories for efficient synthesis of trehalulose in the future. With further research and development, trehalulose holds promise as a valuable component across various industries.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"545 ","pages":"Article 109293"},"PeriodicalIF":2.4,"publicationDate":"2024-10-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142495642","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Chiron approach toward the synthesis of the fused tricyclic core of epi-parvistemonine A","authors":"Esmeralda Marín-Cruz ,&nbsp;Ricardo Tovar-Miranda ,&nbsp;Julio Romero-Ibáñez ,&nbsp;José Alvano Pérez-Bautista ,&nbsp;Alejandro Cordero-Vargas ,&nbsp;Daniel Mendoza-Espinosa ,&nbsp;Rosa L. Meza-León ,&nbsp;Omar Cortezano-Arellano","doi":"10.1016/j.carres.2024.109290","DOIUrl":"10.1016/j.carres.2024.109290","url":null,"abstract":"<div><div>A stereoselective synthesis of fused tricyclic framework of <em>epi</em>-parvistemonine A from D-glucono-δ-lactone is described. The synthetic strategic is based on the stereoselective construction of the 7-membered cyclic skeleton <em>via</em> a cross-metathesis reaction followed by a Michael type cyclization promoted by Tf₂O.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"545 ","pages":"Article 109290"},"PeriodicalIF":2.4,"publicationDate":"2024-10-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142458580","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Picoplatin (II)-loaded chitosan nanocomposites as effective drug delivery systems: Preparation, mechanistic investigation of BSA/5-GMP/GSH binding and biological evaluations","authors":"Noha M. Ahmed ,&nbsp;Mohamed M. Ibrahim ,&nbsp;Ibrahim M. Elmehasseb ,&nbsp;Shaban Y. Shaban","doi":"10.1016/j.carres.2024.109292","DOIUrl":"10.1016/j.carres.2024.109292","url":null,"abstract":"<div><div>The goal of the current study is to improve the characteristics and bioavailability of the drug picoplatin (PPt) by encapsulating it in chitosan nanoparticles (CS NPs) which allows for the targeted delivery of cytotoxic cargo to cancerous tissue, reducing toxic side effects and raising the therapeutic index. When picoplatin was delivered into the CS, it was able to produce a complex with CS (PPt@CS NPs) that had an appropriate particle size of 275 ± 10 nm, a reasonably low PDI of 0.15 ± 0.05, and high stability (ζ = −22.1 ± 0.3 mV). Since almost all pharmaceuticals work by binding to specific proteins or DNA, the in vitro binding mechanism and affinity of bovine serum albumin (BSA), low molecular building units of nucleic acids (5−GMP), and Glutathione (GSH) (considering that cisplatin resistance could be due to a reaction between cisplatin and GSH) to PPt and PPt@CS NPs were examined using stopped-flow and other spectroscopic approaches. Through two reversible processes, a rapid second-order binding followed by a slower first-order isomerization reaction, and a static quenching mechanism, PPt and PPt@CS NPs bind to BSA with relative reactivity of around (PPt)/(PPt@CS NPs) = 1/2.5. The 5−GMP interaction studies demonstrated that, in addition to changing the binding mechanism, PPt's encapsulation in CS increases its rate of reaction through coordination affinity. PPt interacted with 5-GMP via two reversible processes, a rapid second-order binding to phosphate followed by a slower first−order migration to the N7 of pyrimidine moiety. PPt@CS NPs showed weaker binding to GSH compared to PPt and hence PPt@CS NPs exhibits a lower resistance factor. It was also found that the in vitro drug release of PPt@CS NPs in PBS at pH 7.4 was steady, releasing 30 % of the PPt in just 5 h. Nonetheless, 75 % of the release in a pH 5.4 solution containing 10 mM GSH—a solution that mimics the tumor microenvironment—shows that the PPt@CS NPs system is sensitive to GSH and specifically targets malignant tissue. The encapsulation of PPt in CS complex maintained its anticancer activity, as shown by an in vitro cell-survival assay on HepG2 cancer cell lines and also cleavage efficiency toward the minor groove of pBR322 DNA via the hydrolytic way. These findings collectively suggested that inclusion PPt in CS would be an effective strategy to formulate a novel picoplatin formulation intended for use as targeted anticancer treatment.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"545 ","pages":"Article 109292"},"PeriodicalIF":2.4,"publicationDate":"2024-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142458582","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Design of experiments optimization of N,N,N-trimethyl chitosan synthesis using N,N-diisopropylethylamine base","authors":"Vivien Nagy ,&nbsp;Bergthóra S. Snorradóttir ,&nbsp;Héléne Liette Lauzon ,&nbsp;Már Másson","doi":"10.1016/j.carres.2024.109289","DOIUrl":"10.1016/j.carres.2024.109289","url":null,"abstract":"<div><div>This study presents a novel synthesis method of <em>N</em>,<em>N</em>,<em>N</em>-trimethyl chitosan (TMC) by using a non-nucleophilic base and optimizing the solvent system for enhanced scalability, while addressing critical factors such as viscosity management and stirring efficiency. The study objectives also included achieving high <em>N,N,N</em>-trimethylation without O-methylation while minimizing reagent use. Eight bases, three solvent systems, and varying levels of dilution were explored to mitigate viscosity challenges and gas evolution. ¹H NMR spectroscopy was used to characterize the TMC products. The integral values of the peaks at 3.3, 3.0, and 2.8 ppm, corresponding to trimethyl, dimethyl, and monomethyl groups, were used to quantify the methylation degrees. The most promising initial results were obtained with <em>N,N</em>-diisopropylethylamine (DIPEA) base, and DMF as solvent. Using 6 eq methyl iodide (MeI) relative to chitosan and DIPEA as base, up to 68 % DTM was achieved. Applying Design of Experiments (DoE), the method was further optimized under diluted conditions, crucial for industrial scalability and viscosity control. Results from a full factorial design (3²) revealed that diluted medium effectively prevented viscosity concerns, achieving a notably low viscosity of 5.9 cP in the reaction mixture, a 16-fold decrease in viscosity, compared to initial experiments. It was also established that both the MeI reagent and the base addition are significant factors for the DTM response, with both factors showing quadratic effects. The DoE model demonstrated high significance (R = 0.97), high precision for future prediction (Q2 = 0.87), good model validity (0.84) and excellent reproducibility (0.96). The results mark a notable advancement in TMC synthesis, offering an efficient and practical method with significant implications for industrial applications.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"545 ","pages":"Article 109289"},"PeriodicalIF":2.4,"publicationDate":"2024-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142458581","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Seaweed-derived etherified carboxymethyl cellulose for sustainable tissue engineering","authors":"Sobia Naseem ,&nbsp;Muhammad Rizwan","doi":"10.1016/j.carres.2024.109291","DOIUrl":"10.1016/j.carres.2024.109291","url":null,"abstract":"<div><div>Biodegradability, biocompatibility, abundant supply from renewable sources, and affordability are the outstanding properties of cellulose that have prompted substantial studies into its potential in biomedical applications. Beyond terrestrial sources of cellulose, seaweeds have attracted much attention as a potential source of cellulose because they are widely available. Cellulose and its byproducts may be extracted from various macroalgae species, including red, green, and brown algae. The extracted cellulose's qualities vary depending on the algae species, age, and extraction process utilized. Cellulose's characteristics are enhanced through chemical modifications, specifically etherification and esterification, which substitute functional groups for hydroxyl groups, yielding a range of products, including cellulose acetate (CA), cellulose nitrate, cellulose sulfate, methylcellulose, and carboxymethyl cellulose (CMC). The ability to modify CMC characteristics for particular applications is explored through techniques including grafting processes mixing, and cross-linking with other polymers. Moreover, tissue engineering is given significant consideration in the growing use of CMC and its altered forms in biological applications. These alterations allow for the production of scaffolds that promote tissue regeneration and cell proliferation, enabling CMC-based scaffolds for various tissue engineering uses. This review provides a comprehensive overview of CMC's properties, modifications, and potential in tissue engineering.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"545 ","pages":"Article 109291"},"PeriodicalIF":2.4,"publicationDate":"2024-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142495631","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Ultrasound-promoted removal of benzylidene and isopropylidene acetal protection of carbohydrates in presence of sulfonated graphene (GR-SO3H) as a sustainable acid catalyst","authors":"Padmashri Rabha,&nbsp;Rajib Panchadhayee","doi":"10.1016/j.carres.2024.109288","DOIUrl":"10.1016/j.carres.2024.109288","url":null,"abstract":"<div><div>Sulfonated graphene (GR-SO₃H) was prepared and used as an efficient and sustainable catalyst to deprotect <em>O</em>-benzylidene and <em>O</em>-isopropylidene acetal of carbohydrates under ultrasound (US) irradiation. The solid catalyst can recovered by simple filtration and used several times without much loss in reactivity. This methodology not only reduces the reaction time but also increases the yield. Moreover, the work-up and purification procedure is very simple and also effective for large-scale preparation.</div></div>","PeriodicalId":9415,"journal":{"name":"Carbohydrate Research","volume":"545 ","pages":"Article 109288"},"PeriodicalIF":2.4,"publicationDate":"2024-10-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142434223","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}