Biological Evaluation of New Largazole Analogues: Alteration of Macrocyclic Scaffold with Click Chemistry

被引：35

作者：

Li, Xianlin ^{[1
]}

Tu, Zhenchao ^{[1
]}

Li, Hua ^{[1
]}

Liu, Chunping ^{[1
]}

Li, Zheng ^{[2
]}

Sun, Qiao ^{[1
]}

Yao, Yiwu ^{[1
]}

Liu, Jinsong ^{[1
]}

Jiang, Sheng ^{[1
]}

机构：

[1] Chinese Acad Sci, Guangzhou Inst Biomed & Hlth, Lab Regenerat Biol, Guangzhou 510530, Guangdong, Peoples R China

[2] Methodist Hosp, Res Inst, Houston, TX 77030 USA

来源：

ACS MEDICINAL CHEMISTRY LETTERS | 2013年 / 4卷 / 01期

关键词：

HDAC inhibitor; peptides; macrocycles; largazole; click chemistry; HISTONE-DEACETYLASE INHIBITORS; EXPRESSION; CONFORMATION; CANCER; HDACS;

D O I：

10.1021/ml300371t

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

We report the design, synthesis, and biological evaluation of a new series of largazole analogues in which a 4-methylthiazoline moiety was replaced with a triazole and tetrazole ring, respectively. Compound 7 bearing a tetrazole ring was identified to show much better selectivity for HDAC1 over HDAC9 than largazole (10-fold). This work could serve as a foundation for further exploration of selective HDAC inhibitors using a largazole molecular scaffold.

引用

页码：132 / 136

页数：5

共 50 条

[21] Design, synthesis and biological evaluation of novel macrocyclic bisbibenzyl analogues as tubulin polymerization inhibitors
Sun, Bin
Li, Lin
Hu, Qing-wen
Xie, Fei
Zheng, Hong-bo
Niu, Huan-min
Yuan, Hui-qing
Lou, Hong-xiang
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2016, 121 : 484 - 499
[22] Synthesis of new photobactericidal polymers by "click chemistry" and a study of their biological activity
Memmi, Abdelmajid
Granet, Robert
Aouni, Mahjoub
Bakhrouf, Amina
Krausz, Pierre
E-POLYMERS, 2012,
[23] Ceramide-Templated Macrolactams: Total Synthesis and Biological Evaluation of Macrocyclic α-Galactosylceramide Analogues and their Aglycons
Janssens, Jonas
Van der Eycken, Johan
Van Calenbergh, Serge
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (12) : 2253 - 2267
[24] Tyrosine modified analogues of the α4β7 integrin inhibitor biotin-R8ERY prepared via Click Chemistry: Synthesis and biological evaluation
Papst, Stefanie
Noisier, Anais
Brimble, Margaret A.
Yang, Yi
Krissansen, Geoffrey W.
BIOORGANIC & MEDICINAL CHEMISTRY, 2012, 20 (08) : 2638 - 2644
[25] Medicinal Chemistry of Annonaceous Acetogenins: Design, Synthesis, and Biological Evaluation of Novel Analogues
Kojima, Naoto
Tanaka, Tetsuaki
MOLECULES, 2009, 14 (09) : 3621 - 3661
[26] Design, synthesis and biological evaluation of simplified analogues of MraY inhibitory natural product with rigid scaffold
Okamoto, Kazuhiro
Ishikawa, Aoi
Okawa, Ryotaro
Yamamoto, Kazuki
Sato, Toyotaka
Yokota, Shin-ichi
Chiba, Kazuhiro
Ichikawa, Satoshi
BIOORGANIC & MEDICINAL CHEMISTRY, 2022, 55
[27] Synthesis And Biological Evaluation Of New Linear And Cyclic Analogues Of Neurotensin
Manessi-Zoupa, E. M. Z.
Exarchakou, R.
Magafa, V.
Assimomytis, N.
Liapakis, G.
Venihaki, M.
Varvounis, G.
Cordopatis, P.
JOURNAL OF PEPTIDE SCIENCE, 2010, 16 : 159 - 159
[28] Design, synthesis, biological evaluation and molecular modeling study of novel macrocyclic bisbibenzyl analogues as antitubulin agents
Sun, Bin
Li, Lin
Hu, Qing-wen
Zheng, Hong-bo
Tang, Hui
Niu, Huan-min
Yuan, Hui-qing
Lou, Hong-xiang
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2017, 129 : 186 - 208
[29] Design, synthesis, and biological evaluation of new territrem B analogues
Jiang, XR
Ao, L
Zhou, CX
Yang, LX
Zhang, QJ
Li, HB
Sun, LL
Wu, XM
Bai, H
Zhao, Y
CHEMISTRY & BIODIVERSITY, 2005, 2 (04) : 557 - 567
[30] Biological evaluation of new vitamin D2 analogues
Corcorana, Aoife
Bermudez, Maria A.
Seoane, Samuel
Perez-Fernandez, Roman
Krupa, Malgorzata
Pietraszek, Anita
Chodynski, Michal
Kutner, Andrzej
Brown, Geoffrey
Marcinkowska, Ewa
JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY, 2016, 164 : 66 - 71

← 1 2 3 4 5 →