Literature DB >> 32534343

Discovery of novel aminopiperidinyl amide CXCR4 modulators through virtual screening and rational drug design.

Yoon Hyeun Oum1, Steven A Kell2, Younghyoun Yoon1, Zhongxing Liang1, Pieter Burger3, Hyunsuk Shim4.   

Abstract

The C-X-C chemokine receptor type 4 (CXCR4) is a potential therapeutic target for HIV infection, metastatic cancer, and inflammatory autoimmune diseases. In this study, we screened the ZINC chemical database for novel CXCR4 modulators through a series of in silico guided processes. After evaluating the screened compounds for their binding affinities to CXCR4 and inhibitory activities against the chemoattractant CXCL12, we identified a hit compound (ZINC 72372983) showing 100 nM affinity and 69% chemotaxis inhibition at the same concentration (100 nM). To increase the potency of our hit compound, we explored the protein-ligand interactions at an atomic level using molecular dynamics simulation which enabled us to design and synthesize a novel compound (Z7R) with nanomolar affinity (IC50 = 1.25 nM) and improved chemotaxis inhibition (78.5%). Z7R displays promising anti-inflammatory activity (50%) in a mouse edema model by blocking CXCR4-expressed leukocytes, being supported by our immunohistochemistry study.
Copyright © 2020 Elsevier Masson SAS. All rights reserved.

Entities:  

Keywords:  C-X-C chemokine receptor type 4 (CXCR4); Chemokine modulator; Ligand shape similarity; Molecular docking; Molecular dynamics; Structure-based drug design

Mesh:

Substances:

Year:  2020        PMID: 32534343      PMCID: PMC7422936          DOI: 10.1016/j.ejmech.2020.112479

Source DB:  PubMed          Journal:  Eur J Med Chem        ISSN: 0223-5234            Impact factor:   6.514


  59 in total

1.  ZINC--a free database of commercially available compounds for virtual screening.

Authors:  John J Irwin; Brian K Shoichet
Journal:  J Chem Inf Model       Date:  2005 Jan-Feb       Impact factor: 4.956

2.  Studying the binding interactions of allosteric agonists and antagonists of the CXCR4 receptor.

Authors:  Jesús M Planesas; Violeta I Pérez-Nueno; José I Borrell; Jordi Teixidó
Journal:  J Mol Graph Model       Date:  2015-05-30       Impact factor: 2.518

Review 3.  The GPCR Network: a large-scale collaboration to determine human GPCR structure and function.

Authors:  Raymond C Stevens; Vadim Cherezov; Vsevolod Katritch; Ruben Abagyan; Peter Kuhn; Hugh Rosen; Kurt Wüthrich
Journal:  Nat Rev Drug Discov       Date:  2012-12-14       Impact factor: 84.694

Review 4.  An update on small molecules targeting CXCR4 as starting points for the development of anti-cancer therapeutics.

Authors:  Fedora Grande; Gilda Giancotti; Giuseppina Ioele; Maria A Occhiuzzi; Antonio Garofalo
Journal:  Eur J Med Chem       Date:  2017-08-12       Impact factor: 6.514

5.  Comparison of the potential multiple binding modes of bicyclam, monocylam, and noncyclam small-molecule CXC chemokine receptor 4 inhibitors.

Authors:  Rebecca S Y Wong; Veronique Bodart; Markus Metz; Jean Labrecque; Gary Bridger; Simon P Fricker
Journal:  Mol Pharmacol       Date:  2008-09-02       Impact factor: 4.436

6.  Identification of novel 2-(1H-indol-1-yl)-benzohydrazides CXCR4 ligands impairing breast cancer growth and motility.

Authors:  Fedora Grande; Ines Barone; Francesca Aiello; Andrea Brancale; Michela Cancellieri; Mariateresa Badolato; Francesca Chemi; Cinzia Giordano; Valentina Vircillo; Daniela Bonofiglio; Antonio Garofalo; Sebastiano Andò; Stefania Catalano
Journal:  Future Med Chem       Date:  2016-01-25       Impact factor: 3.808

7.  Inhibitory effect of CXC chemokine receptor 4 antagonist AMD3100 on bleomycin induced murine pulmonary fibrosis.

Authors:  Jeong Sup Song; Chun Mi Kang; Hyeon Hui Kang; Hyung Kyu Yoon; Young Kyoon Kim; Kwan Hyung Kim; Hwa Sik Moon; Sung Hak Park
Journal:  Exp Mol Med       Date:  2010-06-30       Impact factor: 8.718

8.  Directory of useful decoys, enhanced (DUD-E): better ligands and decoys for better benchmarking.

Authors:  Michael M Mysinger; Michael Carchia; John J Irwin; Brian K Shoichet
Journal:  J Med Chem       Date:  2012-07-05       Impact factor: 7.446

Review 9.  Calcium signaling and cytotoxicity.

Authors:  G E Kass; S Orrenius
Journal:  Environ Health Perspect       Date:  1999-02       Impact factor: 9.031

10.  Ligand-activated PPARγ downregulates CXCR4 gene expression through a novel identified PPAR response element and inhibits breast cancer progression.

Authors:  Daniela Rovito; Giulia Gionfriddo; Ines Barone; Cinzia Giordano; Fedora Grande; Francesca De Amicis; Marilena Lanzino; Stefania Catalano; Sebastiano Andò; Daniela Bonofiglio
Journal:  Oncotarget       Date:  2016-10-04
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  2 in total

Review 1.  One Century of Study: What We Learned about Paracoccidioides and How This Pathogen Contributed to Advances in Antifungal Therapy.

Authors:  Erika Seki Kioshima; Patrícia de Souza Bonfim de Mendonça; Marcus de Melo Teixeira; Isis Regina Grenier Capoci; André Amaral; Franciele Abigail Vilugron Rodrigues-Vendramini; Bruna Lauton Simões; Ana Karina Rodrigues Abadio; Larissa Fernandes Matos; Maria Sueli Soares Felipe
Journal:  J Fungi (Basel)       Date:  2021-02-02

2.  Computational modeling and experimental validation of the EPI-X4/CXCR4 complex allows rational design of small peptide antagonists.

Authors:  Pandian Sokkar; Mirja Harms; Christina Stürzel; Andrea Gilg; Gönül Kizilsavas; Martina Raasholm; Nico Preising; Manfred Wagner; Frank Kirchhoff; Ludger Ständker; Gilbert Weidinger; Benjamin Mayer; Jan Münch; Elsa Sanchez-Garcia
Journal:  Commun Biol       Date:  2021-09-22
  2 in total

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