Literature DB >> 23606927

3D-QSAR Assisted Design, Synthesis and Evaluation of Novobiocin Analogues.

Huiping Zhao1, Elisabetta Moroni, Bin Yan, Giorgio Colombo, Brian S J Blagg.   

Abstract

Hsp90 is an attractive therapeutic target for the treatment of cancer. Extensive structural modifications to novobiocin, the first Hsp90 C-terminal inhibitor discovered, have produced a library of novobiocin analogues and revealed some structure-activity relationships. Based upon the most potent novobiocin analogues generated from prior studies, a three-dimensional quantitative structure-activity (3D-QSAR) model was built. In addition, a new set of novobiocin analogues containing various structural features supported by the 3D-QSAR model were synthesized and evaluated against two breast cancer cell lines. Several new inhibitors produced anti-proliferative activity at mid nano-molar concentrations, which results through Hsp90 inhibition.

Entities:  

Keywords:  3D-QSAR; Breast cancer; Heat shock protein 90; Hsp90 inhibitors; Novobiocin

Year:  2012        PMID： 23606927      PMCID： PMC3627542          DOI： 10.1021/ml300275g

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


  19 in total

1.  GRid-INdependent descriptors (GRIND): a novel class of alignment-independent three-dimensional molecular descriptors.

Authors:  M Pastor; G Cruciani; I McLay; S Pickett; S Clementi
Journal:  J Med Chem       Date:  2000-08-24       Impact factor: 7.446

2.  Incorporating molecular shape into the alignment-free Grid-Independent Descriptors.

Authors:  Fabien Fontaine; Manuel Pastor; Ferran Sanz
Journal:  J Med Chem       Date:  2004-05-20       Impact factor: 7.446

3.  Development of novobiocin analogues that manifest anti-proliferative activity against several cancer cell lines.

Authors:  Joseph A Burlison; Christopher Avila; George Vielhauer; Donna J Lubbers; Jeffrey Holzbeierlein; Brian S J Blagg
Journal:  J Org Chem       Date:  2008-02-23       Impact factor: 4.354

4.  Development and validation of AMANDA, a new algorithm for selecting highly relevant regions in Molecular Interaction Fields.

Authors:  Angel Durán; Guillermo C Martínez; Manuel Pastor
Journal:  J Chem Inf Model       Date:  2008-08-12       Impact factor: 4.956

5.  Heat shock protein 90: inhibitors in clinical trials.

Authors:  Marco A Biamonte; Ryan Van de Water; Joseph W Arndt; Robert H Scannevin; Daniel Perret; Wen-Cherng Lee
Journal:  J Med Chem       Date:  2010-01-14       Impact factor: 7.446

6.  Identification and initial SAR of silybin: an Hsp90 inhibitor.

Authors:  Huiping Zhao; Gary E Brandt; Lakshmi Galam; Robert L Matts; Brian S J Blagg
Journal:  Bioorg Med Chem Lett       Date:  2010-12-28       Impact factor: 2.823

7.  The heat shock protein 90 antagonist novobiocin interacts with a previously unrecognized ATP-binding domain in the carboxyl terminus of the chaperone.

Authors:  M G Marcu; A Chadli; I Bouhouche; M Catelli; L M Neckers
Journal:  J Biol Chem       Date:  2000-11-24       Impact factor: 5.157

8.  3-Arylcoumarin derivatives manifest anti-proliferative activity through Hsp90 inhibition.

Authors:  Huiping Zhao; Bin Yan; Laura B Peterson; Brian S J Blagg
Journal:  ACS Med Chem Lett       Date:  2012-02-26       Impact factor: 4.345

Review 9.  Hallmarks of cancer: the next generation.

Authors:  Douglas Hanahan; Robert A Weinberg
Journal:  Cell       Date:  2011-03-04       Impact factor: 41.582

10.  Novobiocin: redesigning a DNA gyrase inhibitor for selective inhibition of hsp90.

Authors:  Joseph A Burlison; Len Neckers; Andrew B Smith; Anthony Maxwell; Brian S J Blagg
Journal:  J Am Chem Soc       Date:  2006-12-06       Impact factor: 15.419
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  7 in total

1.  Exploiting conformational dynamics in drug discovery: design of C-terminal inhibitors of Hsp90 with improved activities.

Authors:  Elisabetta Moroni; Huiping Zhao; Brian S J Blagg; Giorgio Colombo
Journal:  J Chem Inf Model       Date:  2014-01-15       Impact factor: 4.956

2.  Novologues containing a benzamide side chain manifest anti-proliferative activity against two breast cancer cell lines.

Authors:  Huiping Zhao; Mercy Anyika; Antwan Girgis; Brian S J Blagg
Journal:  Bioorg Med Chem Lett       Date:  2014-05-16       Impact factor: 2.823

3.  Identification of a new scaffold for hsp90 C-terminal inhibition.

Authors:  Huiping Zhao; Elisabetta Moroni; Giorgio Colombo; Brian S J Blagg
Journal:  ACS Med Chem Lett       Date:  2013-11-26       Impact factor: 4.345

4.  Design, synthesis and biological evaluation of biphenylamide derivatives as Hsp90 C-terminal inhibitors.

Authors:  Huiping Zhao; Gaurav Garg; Jinbo Zhao; Elisabetta Moroni; Antwan Girgis; Lucas S Franco; Swapnil Singh; Giorgio Colombo; Brian S J Blagg
Journal:  Eur J Med Chem       Date:  2014-10-14       Impact factor: 6.514

5.  Exploring the Prominent and Concealed Inhibitory Features for Cytoplasmic Isoforms of Hsp90 Using QSAR Analysis.

Authors:  Magdi E A Zaki; Sami A Al-Hussain; Syed Nasir Abbas Bukhari; Vijay H Masand; Mithilesh M Rathore; Sumer D Thakur; Vaishali M Patil
Journal:  Pharmaceuticals (Basel)       Date:  2022-03-01

6.  Design and synthesis of novel xyloketal derivatives and their protective activities against H2O2-induced HUVEC injury.

Authors:  Shixin Liu; Rong Luo; Qi Xiang; Xianfang Xu; Liqin Qiu; Jiyan Pang
Journal:  Mar Drugs       Date:  2015-02-12       Impact factor: 5.118

7.  Activation of Hsp90 Enzymatic Activity and Conformational Dynamics through Rationally Designed Allosteric Ligands.

Authors:  Sara Sattin; Jiahui Tao; Gerolamo Vettoretti; Elisabetta Moroni; Marzia Pennati; Alessia Lopergolo; Laura Morelli; Antonella Bugatti; Abbey Zuehlke; Mike Moses; Thomas Prince; Toshiki Kijima; Kristin Beebe; Marco Rusnati; Len Neckers; Nadia Zaffaroni; David A Agard; Anna Bernardi; Giorgio Colombo
Journal:  Chemistry       Date:  2015-08-18       Impact factor: 5.236
  7 in total

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