一种新型糖隐体与抗癌药物丝裂霉素C形成的复合物的理论分析、合成及其对正常细胞和癌细胞的生物活性

IF 2.4 3区化学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY

Carbohydrate Research Pub Date : 2025-02-13 DOI:10.1016/j.carres.2025.109425

Marta Hoelm , Stanisław Porwański , Paweł Jóźwiak , Anna Krześlak

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引用次数: 0

摘要

本文介绍了作为抗癌药物丝分裂霉素c的药物载体的1,10-N,N ' -二-（β-d-脲基纤维素生物基）-4,7,13,16-四氧基-1,10-二氮杂环十八烷（TN）的理论、光谱和生物学特性。光谱分析证实了在水中成功形成稳定的1:1配合物。丝裂霉素C与TN的所有功能部分相互作用。通过理论建模，这些发现得到了进一步的支持和阐述。利用密度泛函理论（DFT）方法，估计络合能为−25.8 kcal/mol（−107.95 kJ/mol）。将此值与文献数据进行比较，并附有详细讨论。对TN、丝裂霉素C及其复合物进行的生物学评价表明，在复合物中结合丝裂霉素C可有效降低其对所有分析细胞系的细胞毒性。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Theoretical analysis, synthesis and biological activity against normal and cancer cells of a complex formed by a novel sugar cryptand and anticancer drug mitomycin C

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Theoretical analysis, synthesis and biological activity against normal and cancer cells of a complex formed by a novel sugar cryptand and anticancer drug mitomycin C

This work presents the theoretical, spectroscopic, and biological characterization of cryptand 1,10-N,N′-bis-(β-d-ureidocellobiosyl)-4,7,13,16-tetraoxa-1,10-diazacyclooctadecane (TN) as a drug carrier for the anticancer agent mitomycin C. Spectroscopic analysis confirms the successful formation of a stable 1:1 complex in water, with the preferred configuration involving interactions between mitomycin C and all functional moieties of TN. These findings are further supported and elaborated upon through theoretical modeling. Using the density functional theory (DFT) method, the complexation energy was estimated at −25.8 kcal/mol (−107.95 kJ/mol). This value is compared with the literature data, accompanied by a detailed discussion. The biological assessment conducted for TN, mitomycin C, and their complex demonstrates that binding mitomycin C in a complex effectively reduces its cytotoxicity toward all analyzed cell lines.

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来源期刊

Carbohydrate Research 化学-生化与分子生物学

CiteScore

5.00

自引率

3.20%

发文量

183

审稿时长

3.6 weeks

期刊介绍： Carbohydrate Research publishes reports of original research in the following areas of carbohydrate science: action of enzymes, analytical chemistry, biochemistry (biosynthesis, degradation, structural and functional biochemistry, conformation, molecular recognition, enzyme mechanisms, carbohydrate-processing enzymes, including glycosidases and glycosyltransferases), chemical synthesis, isolation of natural products, physicochemical studies, reactions and their mechanisms, the study of structures and stereochemistry, and technological aspects. Papers on polysaccharides should have a "molecular" component; that is a paper on new or modified polysaccharides should include structural information and characterization in addition to the usual studies of rheological properties and the like. A paper on a new, naturally occurring polysaccharide should include structural information, defining monosaccharide components and linkage sequence. Papers devoted wholly or partly to X-ray crystallographic studies, or to computational aspects (molecular mechanics or molecular orbital calculations, simulations via molecular dynamics), will be considered if they meet certain criteria. For computational papers the requirements are that the methods used be specified in sufficient detail to permit replication of the results, and that the conclusions be shown to have relevance to experimental observations - the authors'' own data or data from the literature. Specific directions for the presentation of X-ray data are given below under Results and "discussion".