Elucidation of Hydrogen Bonding Patterns in Ligand-Free, Lactose- and Glycerol-Bound Galectin-3C by Neutron Crystallography to Guide Drug Design

Manzoni, Francesco; Wallerstein, Johan; Schrader, Tobias E.; Ostermann, Andreas; Coates, Leighton; Akke, Mikael; Blakeley, Matthew P.; Oksanen, Esko; Logan, Derek T.

doi:10.1021/acs.jmedchem.8b00081

Title: Elucidation of Hydrogen Bonding Patterns in Ligand-Free, Lactose- and Glycerol-Bound Galectin-3C by Neutron Crystallography to Guide Drug Design

Authors:

Manzoni, Francesco ^[1]; Wallerstein, Johan ^[2];

^[3]; Ostermann, Andreas ^[4];

^[5];

^[2]; Blakeley, Matthew P. ^[6]; Oksanen, Esko ^[7];

^[1]

Department of Biochemistry & Structural Biology, Lund University, S-221 00 Lund, Sweden
Department of Biophysical Chemistry, Lund University, S-221 00 Lund, Sweden
Jülich Centre for Neutron Science (JCNS) at Heinz Maier-Leibnitz Zentrum (MLZ), Forschungszentrum Jülich GmbH, Lichtenbergstrasse 1, 85747 Garching, Germany
Heinz Maier-Leibnitz Zentrum (MLZ), Technische Universität München, Lichtenbergstrasse 1, 85748 Garching, Germany
Neutron Scattering Division, Oak Ridge National Laboratory, 1 Bethel Valley Road, Oak Ridge, Tennessee 37831, United States
Institut Laue-Langevin, 71 avenue des Martyrs, 38000 Grenoble, France
Department of Biochemistry & Structural Biology, Lund University, S-221 00 Lund, Sweden, Instrument Division, European Spallation Source ERIC, Box 176, S-221 00 Lund, Sweden

Publication Date:: Thu Apr 19 00:00:00 EDT 2018

Sponsoring Org.:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

OSTI Identifier:: 1438966

Resource Type:: Published Article

Journal Name:: Journal of Medicinal Chemistry

Additional Journal Information:: Journal Name: Journal of Medicinal Chemistry Journal Volume: 61 Journal Issue: 10; Journal ID: ISSN 0022-2623

Publisher:: American Chemical Society

Country of Publication:: United States

Language:: English

Citation Formats


                    Manzoni, Francesco, Wallerstein, Johan, Schrader, Tobias E., Ostermann, Andreas, Coates, Leighton, Akke, Mikael, Blakeley, Matthew P., Oksanen, Esko, and Logan, Derek T. Elucidation of Hydrogen Bonding Patterns in Ligand-Free, Lactose- and Glycerol-Bound Galectin-3C by Neutron Crystallography to Guide Drug Design.  United States: N. p., 2018. 
Web.  doi:10.1021/acs.jmedchem.8b00081.

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                    Manzoni, Francesco, Wallerstein, Johan, Schrader, Tobias E., Ostermann, Andreas, Coates, Leighton, Akke, Mikael, Blakeley, Matthew P., Oksanen, Esko, & Logan, Derek T. Elucidation of Hydrogen Bonding Patterns in Ligand-Free, Lactose- and Glycerol-Bound Galectin-3C by Neutron Crystallography to Guide Drug Design.  United States.  https://doi.org/10.1021/acs.jmedchem.8b00081

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                    Manzoni, Francesco, Wallerstein, Johan, Schrader, Tobias E., Ostermann, Andreas, Coates, Leighton, Akke, Mikael, Blakeley, Matthew P., Oksanen, Esko, and Logan, Derek T. Thu .  
"Elucidation of Hydrogen Bonding Patterns in Ligand-Free, Lactose- and Glycerol-Bound Galectin-3C by Neutron Crystallography to Guide Drug Design".  United States.  https://doi.org/10.1021/acs.jmedchem.8b00081.

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@article{osti_1438966,

  title        = {Elucidation of Hydrogen Bonding Patterns in Ligand-Free, Lactose- and Glycerol-Bound Galectin-3C by Neutron Crystallography to Guide Drug Design},

  author       = {Manzoni, Francesco and Wallerstein, Johan and Schrader, Tobias E. and Ostermann, Andreas and Coates, Leighton and Akke, Mikael and Blakeley, Matthew P. and Oksanen, Esko and Logan, Derek T.},

  abstractNote = {},

  doi          = {10.1021/acs.jmedchem.8b00081},

  journal      = {Journal of Medicinal Chemistry},

  number       = 10,

  volume       = 61,

  place        = {United States},

  year         = {Thu Apr 19 00:00:00 EDT 2018},

  month        = {Thu Apr 19 00:00:00 EDT 2018}

}

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https://doi.org/10.1021/acs.jmedchem.8b00081

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Title: Elucidation of Hydrogen Bonding Patterns in Ligand-Free, Lactose- and Glycerol-Bound Galectin-3C by Neutron Crystallography to Guide Drug Design

Citation Formats

Biophysical and structural characterization of mono/di-arylated lactosamine derivatives interaction with human galectin-3 journal, July 2017

Comparison of hydrogen determination with X-ray and neutron crystallography in a human aldose reductase–inhibitor complex journal, April 2006

Introduction to galectins journal, January 2002

Overview of the CCP 4 suite and current developments journal, March 2011

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Structural and Thermodynamic Studies on Cation−Π Interactions in Lectin−Ligand Complexes: High-Affinity Galectin-3 Inhibitors through Fine-Tuning of an Arginine−Arene Interaction journal, February 2005

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Ultrahigh resolution drug design I: Details of interactions in human aldose reductase-inhibitor complex at 0.66 Å journal, April 2004

Features and development of Coot journal, March 2010

1H-1,2,3-Triazol-1-yl thiodigalactoside derivatives as high affinity galectin-3 inhibitors journal, July 2010

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PHENIX: a comprehensive Python-based system for macromolecular structure solution journal, January 2010

Determination of the tautomeric form of the imidazole ring of L-histidine in basic solution by carbon-13 magnetic resonance spectroscopy journal, January 1973

Orientational Disorder and Entropy of Water in Protein Cavities journal, November 1997

An Emerging Role for Galectins in Tuning the Immune Response: Lessons from Experimental Models of Inflammatory Disease, Autoimmunity and Cancer journal, August 2007

Systematic Tuning of Fluoro-galectin-3 Interactions Provides Thiodigalactoside Derivatives with Single-Digit nM Affinity and High Selectivity journal, January 2018

NMRPipe: A multidimensional spectral processing system based on UNIX pipes journal, November 1995

Galectin-3-Binding Glycomimetics that Strongly Reduce Bleomycin-Induced Lung Fibrosis and Modulate Intracellular Glycan Recognition journal, August 2016

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Galectins as modulators of tumour progression journal, January 2005

The Carbohydrate-Binding Site in Galectin-3 Is Preorganized To Recognize a Sugarlike Framework of Oxygens: Ultra-High-Resolution Structures and Water Dynamics journal, December 2011

Slow diffusion of lactose out of galectin-3 crystals monitored by X-ray crystallography: possible implications for ligand-exchange protocols journal, February 2007

Perdeuteration, crystallization, data collection and comparison of five neutron diffraction data sets of complexes of human galectin-3C journal, October 2016

Scaling and assessment of data quality journal, December 2005

The CCPN data model for NMR spectroscopy: Development of a software pipeline journal, April 2005

XDS journal, January 2010

Joint X-ray and neutron refinement with phenix.refine journal, October 2010

Investigation into the Feasibility of Thioditaloside as a Novel Scaffold for Galectin-3-Specific Inhibitors journal, July 2013

Dual thio-digalactoside-binding modes of human galectins as the structural basis for the design of potent and selective inhibitors journal, July 2016

Taloside Inhibitors of Galectin-1 and Galectin-3: Taloside Inhibitors of Galectins journal, January 2012

Protein Flexibility and Conformational Entropy in Ligand Design Targeting the Carbohydrate Recognition Domain of Galectin-3 journal, October 2010

Biophysical and structural characterization of mono/di-arylated lactosamine derivatives interaction with human galectin-3
journal, July 2017

Comparison of hydrogen determination with X-ray and neutron crystallography in a human aldose reductase–inhibitor complex
journal, April 2006

Introduction to galectins
journal, January 2002

Overview of the CCP 4 suite and current developments
journal, March 2011

Galectin-3 in diabetic patients
journal, January 2014

Structural and Thermodynamic Studies on Cation−Π Interactions in Lectin−Ligand Complexes: High-Affinity Galectin-3 Inhibitors through Fine-Tuning of an Arginine−Arene Interaction
journal, February 2005

Galectin-3 Interactions with Glycosphingolipids
journal, April 2014

Galectins as inflammatory mediators
journal, January 2002

Ultrahigh resolution drug design I: Details of interactions in human aldose reductase-inhibitor complex at 0.66 Å
journal, April 2004

Features and development of Coot
journal, March 2010

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journal, July 2010

Tuning the Preference of Thiodigalactoside- and Lactosamine-Based Ligands to Galectin-3 over Galectin-1
journal, January 2013

Regulatory Roles of Galectins in the Immune Response
journal, January 2005

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journal, January 1973

Orientational Disorder and Entropy of Water in Protein Cavities
journal, November 1997

An Emerging Role for Galectins in Tuning the Immune Response: Lessons from Experimental Models of Inflammatory Disease, Autoimmunity and Cancer
journal, August 2007

Systematic Tuning of Fluoro-galectin-3 Interactions Provides Thiodigalactoside Derivatives with Single-Digit nM Affinity and High Selectivity
journal, January 2018

NMRPipe: A multidimensional spectral processing system based on UNIX pipes
journal, November 1995

Galectin-3-Binding Glycomimetics that Strongly Reduce Bleomycin-Induced Lung Fibrosis and Modulate Intracellular Glycan Recognition
journal, August 2016

Galectin-3: An open-ended story
journal, April 2006

Galectins as modulators of tumour progression
journal, January 2005

The Carbohydrate-Binding Site in Galectin-3 Is Preorganized To Recognize a Sugarlike Framework of Oxygens: Ultra-High-Resolution Structures and Water Dynamics
journal, December 2011

Slow diffusion of lactose out of galectin-3 crystals monitored by X-ray crystallography: possible implications for ligand-exchange protocols
journal, February 2007

Perdeuteration, crystallization, data collection and comparison of five neutron diffraction data sets of complexes of human galectin-3C
journal, October 2016

Scaling and assessment of data quality
journal, December 2005

The CCPN data model for NMR spectroscopy: Development of a software pipeline
journal, April 2005

XDS
journal, January 2010

Joint X-ray and neutron refinement with phenix.refine
journal, October 2010

Investigation into the Feasibility of Thioditaloside as a Novel Scaffold for Galectin-3-Specific Inhibitors
journal, July 2013

Dual thio-digalactoside-binding modes of human galectins as the structural basis for the design of potent and selective inhibitors
journal, July 2016

Taloside Inhibitors of Galectin-1 and Galectin-3: Taloside Inhibitors of Galectins
journal, January 2012

Protein Flexibility and Conformational Entropy in Ligand Design Targeting the Carbohydrate Recognition Domain of Galectin-3
journal, October 2010