Literature DB >> 24035339

Synthesis and HDAC inhibitory activity of isosteric thiazoline-oxazole largazole analogs.

Jennifer M Guerra-Bubb1, Albert A Bowers, William B Smith, Ronald Paranal, Guillermina Estiu, Olaf Wiest, James E Bradner, Robert M Williams.   

Abstract

The synthesis of an isosteric analog of the natural product and HDAC inhibitor largazole is described. The sulfur atom in the thizaole ring of the natural product has been replaced with an oxygen atom, constituting an oxazole ring. The biochemical activity and cytotoxicity of this species is described.
Copyright © 2013 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  Conformation; HDAC; Isostere; Largazole; Oxazole

Mesh：

Substances：

Year:  2013        PMID： 24035339      PMCID： PMC3859309          DOI： 10.1016/j.bmcl.2013.06.012

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  10 in total

1.  Structure and activity of largazole, a potent antiproliferative agent from the Floridian marine cyanobacterium Symploca sp.

Authors:  Kanchan Taori; Valerie J Paul; Hendrik Luesch
Journal:  J Am Chem Soc       Date:  2008-01-19       Impact factor: 15.419

2.  On the inhibition of histone deacetylase 8.

Authors:  Guillermina Estiu; Nathan West; Ralph Mazitschek; Edward Greenberg; James E Bradner; Olaf Wiest
Journal:  Bioorg Med Chem       Date:  2010-04-03       Impact factor: 3.641

3.  Structural origin of selectivity in class II-selective histone deacetylase inhibitors.

Authors:  Guillermina Estiu; Edward Greenberg; Christopher B Harrison; Nicholas P Kwiatkowski; Ralph Mazitschek; James E Bradner; Olaf Wiest
Journal:  J Med Chem       Date:  2008-04-16       Impact factor: 7.446

Review 4.  Discovery, biological activity, synthesis and potential therapeutic utility of naturally occurring histone deacetylase inhibitors.

Authors:  Tenaya L Newkirk; Albert A Bowers; Robert M Williams
Journal:  Nat Prod Rep       Date:  2009-08-03       Impact factor: 13.423

5.  Inhibitors of human histone deacetylase: synthesis and enzyme and cellular activity of straight chain hydroxamates.

Authors:  Stacy W Remiszewski; Lidia C Sambucetti; Peter Atadja; Kenneth W Bair; Wendy D Cornell; Michael A Green; Kobporn Lulu Howell; Manfred Jung; Paul Kwon; Nancy Trogani; Heather Walker
Journal:  J Med Chem       Date:  2002-02-14       Impact factor: 7.446

6.  Synthesis and histone deacetylase inhibitory activity of largazole analogs: alteration of the zinc-binding domain and macrocyclic scaffold.

Authors:  Albert A Bowers; Nathan West; Tenaya L Newkirk; Annie E Troutman-Youngman; Stuart L Schreiber; Olaf Wiest; James E Bradner; Robert M Williams
Journal:  Org Lett       Date:  2009-03-19       Impact factor: 6.005

7.  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

8.  Total synthesis and biological mode of action of largazole: a potent class I histone deacetylase inhibitor.

Authors:  Albert Bowers; Nathan West; Jack Taunton; Stuart L Schreiber; James E Bradner; Robert M Williams
Journal:  J Am Chem Soc       Date:  2008-07-19       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

Review 10.  The role of HDAC6 in cancer.

Authors:  Grace I Aldana-Masangkay; Kathleen M Sakamoto
Journal:  J Biomed Biotechnol       Date:  2010-11-07
  10 in total
  6 in total

1.  Modular synthesis and biological activity of pyridyl-based analogs of the potent Class I Histone Deacetylase Inhibitor Largazole.

Authors:  Dane J Clausen; William B Smith; Brandon E Haines; Olaf Wiest; James E Bradner; Robert M Williams
Journal:  Bioorg Med Chem       Date:  2015-03-31       Impact factor: 3.641

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.  Comparative pharmacokinetic properties and antitumor activity of the marine HDACi Largazole and Largazole peptide isostere.

Authors:  John L Pilon; Dane J Clausen; Ryan J Hansen; Paul J Lunghofer; Brad Charles; Barbara J Rose; Douglas H Thamm; Daniel L Gustafson; James E Bradner; Robert M Williams
Journal:  Cancer Chemother Pharmacol       Date:  2015-01-24       Impact factor: 3.333

5.  Synthesis and biological evaluation of largazole analogues with modified surface recognition cap groups.

Authors:  Pravin Bhansali; Christin L Hanigan; Lalith Perera; Robert A Casero; L M Viranga Tillekeratne
Journal:  Eur J Med Chem       Date:  2014-09-06       Impact factor: 6.514

6.  Exploration of Novel Inhibitors for Class I Histone Deacetylase Isoforms by QSAR Modeling and Molecular Dynamics Simulation Assays.

Authors:  Zainab Noor; Noreen Afzal; Sajid Rashid
Journal:  PLoS One       Date:  2015-10-02       Impact factor: 3.240
  6 in total

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