Literature DB >> 24900575

Biological evaluation of new largazole analogues: alteration of macrocyclic scaffold with click chemistry.

Xianlin Li1, Zhenchao Tu1, Hua Li1, Chunping Liu1, Zheng Li2, Qiao Sun1, Yiwu Yao1, Jinsong Liu1, Sheng Jiang1.   

Abstract

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.

Entities:  

Keywords:  HDAC inhibitor; click chemistry; largazole; macrocycles; peptides

Year:  2012        PMID： 24900575      PMCID： PMC4027506          DOI： 10.1021/ml300371t

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  40 in total

Review 1.  Class II histone deacetylases: versatile regulators.

Authors:  Eric Verdin; Franck Dequiedt; Herbert G Kasler
Journal:  Trends Genet       Date:  2003-05       Impact factor: 11.639

2.  Vorinostat.

Authors:  Steven Grant; Chris Easley; Peter Kirkpatrick
Journal:  Nat Rev Drug Discov       Date:  2007-01       Impact factor: 84.694

3.  Synthesis and biological activity of largazole and derivatives.

Authors:  Tobias Seiser; Faustin Kamena; Nicolai Cramer
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

4.  Total synthesis of largazole and analogues: HDAC inhibition, antiproliferative activity and metabolic stability.

Authors:  Hanae Benelkebir; Sabrina Marie; Annette L Hayden; Jason Lyle; Paul M Loadman; Simon J Crabb; Graham Packham; A Ganesan
Journal:  Bioorg Med Chem       Date:  2011-02-17       Impact factor: 3.641

Review 5.  Romidepsin for the treatment of cutaneous T-cell lymphoma.

Authors:  Clara Campas-Moya
Journal:  Drugs Today (Barc)       Date:  2009-11       Impact factor: 2.245

6.  Class I histone deacetylase expression has independent prognostic impact in human colorectal cancer: specific role of class I histone deacetylases in vitro and in vivo.

Authors:  Wilko Weichert; Annika Röske; Silvia Niesporek; Aurelia Noske; Ann-Christin Buckendahl; Manfred Dietel; Volker Gekeler; Markus Boehm; Thomas Beckers; Carsten Denkert
Journal:  Clin Cancer Res       Date:  2008-03-15       Impact factor: 12.531

7.  Expression of hypoxia-inducible factor-1alpha, histone deacetylase 1, and metastasis-associated protein 1 in pancreatic carcinoma: correlation with poor prognosis with possible regulation.

Authors:  Kotaro Miyake; Tomoharu Yoshizumi; Satoru Imura; Koji Sugimoto; Erdenebulgan Batmunkh; Hirofumi Kanemura; Yuji Morine; Mitsuo Shimada
Journal:  Pancreas       Date:  2008-04       Impact factor: 3.327

8.  Total synthesis and molecular target of largazole, a histone deacetylase inhibitor.

Authors:  Yongcheng Ying; Kanchan Taori; Hyoungsu Kim; Jiyong Hong; Hendrik Luesch
Journal:  J Am Chem Soc       Date:  2008-05-29       Impact factor: 15.419

9.  Synthesis and conformation-activity relationships of the peptide isosteres of FK228 and largazole.

Authors:  Albert A Bowers; Thomas J Greshock; Nathan West; Guillermina Estiu; Stuart L Schreiber; Olaf Wiest; Robert M Williams; James E Bradner
Journal:  J Am Chem Soc       Date:  2009-03-04       Impact factor: 15.419

10.  Histone deacetylases 1, 2 and 3 are highly expressed in prostate cancer and HDAC2 expression is associated with shorter PSA relapse time after radical prostatectomy.

Authors:  W Weichert; A Röske; V Gekeler; T Beckers; C Stephan; K Jung; F R Fritzsche; S Niesporek; C Denkert; M Dietel; G Kristiansen
Journal:  Br J Cancer       Date:  2008-01-22       Impact factor: 7.640
View more
  8 in total

Review 1.  An overview of naturally occurring histone deacetylase inhibitors.

Authors:  Bumki Kim; Jiyong Hong
Journal:  Curr Top Med Chem       Date:  2015       Impact factor: 3.295

2.  Variable active site loop conformations accommodate the binding of macrocyclic largazole analogues to HDAC8.

Authors:  Christophe Decroos; Dane J Clausen; Brandon E Haines; Olaf Wiest; Robert M Williams; David W Christianson
Journal:  Biochemistry       Date:  2015-03-20       Impact factor: 3.162

3.  Synthesis and biological evaluation of largazole zinc-binding group analogs.

Authors:  Bumki Kim; Ranjala Ratnayake; Hyunji Lee; Guqin Shi; Sabrina L Zeller; Chenglong Li; Hendrik Luesch; Jiyong Hong
Journal:  Bioorg Med Chem       Date:  2017-04-04       Impact factor: 3.641

4.  Potent and orally efficacious bisthiazole-based histone deacetylase inhibitors.

Authors:  Fei Chen; Hui Chai; Ming-Bo Su; Yang-Ming Zhang; Jia Li; Xin Xie; Fa-Jun Nan
Journal:  ACS Med Chem Lett       Date:  2014-04-04       Impact factor: 4.345

5.  Evaluation of class I HDAC isoform selectivity of largazole analogues.

Authors:  Bumki Kim; Heekwang Park; Lilibeth A Salvador; Patrick E Serrano; Jason C Kwan; Sabrina L Zeller; Qi-Yin Chen; Soyoung Ryu; Yanxia Liu; Seongrim Byeon; Hendrik Luesch; Jiyong Hong
Journal:  Bioorg Med Chem Lett       Date:  2014-07-09       Impact factor: 2.823

6.  Thiazole-amino acids: influence of thiazole ring on conformational properties of amino acid residues.

Authors:  Monika Staś; Małgorzata A Broda; Dawid Siodłak
Journal:  Amino Acids       Date:  2021-04-10       Impact factor: 3.520

Review 7.  The application of click chemistry in the synthesis of agents with anticancer activity.

Authors:  Nan Ma; Ying Wang; Bing-Xin Zhao; Wen-Cai Ye; Sheng Jiang
Journal:  Drug Des Devel Ther       Date:  2015-03-12       Impact factor: 4.162

Review 8.  Marine Power on Cancer: Drugs, Lead Compounds, and Mechanisms.

Authors:  Lichuan Wu; Ke Ye; Sheng Jiang; Guangbiao Zhou
Journal:  Mar Drugs       Date:  2021-08-27       Impact factor: 5.118
  8 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.