Literature DB >> 24126093

Design and evaluation of xanthine based adenosine receptor antagonists: potential hypoxia targeted immunotherapies.

Rhiannon Thomas1, Joslynn Lee, Vincent Chevalier, Sara Sadler, Kaisa Selesniemi, Stephen Hatfield, Michail Sitkovsky, Mary Jo Ondrechen, Graham B Jones.   

Abstract

Molecular modeling techniques were applied to the design, synthesis and optimization of a new series of xanthine based adenosine A(2A) receptor antagonists. The optimized lead compound was converted to a PEG derivative and a functional in vitro bioassay used to confirm efficacy. Additionally, the PEGylated version showed enhanced aqueous solubility and was inert to photoisomerization, a known limitation of existing antagonists of this class.
Copyright © 2013 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  A(2A); Adenosine receptor; Hypoxia; KW-6002; Synthesis; Xanthine

Mesh：

Substances：

Year:  2013        PMID： 24126093      PMCID： PMC4346301          DOI： 10.1016/j.bmc.2013.09.043

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


  22 in total

1.  PRODRG: a tool for high-throughput crystallography of protein-ligand complexes.

Authors:  Alexander W Schüttelkopf; Daan M F van Aalten
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2004-07-21

2.  Prediction of Absolute Solvation Free Energies using Molecular Dynamics Free Energy Perturbation and the OPLS Force Field.

Authors:  Devleena Shivakumar; Joshua Williams; Yujie Wu; Wolfgang Damm; John Shelley; Woody Sherman
Journal:  J Chem Theory Comput       Date:  2010-04-14       Impact factor: 6.006

3.  The SWISS-MODEL workspace: a web-based environment for protein structure homology modelling.

Authors:  Konstantin Arnold; Lorenza Bordoli; Jürgen Kopp; Torsten Schwede
Journal:  Bioinformatics       Date:  2005-11-13       Impact factor: 6.937

4.  Extra precision glide: docking and scoring incorporating a model of hydrophobic enclosure for protein-ligand complexes.

Authors:  Richard A Friesner; Robert B Murphy; Matthew P Repasky; Leah L Frye; Jeremy R Greenwood; Thomas A Halgren; Paul C Sanschagrin; Daniel T Mainz
Journal:  J Med Chem       Date:  2006-10-19       Impact factor: 7.446

5.  A2A adenosine receptor protects tumors from antitumor T cells.

Authors:  Akio Ohta; Elieser Gorelik; Simon J Prasad; Franca Ronchese; Dmitriy Lukashev; Michael K K Wong; Xiaojun Huang; Sheila Caldwell; Kebin Liu; Patrick Smith; Jiang-Fan Chen; Edwin K Jackson; Sergey Apasov; Scott Abrams; Michail Sitkovsky
Journal:  Proc Natl Acad Sci U S A       Date:  2006-08-17       Impact factor: 11.205

6.  An efficient route to xanthine based A(2A) adenosine receptor antagonists and functional derivatives.

Authors:  Paul Labeaume; Ma Dong; Michail Sitkovsky; Elizabeth V Jones; Rhiannon Thomas; Sara Sadler; Amy E Kallmerten; Graham B Jones
Journal:  Org Biomol Chem       Date:  2010-07-23       Impact factor: 3.876

7.  T regulatory cells: hypoxia-adenosinergic suppression and re-direction of the immune response.

Authors:  Michail V Sitkovsky
Journal:  Trends Immunol       Date:  2009-02-07       Impact factor: 16.687

8.  The 2.6 angstrom crystal structure of a human A2A adenosine receptor bound to an antagonist.

Authors:  Veli-Pekka Jaakola; Mark T Griffith; Michael A Hanson; Vadim Cherezov; Ellen Y T Chien; J Robert Lane; Adriaan P Ijzerman; Raymond C Stevens
Journal:  Science       Date:  2008-10-02       Impact factor: 47.728

9.  Adenosine receptor subtype-selective antagonists in inflammation and hyperalgesia.

Authors:  Andras Bilkei-Gorzo; Osama M Abo-Salem; Alaa M Hayallah; Kerstin Michel; Christa E Müller; Andreas Zimmer
Journal:  Naunyn Schmiedebergs Arch Pharmacol       Date:  2008-01-10       Impact factor: 3.000

10.  From "Hellstrom Paradox" to anti-adenosinergic cancer immunotherapy.

Authors:  Dmitriy Lukashev; Michail Sitkovsky; Akio Ohta
Journal:  Purinergic Signal       Date:  2007-01-24       Impact factor: 3.765
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  3 in total

Review 1.  A2A adenosine receptor antagonists to weaken the hypoxia-HIF-1α driven immunosuppression and improve immunotherapies of cancer.

Authors:  Stephen M Hatfield; Michail Sitkovsky
Journal:  Curr Opin Pharmacol       Date:  2016-07-17       Impact factor: 5.547

2.  Fluorinated Adenosine A2A Receptor Antagonists Inspired by Preladenant as Potential Cancer Immunotherapeutics.

Authors:  Gengyang Yuan; Tanner C Jankins; Christopher G Patrick; Phaethon Philbrook; Olivia Sears; Stephen Hatfield; Michail Sitkovsky; Neil Vasdev; Steven H Liang; Mary Jo Ondrechen; Michael P Pollastri; Graham B Jones
Journal:  Int J Med Chem       Date:  2017-10-19

3.  Synthesis and anticancer activity of multisubstituted purines and xanthines with one or two propynylthio and aminobutynylthio groups.

Authors:  Alicja Kowalska; Krystian Pluta; Małgorzata Latocha
Journal:  Med Chem Res       Date:  2018-03-06       Impact factor: 1.965
  3 in total

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