Synthesis of glucoconjugates of oleanolic acid as inhibitors of glycogen phosphorylase

被引：72

作者：

Cheng, Keguang ^{[1
,2
]}

Liu, Jun ^{[3
]}

Liu, Xiaofeng ^{[4
]}

Li, Honglin ^{[4
,5
]}

Sun, Hongbin ^{[1
]}

Xie, Juan ^{[2
]}

机构：

[1] China Pharmaceut Univ, Coll Pharm, Ctr Drug Discovery, Nanjing 210009, Peoples R China

[2] UniverSud, CNRS, ENS Cachan, PPSM, F-94230 Cachan, France

[3] China Pharmaceut Univ, Jiangsu Ctr Drug Screening, Nanjing 210038, Peoples R China

[4] Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Drug Discovery & Design Ctr, Shanghai 201203, Peoples R China

[5] E China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R China

来源：

CARBOHYDRATE RESEARCH | 2009年 / 344卷 / 07期

基金：

中国国家自然科学基金;

关键词：

Glycogen phosphorylase; Oleanolic acid; Glucoconjugate; Inhibitor; Diabetes; Click chemistry; GLUCOSE ANALOG INHIBITORS; PENTACYCLIC TRITERPENES; CLICK CHEMISTRY; BINDING; DERIVATIVES; DESIGN; TARGET;

D O I：

10.1016/j.carres.2009.02.012

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

070307 [化学生物学]; 071010 [生物化学与分子生物学];

摘要：

Synthesis and biological evaluation of glucoconjugates of oleanolic acid, linked by either a triazole moiety or an ester function, as novel inhibitors of glycogen phosphorylase have been described. Several triterpene-glycoside conjugates exhibited moderate-to-good inhibitory activity against rabbit muscle GPa. Compound 12 showed the best inhibition with an IC50 value of 1.14 mu M. Structure-activity relationship (SAR) analysis of these inhibitors is also discussed. Possible binding modes of compound 12 were explored by molecular docking simulations. (C) 2009 Elsevier Ltd. All rights reserved.

引用

收藏

页码：841 / 850

页数：10

相关论文

共 35 条

[1]

New hepatic targets for glycaemic control in diabetes [J].

Agius, Loranne .

BEST PRACTICE & RESEARCH CLINICAL ENDOCRINOLOGY & METABOLISM, 2007, 21 (04) :587-605

[2]

Glycogen phosphorylase inhibition as a therapeutic target: a review of the recent patent literature [J].

Baker, DJ ;

Greenhaff, PL ;

Timmons, JA .

EXPERT OPINION ON THERAPEUTIC PATENTS, 2006, 16 (04) :459-466

[3]

The Protein Data Bank [J].

Berman, HM ;

Westbrook, J ;

Feng, Z ;

Gilliland, G ;

Bhat, TN ;

Weissig, H ;

Shindyalov, IN ;

Bourne, PE .

NUCLEIC ACIDS RESEARCH, 2000, 28 (01) :235-242

[4]

Development of potent, orally active 1-substituted-3,4-dihydro-2-quinolone glycogen phosphorylase inhibitors [J].

Birch, Alan M. ;

Kenny, Peter W. ;

Oikonomakos, Nikos G. ;

Otterbein, Ludovic ;

Schofield, Paul ;

Whittamore, Paul R. O. ;

Whalley, Dave P. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (02) :394-399

[5]

Pentacyclic triterpenes. Part 3: Synthesis and biological evaluation of oleanolic acid derivatives as novel inhibitors of glycogen phosphorylase [J].

Chen, J ;

Liu, J ;

Zhang, LY ;

Wu, GZ ;

Hua, WY ;

Wu, XM ;

Sun, HB .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (11) :2915-2919

[6]

Practical Synthesis of Bredemolic Acid, a Natural Inhibitor of Glycogen Phosphorylase [J].

Cheng, Keguang ;

Zhang, Pu ;

Liu, Jun ;

Xie, Juan ;

Sun, Hongbin .

JOURNAL OF NATURAL PRODUCTS, 2008, 71 (11) :1877-1880

[7]

Kinetic and crystallographic studies on 2-(β-D-glucopyranosyl)-5-methyl-1,3,4-oxadiazole, -benzothiazole, and -benzimidazole, inhibitors of muscle glycogen phosphorylase b.: Evidence for a new binding site [J].

Chrysina, ED ;

Kosmopoulou, MN ;

Tiraidis, C ;

Kardakaris, R ;

Bischler, N ;

Leonidas, DD ;

Hadady, Z ;

Somsak, L ;

Docsa, T ;

Gergely, P ;

Oikonomakos, NG .

PROTEIN SCIENCE, 2005, 14 (04) :873-888

[8]

Hantzsch-type three-component approach to a new family of carbon-linked glycosyl amino acids. synthesis of C-glycosylmethyl pyridylalanines [J].

Dondoni, Alessandro ;

Massi, Alessandro ;

Aldhoun, Mohammad .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (20) :7677-7687

[9]

Pharmacological activities of natural triterpenoids and their therapeutic implications [J].

Dzubak, Petr ;

Hajduch, Marian ;

Vydra, David ;

Hustova, Alica ;

Kvasnica, Miroslav ;

Biedermann, David ;

Markova, Lenka ;

Urban, Milan ;

Sarek, Jan .

NATURAL PRODUCT REPORTS, 2006, 23 (03) :394-411

[10]

Glide: A new approach for rapid, accurate docking and scoring. 1. Method and assessment of docking accuracy [J].

Friesner, RA ;

Banks, JL ;

Murphy, RB ;

Halgren, TA ;

Klicic, JJ ;

Mainz, DT ;

Repasky, MP ;

Knoll, EH ;

Shelley, M ;

Perry, JK ;

Shaw, DE ;

Francis, P ;

Shenkin, PS .

JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (07) :1739-1749

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