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Literature DB >> 19239241

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

Albert A Bowers¹, Nathan West, Tenaya L Newkirk, Annie E Troutman-Youngman, Stuart L Schreiber, Olaf Wiest, James E Bradner, Robert M Williams.

Abstract

Fourteen analogs of the marine natural product largazole have been prepared and assayed against histone deacetylases (HDACs) 1, 2, 3, and 6. Olefin cross-metathesis was used to efficiently access six variants of the side-chain zinc-binding domain, while adaptation of our previously reported modular synthesis allowed probing of the macrocyclic cap group.

Entities: Chemical Disease Gene Species

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Year: 2009 PMID： 19239241 PMCID： PMC2673910 DOI： 10.1021/ol900078k

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

33 in total

1. Cyclic tetrapeptides bearing a sulfhydryl group potently inhibit histone deacetylases.

Authors: Norikazu Nishino; Binoy Jose; Shinji Okamura; Shutoku Ebisusaki; Tamaki Kato; Yuko Sumida; Minoru Yoshida
Journal: Org Lett Date: 2003-12-25 Impact factor: 6.005

Review 2. Histone deacetylase inhibitors.

Authors: Thomas A Miller; David J Witter; Sandro Belvedere
Journal: J Med Chem Date: 2003-11-20 Impact factor: 7.446

3. FR901228, a novel antitumor bicyclic depsipeptide produced by Chromobacterium violaceum No. 968. I. Taxonomy, fermentation, isolation, physico-chemical and biological properties, and antitumor activity.

Authors: H Ueda; H Nakajima; Y Hori; T Fujita; M Nishimura; T Goto; M Okuhara
Journal: J Antibiot (Tokyo) Date: 1994-03 Impact factor: 2.649

4. Potent and specific inhibition of mammalian histone deacetylase both in vivo and in vitro by trichostatin A.

Authors: M Yoshida; M Kijima; M Akita; T Beppu
Journal: J Biol Chem Date: 1990-10-05 Impact factor: 5.157

Review 5. Histone-deacetylase inhibitors: novel drugs for the treatment of cancer.

Authors: Ricky W Johnstone
Journal: Nat Rev Drug Discov Date: 2002-04 Impact factor: 84.694

6. Histone deacetylase inhibitors--a new tool to treat cancer.

Authors: Raz Somech; Shai Izraeli; Amos J Simon
Journal: Cancer Treat Rev Date: 2004-08 Impact factor: 12.111

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 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

Review 9. Novel hydroxamate and anilide derivatives as potent histone deacetylase inhibitors: synthesis and antiproliferative evaluation.

Authors: Giliane Bouchain; Daniel Delorme
Journal: Curr Med Chem Date: 2003-11 Impact factor: 4.530

10. Potent histone deacetylase inhibitors built from trichostatin A and cyclic tetrapeptide antibiotics including trapoxin.

Authors: R Furumai; Y Komatsu; N Nishino; S Khochbin; M Yoshida; S Horinouchi
Journal: Proc Natl Acad Sci U S A Date: 2001-01-02 Impact factor: 11.205

33 in total

1. Histone deacetylase inhibitors are potent inducers of gene expression in latent EBV and sensitize lymphoma cells to nucleoside antiviral agents.

Authors: Sajal K Ghosh; Susan P Perrine; Robert M Williams; Douglas V Faller
Journal: Blood Date: 2011-12-07 Impact factor: 22.113

Review 2. 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

3. 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

8. 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

9. 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

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