Literature DB >> 31312965

Rational Design, synthesis and biological evaluation of novel triazole derivatives as potent and selective PRMT5 inhibitors with antitumor activity.

Kongkai Zhu1, Jingwei Shao2, Hongrui Tao3, Xue Yan3, Cheng Luo4, Hua Zhang5, Wenhu Duan6.   

Abstract

Protein arginine methyltransferase 5 (PRMT5) is responsible for the mono-methylation and symmetric dimethylation of arginine, and its expression level and methyl transferring activity have been demonstrated to have a close relationship with tumorigenesis, development and poor clinical outcomes of human cancers. Two PRMT5 small molecule inhibitors (GSK3326595 and JNJ-64619178) have been put forward into clinical trials. Here, we describe the design, synthesis and biological evaluation of a series of novel, potent and selective PRMT5 inhibitors with antiproliferative activity against Z-138 mantle cell lymphoma cell line. Among them, compound C_4 exhibited the highest potency with enzymatic and cellular level IC50 values of 0.72 and 2.6 μM, respectively, and displayed more than 270-fold selectivity toward PRMT5 over several other isoenzymes (PRMT1, PRMT4 and PRMT6). Besides, C_4 demonstrated obvious cell apoptotic effect while reduced the cellular symmetric arginine dimethylation levels of SmD3 protein. The potency, small size, and synthetic accessibility of this compound class provide promising hit scaffold for medicinal chemists to further explore this series of PRMT5 inhibitors.

Entities:  

Keywords:  Anti-proliferative; Cellular target validation; Design and synthesis; PRMT5 inhibitor

Year:  2019        PMID: 31312965     DOI: 10.1007/s10822-019-00214-y

Source DB:  PubMed          Journal:  J Comput Aided Mol Des        ISSN: 0920-654X            Impact factor:   3.686


  37 in total

1.  Protein arginine methyltransferase 5 is a potential oncoprotein that upregulates G1 cyclins/cyclin-dependent kinases and the phosphoinositide 3-kinase/AKT signaling cascade.

Authors:  Tong-You W Wei; Chi-Chang Juan; Jiun-Yi Hisa; Li-Jen Su; Yuan-Chii G Lee; Hsiang-Yun Chou; Jo-Mei M Chen; Yu-Chung Wu; Shao-Chih Chiu; Chung-Ping Hsu; Kuo-Lin Liu; Chang-Tze R Yu
Journal:  Cancer Sci       Date:  2012-08-08       Impact factor: 6.716

2.  The protein arginine methyltransferase Prmt5 is required for myogenesis because it facilitates ATP-dependent chromatin remodeling.

Authors:  Caroline S Dacwag; Yasuyuki Ohkawa; Sharmistha Pal; Saïd Sif; Anthony N Imbalzano
Journal:  Mol Cell Biol       Date:  2006-10-16       Impact factor: 4.272

3.  Genetic deletion or small-molecule inhibition of the arginine methyltransferase PRMT5 exhibit anti-tumoral activity in mouse models of MLL-rearranged AML.

Authors:  S Kaushik; F Liu; K J Veazey; G Gao; P Das; L F Neves; K Lin; Y Zhong; Y Lu; V Giuliani; M T Bedford; S D Nimer; M A Santos
Journal:  Leukemia       Date:  2017-06-30       Impact factor: 11.528

Review 4.  Molecular pathways: protein methyltransferases in cancer.

Authors:  Robert A Copeland
Journal:  Clin Cancer Res       Date:  2013-08-19       Impact factor: 12.531

5.  Identification of 5-benzylidene-2-phenylthiazolones as potent PRMT5 inhibitors by virtual screening, structural optimization and biological evaluations.

Authors:  Kongkai Zhu; Hongrui Tao; Jia-Li Song; Lu Jin; Yuanyuan Zhang; Jingqiu Liu; Zhifeng Chen; Cheng-Shi Jiang; Cheng Luo; Hua Zhang
Journal:  Bioorg Chem       Date:  2018-08-20       Impact factor: 5.275

6.  Robust light emission from cyclic alkylaminoluciferin substrates for firefly luciferase.

Authors:  Gadarla Randheer Reddy; Walter C Thompson; Stephen C Miller
Journal:  J Am Chem Soc       Date:  2010-10-06       Impact factor: 15.419

7.  Protein arginine methyltransferase 5 suppresses the transcription of the RB family of tumor suppressors in leukemia and lymphoma cells.

Authors:  Li Wang; Sharmistha Pal; Saïd Sif
Journal:  Mol Cell Biol       Date:  2008-08-11       Impact factor: 4.272

8.  Arginine methylation controls growth regulation by E2F-1.

Authors:  Er-Chieh Cho; Shunsheng Zheng; Shonagh Munro; Geng Liu; Simon M Carr; Jutta Moehlenbrink; Yi-Chien Lu; Lindsay Stimson; Omar Khan; Rebecca Konietzny; Joanna McGouran; Amanda S Coutts; Benedikt Kessler; David J Kerr; Nicholas B La Thangue
Journal:  EMBO J       Date:  2012-02-10       Impact factor: 11.598

9.  PRMT5 promotes cell proliferation by inhibiting BTG2 expression via the ERK signaling pathway in hepatocellular carcinoma.

Authors:  Hai Jiang; Yue Zhu; Zhenyu Zhou; Junyang Xu; Shaowen Jin; Kang Xu; Heyun Zhang; Qing Sun; Jie Wang; Junyao Xu
Journal:  Cancer Med       Date:  2018-02-14       Impact factor: 4.452

10.  Selective small-chemical inhibitors of protein arginine methyltransferase 5 with anti-lung cancer activity.

Authors:  Gui-Mei Kong; Min Yu; Zhongping Gu; Zhi Chen; Rui-Ming Xu; Deon O'Bryant; Zhengxin Wang
Journal:  PLoS One       Date:  2017-08-14       Impact factor: 3.240

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  1 in total

1.  Acquired resistance to PRMT5 inhibition induces concomitant collateral sensitivity to paclitaxel.

Authors:  Helen S Mueller; Colin E Fowler; Simona Dalin; Enrico Moiso; Tee Udomlumleart; Salil Garg; Michael T Hemann; Jacqueline A Lees
Journal:  Proc Natl Acad Sci U S A       Date:  2021-08-24       Impact factor: 11.205

  1 in total

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