Amadori and Heyns rearrangement products of bioactive peptides as potential new ligands of galectin-3

IF 2.4 3区化学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY

Carbohydrate Research Pub Date : 2024-06-18 DOI:10.1016/j.carres.2024.109195

Andreja Jakas , Ramya Ayyalasomayajula , Mare Cudic

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Abstract

Non-enzymatic cascade reactions between amines and reducing sugars are known as Maillard reaction. The late phase of these reactions consists of advanced glycation end products (AGEs), which have been implicated in the pathogenesis of numerous human diseases. Recent evidence suggests that galectin-3 acts as a receptor for AGEs and some early products of the Maillard reaction. The early phase of the Maillard reaction, which consists of 1-amino-1-deoxyketoses (Amadori compounds) and 2-amino-2-deoxyaldoses (Heyns compounds), was the subject of our study. The binding interactions between galectin-3 and the Amadori and Heyns compounds of leucine-enkephalin (YGGFL), leucine-enkephalin methyl ester (YGGFL-OMe), truncated enkephalin (YGG and Y) and tetrapeptide (LSKL) were measured using the AlphaScreen competitive binding assay. The affinity of galectin-3 for Amadori and Heyns compounds depends on both the sugar moiety and the amino acid sequence of the model compounds. The best results were obtained with Leu-enkephalin derivatives of Amadori (IC₅₀ = 6.06 μm) and Heyns (IC₅₀ = 8.6 μm) compound, respectively.

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生物活性肽的 Amadori 和 Heyns 重排产物作为 galectin-3 的潜在新配体

胺和还原糖之间的非酶级联反应被称为马氏反应（Maillard reaction）。这些反应的后期阶段由高级糖化终产物（AGEs）组成，与许多人类疾病的发病机制有关。最近的证据表明，galectin-3 是 AGEs 和一些马氏反应早期产物的受体。麦拉德反应的早期产物包括 1-氨基-1-脱氧酮（Amadori 化合物）和 2-氨基-2-脱氧醛（Heyns 化合物），这是我们研究的主题。利用 AlphaScreen 竞争性结合试验测定了半凝集素-3 与亮氨酸脑啡肽（YGGFL）、亮氨酸脑啡肽甲酯（YGGFL-OMe）、截短脑啡肽（YGG 和 Y）和四肽（LSKL）的 Amadori 和 Heyns 化合物之间的结合相互作用。Galectin-3 与 Amadori 和 Heyns 化合物的亲和力取决于模型化合物的糖分子和氨基酸序列。Amadori（IC50 = 6.06 μm）和 Heyns（IC50 = 8.6 μm）化合物的亮烯酮脑啡肽衍生物分别获得了最佳结果。

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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".