Methionine-enkephalin related glycoconjugates. Synthesis and biological activity.

S Horvat, J Horvat, L Varga-Defterdarović, K Pavelić, N N Chung, P W Schiller
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Abstract

A series of glycoconjugates, in which [Met5]enkephalin or [D-Ala2,Met5]enkephalin have been linked through an ester bond to the HO-6 of various D-glycopyranose moieties, were synthesized by classical solution methods. The biological activities of these compounds were determined on selective pharmacological preparations: guinea pig ileum and mouse vas deferens for opioid activity, and two mouse cell lines, fibroblasts L929 and melanoma B16BL6, to study the influence on growth processes. The results reported in this study demonstrate the differential effect of the carbohydrate part in enkephalin-related glycoconjugates on receptor recognition. In addition, synthesized neo-glycopeptides stimulate growth of the examined mouse cell lines, whereas parent peptide demonstrated some growth inhibitory properties. Full growth curves showed a dose-dependent effect at concentrations of 10(-7) to 10(-10) M.

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蛋氨酸-脑啡肽相关糖缀合物。合成及生物活性。
通过经典溶液法合成了一系列糖缀合物,其中[Met5]脑啡肽或[D-Ala2,Met5]脑啡肽通过酯键与各种d -甘氨糖基团的HO-6相连。在豚鼠回肠和小鼠输精管中测定这些化合物的生物活性,并在两种小鼠细胞系成纤维细胞L929和黑色素瘤B16BL6中测定其对生长过程的影响。本研究报告的结果表明,脑啡肽相关糖缀合物中碳水化合物部分对受体识别的不同影响。此外,合成的新糖肽刺激小鼠细胞系的生长,而母体肽则表现出一定的生长抑制特性。在10(-7)~ 10(-10)M的浓度下,全生长曲线显示出剂量依赖性。
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