Literature DB >> 23993674

Hydroxyquinoline-derived compounds and analoguing of selective Mcl-1 inhibitors using a functional biomarker.

David J Richard1, Ryan Lena, Thomas Bannister, Noel Blake, William E Pierceall, Nicole E Carlson, Christina Eberhart Keller, Marcel Koenig, Yuanjun He, Dmitriy Minond, Jitendra Mishra, Michael Cameron, Timothy Spicer, Peter Hodder, Michael H Cardone.   

Abstract

Anti-apoptotic Bcl-2 family proteins are important oncology therapeutic targets. To date, BH3 mimetics that abrogate anti-apoptotic activity have largely been directed at Bcl-2 and/or Bcl-xL. One observed mechanism of resistance to these inhibitors is increased Mcl-1 levels in cells exposed to such therapeutics. For this reason, and because Mcl-1 is important in the onset of lymphoid, myeloid, and other cancers, it has become a target of great interest. However, small molecule inhibitors displaying potency and selectivity for Mcl-1 are lacking. Identifying such compounds has been challenging due to difficulties in translating the target selectivity observed at the biochemical level to the cellular level. Herein we report the results of an HTS strategy coupled with directed hit optimization. Compounds identified have selective Mcl-1 inhibitory activity with greater than 100-fold reduced affinity for Bcl-xL. The selectivity of these compounds at the cellular level was validated using BH3 profiling, a novel personalized diagnostic approach. This assay provides an important functional biomarker that allows for the characterization of cells based upon their dependencies on various anti-apoptotic Bcl-2 proteins. We demonstrate that cells dependent on Mcl-1 or Bcl-2/Bcl-xL for survival are commensurately responsive to compounds that genuinely target those proteins. The identification of compound 9 with uniquely validated and selective Mcl-1 inhibitory activity provides a valuable tool to those studying the intrinsic apoptosis pathway and highlights an important approach in the development of a first-in-class cancer therapeutic.
Copyright © 2013 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  Apoptosis; Biomarkers; Cell-based activity; Mcl-1; Oncology

Mesh:

Substances:

Year:  2013        PMID: 23993674      PMCID: PMC3831274          DOI: 10.1016/j.bmc.2013.08.017

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN: 0968-0896            Impact factor:   3.641


  34 in total

1.  Anti-apoptotic Mcl-1 is essential for the development and sustained growth of acute myeloid leukemia.

Authors:  Stefan P Glaser; Erinna F Lee; Evelyn Trounson; Philippe Bouillet; Andrew Wei; W Douglas Fairlie; David J Izon; Johannes Zuber; Amy R Rappaport; Marco J Herold; Warren S Alexander; Scott W Lowe; Lorraine Robb; Andreas Strasser
Journal:  Genes Dev       Date:  2012-01-15       Impact factor: 11.361

2.  Mitochondria primed by death signals determine cellular addiction to antiapoptotic BCL-2 family members.

Authors:  Michael Certo; Victoria Del Gaizo Moore; Mari Nishino; Guo Wei; Stanley Korsmeyer; Scott A Armstrong; Anthony Letai
Journal:  Cancer Cell       Date:  2006-05       Impact factor: 31.743

3.  Mcl-1 expression has in vitro and in vivo significance in chronic lymphocytic leukemia and is associated with other poor prognostic markers.

Authors:  Chris Pepper; Thet Thet Lin; Guy Pratt; Saman Hewamana; Paul Brennan; Louise Hiller; Robert Hills; Rachel Ward; Jane Starczynski; Belinda Austen; Laura Hooper; Tatjana Stankovic; Chris Fegan
Journal:  Blood       Date:  2008-07-03       Impact factor: 22.113

4.  Acquired resistance to ABT-737 in lymphoma cells that up-regulate MCL-1 and BFL-1.

Authors:  Derek Yecies; Nicole E Carlson; Jing Deng; Anthony Letai
Journal:  Blood       Date:  2010-03-02       Impact factor: 22.113

5.  Molecular dynamics study of small molecule inhibitors of the Bcl-2 family.

Authors:  Stéphane Acoca; Qizhi Cui; Gordon C Shore; Enrico O Purisima
Journal:  Proteins       Date:  2011-06-30

6.  Pretreatment mitochondrial priming correlates with clinical response to cytotoxic chemotherapy.

Authors:  Triona Ni Chonghaile; Kristopher A Sarosiek; Thanh-Trang Vo; Jeremy A Ryan; Anupama Tammareddi; Victoria Del Gaizo Moore; Jing Deng; Kenneth C Anderson; Paul Richardson; Yu-Tzu Tai; Constantine S Mitsiades; Ursula A Matulonis; Ronny Drapkin; Richard Stone; Daniel J Deangelo; David J McConkey; Stephen E Sallan; Lewis Silverman; Michelle S Hirsch; Daniel Ruben Carrasco; Anthony Letai
Journal:  Science       Date:  2011-10-27       Impact factor: 47.728

7.  Heightened mitochondrial priming is the basis for apoptotic hypersensitivity of CD4+ CD8+ thymocytes.

Authors:  Jeremy A Ryan; Joslyn K Brunelle; Anthony Letai
Journal:  Proc Natl Acad Sci U S A       Date:  2010-07-06       Impact factor: 11.205

8.  Myeloid cell factor-1 is a critical survival factor for multiple myeloma.

Authors:  Bin Zhang; Ivana Gojo; Robert G Fenton
Journal:  Blood       Date:  2002-03-15       Impact factor: 22.113

9.  Different forms of cell death induced by putative BCL2 inhibitors.

Authors:  M Vogler; K Weber; D Dinsdale; I Schmitz; K Schulze-Osthoff; M J S Dyer; G M Cohen
Journal:  Cell Death Differ       Date:  2009-04-24       Impact factor: 15.828

10.  Mcl-1 is regulated by IL-6 and mediates the survival activity of the cytokine in a model of late stage prostate carcinoma.

Authors:  Ilaria Teresa Cavarretta; Hannes Neuwirt; Mohamed H Zaki; Hannes Steiner; Alfred Hobisch; Jeffrey A Nemeth; Zoran Culig
Journal:  Adv Exp Med Biol       Date:  2008       Impact factor: 2.622

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  24 in total

Review 1.  Attacking cancer's Achilles heel: antagonism of anti-apoptotic BCL-2 family members.

Authors:  Joseph T Opferman
Journal:  FEBS J       Date:  2015-09-15       Impact factor: 5.542

2.  Structure-based design of N-substituted 1-hydroxy-4-sulfamoyl-2-naphthoates as selective inhibitors of the Mcl-1 oncoprotein.

Authors:  Maryanna E Lanning; Wenbo Yu; Jeremy L Yap; Jay Chauhan; Lijia Chen; Ellis Whiting; Lakshmi S Pidugu; Tyler Atkinson; Hala Bailey; Willy Li; Braden M Roth; Lauren Hynicka; Kirsty Chesko; Eric A Toth; Paul Shapiro; Alexander D MacKerell; Paul T Wilder; Steven Fletcher
Journal:  Eur J Med Chem       Date:  2016-02-04       Impact factor: 6.514

3.  Discovery and biological characterization of potent myeloid cell leukemia-1 inhibitors.

Authors:  Taekyu Lee; Zhiguo Bian; Bin Zhao; Leah J Hogdal; John L Sensintaffar; Craig M Goodwin; Johannes Belmar; Subrata Shaw; James C Tarr; Nagarathanam Veerasamy; Shannon M Matulis; Brian Koss; Melissa A Fischer; Allison L Arnold; DeMarco V Camper; Carrie F Browning; Olivia W Rossanese; Amit Budhraja; Joseph Opferman; Lawrence H Boise; Michael R Savona; Anthony Letai; Edward T Olejniczak; Stephen W Fesik
Journal:  FEBS Lett       Date:  2016-12-19       Impact factor: 4.124

Review 4.  Targeting multiple signaling pathways: the new approach to acute myeloid leukemia therapy.

Authors:  Jenna L Carter; Katie Hege; Jay Yang; Hasini A Kalpage; Yongwei Su; Holly Edwards; Maik Hüttemann; Jeffrey W Taub; Yubin Ge
Journal:  Signal Transduct Target Ther       Date:  2020-12-18

Review 5.  From basic apoptosis discoveries to advanced selective BCL-2 family inhibitors.

Authors:  Avi Ashkenazi; Wayne J Fairbrother; Joel D Leverson; Andrew J Souers
Journal:  Nat Rev Drug Discov       Date:  2017-02-17       Impact factor: 84.694

6.  Single Diastereomer of a Macrolactam Core Binds Specifically to Myeloid Cell Leukemia 1 (MCL1).

Authors:  Chao Fang; Brendan D'Souza; Christopher F Thompson; Matthew C Clifton; James W Fairman; Ben Fulroth; Alison Leed; Patrick McCarren; Lili Wang; Yikai Wang; Clementine Feau; Virendar K Kaushik; Michelle Palmer; Guo Wei; Todd R Golub; Brian K Hubbard; Michael H Serrano-Wu
Journal:  ACS Med Chem Lett       Date:  2014-11-11       Impact factor: 4.345

7.  Mcl-1 mediates TWEAK/Fn14-induced non-small cell lung cancer survival and therapeutic response.

Authors:  Timothy G Whitsett; Ian T Mathews; Michael H Cardone; Ryan J Lena; William E Pierceall; Michael Bittner; Chao Sima; Janine LoBello; Glen J Weiss; Nhan L Tran
Journal:  Mol Cancer Res       Date:  2014-01-27       Impact factor: 5.852

Review 8.  Small molecule Mcl-1 inhibitors for the treatment of cancer.

Authors:  Johannes Belmar; Stephen W Fesik
Journal:  Pharmacol Ther       Date:  2014-08-27       Impact factor: 12.310

Review 9.  Targeting MCL-1 in hematologic malignancies: Rationale and progress.

Authors:  Andrew H Wei; Andrew W Roberts; Andrew Spencer; Aaron Seth Rosenberg; David Siegel; Roland B Walter; Sean Caenepeel; Paul Hughes; Zach McIver; Khalid Mezzi; Phuong Khanh Morrow; Anthony Stein
Journal:  Blood Rev       Date:  2020-02-21       Impact factor: 8.250

10.  Structural Re-engineering of the α-Helix Mimetic JY-1-106 into Small Molecules: Disruption of the Mcl-1-Bak-BH3 Protein-Protein Interaction with 2,6-Di-Substituted Nicotinates.

Authors:  Brandon Drennen; Jacob A Scheenstra; Jeremy L Yap; Lijia Chen; Maryanna E Lanning; Braden M Roth; Paul T Wilder; Steven Fletcher
Journal:  ChemMedChem       Date:  2016-02-04       Impact factor: 3.466

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