Literature DB >> 19193120

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

Albert A Bowers1, Thomas J Greshock, Nathan West, Guillermina Estiu, Stuart L Schreiber, Olaf Wiest, Robert M Williams, James E Bradner.   

Abstract

The peptide isosteres (10 and 11) of the naturally occurring and potent histone deacetylase (HDAC) inhibitors FK228 and largazole have been synthesized and evaluated side-by-side with FK228, largazole, and SAHA for inhibition of the class I HDACs 1, 2, 3, and 6.

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Year:  2009        PMID： 19193120      PMCID： PMC2880701          DOI： 10.1021/ja807772w

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  30 in total

Review 1.  The cyclization of peptides and depsipeptides.

Authors:  John S Davies
Journal:  J Pept Sci       Date:  2003-08       Impact factor: 1.905

Review 2.  Histone deacetylase inhibitors and the promise of epigenetic (and more) treatments for cancer.

Authors:  Saverio Minucci; Pier Giuseppe Pelicci
Journal:  Nat Rev Cancer       Date:  2006-01       Impact factor: 60.716

3.  Total synthesis of azumamides A and E.

Authors:  Irene Izzo; Nakia Maulucci; Giuseppe Bifulco; Francesco De Riccardis
Journal:  Angew Chem Int Ed Engl       Date:  2006-11-20       Impact factor: 15.336

4.  Extra precision glide: docking and scoring incorporating a model of hydrophobic enclosure for protein-ligand complexes.

Authors:  Richard A Friesner; Robert B Murphy; Matthew P Repasky; Leah L Frye; Jeremy R Greenwood; Thomas A Halgren; Paul C Sanschagrin; Daniel T Mainz
Journal:  J Med Chem       Date:  2006-10-19       Impact factor: 7.446

5.  Total synthesis of azumamide A and azumamide E, evaluation as histone deacetylase inhibitors, and design of a more potent analogue.

Authors:  Shijun Wen; Krystle L Carey; Yoichi Nakao; Nobuhiro Fusetani; Graham Packham; A Ganesan
Journal:  Org Lett       Date:  2007-02-21       Impact factor: 6.005

6.  Improved total synthesis of the potent HDAC inhibitor FK228 (FR-901228).

Authors:  Thomas J Greshock; Deidre M Johns; Yasuo Noguchi; Robert M Williams
Journal:  Org Lett       Date:  2008-01-19       Impact factor: 6.005

7.  Trapoxin, an antitumor cyclic tetrapeptide, is an irreversible inhibitor of mammalian histone deacetylase.

Authors:  M Kijima; M Yoshida; K Sugita; S Horinouchi; T Beppu
Journal:  J Biol Chem       Date:  1993-10-25       Impact factor: 5.157

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.  Total synthesis of spiruchostatin A, a potent histone deacetylase inhibitor.

Authors:  Alexander Yurek-George; Fay Habens; Matthew Brimmell; Graham Packham; A Ganesan
Journal:  J Am Chem Soc       Date:  2004-02-04       Impact factor: 15.419

10.  A mammalian histone deacetylase related to the yeast transcriptional regulator Rpd3p.

Authors:  J Taunton; C A Hassig; S L Schreiber
Journal:  Science       Date:  1996-04-19       Impact factor: 47.728
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  35 in total

Review 1.  Macrocyclic histone deacetylase inhibitors.

Authors:  Sandra C Mwakwari; Vishal Patil; William Guerrant; Adegboyega K Oyelere
Journal:  Curr Top Med Chem       Date:  2010       Impact factor: 3.295

2.  Largazole and analogues with modified metal-binding motifs targeting histone deacetylases: synthesis and biological evaluation.

Authors:  Pravin Bhansali; Christin L Hanigan; Robert A Casero; L M Viranga Tillekeratne
Journal:  J Med Chem       Date:  2011-10-10       Impact factor: 7.446

Review 3.  Discovery and mechanism of natural products as modulators of histone acetylation.

Authors:  Lilibeth A Salvador; Hendrik Luesch
Journal:  Curr Drug Targets       Date:  2012-07       Impact factor: 3.465

Review 4.  Microbial natural products: molecular blueprints for antitumor drugs.

Authors:  Lesley-Ann Giddings; David J Newman
Journal:  J Ind Microbiol Biotechnol       Date:  2013-09-03       Impact factor: 3.346

Review 5.  Natural products synthesis: enabling tools to penetrate Nature's secrets of biogenesis and biomechanism.

Authors:  Robert M Williams
Journal:  J Org Chem       Date:  2011-04-12       Impact factor: 4.354

Review 6.  An overview of naturally occurring histone deacetylase inhibitors.

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

7.  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

8.  Computational exploration of zinc binding groups for HDAC inhibition.

Authors:  Kai Chen; Liping Xu; Olaf Wiest
Journal:  J Org Chem       Date:  2013-04-29       Impact factor: 4.354

9.  Chemical phylogenetics of histone deacetylases.

Authors:  James E Bradner; Nathan West; Melissa L Grachan; Edward F Greenberg; Stephen J Haggarty; Tandy Warnow; Ralph Mazitschek
Journal:  Nat Chem Biol       Date:  2010-02-07       Impact factor: 15.040

Review 10.  Thiazole and oxazole alkaloids: isolation and synthesis.

Authors:  Danilo Davyt; Gloria Serra
Journal:  Mar Drugs       Date:  2010-11-05       Impact factor: 5.118
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