Literature DB >> 36154172

Discovery and Optimization of the First Highly Effective and Orally Available Galectin-3 Inhibitors for Treatment of Fibrotic Disease.

Fredrik R Zetterberg1, Alison MacKinnon2, Thomas Brimert3,4, Lise Gravelle5, Richard E Johnsson3, Barbro Kahl-Knutson4, Hakon Leffler6, Ulf J Nilsson1,7, Anders Pedersen5, Kristoffer Peterson1,7, James A Roper8, Hans Schambye5, Robert J Slack8, Susan Tantawi5.   

Abstract

Galectin-3 is a carbohydrate-binding protein central to regulating mechanisms of diseases such as fibrosis, cancer, metabolic, inflammatory, and heart disease. We recently found a high affinity (nM) thiodigalactoside GB0139 which currently is in clinical development (PhIIb) as an inhaled treatment of idiopathic pulmonary fibrosis. To enable treatment of systemically galectin-3 driven disease, we here present the first series of selective galectin-3 inhibitors combining high affinity (nM) with oral bioavailability. This was achieved by optimizing galectin-3 specificity and physical chemical parameters for a series of disubstituted monogalactosides. Further characterization showed that this class of compounds reduced profibrotic gene expression in liver myofibroblasts and displayed antifibrotic activity in CCl4-induced liver fibrosis and bleomycin-induced lung fibrosis mouse models. On the basis of the overall pharmacokinetic, pharmacodynamic, and safety profile, GB1211 was selected as the clinical candidate and is currently in phase IIa clinical trials as a potential therapy for liver cirrhosis and cancer.

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Year:  2022        PMID: 36154172      PMCID: PMC9574852          DOI: 10.1021/acs.jmedchem.2c00660

Source DB:  PubMed          Journal:  J Med Chem        ISSN: 0022-2623            Impact factor:   8.039


  31 in total

Review 1.  Coexistence of passive and carrier-mediated processes in drug transport.

Authors:  Kiyohiko Sugano; Manfred Kansy; Per Artursson; Alex Avdeef; Stefanie Bendels; Li Di; Gerhard F Ecker; Bernard Faller; Holger Fischer; Grégori Gerebtzoff; Hans Lennernaes; Frank Senner
Journal:  Nat Rev Drug Discov       Date:  2010-08       Impact factor: 84.694

Review 2.  Molecular recognition in chemical and biological systems.

Authors:  Elke Persch; Oliver Dumele; François Diederich
Journal:  Angew Chem Int Ed Engl       Date:  2015-01-28       Impact factor: 15.336

Review 3.  Hydroxyl Groups in Synthetic and Natural-Product-Derived Therapeutics: A Perspective on a Common Functional Group.

Authors:  Jonathan Cramer; Christoph P Sager; Beat Ernst
Journal:  J Med Chem       Date:  2019-05-28       Impact factor: 7.446

4.  Principles and applications of halogen bonding in medicinal chemistry and chemical biology.

Authors:  Rainer Wilcken; Markus O Zimmermann; Andreas Lange; Andreas C Joerger; Frank M Boeckler
Journal:  J Med Chem       Date:  2013-01-03       Impact factor: 7.446

5.  Synthesis of a phenyl thio-beta-D-galactopyranoside library from 1,5-difluoro-2,4-dinitrobenzene: discovery of efficient and selective monosaccharide inhibitors of galectin-7.

Authors:  Ian Cumpstey; Susanne Carlsson; Hakon Leffler; Ulf J Nilsson
Journal:  Org Biomol Chem       Date:  2005-04-14       Impact factor: 3.876

6.  Systematic Tuning of Fluoro-galectin-3 Interactions Provides Thiodigalactoside Derivatives with Single-Digit nM Affinity and High Selectivity.

Authors:  Kristoffer Peterson; Rohit Kumar; Olof Stenström; Priya Verma; Prashant R Verma; Maria Håkansson; Barbro Kahl-Knutsson; Fredrik Zetterberg; Hakon Leffler; Mikael Akke; Derek T Logan; Ulf J Nilsson
Journal:  J Med Chem       Date:  2018-01-11       Impact factor: 7.446

7.  Regulation of alternative macrophage activation by galectin-3.

Authors:  Alison C MacKinnon; Sarah L Farnworth; Philip S Hodkinson; Neil C Henderson; Kirsten M Atkinson; Hakon Leffler; Ulf J Nilsson; Christopher Haslett; Stuart J Forbes; Tariq Sethi
Journal:  J Immunol       Date:  2008-02-15       Impact factor: 5.422

8.  Predictive Biomarkers for Checkpoint Inhibitor-Based Immunotherapy: The Galectin-3 Signature in NSCLCs.

Authors:  Carlo Capalbo; Giorgia Scafetta; Marco Filetti; Paolo Marchetti; Armando Bartolazzi
Journal:  Int J Mol Sci       Date:  2019-03-31       Impact factor: 5.923

9.  Inhibition of galectin-3 reduces atherosclerosis in apolipoprotein E-deficient mice.

Authors:  Alison C MacKinnon; Xiaojun Liu; Patrick Wf Hadoke; Mark R Miller; David E Newby; Tariq Sethi
Journal:  Glycobiology       Date:  2013-02-19       Impact factor: 4.313

10.  Usefulness of Enhanced Liver Fibrosis, Glycosylation Isomer of Mac-2 Binding Protein, Galectin-3, and Soluble Suppression of Tumorigenicity 2 for Assessing Liver Fibrosis in Chronic Liver Diseases.

Authors:  Hee Won Moon; Mikyoung Park; Mina Hur; Hanah Kim; Won Hyeok Choe; Yeo Min Yun
Journal:  Ann Lab Med       Date:  2018-07       Impact factor: 3.464

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