Synthesis and preliminary biological assay of uridine glycoconjugate derivatives containing amide and/or 1,2,3-triazole linkers

被引：12

作者：

Pastuch-Gawolek, Gabriela ^{[1
,2
]}

Plesniak, Mateusz ^{[1
]}

Komor, Roman ^{[1
]}

Byczek-Wyrostek, Anna ^{[1
]}

Erfurt, Karol ^{[3
]}

Szeja, Wieslaw ^{[1
,2
]}

机构：

[1] Silesian Tech Univ, Dept Organ Chem Bioorgan Chem & Biotechnol, B Krzywoustego 4, PL-44100 Gliwice, Poland

[2] Silesian Tech Univ, Biotechnol Ctr, Krzywoustego 8, PL-44100 Gliwice, Poland

[3] Silesian Tech Univ, Dept Chem Organ Technol & Petrochem, B Krzywoustego 4, PL-44100 Gliwice, Poland

来源：

BIOORGANIC CHEMISTRY | 2017年 / 72卷

关键词：

Glycoconjugates; Uridine derivatives; Glycosyltransferase inhibitors; Click chemistry; GLYCOSYLTRANSFERASE INHIBITORS; CLICK-CHEMISTRY; POTENTIAL INHIBITORS; DIPHOSPHATE SUGARS; CONDENSING AGENT; ANALOGS; CANCER; ACIDS; CYCLOADDITION; GLYCOSYLATION;

D O I：

10.1016/j.bioorg.2017.03.015

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A series of UDP-sugar analogues was synthesized and their preliminary biological activity was evaluated. Glycoconjugates of uridine 1 and 2 were synthesized by condensation of uridine-5'-carboxylic acid and 1-amino sugars derivatives of D-glucose and D-galactose, glycoconjugates 3 and 4 were synthesized by azide-alkyne 1,3-dipolar cycloaddition (CuAAC) of 1-azido sugars and propargylamide derivatives of uridine while glycoconjugates 5 and 6 were synthesized by CuAAC of propargyl beta-O-glycosides and 5'-azido uridine. Evaluation of inhibitory activity of compounds 1-6 against commercially available beta-1,4-galacto syltransferase I (beta 4GalT) show that compound 5 inhibited the enzyme in ae molar range. Additionally, the antitumor activity of the obtained glycoconjugates 1-6 were tested using MTT assay. (C) 2017 Elsevier Inc. All rights reserved.

引用

页码：80 / 88

页数：9

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