作为半乳糖凝集素-3高亲和力抑制剂的C2对称硫代二半乳糖苷双苯甲酰胺衍生物：通过双精氨酸-芳烃相互作用实现高效的凝集素抑制作用 - Suppr

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C2-symmetrical thiodigalactoside bis-benzamido derivatives as high-affinity inhibitors of galectin-3: efficient lectin inhibition through double arginine-arene interactions.

作者信息

Cumpstey Ian, Sundin Anders, Leffler Hakon, Nilsson Ulf J

机构信息

Organic Chemistry, Lund University, Box 124, 221 00 Lund, Sweden.

出版信息

Angew Chem Int Ed Engl. 2005 Aug 12;44(32):5110-2. doi: 10.1002/anie.200500627.

DOI:10.1002/anie.200500627

PMID:16007713

Abstract

摘要

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C2-symmetrical thiodigalactoside bis-benzamido derivatives as high-affinity inhibitors of galectin-3: efficient lectin inhibition through double arginine-arene interactions.

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C2-symmetrical thiodigalactoside bis-benzamido derivatives as high-affinity inhibitors of galectin-3: efficient lectin inhibition through double arginine-arene interactions.

作者信息

Cumpstey Ian, Sundin Anders, Leffler Hakon, Nilsson Ulf J

机构信息

Organic Chemistry, Lund University, Box 124, 221 00 Lund, Sweden.

出版信息

Angew Chem Int Ed Engl. 2005 Aug 12;44(32):5110-2. doi: 10.1002/anie.200500627.

DOI:10.1002/anie.200500627

PMID:16007713

Abstract

摘要

相似文献

C2-symmetrical thiodigalactoside bis-benzamido derivatives as high-affinity inhibitors of galectin-3: efficient lectin inhibition through double arginine-arene interactions.

Angew Chem Int Ed Engl. 2005 Aug 12;44(32):5110-2. doi: 10.1002/anie.200500627.

1H-1,2,3-triazol-1-yl thiodigalactoside derivatives as high affinity galectin-3 inhibitors.

Bioorg Med Chem. 2010 Jul 15;18(14):5367-78. doi: 10.1016/j.bmc.2010.05.040. Epub 2010 May 20.

Tuning the preference of thiodigalactoside- and lactosamine-based ligands to galectin-3 over galectin-1.

J Med Chem. 2013 Feb 14;56(3):1350-4. doi: 10.1021/jm301677r. Epub 2013 Jan 23.

Synthesis and evaluation of new thiodigalactoside-based chemical probes to label galectin-3.

Chembiochem. 2009 Jul 6;10(10):1724-33. doi: 10.1002/cbic.200900198.

Arginine binding motifs: design and synthesis of galactose-derived arginine tweezers as galectin-3 inhibitors.

J Med Chem. 2008 Apr 10;51(7):2297-301. doi: 10.1021/jm701266y. Epub 2008 Mar 5.

Structural and thermodynamic studies on cation-Pi interactions in lectin-ligand complexes: high-affinity galectin-3 inhibitors through fine-tuning of an arginine-arene interaction.

J Am Chem Soc. 2005 Feb 16;127(6):1737-43. doi: 10.1021/ja043475p.

Double affinity amplification of galectin-ligand interactions through arginine-arene interactions: synthetic, thermodynamic, and computational studies with aromatic diamido thiodigalactosides.

Chemistry. 2008;14(14):4233-45. doi: 10.1002/chem.200701932.

A Selective Galactose-Coumarin-Derived Galectin-3 Inhibitor Demonstrates Involvement of Galectin-3-glycan Interactions in a Pulmonary Fibrosis Model.

J Med Chem. 2016 Sep 8;59(17):8141-7. doi: 10.1021/acs.jmedchem.6b00957. Epub 2016 Aug 23.

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

J Med Chem. 2018 Feb 8;61(3):1164-1175. doi: 10.1021/acs.jmedchem.7b01626. Epub 2018 Jan 11.

Arene-anion based arginine-binding motif on a galactose scaffold: structure-activity relationships of interactions with arginine-rich galectins.

Chemistry. 2011 Jul 11;17(29):8139-44. doi: 10.1002/chem.201003247. Epub 2011 Jun 7.

引用本文的文献

Structural Insights Into Galectin-3 Recognition of a Selenoglycomimetic.

ChemMedChem. 2025 May 19;20(10):e202401005. doi: 10.1002/cmdc.202401005. Epub 2025 Mar 6.

Ligand Sulfur Oxidation State Progressively Alters Galectin-3-Ligand Complex Conformations To Induce Affinity-Influencing Hydrogen Bonds.

J Med Chem. 2023 Nov 9;66(21):14716-14723. doi: 10.1021/acs.jmedchem.3c01223. Epub 2023 Oct 25.

Glycomimetics for the inhibition and modulation of lectins.

Chem Soc Rev. 2023 Jun 6;52(11):3663-3740. doi: 10.1039/d2cs00954d.

Galectin-1: A Traditionally Immunosuppressive Protein Displays Context-Dependent Capacities.

Int J Mol Sci. 2023 Mar 30;24(7):6501. doi: 10.3390/ijms24076501.

Design and synthesis of novel 3-triazolyl-1-thiogalactosides as galectin-1, -3 and -8 inhibitors.

RSC Adv. 2022 Jun 30;12(29):18973-18984. doi: 10.1039/d2ra03163a. eCollection 2022 Jun 22.

Understanding the role of galectin inhibitors as potential candidates for SARS-CoV-2 spike protein: studies.

RSC Adv. 2020 Aug 13;10(50):29873-29884. doi: 10.1039/d0ra04795c. eCollection 2020 Aug 10.

Synthesis of tricyclic carbohydrate-benzene hybrids as selective inhibitors of galectin-1 and galectin-8 N-terminal domains.

RSC Adv. 2020 May 22;10(33):19636-19642. doi: 10.1039/d0ra03144e. eCollection 2020 May 20.

Design, Synthesis, and Anticancer Activity of a Selenium-Containing Galectin-3 and Galectin-9N Inhibitor.

Int J Mol Sci. 2022 Feb 25;23(5):2581. doi: 10.3390/ijms23052581.

Investigation of the Molecular Details of the Interactions of Selenoglycosides and Human Galectin-3.

Int J Mol Sci. 2022 Feb 24;23(5):2494. doi: 10.3390/ijms23052494.

Galectin 3 enhances platelet aggregation and thrombosis via Dectin-1 activation: a translational study.

Eur Heart J. 2022 Oct 7;43(37):3556-3574. doi: 10.1093/eurheartj/ehac034.