Literature DB >> 21889343

The structural requirements of histone deacetylase inhibitors: Suberoylanilide hydroxamic acid analogs modified at the C3 position display isoform selectivity.

Sun Ea Choi1, Sujith V W Weerasinghe, Mary Kay H Pflum.   

Abstract

The FDA-approved drug suberoylanilide hydroxamic acid (SAHA, Vorinostat) was modified to improve its selectivity for a single histone deaetylase (HDAC) isoform. We show that attaching an ethyl group at the C3 position transforms SAHA from nonselective to an HDAC6-selective inhibitor. Theses results indicate that small structural changes in SAHA can significantly influence selectivity, which will lead future anti-cancer design efforts targeting HDAC proteins.
Copyright © 2011 Elsevier Ltd. All rights reserved.

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Year:  2011        PMID： 21889343      PMCID： PMC3842171          DOI： 10.1016/j.bmcl.2011.08.027

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


  32 in total

Review 1.  Deacetylase enzymes: biological functions and the use of small-molecule inhibitors.

Authors:  Christina M Grozinger; Stuart L Schreiber
Journal:  Chem Biol       Date:  2002-01

2.  Vorinostat.

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

Review 3.  Epigenetic therapy of cancer: past, present and future.

Authors:  Christine B Yoo; Peter A Jones
Journal:  Nat Rev Drug Discov       Date:  2006-01       Impact factor: 84.694

4.  Identification of novel isoform-selective inhibitors within class I histone deacetylases.

Authors:  Erding Hu; Edward Dul; Chiu-Mei Sung; Zunxuan Chen; Robert Kirkpatrick; Gui-Feng Zhang; Kyung Johanson; Ronggang Liu; Amparo Lago; Glenn Hofmann; Ricardo Macarron; Maite de los Frailes; Paloma Perez; John Krawiec; James Winkler; Michael Jaye
Journal:  J Pharmacol Exp Ther       Date:  2003-09-15       Impact factor: 4.030

5.  Structural snapshots of human HDAC8 provide insights into the class I histone deacetylases.

Authors:  John R Somoza; Robert J Skene; Bradley A Katz; Clifford Mol; Joseph D Ho; Andy J Jennings; Christine Luong; Andrew Arvai; Joseph J Buggy; Ellen Chi; Jie Tang; Bi-Ching Sang; Erik Verner; Robert Wynands; Ellen M Leahy; Douglas R Dougan; Gyorgy Snell; Marc Navre; Mark W Knuth; Ronald V Swanson; Duncan E McRee; Leslie W Tari
Journal:  Structure       Date:  2004-07       Impact factor: 5.006

6.  Distinct pharmacological properties of second generation HDAC inhibitors with the benzamide or hydroxamate head group.

Authors:  Thomas Beckers; Carmen Burkhardt; Heike Wieland; Petra Gimmnich; Thomas Ciossek; Thomas Maier; Karl Sanders
Journal:  Int J Cancer       Date:  2007-09-01       Impact factor: 7.396

7.  Crystal structure of a eukaryotic zinc-dependent histone deacetylase, human HDAC8, complexed with a hydroxamic acid inhibitor.

Authors:  Alessandro Vannini; Cinzia Volpari; Gessica Filocamo; Elena Caroli Casavola; Mirko Brunetti; Debora Renzoni; Prasun Chakravarty; Chantal Paolini; Raffaele De Francesco; Paola Gallinari; Christian Steinkühler; Stefania Di Marco
Journal:  Proc Natl Acad Sci U S A       Date:  2004-10-11       Impact factor: 11.205

8.  Molecular evolution of the histone deacetylase family: functional implications of phylogenetic analysis.

Authors:  Ivan V Gregoretti; Yun-Mi Lee; Holly V Goodson
Journal:  J Mol Biol       Date:  2004-04-16       Impact factor: 5.469

9.  The cytoplasmic deacetylase HDAC6 is required for efficient oncogenic tumorigenesis.

Authors:  Yi-Shan Lee; Kian-Huat Lim; Xing Guo; Yoshiharu Kawaguchi; Yasheng Gao; Tomasa Barrientos; Peter Ordentlich; Xiao-Fan Wang; Christopher M Counter; Tso-Pang Yao
Journal:  Cancer Res       Date:  2008-09-15       Impact factor: 12.701

10.  Design and synthesis of a potent histone deacetylase inhibitor.

Authors:  Tao Liu; Galina Kapustin; Felicia A Etzkorn
Journal:  J Med Chem       Date:  2007-04-10       Impact factor: 7.446
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  10 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.  Structural Requirements of HDAC Inhibitors: SAHA Analogues Modified at the C2 Position Display HDAC6/8 Selectivity.

Authors:  Ahmed T Negmeldin; Geetha Padige; Anton V Bieliauskas; Mary Kay H Pflum
Journal:  ACS Med Chem Lett       Date:  2017-02-07       Impact factor: 4.345

Review 3.  Targeted cancer therapy: giving histone deacetylase inhibitors all they need to succeed.

Authors:  Berkley E Gryder; Quaovi H Sodji; Adegboyega K Oyelere
Journal:  Future Med Chem       Date:  2012-03       Impact factor: 3.808

4.  The structural requirements of histone deacetylase inhibitors: SAHA analogs modified at the C5 position display dual HDAC6/8 selectivity.

Authors:  Ahmed T Negmeldin; Mary Kay H Pflum
Journal:  Bioorg Med Chem Lett       Date:  2017-06-13       Impact factor: 2.823

5.  Structural Requirements of Histone Deacetylase Inhibitors: SAHA Analogs Modified on the Hydroxamic Acid.

Authors:  Anton V Bieliauskas; Sujith V W Weerasinghe; Ahmed T Negmeldin; Mary Kay H Pflum
Journal:  Arch Pharm (Weinheim)       Date:  2016-04-09       Impact factor: 3.751

6.  The structural requirements of histone deacetylase inhibitors: C4-modified SAHA analogs display dual HDAC6/HDAC8 selectivity.

Authors:  Ahmed T Negmeldin; Joseph R Knoff; Mary Kay H Pflum
Journal:  Eur J Med Chem       Date:  2017-10-31       Impact factor: 6.514

7.  The structural requirements of histone deacetylase inhibitors: suberoylanilide hydroxamic acid analogs modified at the C6 position.

Authors:  Sun Ea Choi; Mary Kay H Pflum
Journal:  Bioorg Med Chem Lett       Date:  2012-10-02       Impact factor: 2.823

8.  Mutagenesis studies of the 14 Å internal cavity of histone deacetylase 1: insights toward the acetate-escape hypothesis and selective inhibitor design.

Authors:  Magdalene K Wambua; Dhanusha A Nalawansha; Ahmed T Negmeldin; Mary Kay H Pflum
Journal:  J Med Chem       Date:  2014-01-27       Impact factor: 7.446

Review 9.  A Therapeutic Perspective of HDAC8 in Different Diseases: An Overview of Selective Inhibitors.

Authors:  Anna Fontana; Ilaria Cursaro; Gabriele Carullo; Sandra Gemma; Stefania Butini; Giuseppe Campiani
Journal:  Int J Mol Sci       Date:  2022-09-02       Impact factor: 6.208

10.  Design and Evaluation of Tumor-Specific Dendrimer Epigenetic Therapeutics.

Authors:  Hong Zong; Dhavan Shah; Katherine Selwa; Ryan E Tsuchida; Rahul Rattan; Jay Mohan; Adam B Stein; James B Otis; Sascha N Goonewardena
Journal:  ChemistryOpen       Date:  2015-04-13       Impact factor: 2.911
  10 in total

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