Synthesis of glucoconjugates of oleanolic acid as inhibitors of glycogen phosphorylase

Keguang Cheng; Jun Liu; Xiaofeng Liu; Honglin Li; Hongbin Sun; Juan Xie

doi:10.1016/j.carres.2009.02.012

Synthesis of glucoconjugates of oleanolic acid as inhibitors of glycogen phosphorylase

Keguang Cheng
, Jun Liu
, Xiaofeng Liu
, Honglin Li
, Hongbin Sun^*
, Juan Xie

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

67 Scopus citations

Abstract

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 μM. Structure-activity relationship (SAR) analysis of these inhibitors is also discussed. Possible binding modes of compound 12 were explored by molecular docking simulations.

Original language	English
Pages (from-to)	841-850
Number of pages	10
Journal	Carbohydrate Research
Volume	344
Issue number	7
DOIs	https://doi.org/10.1016/j.carres.2009.02.012
State	Published - 12 May 2009
Externally published	Yes

Keywords

Click chemistry
Diabetes
Glucoconjugate
Glycogen phosphorylase
Inhibitor
Oleanolic acid

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.carres.2009.02.012

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title = "Synthesis of glucoconjugates of oleanolic acid as inhibitors of glycogen phosphorylase",

abstract = "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 μM. Structure-activity relationship (SAR) analysis of these inhibitors is also discussed. Possible binding modes of compound 12 were explored by molecular docking simulations.",

keywords = "Click chemistry, Diabetes, Glucoconjugate, Glycogen phosphorylase, Inhibitor, Oleanolic acid",

author = "Keguang Cheng and Jun Liu and Xiaofeng Liu and Honglin Li and Hongbin Sun and Juan Xie",

year = "2009",

month = may,

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doi = "10.1016/j.carres.2009.02.012",

language = "英语",

volume = "344",

pages = "841--850",

journal = "Carbohydrate Research",

issn = "0008-6215",

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TY - JOUR

T1 - Synthesis of glucoconjugates of oleanolic acid as inhibitors of glycogen phosphorylase

AU - Cheng, Keguang

AU - Liu, Jun

AU - Liu, Xiaofeng

AU - Li, Honglin

AU - Sun, Hongbin

AU - Xie, Juan

PY - 2009/5/12

Y1 - 2009/5/12

N2 - 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 μM. Structure-activity relationship (SAR) analysis of these inhibitors is also discussed. Possible binding modes of compound 12 were explored by molecular docking simulations.

AB - 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 μM. Structure-activity relationship (SAR) analysis of these inhibitors is also discussed. Possible binding modes of compound 12 were explored by molecular docking simulations.

KW - Click chemistry

KW - Diabetes

KW - Glucoconjugate

KW - Glycogen phosphorylase

KW - Inhibitor

KW - Oleanolic acid

UR - https://www.scopus.com/pages/publications/65249125749

U2 - 10.1016/j.carres.2009.02.012

DO - 10.1016/j.carres.2009.02.012

M3 - 文章

C2 - 19269628

AN - SCOPUS:65249125749

SN - 0008-6215

VL - 344

SP - 841

EP - 850

JO - Carbohydrate Research

JF - Carbohydrate Research

IS - 7

ER -

Synthesis of glucoconjugates of oleanolic acid as inhibitors of glycogen phosphorylase

Abstract

Keywords

UN SDGs

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