Design, synthesis and evaluation of PPAR gamma binding activity of 2-thioxo-4-thiazolidinone derivatives

Li Zhou; Ye Zhong; Meng Zhu Xue; Dong Kuang; Xian Wen Cao; Zhen Jiang Zhao; Hong Lin Li; Yu Fang Xu; Rui Wang

doi:10.1016/j.cclet.2014.10.008

Design, synthesis and evaluation of PPAR gamma binding activity of 2-thioxo-4-thiazolidinone derivatives

Li Zhou, Ye Zhong, Meng Zhu Xue, Dong Kuang, Xian Wen Cao, Zhen Jiang Zhao, Hong Lin Li, Yu Fang Xu, Rui Wang

East China University of Science and Technology

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

21 Scopus citations

Abstract

We designed and synthesized a series of 2-thioxo-4-thiazolidinone derivatives and evaluated them on peroxisome proliferator activated receptor γ (PPARγ) binding activities. Through the biological assays, compounds 18 and 38 were highlighted with K_i values of 12.15 nmol/L and 14.46 nmol/L, respectively. Then structure-activity relationship (SAR) was analyzed to screen privileged structural modifications. Moreover, molecular fitting of these compounds onto the approved drug Rosiglitazone in the PPARγ ligand binding domain was performed to elucidate the SAR and explore potential receptor-ligand interactions. These results demonstrate that the 2-thioxo-4-thiazolidinones can be considered as new promising molecular probes with excellent binding activities to PPARγ.

Original language	English
Pages (from-to)	63-68
Number of pages	6
Journal	Chinese Chemical Letters
Volume	26
Issue number	1
DOIs	https://doi.org/10.1016/j.cclet.2014.10.008
State	Published - Jan 2015
Externally published	Yes

Keywords

2-Thioxo-4-thiazolidinone
Binding activities
Molecular docking
Peroxisome proliferator activated receptor
SAR
γ

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10.1016/j.cclet.2014.10.008

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title = "Design, synthesis and evaluation of PPAR gamma binding activity of 2-thioxo-4-thiazolidinone derivatives",

abstract = "We designed and synthesized a series of 2-thioxo-4-thiazolidinone derivatives and evaluated them on peroxisome proliferator activated receptor γ (PPARγ) binding activities. Through the biological assays, compounds 18 and 38 were highlighted with Ki values of 12.15 nmol/L and 14.46 nmol/L, respectively. Then structure-activity relationship (SAR) was analyzed to screen privileged structural modifications. Moreover, molecular fitting of these compounds onto the approved drug Rosiglitazone in the PPARγ ligand binding domain was performed to elucidate the SAR and explore potential receptor-ligand interactions. These results demonstrate that the 2-thioxo-4-thiazolidinones can be considered as new promising molecular probes with excellent binding activities to PPARγ.",

keywords = "2-Thioxo-4-thiazolidinone, Binding activities, Molecular docking, Peroxisome proliferator activated receptor, SAR, γ",

author = "Li Zhou and Ye Zhong and Xue, \{Meng Zhu\} and Dong Kuang and Cao, \{Xian Wen\} and Zhao, \{Zhen Jiang\} and Li, \{Hong Lin\} and Xu, \{Yu Fang\} and Rui Wang",

note = "Publisher Copyright: {\textcopyright} 2014 Rui Wang and Yu-Fang Xu. Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. All rights reserved.",

year = "2015",

month = jan,

doi = "10.1016/j.cclet.2014.10.008",

language = "英语",

volume = "26",

pages = "63--68",

journal = "Chinese Chemical Letters",

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T1 - Design, synthesis and evaluation of PPAR gamma binding activity of 2-thioxo-4-thiazolidinone derivatives

AU - Zhou, Li

AU - Zhong, Ye

AU - Xue, Meng Zhu

AU - Kuang, Dong

AU - Cao, Xian Wen

AU - Zhao, Zhen Jiang

AU - Li, Hong Lin

AU - Xu, Yu Fang

AU - Wang, Rui

N1 - Publisher Copyright: © 2014 Rui Wang and Yu-Fang Xu. Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. All rights reserved.

PY - 2015/1

Y1 - 2015/1

N2 - We designed and synthesized a series of 2-thioxo-4-thiazolidinone derivatives and evaluated them on peroxisome proliferator activated receptor γ (PPARγ) binding activities. Through the biological assays, compounds 18 and 38 were highlighted with Ki values of 12.15 nmol/L and 14.46 nmol/L, respectively. Then structure-activity relationship (SAR) was analyzed to screen privileged structural modifications. Moreover, molecular fitting of these compounds onto the approved drug Rosiglitazone in the PPARγ ligand binding domain was performed to elucidate the SAR and explore potential receptor-ligand interactions. These results demonstrate that the 2-thioxo-4-thiazolidinones can be considered as new promising molecular probes with excellent binding activities to PPARγ.

AB - We designed and synthesized a series of 2-thioxo-4-thiazolidinone derivatives and evaluated them on peroxisome proliferator activated receptor γ (PPARγ) binding activities. Through the biological assays, compounds 18 and 38 were highlighted with Ki values of 12.15 nmol/L and 14.46 nmol/L, respectively. Then structure-activity relationship (SAR) was analyzed to screen privileged structural modifications. Moreover, molecular fitting of these compounds onto the approved drug Rosiglitazone in the PPARγ ligand binding domain was performed to elucidate the SAR and explore potential receptor-ligand interactions. These results demonstrate that the 2-thioxo-4-thiazolidinones can be considered as new promising molecular probes with excellent binding activities to PPARγ.

KW - 2-Thioxo-4-thiazolidinone

KW - Binding activities

KW - Molecular docking

KW - Peroxisome proliferator activated receptor

KW - SAR

KW - γ

UR - https://www.scopus.com/pages/publications/84921025121

U2 - 10.1016/j.cclet.2014.10.008

DO - 10.1016/j.cclet.2014.10.008

M3 - 文章

AN - SCOPUS:84921025121

SN - 1001-8417

VL - 26

SP - 63

EP - 68

JO - Chinese Chemical Letters

JF - Chinese Chemical Letters

IS - 1

ER -

Design, synthesis and evaluation of PPAR gamma binding activity of 2-thioxo-4-thiazolidinone derivatives

Abstract

Keywords

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