Journal of Carbohydrate Chemistry最新文献

英文中文

Molecular mechanisms underlying endoplasmic reticulum stress-triggered apoptosis induced by Trichoderma pseudokoningii exopolysaccharide in WEHI-3 mouse myeloid leukemic cells 假康宁木霉胞外多糖诱导WEHI-3小鼠髓性白血病细胞内质网应激引发凋亡的分子机制

IF 2.2 4区化学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY

Journal of Carbohydrate Chemistry

Pub Date : 2025-07-24 DOI: 10.1080/07328303.2025.2528127

Jingbo Lu , Xianfeng Zhang , Kaoshan Chen

In this work, the anticancer activities of an exopolysaccharide (EPS) from Trichoderma pseudokoningii, as well as its influence on WEHI-3 mouse myeloid leukemia cells, were investigated. This EPS not only inhibited the proliferation of WEHI-3 cells in a time- and concentration-dependent manner but also altered the morphology of WEHI-3 cells in a manner similar to that of apoptotic cells, as demonstrated by fluorescence staining experiments. Moreover, flow cytometry analysis also revealed that the EPS induced apoptosis in WEHI-3 cells. Additionally, the results indicated that the endoplasmic reticulum (ER) stress may be involved in this apoptotic process. Apoptotic factors related to the ER pathway were assessed subsequently. The results revealed that after treatment with the EPS for 48 h, the concentration of intracellular calcium in WEHI-3 cells increased. Exposure of WEHI-3 cells to different concentrations of the EPS (0.25, 0.50, and 1.0 mg/mL) resulted in decreased GRP78 mRNA transcription and increased CHOP mRNA expression in relation to the ER pathway. In addition, the Western blot results revealed that EPS significantly increased the p-PERK/PERK ratio, decreased the protein levels of GRP78 and Bcl-2, and increased the protein levels of CHOP and Bax. Caspase activity analysis also revealed that EPS treatment of WEHI-3 cells resulted in a dose-dependent increase in the activities of caspase-4 and caspase-3. Taking all together, these results provide evidence that the endoplasmic reticulum pathway is one of the potential pathways for the EPS-induced apoptosis in WEHI-3 cells.

本文研究了伪康宁木霉胞外多糖（EPS）的抗癌活性及其对小鼠髓系白血病细胞WEHI-3的影响。荧光染色实验表明，EPS不仅能以时间和浓度依赖性的方式抑制WEHI-3细胞的增殖，而且能以类似凋亡细胞的方式改变WEHI-3细胞的形态。流式细胞术分析也显示EPS诱导WEHI-3细胞凋亡。此外，内质网应激可能参与了这一凋亡过程。随后评估与内质网通路相关的凋亡因子。结果显示，EPS作用48 h后，WEHI-3细胞内钙浓度升高。不同浓度的EPS（0.25、0.50和1.0 mg/mL）使WEHI-3细胞GRP78 mRNA转录降低，CHOP mRNA表达增加。此外，Western blot结果显示，EPS显著提高了p-PERK/PERK比值，降低了GRP78和Bcl-2蛋白水平，增加了CHOP和Bax蛋白水平。Caspase活性分析还显示，EPS处理WEHI-3细胞导致Caspase -4和Caspase -3活性呈剂量依赖性增加。综上所述，这些结果证明内质网途径是eps诱导WEHI-3细胞凋亡的潜在途径之一。

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引用次数: 0

Formulation approaches and pharmaceutical applications of chitosan and thiolated chitosan nanoparticles 壳聚糖及硫代壳聚糖纳米颗粒的制备方法及医药应用

IF 1.2 4区化学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY

Journal of Carbohydrate Chemistry

Pub Date : 2025-03-24 DOI: 10.1080/07328303.2025.2451825

Zoya Saifi , Tanya Ralli , Divya Vohora , Showkat R. Mir , Saima Amin

Effective oral drug delivery is highly desirable for a controlled drug release using various polymers. Among different polymers, chitosan is known to be a safe, nontoxic material that has served as an efficient drug carrier. It is biocompatible, biodegradable, and obtained by hydrolyzing the amino acetyl groups of chitins. Structurally chitosan does not possess any thiol group but is modified chemically to add free thiol groups to its structure. This derivatization makes it an ideal carrier with properties such as mucoadhesion and permeation of drugs. Recently it has been used for immune modulation and bone resorption because of the excessive charge on its surface that helps its binding with the charged surfaces. As a result, the current research thoroughly assesses the efficacy of chitosan and thiolated chitosan nanoparticles for oral drug administration in medicine, particularly in bone tissue regeneration for osteoporosis treatment.

有效的口服药物递送是非常理想的，以控制药物释放使用各种聚合物。在不同的聚合物中，壳聚糖被认为是一种安全、无毒的材料，是一种有效的药物载体。它具有生物相容性，可生物降解性，可通过水解几丁质的氨基乙酰基获得。壳聚糖在结构上不含任何巯基，而是通过化学修饰在其结构上加入游离巯基。这种衍生化使其成为具有黏附性和药物渗透性等特性的理想载体。最近，由于其表面的过量电荷有助于其与带电表面的结合，它已被用于免疫调节和骨吸收。因此，目前的研究彻底评估了壳聚糖和硫代壳聚糖纳米颗粒在医学口服给药方面的功效，特别是在骨质疏松症治疗的骨组织再生方面。

引用次数: 0

Supramolecular assembly of antibody-rhamnose complex to enhance the complement-dependent cytotoxicity for cancer immunotherapy 抗体-鼠李糖复合物的超分子组装增强补体依赖性细胞毒性用于癌症免疫治疗

IF 1.2 4区化学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY

Journal of Carbohydrate Chemistry

Pub Date : 2025-03-24 DOI: 10.1080/07328303.2024.2418526

Haofei Hong , Kun Zhou , Han Lin , Zhimeng Wu

Enhancing the complement-dependent cytotoxicity (CDC) of monoclonal antibodies (mAbs) has the potential to improve their clinical performance. In this study, we describe an innovative antibody-hapten supramolecular complex strategy to amplify CDC activity. We selected Rituximab (RTX), an approved anti-CD20 mAb, and conjugated it with adamantane (Ada) to generate RTX-Ada. After targeting CD20-positive cells, this conjugate can interact with rhamnose (Rha)-modified β-cyclodextrin via host-guest interaction, in situ forming a supramolecular complex that can recruit anti-Rha antibodies onto CD20-positive cancer cells. This complex provides a larger number of Fc domains for complement system activation, leading to enhanced CDC. Our study demonstrates the potential of antibody-based supramolecular complexes for cancer immunotherapy, offering a promising approach to improve the efficacy of mAb-based cancer treatments.

增强单克隆抗体（mab）的补体依赖性细胞毒性（CDC）有可能改善其临床性能。在这项研究中，我们描述了一种创新的抗体-半抗原超分子复合物策略来增强CDC活性。我们选择了一种被批准的抗cd20单抗Rituximab (RTX)，并将其与adamantane （Ada）偶联生成RTX-Ada。在靶向cd20阳性细胞后，该缀合物可以通过主客体相互作用与鼠李糖修饰的β-环糊精相互作用，在原位形成一个超分子复合物，可以将抗Rha抗体募集到cd20阳性癌细胞上。该复合物为补体系统激活提供了大量的Fc结构域，从而增强了CDC。我们的研究证明了基于抗体的超分子复合物在癌症免疫治疗中的潜力，为提高基于单克隆抗体的癌症治疗的疗效提供了一种有希望的方法。

引用次数: 0

Ring opening of cyclopropylmethylidene with trimethylaluminum: Synthesis of 1-cyclopropylethyl ether as an acid labile protecting group for hydroxyl Protection and carbohydrate synthesis 环丙基甲基乙烯与三甲基铝开环：1-环丙基乙醚的合成，作为羟基保护和碳水化合物合成的酸不稳定保护基团

IF 1.2 4区化学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY

Journal of Carbohydrate Chemistry

Pub Date : 2025-03-24 DOI: 10.1080/07328303.2025.2471354

Madhav Poudel , Zainab Bustani , Xiaohua Li , Jianglong Zhu

The 4,6-O-cyclopropylmethylidene (CPMD) moiety of a methyl α-glucoside derivative can be regioselectively opened by trimethylaluminum to afford a corresponding 1-cyclopropylethyl (CPE) ether at C4 and a free alcohol at C6. This 1-CPE ether was found to be an acid-labile hydroxyl protecting group and can be readily cleaved using 10% trifluoracetic acid in dichloromethane at room temperature. The utilization of 1-CPE ether as a hydroxyl protecting group has been demonstrated in the efficient synthesis of a trisaccharide.

甲基α-葡萄糖苷衍生物的4,6- o -环丙基甲基（CPMD）部分可以被三甲基铝选择性地打开，在C4上得到相应的1-环丙基乙基（CPE）醚和在C6上得到游离醇。该1-CPE醚被发现是一种酸不稳定的羟基保护基团，在室温下用10%的三氟乙酸在二氯甲烷中很容易裂解。利用1-CPE醚作为羟基保护基团，有效合成了一种三糖。

引用次数: 0

Inhibition of lipopolysaccharide layer by plant-derived molecules: A novel approach to combat Helicobacter pylori 植物源性分子抑制脂多糖层：一种对抗幽门螺杆菌的新方法

IF 1.2 4区化学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY

Journal of Carbohydrate Chemistry

Pub Date : 2025-03-24 DOI: 10.1080/07328303.2025.2459914

Abhishek Sharma , Pragati Mahur , Amit Kumar Singh , Jayaraman Muthukumaran , Monika Jain

The WHO classifies H. pylori as a critical public health issue. H. pylori is a gram-negative bacterium that causes infections in the stomach lining, contributing to conditions such as gastritis, peptic ulcers, and gastric cancer. The emergence of multidrug resistance in H. pylori presents a major obstacle in treatment, resulting in ineffective therapies and prolonged infections. The lipopolysaccharide biosynthesis pathway plays a crucial role in the survival of H. pylori. UDP-3-O-acyl-N-acetylglucosamine deacetylase (LpxC) is an essential enzyme, and its crucial role in disease pathogenesis has positioned LpxC as a highly promising druggable target for targeting H. pylori infection. In this study, we utilized structure-based virtual high-throughput screening of phytochemicals to discover potential inhibitors of LpxC. The selection of hits was initially based on their compliance with the Lipinski rule of 5, along with their toxicological, pharmacokinetic properties, and other drug-like attributes. This was followed by 100 ns molecular dynamics simulations in triplicate and MM/PBSA based binding free energy calculations. These findings indicated that Panicutine interacts strongly and enhances the stability of the LpxC structure, suggesting it as potential inhibitor of LpxC. The outcomes point to future studies to enhance their effectiveness as innovative and cost-effective treatments for H. pylori infections.

世界卫生组织将幽门螺旋杆菌列为严重的公共卫生问题。幽门螺杆菌是一种革兰氏阴性细菌，会引起胃粘膜感染，导致胃炎、消化性溃疡和胃癌等疾病。幽门螺杆菌多药耐药的出现是治疗的主要障碍，导致治疗无效和长期感染。脂多糖生物合成途径在幽门螺杆菌的生存中起着至关重要的作用。udp -3- o -酰基- n -乙酰氨基葡萄糖脱乙酰酶（LpxC）是一种必需的酶，其在疾病发病机制中的重要作用使LpxC成为一种非常有前途的靶向幽门螺杆菌感染的药物靶点。在这项研究中，我们利用基于结构的虚拟高通量植物化学物质筛选来发现LpxC的潜在抑制剂。药物的选择最初是基于它们是否符合Lipinski规则5，以及它们的毒理学、药代动力学特性和其他类似药物的属性。随后进行了100 ns三次分子动力学模拟和基于MM/PBSA的结合自由能计算。这些结果表明，Panicutine与LpxC的相互作用强，增强了LpxC结构的稳定性，提示其可能是LpxC的潜在抑制剂。这些结果表明，未来的研究将提高它们作为幽门螺杆菌感染的创新和经济有效的治疗方法的有效性。

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引用次数: 0

A glycosylated naphthalimide conjugate preferentially accumulates in metastatic hepatocellular carcinoma as ROS-mediated mitochondrial-targeted antimetastatic agent 糖基化萘酰亚胺缀合物优先在转移性肝癌中积累，作为ros介导的线粒体靶向抗转移剂

IF 1.2 4区化学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY

Journal of Carbohydrate Chemistry

Pub Date : 2025-03-24 DOI: 10.1080/07328303.2025.2468188

Na. Li , Bin Hu , Kexin Du , Yi. Cao , Zhongzhe Zhang , Binhao Guo , Chuanchuan Liu , Songshen Chu , Jinhua Gao , Chaojie Wang , Jing Ma , Lingling Di , Songqiang Xie

For patients with hepatocellular carcinoma (HCC), recurrence and metastasis lead to approximately 90% deaths, even after various standard therapies, indicating the need for novel therapies and antimetastatic drugs. Recently, mitochondrial dysfunction has been shown to be closely associated with HCC recurrence and metastasis. Herein, a novel glycosylated naphthalimide conjugate 4a was explored to target HCC and HCC metastasis by inducing ROS-mediated mitochondrial metabolic programs in HCC, remarkably improving the efficacy of amonafide and prolonging the survival of mice. Mechanistically, 4a, as a potential fluorescent chemical probe, could target mitochondria, which is completely different from amonafide. Preliminary investigation into the mechanism of 4a indicates that it localizes in the mitochondria and selectively causes reactive oxygen species (ROS) overproduction in HCC instead of the matched normal liver cells, leading to HCC cell apoptosis and migration inhibition via multiple ROS-mediated signaling pathways. In addition to exposing a previously undefined mitochondrial metabolic program in HCC, our study further illuminates an unrecognized naphthalimide-based tumor therapeutic strategy to prolong the life of terminal HCC in a completely new field.

对于肝细胞癌（HCC）患者，即使在各种标准治疗后，复发和转移导致约90%的死亡，这表明需要新的治疗方法和抗转移药物。近年来，线粒体功能障碍已被证明与HCC的复发和转移密切相关。本研究探索一种新型糖基化萘酰亚胺偶联物4a，通过诱导ros介导的肝癌线粒体代谢程序，靶向肝癌及肝癌转移，显著提高氨那定的疗效，延长小鼠生存期。从机制上讲，4a作为一种潜在的荧光化学探针，可以靶向线粒体，这与氨氮完全不同。对4a机制的初步研究表明，它定位于线粒体，在HCC中选择性地导致活性氧（ROS）过量产生，而不是匹配的正常肝细胞，通过多种ROS介导的信号通路导致HCC细胞凋亡和迁移抑制。除了揭示HCC中先前未定义的线粒体代谢程序外，我们的研究进一步阐明了一种未被认识的基于萘酰亚胺的肿瘤治疗策略，可以在一个全新的领域延长晚期HCC的生命。

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引用次数: 0

Lectins: Versatile proteins in plant life with diverse applications in immunomodulation, antibacterial defense, and disease-fighting 凝集素：植物生命中的多功能蛋白质，在免疫调节、抗菌防御和抗病方面具有多种应用

IF 2.2 4区化学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY

Journal of Carbohydrate Chemistry

Pub Date : 2024-11-21 DOI: 10.1080/07328303.2024.2410792

Sivakamavalli Jeyachandran , Prachi Vibhute

Lectins, diverse proteins adept at detecting and binding carbohydrates without altering them, are pivotal in plant life. They facilitate cell communication, development, and defense mechanisms. This article explores lectins’ varied biological roles, focusing on their versatility and significance. Plant lectins exhibit diverse biochemical traits, impacting immune regulation and possessing antibacterial properties vital in plant defense. Additionally, they showcase disease-fighting potential. Their multifaceted nature, spanning biochemical properties, and functional roles underscores their importance in intricate biological processes. This concise review highlights wide-ranging applications of plant lectins, emphasizing their crucial role in immunomodulation, antibacterial functions, and contributions to plant health and defense mechanisms.

凝集素是一种不同的蛋白质，擅长探测和结合碳水化合物而不改变它们，在植物生命中起着关键作用。它们促进细胞通讯、发育和防御机制。本文探讨了凝集素的多种生物学作用，重点介绍了它们的多功能性和意义。植物凝集素具有多种生物化学特性，影响免疫调节，并具有在植物防御中至关重要的抗菌特性。此外，它们还显示出对抗疾病的潜力。它们的多面性，跨越生化特性和功能角色强调了它们在复杂的生物过程中的重要性。本文简要介绍了植物凝集素的广泛应用，强调了它们在免疫调节、抗菌功能以及对植物健康和防御机制的贡献方面的重要作用。

引用次数: 0

On the relevance of glycosyl oxonium ions to 1,2-cis-selective O-glycosylation in ether solvents 乙醚溶剂中糖基氧鎓离子与1,2-顺式选择性o糖基化的相关性

IF 2.2 4区化学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY

Journal of Carbohydrate Chemistry

Pub Date : 2024-11-21 DOI: 10.1080/07328303.2024.2410800

Varad Agarkar , Ava E. Hart , Justin R. Ragains

Since no later than the 1970s, organic chemists have speculated on the role of glycosyl oxonium ions in chemical O-glycosylation. Such species result from the attack of ethers on glycosyl oxocarbenium ions and are invoked to explain 1,2-cis-selectivity in ether solvents. However, a systematic study to probe this phenomenon appears to be lacking in the chemical literature. Herein, we study the effects of solvent, counteranion, protecting group electron-withdrawing effects, and acceptor on O-glycosylation stereoselectivity with D-glucosyl trichloroacetimidate donors. While many of these transformations proceed with 1,2-cis-selectivity, our results suggest that glycosyl oxonium ions play minimal, if any, role in O-glycosylation.

早在20世纪70年代，有机化学家就开始推测糖基氧鎓离子在化学o -糖基化中的作用。这些物质是由醚对糖基氧羰基离子的攻击产生的，并被用来解释醚溶剂中的1,2-顺式选择性。然而，在化学文献中似乎缺乏对这一现象的系统研究。本文研究了溶剂、反阴离子、保护基吸电子效应和受体对d -葡萄糖基三氯乙酸酯给体o -糖基化立体选择性的影响。虽然许多这些转化进行1,2-顺式选择性，我们的结果表明，糖基氧鎓离子在o -糖基化中发挥最小的作用，如果有的话。

引用次数: 0

Stereoselective synthesis of phomopsolidone B from L-Arabinose l -阿拉伯糖立体选择性合成硫固酮B

IF 2.2 4区化学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY

Journal of Carbohydrate Chemistry

Pub Date : 2024-11-21 DOI: 10.1080/07328303.2024.2407803

Jun Liu , Minhao Chen , Pengpeng Nie , Yuanfang Liu , Yuguo Du

An efficient and concise synthesis of phomopsolidone B was accomplished in nine longest linear steps from readily available chiral template, L-arabinose and L-ethyl lactate. The synthesis features rapid access to the key chiral backbone from chiral pools and the formation of furanone skeleton employing a late-stage olefin cross-metathesis.

以现成的手性模板、l -阿拉伯糖和l -乳酸乙酯为原料，经过9个最长的线性步骤，高效、简洁地合成了磷硫固酮B。该合成方法的特点是从手性池中快速获得关键的手性骨架，并通过后期烯烃交叉复分解形成呋喃酮骨架。

引用次数: 0

Mercury(II) triflate catalyzed direct α-stereoselective synthesis of 2-deoxyglycosides from glycals 三酸汞催化糖基直接α-立体选择性合成2-脱氧糖苷

IF 2.2 4区化学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY

Journal of Carbohydrate Chemistry

Pub Date : 2024-11-21 DOI: 10.1080/07328303.2025.2451830

Miaomiao Zhang , Haoru Zhuang , Yongshun Qiu , Yuanyuan Li , Shuting Liu , Tong Li , Tianlu Li , Peng Peng

A novel and efficient approach was established for the formation of α-2-deoxyglycosidic bonds directly from glycals, utilizing catalytic amounts of Hg(OTf)₂. This robust method enabled the synthesis of corresponding 2-deoxyglycosides with excellent yields and high α-selectivity rapidly (within 10 min) under mild conditions, employing various glycal donors and alcohol acceptors. The versatility of this methodology was demonstrated in the synthesis of saponins, glycosyl amino acids, and oligosaccharides. Mechanistic investigations and DFT calculations revealed that Hg(II) played a pivotal role in facilitating efficient catalysis and stereoselectivity by activating both the glycal donors and the acceptors.

利用Hg(OTf)2的催化量，建立了一种新的、高效的由糖基直接形成α-2-脱氧糖苷键的方法。该方法采用多种糖给体和醇受体，在温和的条件下快速（10 min内）合成了相应的2-脱氧糖苷，收率高，α-选择性高。这种方法的多功能性在皂苷、糖基氨基酸和低聚糖的合成中得到了证明。机理研究和DFT计算表明，Hg（II）通过激活糖供体和受体，在促进高效催化和立体选择性中发挥了关键作用。

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