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

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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Abstract

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".