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Literature DB >> 19475493

Synthesis, molecular docking and biological evaluation as HDAC inhibitors of cyclopeptide mimetics by a tandem three-component reaction and intramolecular [3+2] cycloaddition.

Tracey Pirali¹, Valeria Faccio, Riccardo Mossetti, Ambra A Grolla, Simone Di Micco, Giuseppe Bifulco, Armando A Genazzani, Gian Cesare Tron.

Abstract

Novel macrocyclic peptide mimetics have been synthesized by exploiting a three-component reaction and an azide-alkyne [3 + 2] cycloaddition. The prepared compounds were screened as HDAC inhibitors allowing us to identify a new compound with promising biological activity. In order to rationalize the biological results, computational studies have also been performed.

Entities: Chemical

Mesh：

Substances：

Year: 2009 PMID： 19475493 DOI： 10.1007/s11030-009-9153-9

Source DB: PubMed Journal: Mol Divers ISSN： 1381-1991 Impact factor: 2.943

20 in total

1. Development of a scintillation proximity assay for histone deacetylase using a biotinylated peptide derived from histone-H4.

Authors: B Nare; J J Allocco; R Kuningas; S Galuska; R W Myers; M A Bednarek; D M Schmatz
Journal: Anal Biochem Date: 1999-02-15 Impact factor: 3.365

2. One-pot synthesis of macrocycles by a tandem three-component reaction and intramolecular [3+2] cycloaddition.

Authors: Tracey Pirali; Gian Cesare Tron; Jieping Zhu
Journal: Org Lett Date: 2006-08-31 Impact factor: 6.005

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

Review 4. The exploration of macrocycles for drug discovery--an underexploited structural class.

Authors: Edward M Driggers; Stephen P Hale; Jinbo Lee; Nicholas K Terrett
Journal: Nat Rev Drug Discov Date: 2008-07 Impact factor: 84.694

Review 5. 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

6. Homology modeling, force field design, and free energy simulation studies to optimize the activities of histone deacetylase inhibitors.

Authors: Hwangseo Park; Sangyoub Lee
Journal: J Comput Aided Mol Des Date: 2004-06 Impact factor: 3.686

7. Molecular insights into azumamide e histone deacetylases inhibitory activity.

Authors: Nakia Maulucci; Maria Giovanna Chini; Simone Di Micco; Irene Izzo; Emiddio Cafaro; Adele Russo; Paola Gallinari; Chantal Paolini; Maria Chiara Nardi; Agostino Casapullo; Raffaele Riccio; Giuseppe Bifulco; Francesco De Riccardis
Journal: J Am Chem Soc Date: 2007-02-21 Impact factor: 15.419

8. A chemical switch for the modulation of the functional activity of higher homologues of histamine on the human histamine H3 receptor: effect of various substitutions at the primary amino function.

Authors: Marinella Govoni; Herman D Lim; Dris El-Atmioui; Wiro M P B Menge; Henk Timmerman; Remko A Bakker; Rob Leurs; Iwan J P De Esch
Journal: J Med Chem Date: 2006-04-20 Impact factor: 7.446

9. 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. Virtual Fragment Screening Identification of a Quinoline-5,8-dicarboxylic Acid Derivative as a Selective JMJD3 Inhibitor.

Authors: Assunta Giordano; Federica Del Gaudio; Catrine Johansson; Raffaele Riccio; Udo Oppermann; Simone Di Micco
Journal: ChemMedChem Date: 2018-05-22 Impact factor: 3.466

6 in total

Synthesis, molecular docking and biological evaluation as HDAC inhibitors of cyclopeptide mimetics by a tandem three-component reaction and intramolecular [3+2] cycloaddition.

1. Development of a scintillation proximity assay for histone deacetylase using a biotinylated peptide derived from histone-H4.

2. One-pot synthesis of macrocycles by a tandem three-component reaction and intramolecular [3+2] cycloaddition.

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

Review 4. The exploration of macrocycles for drug discovery--an underexploited structural class.

Review 5. Dimethyl sulfoxide to vorinostat: development of this histone deacetylase inhibitor as an anticancer drug.

6. Homology modeling, force field design, and free energy simulation studies to optimize the activities of histone deacetylase inhibitors.

7. Molecular insights into azumamide e histone deacetylases inhibitory activity.

8. A chemical switch for the modulation of the functional activity of higher homologues of histamine on the human histamine H3 receptor: effect of various substitutions at the primary amino function.

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

10. Solution-phase parallel synthesis and biological evaluation of combretatriazoles.

Review 1. Macrocyclic histone deacetylase inhibitors.

2. Insights from comprehensive multiple receptor docking to HDAC8.

3. Synthesis of novel 6-triazologlycolipids via click chemistry and their preliminary cytotoxicity assessments.

Review 4. Synthesis of Biologically Active Molecules through Multicomponent Reactions.

5. Benzimidazole-2-one: a novel anchoring principle for antagonizing p53-Mdm2.

6. Virtual Fragment Screening Identification of a Quinoline-5,8-dicarboxylic Acid Derivative as a Selective JMJD3 Inhibitor.