Literature DB >> 15149697

Thiol-based SAHA analogues as potent histone deacetylase inhibitors.

Takayoshi Suzuki1, Akiyasu Kouketsu, Azusa Matsuura, Arihiro Kohara, Shin-Ichi Ninomiya, Kohfuku Kohda, Naoki Miyata.   

Abstract

In order to find novel nonhydroxamate histone deacetylase (HDAC) inhibitors, a series of thiol-based compounds modeled after suberoylanilide hydroxamic acid (SAHA) was synthesized, and their inhibitory effect on HDACs was evaluated. Compound 6, in which the hydroxamic acid of SAHA was replaced by a thiol, was found to be as potent as SAHA, and optimization of this series led to the identification of HDAC inhibitors more potent than SAHA.

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Year:  2004        PMID: 15149697     DOI: 10.1016/j.bmcl.2004.03.063

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


  17 in total

1.  Synthesis and evaluation of N⁸-acetylspermidine analogues as inhibitors of bacterial acetylpolyamine amidohydrolase.

Authors:  Christophe Decroos; Christine M Bowman; David W Christianson
Journal:  Bioorg Med Chem       Date:  2013-06-01       Impact factor: 3.641

2.  Structural requirements of HDAC inhibitors: SAHA analogs functionalized adjacent to the hydroxamic acid.

Authors:  Anton V Bieliauskas; Sujith V W Weerasinghe; Mary Kay H Pflum
Journal:  Bioorg Med Chem Lett       Date:  2007-02-08       Impact factor: 2.823

Review 3.  Metabolism as a key to histone deacetylase inhibition.

Authors:  Praveen Rajendran; David E Williams; Emily Ho; Roderick H Dashwood
Journal:  Crit Rev Biochem Mol Biol       Date:  2011-04-05       Impact factor: 8.250

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.  In vitro plasma stability, permeability and solubility of mercaptoacetamide histone deacetylase inhibitors.

Authors:  Roula Konsoula; Mira Jung
Journal:  Int J Pharm       Date:  2008-05-13       Impact factor: 5.875

6.  Binding ensemble profiling with photoaffinity labeling (BEProFL) approach: mapping the binding poses of HDAC8 inhibitors.

Authors:  Bai He; Subash Velaparthi; Gilles Pieffet; Chris Pennington; Aruna Mahesh; Denise L Holzle; Michael Brunsteiner; Richard van Breemen; Sylvie Y Blond; Pavel A Petukhov
Journal:  J Med Chem       Date:  2009-11-26       Impact factor: 7.446

7.  Pharmacokinetics-pharmacodynamics and antitumor activity of mercaptoacetamide-based histone deacetylase inhibitors.

Authors:  Zacharoula Konsoula; Hong Cao; Alfredo Velena; Mira Jung
Journal:  Mol Cancer Ther       Date:  2009-09-29       Impact factor: 6.261

8.  Allyl mercaptan, a garlic-derived organosulfur compound, inhibits histone deacetylase and enhances Sp3 binding on the P21WAF1 promoter.

Authors:  Hui Nian; Barbara Delage; John T Pinto; Roderick H Dashwood
Journal:  Carcinogenesis       Date:  2008-07-14       Impact factor: 4.944

9.  Thiol versus hydroxamate as zinc binding group in HDAC inhibition: An ab initio QM/MM molecular dynamics study.

Authors:  Wenjing Gong; Ruibo Wu; Yingkai Zhang
Journal:  J Comput Chem       Date:  2015-10-09       Impact factor: 3.376

10.  Hydroxamic acid derivatives as histone deacetylase inhibitors: a DFT study of their tautomerism and metal affinities/selectivities.

Authors:  D Cheshmedzhieva; N Toshev; M Gerova; O Petrov; T Dudev
Journal:  J Mol Model       Date:  2018-04-24       Impact factor: 1.810

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