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Literature DB >> 24900543

Macrocyclic peptoid-Peptide hybrids as inhibitors of class I histone deacetylases.

Christian A Olsen¹, Ana Montero¹, Luke J Leman¹, M Reza Ghadiri¹.

Abstract

We report the design, synthesis, and biological evaluation of the first macrocyclic peptoid-containing histone deacetylase (HDAC) inhibitors. The compounds selectively inhibit human class I HDAC isoforms in vitro, with no inhibition of the tubulin deacetylase activity associated with class IIb HDAC6 in cultured Jurkat cells. Compared to the natural product apicidin (1), one inhibitor (compound 10) showed equivalent potency against K-562 cells, but was more cytoselective across a panel of cancer cell lines.

Entities: Chemical Disease Species

Keywords: HDAC inhibitors; apicidin; macrocycles; peptides; peptoids

Year: 2012 PMID： 24900543 PMCID： PMC4025818 DOI： 10.1021/ml300162r

Source DB: PubMed Journal: ACS Med Chem Lett ISSN： 1948-5875 Impact factor: 4.345

40 in total

Review 1. 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

2. Antiplasmodial and prehemolytic activities of alpha-peptide-beta-peptoid chimeras.

Authors: Line Vedel; Gitte Bonke; Camilla Foged; Hanne Ziegler; Henrik Franzyk; Jerzy W Jaroszewski; Christian A Olsen
Journal: Chembiochem Date: 2007-10-15 Impact factor: 3.164

Review 3. Dimethyl sulfoxide to vorinostat: development of this histone deacetylase inhibitor as an anticancer drug.

Authors: Paul A Marks; Ronald Breslow
Journal: Nat Biotechnol Date: 2007-01 Impact factor: 54.908

4. Extraordinarily robust polyproline type I peptoid helices generated via the incorporation of α-chiral aromatic N-1-naphthylethyl side chains.

Authors: Joseph R Stringer; J Aaron Crapster; Ilia A Guzei; Helen E Blackwell
Journal: J Am Chem Soc Date: 2011-09-13 Impact factor: 15.419

Review 5. Inside HDAC with HDAC inhibitors.

Authors: Philippe Bertrand
Journal: Eur J Med Chem Date: 2010-02-14 Impact factor: 6.514

6. Design, synthesis and antimicrobial properties of non-hemolytic cationic alpha-cyclopeptoids.

Authors: Daniela Comegna; Monica Benincasa; Renato Gennaro; Irene Izzo; Francesco De Riccardis
Journal: Bioorg Med Chem Date: 2010-01-15 Impact factor: 3.641

7. Apicidin: a novel antiprotozoal agent that inhibits parasite histone deacetylase.

Authors: S J Darkin-Rattray; A M Gurnett; R W Myers; P M Dulski; T M Crumley; J J Allocco; C Cannova; P T Meinke; S L Colletti; M A Bednarek; S B Singh; M A Goetz; A W Dombrowski; J D Polishook; D M Schmatz
Journal: Proc Natl Acad Sci U S A Date: 1996-11-12 Impact factor: 11.205

Review 8. Peptoid-Peptide hybrid backbone architectures.

Authors: Christian A Olsen
Journal: Chembiochem Date: 2010-01-25 Impact factor: 3.164

9. Peptoids that mimic the structure, function, and mechanism of helical antimicrobial peptides.

Authors: Nathaniel P Chongsiriwatana; James A Patch; Ann M Czyzewski; Michelle T Dohm; Andrey Ivankin; David Gidalevitz; Ronald N Zuckermann; Annelise E Barron
Journal: Proc Natl Acad Sci U S A Date: 2008-02-19 Impact factor: 11.205

10. Discovery of potent and selective histone deacetylase inhibitors via focused combinatorial libraries of cyclic alpha3beta-tetrapeptides.

Authors: Christian A Olsen; M Reza Ghadiri
Journal: J Med Chem Date: 2009-12-10 Impact factor: 7.446

8 in total

Review 1. HDACs and HDAC Inhibitors in Cancer Development and Therapy.

Authors: Yixuan Li; Edward Seto
Journal: Cold Spring Harb Perspect Med Date: 2016-10-03 Impact factor: 6.915

2. Anthranilic acid-containing cyclic tetrapeptides: at the crossroads of conformational rigidity and synthetic accessibility.

Authors: Dongyue Xin; Kevin Burgess
Journal: Org Biomol Chem Date: 2016-05-13 Impact factor: 3.876

Macrocyclic peptoid-Peptide hybrids as inhibitors of class I histone deacetylases.

Review 1. Histone deacetylase inhibitors and the promise of epigenetic (and more) treatments for cancer.

2. Antiplasmodial and prehemolytic activities of alpha-peptide-beta-peptoid chimeras.

Review 3. Dimethyl sulfoxide to vorinostat: development of this histone deacetylase inhibitor as an anticancer drug.

4. Extraordinarily robust polyproline type I peptoid helices generated via the incorporation of α-chiral aromatic N-1-naphthylethyl side chains.

Review 5. Inside HDAC with HDAC inhibitors.

6. Design, synthesis and antimicrobial properties of non-hemolytic cationic alpha-cyclopeptoids.

7. Apicidin: a novel antiprotozoal agent that inhibits parasite histone deacetylase.

Review 8. Peptoid-Peptide hybrid backbone architectures.

9. Peptoids that mimic the structure, function, and mechanism of helical antimicrobial peptides.

10. Discovery of potent and selective histone deacetylase inhibitors via focused combinatorial libraries of cyclic alpha3beta-tetrapeptides.

Review 1. HDACs and HDAC Inhibitors in Cancer Development and Therapy.

2. Anthranilic acid-containing cyclic tetrapeptides: at the crossroads of conformational rigidity and synthetic accessibility.

3. Development of N-Hydroxycinnamamide-Based Histone Deacetylase Inhibitors with Indole-Containing Cap Group.

4. Template-induced macrocycle diversity through large ring-forming alkylations of tryptophan.

Review 5. Recent Advances in the Synthesis of Peptoid Macrocycles.

6. Solid-Phase Insertion of N-mercaptoalkylglycine Residues into Peptides.

Review 7. Therapeutic peptides: current applications and future directions.

8. Chiral, sequence-definable foldamer-derived macrocycles.