Literature DB >> 29790770

Multicomponent Synthesis and Binding Mode of Imidazo[1,2- a]pyridine-Capped Selective HDAC6 Inhibitors.

Marcel K W Mackwitz1, Alexandra Hamacher2, Jeremy D Osko3, Jana Held4, Andrea Schöler1, David W Christianson3, Matthias U Kassack2, Finn K Hansen1.   

Abstract

The multicomponent synthesis of a mini-library of histone deacetylase inhibitors with imidazo[1,2- a]pyridine-based cap groups is presented. The biological evaluation led to the discovery of the hit compound MAIP-032 as a selective HDAC6 inhibitor with promising anticancer activity. The X-ray structure of catalytic domain 2 from Danio rerio HDAC6 complexed with MAIP-032 revealed a monodentate zinc-binding mode.

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Year:  2018        PMID： 29790770      PMCID： PMC5999327          DOI： 10.1021/acs.orglett.8b01118

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


  21 in total

1.  Nonisotopic substrate for assaying both human zinc and NAD+-dependent histone deacetylases.

Authors:  Birgit Heltweg; Franck Dequiedt; Eric Verdin; Manfred Jung
Journal:  Anal Biochem       Date:  2003-08-01       Impact factor: 3.365

2.  Rational design and diversity-oriented synthesis of peptoid-based selective HDAC6 inhibitors.

Authors:  D Diedrich; A Hamacher; C G W Gertzen; L A Alves Avelar; G J Reiss; T Kurz; H Gohlke; M U Kassack; F K Hansen
Journal:  Chem Commun (Camb)       Date:  2016-02-21       Impact factor: 6.222

Review 3.  Competitive or noncompetitive, that's the question: research toward histone deacetylase inhibitors.

Authors:  Hong Su; Lucia Altucci; Qidong You
Journal:  Mol Cancer Ther       Date:  2008-05       Impact factor: 6.261

4.  Unusual zinc-binding mode of HDAC6-selective hydroxamate inhibitors.

Authors:  Nicholas J Porter; Adaickapillai Mahendran; Ronald Breslow; David W Christianson
Journal:  Proc Natl Acad Sci U S A       Date:  2017-12-04       Impact factor: 11.205

5.  Design and synthesis of orally bioavailable aminopyrrolidinone histone deacetylase 6 inhibitors.

Authors:  Xianfeng Lin; Wenming Chen; Zongxing Qiu; Lei Guo; Wei Zhu; Wentao Li; Zhanguo Wang; Weixing Zhang; Zhenshan Zhang; Yiping Rong; Meifang Zhang; Lingjie Yu; Sheng Zhong; Rong Zhao; Xihan Wu; Jason C Wong; Guozhi Tang
Journal:  J Med Chem       Date:  2015-03-13       Impact factor: 7.446

Review 6.  Groebke-Blackburn-Bienaymé multicomponent reaction: emerging chemistry for drug discovery.

Authors:  Saad Shaaban; Bakr F Abdel-Wahab
Journal:  Mol Divers       Date:  2015-05-28       Impact factor: 2.943

7.  Bicyclic-Capped Histone Deacetylase 6 Inhibitors with Improved Activity in a Model of Axonal Charcot-Marie-Tooth Disease.

Authors:  Sida Shen; Veronick Benoy; Joel A Bergman; Jay H Kalin; Mariana Frojuello; Giulio Vistoli; Wanda Haeck; Ludo Van Den Bosch; Alan P Kozikowski
Journal:  ACS Chem Neurosci       Date:  2015-12-07       Impact factor: 4.418

8.  AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility.

Authors:  Garrett M Morris; Ruth Huey; William Lindstrom; Michel F Sanner; Richard K Belew; David S Goodsell; Arthur J Olson
Journal:  J Comput Chem       Date:  2009-12       Impact factor: 3.376

Review 9.  Histone deacetylases and the immunological network: implications in cancer and inflammation.

Authors:  A Villagra; E M Sotomayor; E Seto
Journal:  Oncogene       Date:  2009-10-26       Impact factor: 9.867

10.  Exploration of thiaheterocyclic hHDAC6 inhibitors as potential antiplasmodial agents.

Authors:  Rob De Vreese; Carmen de Kock; Peter J Smith; Kelly Chibale; Matthias D'hooghe
Journal:  Future Med Chem       Date:  2017-03-06       Impact factor: 3.808
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  18 in total

Review 1.  Structure, mechanism, and inhibition of the zinc-dependent histone deacetylases.

Authors:  Nicholas J Porter; David W Christianson
Journal:  Curr Opin Struct Biol       Date:  2019-02-08       Impact factor: 6.809

2.  Discovery of the First-in-Class Dual Histone Deacetylase-Proteasome Inhibitor.

Authors:  Sanil Bhatia; Viktoria Krieger; Michael Groll; Jeremy D Osko; Nina Reßing; Heinz Ahlert; Arndt Borkhardt; Thomas Kurz; David W Christianson; Julia Hauer; Finn K Hansen
Journal:  J Med Chem       Date:  2018-11-08       Impact factor: 7.446

3.  Histone Deacetylase 6-Selective Inhibitors and the Influence of Capping Groups on Hydroxamate-Zinc Denticity.

Authors:  Nicholas J Porter; Jeremy D Osko; Daniela Diedrich; Thomas Kurz; Jacob M Hooker; Finn K Hansen; David W Christianson
Journal:  J Med Chem       Date:  2018-08-17       Impact factor: 7.446

4.  Structural Basis for the Selective Inhibition of HDAC10, the Cytosolic Polyamine Deacetylase.

Authors:  Corey J Herbst-Gervasoni; Raphael R Steimbach; Michael Morgen; Aubry K Miller; David W Christianson
Journal:  ACS Chem Biol       Date:  2020-07-23       Impact factor: 5.100

5.  Multicomponent Synthesis, Binding Mode, and Structure-Activity Relationship of Selective Histone Deacetylase 6 (HDAC6) Inhibitors with Bifurcated Capping Groups.

Authors:  Nina Reßing; Melf Sönnichsen; Jeremy D Osko; Andrea Schöler; Julian Schliehe-Diecks; Alexander Skerhut; Arndt Borkhardt; Julia Hauer; Matthias U Kassack; David W Christianson; Sanil Bhatia; Finn K Hansen
Journal:  J Med Chem       Date:  2020-09-01       Impact factor: 7.446

6.  Binding of inhibitors to active-site mutants of CD1, the enigmatic catalytic domain of histone deacetylase 6.

Authors:  Jeremy D Osko; David W Christianson
Journal:  Acta Crystallogr F Struct Biol Commun       Date:  2020-08-19       Impact factor: 1.056

7.  Structural and in Vivo Characterization of Tubastatin A, a Widely Used Histone Deacetylase 6 Inhibitor.

Authors:  Sida Shen; Michal Svoboda; Guangming Zhang; Maria A Cavasin; Lucia Motlova; Timothy A McKinsey; James H Eubanks; Cyril Bařinka; Alan P Kozikowski
Journal:  ACS Med Chem Lett       Date:  2020-01-15       Impact factor: 4.345

8.  Methods for the expression, purification, and crystallization of histone deacetylase 6-inhibitor complexes.

Authors:  Jeremy D Osko; David W Christianson
Journal:  Methods Enzymol       Date:  2019-07-18       Impact factor: 1.600

9.  Design, synthesis and biological evaluation of β-peptoid-capped HDAC inhibitors with anti-neuroblastoma and anti-glioblastoma activity.

Authors:  Nina Reßing; Viktoria Marquardt; Christoph G W Gertzen; Andrea Schöler; Alexander Schramm; Thomas Kurz; Holger Gohlke; Achim Aigner; Marc Remke; Finn K Hansen
Journal:  Medchemcomm       Date:  2018-10-23       Impact factor: 3.597

Review 10.  Structural determinants of affinity and selectivity in the binding of inhibitors to histone deacetylase 6.

Authors:  Jeremy D Osko; David W Christianson
Journal:  Bioorg Med Chem Lett       Date:  2020-02-11       Impact factor: 2.823
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