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Extracellular and intracellular small-molecule galectin-3 inhibitors.

Stegmayr J, Zetterberg F, Carlsson MC, Huang X, Sharma G, Kahl-Knutson B, Schambye H, Nilsson UJ, Oredsson S, Leffler H.

Sci Rep. 2019 Feb 18;9(1):2186. doi: 10.1038/s41598-019-38497-8.


Human trophoblast requires galectin-3 for cell migration and invasion.

Bojić-Trbojević Ž, Jovanović Krivokuća M, Vilotić A, Kolundžić N, Stefanoska I, Zetterberg F, Nilsson UJ, Leffler H, Vićovac L.

Sci Rep. 2019 Feb 14;9(1):2136. doi: 10.1038/s41598-018-38374-w.


An orally active galectin-3 antagonist inhibits lung adenocarcinoma growth and augments response to PD-L1 blockade.

Vuong L, Kouverianou E, Rooney CM, McHugh BJ, Howie SE, Gregory CD, Forbes SJ, Henderson NC, Zetterberg FR, Nilsson UJ, Leffler H, Ford P, Pederson A, Gravelle L, Tantawi S, Schambye H, Sethi T, Mackinnon AC.

Cancer Res. 2019 Jan 23. pii: canres.2244.2018. doi: 10.1158/0008-5472.CAN-18-2244. [Epub ahead of print]


Substituted polyfluoroaryl interactions with an arginine side chain in galectin-3 are governed by steric-, desolvation and electronic conjugation effects.

Kumar R, Peterson K, Misini Ignjatović M, Leffler H, Ryde U, Nilsson UJ, Logan DT.

Org Biomol Chem. 2019 Jan 31;17(5):1081-1089. doi: 10.1039/c8ob02888e.


Interplay between Conformational Entropy and Solvation Entropy in Protein-Ligand Binding.

Verteramo ML, Stenström O, Ignjatović MM, Caldararu O, Olsson MA, Manzoni F, Leffler H, Oksanen E, Logan DT, Nilsson UJ, Ryde U, Akke M.

J Am Chem Soc. 2019 Feb 6;141(5):2012-2026. doi: 10.1021/jacs.8b11099. Epub 2019 Jan 23.


Galectin binding to cells and glycoproteins with genetically modified glycosylation reveals galectin-glycan specificities in a natural context.

Nielsen MI, Stegmayr J, Grant OC, Yang Z, Nilsson UJ, Boos I, Carlsson MC, Woods RJ, Unverzagt C, Leffler H, Wandall HH.

J Biol Chem. 2018 Dec 28;293(52):20249-20262. doi: 10.1074/jbc.RA118.004636. Epub 2018 Nov 1.


Quinoline-galactose hybrids bind selectively with high affinity to a galectin-8 N-terminal domain.

Pal KB, Mahanti M, Huang X, Persson S, Sundin AP, Zetterberg FR, Oredsson S, Leffler H, Nilsson UJ.

Org Biomol Chem. 2018 Aug 29;16(34):6295-6305. doi: 10.1039/c8ob01354c.


N,N'-Bis(2-mercaptoethyl)isophthalamide Binds Electrophilic Paracetamol Metabolites and Prevents Paracetamol-Induced Liver Toxicity.

Nilsson JLÅ, Blomgren A, Nilsson UJ, Högestätt ED, Grundemar L.

Basic Clin Pharmacol Toxicol. 2018 Nov;123(5):589-593. doi: 10.1111/bcpt.13058. Epub 2018 Jul 9.


Substrate-bound outward-open structure of a Na+-coupled sialic acid symporter reveals a new Na+ site.

Wahlgren WY, Dunevall E, North RA, Paz A, Scalise M, Bisignano P, Bengtsson-Palme J, Goyal P, Claesson E, Caing-Carlsson R, Andersson R, Beis K, Nilsson UJ, Farewell A, Pochini L, Indiveri C, Grabe M, Dobson RCJ, Abramson J, Ramaswamy S, Friemann R.

Nat Commun. 2018 May 1;9(1):1753. doi: 10.1038/s41467-018-04045-7.


Designing interactions by control of protein-ligand complex conformation: tuning arginine-arene interaction geometry for enhanced electrostatic protein-ligand interactions.

Noresson AL, Aurelius O, Öberg CT, Engström O, Sundin AP, Håkansson M, Stenström O, Akke M, Logan DT, Leffler H, Nilsson UJ.

Chem Sci. 2017 Dec 4;9(4):1014-1021. doi: 10.1039/c7sc04749e. eCollection 2018 Jan 28.


Arynes in the Monoarylation of Unprotected Carbohydrate Amines.

Pal KB, Mahanti M, Nilsson UJ.

Org Lett. 2018 Feb 2;20(3):616-619. doi: 10.1021/acs.orglett.7b03741. Epub 2018 Jan 23.


Galectin-3 is an amplifier of the interleukin-1β-mediated inflammatory response in corneal keratinocytes.

Uchino Y, Woodward AM, Mauris J, Peterson K, Verma P, Nilsson UJ, Rajaiya J, Argüeso P.

Immunology. 2018 Jul;154(3):490-499. doi: 10.1111/imm.12899. Epub 2018 Feb 15.


Galectin-3 type-C self-association on neutrophil surfaces; The carbohydrate recognition domain regulates cell function.

Sundqvist M, Welin A, Elmwall J, Osla V, Nilsson UJ, Leffler H, Bylund J, Karlsson A.

J Leukoc Biol. 2018 Feb;103(2):341-353. doi: 10.1002/JLB.3A0317-110R. Epub 2018 Jan 10.


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

Peterson K, Kumar R, Stenström O, Verma P, Verma PR, Håkansson M, Kahl-Knutsson B, Zetterberg F, Leffler H, Akke M, Logan DT, Nilsson UJ.

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


Monosaccharide Derivatives with Low-Nanomolar Lectin Affinity and High Selectivity Based on Combined Fluorine-Amide, Phenyl-Arginine, Sulfur-π, and Halogen Bond Interactions.

Zetterberg FR, Peterson K, Johnsson RE, Brimert T, Håkansson M, Logan DT, Leffler H, Nilsson UJ.

ChemMedChem. 2018 Jan 22;13(2):133-137. doi: 10.1002/cmdc.201700744. Epub 2018 Jan 15.


Rationally Designed Chemically Modified Glycodendrimer Inhibits Streptococcus suis Adhesin SadP at Picomolar Concentrations.

Haataja S, Verma P, Fu O, Papageorgiou AC, Pöysti S, Pieters RJ, Nilsson UJ, Finne J.

Chemistry. 2018 Feb 6;24(8):1905-1912. doi: 10.1002/chem.201704493. Epub 2018 Jan 5.


Spindle pole cohesion requires glycosylation-mediated localization of NuMA.

Magescas J, Sengmanivong L, Viau A, Mayeux A, Dang T, Burtin M, Nilsson UJ, Leffler H, Poirier F, Terzi F, Delacour D.

Sci Rep. 2017 May 3;7(1):1474. doi: 10.1038/s41598-017-01614-6.


Galectin-3 Inhibition by a Small-Molecule Inhibitor Reduces Both Pathological Corneal Neovascularization and Fibrosis.

Chen WS, Cao Z, Leffler H, Nilsson UJ, Panjwani N.

Invest Ophthalmol Vis Sci. 2017 Jan 1;58(1):9-20. doi: 10.1167/iovs.16-20009.


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

Manzoni F, Saraboji K, Sprenger J, Kumar R, Noresson AL, Nilsson UJ, Leffler H, Fisher SZ, Schrader TE, Ostermann A, Coates L, Blakeley MP, Oksanen E, Logan DT.

Acta Crystallogr D Struct Biol. 2016 Nov 1;72(Pt 11):1194-1202. Epub 2016 Oct 28.


Efficient O-Functionalization of Carbohydrates with Electrophilic Reagents.

Tolnai GL, Nilsson UJ, Olofsson B.

Angew Chem Int Ed Engl. 2016 Sep 5;55(37):11226-30. doi: 10.1002/anie.201605999. Epub 2016 Aug 16.


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

Rajput VK, MacKinnon A, Mandal S, Collins P, Blanchard H, Leffler H, Sethi T, Schambye H, Mukhopadhyay B, Nilsson UJ.

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


Erratum: Pathological lymphangiogenesis is modulated by galectin-8-dependent crosstalk between podoplanin and integrin-associated VEGFR-3.

Chen WS, Cao Z, Sugaya S, Lopez MJ, Sendra VG, Laver N, Leffler H, Nilsson UJ, Fu J, Song J, Xia L, Hamrah P, Panjwani N.

Nat Commun. 2016 Jul 19;7:12063. doi: 10.1038/ncomms12063. No abstract available.


Galectin-3-Binding Glycomimetics that Strongly Reduce Bleomycin-Induced Lung Fibrosis and Modulate Intracellular Glycan Recognition.

Delaine T, Collins P, MacKinnon A, Sharma G, Stegmayr J, Rajput VK, Mandal S, Cumpstey I, Larumbe A, Salameh BA, Kahl-Knutsson B, van Hattum H, van Scherpenzeel M, Pieters RJ, Sethi T, Schambye H, Oredsson S, Leffler H, Blanchard H, Nilsson UJ.

Chembiochem. 2016 Sep 15;17(18):1759-70. doi: 10.1002/cbic.201600285. Epub 2016 Aug 12.


Low or No Inhibitory Potency of the Canonical Galectin Carbohydrate-binding Site by Pectins and Galactomannans.

Stegmayr J, Lepur A, Kahl-Knutson B, Aguilar-Moncayo M, Klyosov AA, Field RA, Oredsson S, Nilsson UJ, Leffler H.

J Biol Chem. 2016 Jun 17;291(25):13318-34. doi: 10.1074/jbc.M116.721464. Epub 2016 Apr 26.


Pathological lymphangiogenesis is modulated by galectin-8-dependent crosstalk between podoplanin and integrin-associated VEGFR-3.

Chen WS, Cao Z, Sugaya S, Lopez MJ, Sendra VG, Laver N, Leffler H, Nilsson UJ, Fu J, Song J, Xia L, Hamrah P, Panjwani N.

Nat Commun. 2016 Apr 12;7:11302. doi: 10.1038/ncomms11302. Erratum in: Nat Commun. 2016 Jul 19;7:12063.


Flap Dynamics in Aspartic Proteases: A Computational Perspective.

Mahanti M, Bhakat S, Nilsson UJ, Söderhjelm P.

Chem Biol Drug Des. 2016 Aug;88(2):159-77. doi: 10.1111/cbdd.12745. Epub 2016 Mar 15.


Hydrophobic ion pairing of a minocycline/Ca(2+)/AOT complex for preparation of drug-loaded PLGA nanoparticles with improved sustained release.

Holmkvist AD, Friberg A, Nilsson UJ, Schouenborg J.

Int J Pharm. 2016 Feb 29;499(1-2):351-357. doi: 10.1016/j.ijpharm.2016.01.011. Epub 2016 Jan 7.


Haemophilus influenzae surface fibril (Hsf) is a unique twisted hairpin-like trimeric autotransporter.

Singh B, Jubair TA, Mörgelin M, Sundin A, Linse S, Nilsson UJ, Riesbeck K.

Int J Med Microbiol. 2015 Jan;305(1):27-37. doi: 10.1016/j.ijmm.2014.10.004. Epub 2014 Oct 27.


Synthesis and evaluation of iminocoumaryl and coumaryl derivatized glycosides as galectin antagonists.

Rajput VK, Leffler H, Nilsson UJ, Mukhopadhyay B.

Bioorg Med Chem Lett. 2014 Aug 1;24(15):3516-20. doi: 10.1016/j.bmcl.2014.05.063. Epub 2014 Jun 9.


Tri-isopropylsilyl thioglycosides as masked glycosyl thiol nucleophiles for the synthesis of S-linked glycosides and glyco-conjugates.

Mandal S, Nilsson UJ.

Org Biomol Chem. 2014 Jul 21;12(27):4816-9. doi: 10.1039/c4ob00741g.


Investigation into the feasibility of thioditaloside as a novel scaffold for galectin-3-specific inhibitors.

Bum-Erdene K, Gagarinov IA, Collins PM, Winger M, Pearson AG, Wilson JC, Leffler H, Nilsson UJ, Grice ID, Blanchard H.

Chembiochem. 2013 Jul 22;14(11):1331-42. doi: 10.1002/cbic.201300245.


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

van Hattum H, Branderhorst HM, Moret EE, Nilsson UJ, Leffler H, Pieters RJ.

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


Galectin-3 deficiency protects pancreatic islet cells from cytokine-triggered apoptosis in vitro.

Saksida T, Nikolic I, Vujicic M, Nilsson UJ, Leffler H, Lukic ML, Stojanovic I, Stosic-Grujicic S.

J Cell Physiol. 2013 Jul;228(7):1568-76. doi: 10.1002/jcp.24318.


Bacterial Adhesion of Streptococcus suis to Host Cells and Its Inhibition by Carbohydrate Ligands.

Kouki A, Pieters RJ, Nilsson UJ, Loimaranta V, Finne J, Haataja S.

Biology (Basel). 2013 Jul 1;2(3):918-35. doi: 10.3390/biology2030918.


Ligand induced galectin-3 protein self-association.

Lepur A, Salomonsson E, Nilsson UJ, Leffler H.

J Biol Chem. 2012 Jun 22;287(26):21751-6. doi: 10.1074/jbc.C112.358002. Epub 2012 May 1.


Galectin-3 endocytosis by carbohydrate independent and dependent pathways in different macrophage like cell types.

Lepur A, Carlsson MC, Novak R, Dumić J, Nilsson UJ, Leffler H.

Biochim Biophys Acta. 2012 Jul;1820(7):804-18. doi: 10.1016/j.bbagen.2012.02.018. Epub 2012 Mar 17.


Taloside inhibitors of galectin-1 and galectin-3.

Collins PM, Oberg CT, Leffler H, Nilsson UJ, Blanchard H.

Chem Biol Drug Des. 2012 Mar;79(3):339-46. doi: 10.1111/j.1747-0285.2011.01283.x. Epub 2012 Jan 11.


The carbohydrate-binding site in galectin-3 is preorganized to recognize a sugarlike framework of oxygens: ultra-high-resolution structures and water dynamics.

Saraboji K, Håkansson M, Genheden S, Diehl C, Qvist J, Weininger U, Nilsson UJ, Leffler H, Ryde U, Akke M, Logan DT.

Biochemistry. 2012 Jan 10;51(1):296-306. doi: 10.1021/bi201459p. Epub 2011 Dec 7.


Regulation of transforming growth factor-β1-driven lung fibrosis by galectin-3.

Mackinnon AC, Gibbons MA, Farnworth SL, Leffler H, Nilsson UJ, Delaine T, Simpson AJ, Forbes SJ, Hirani N, Gauldie J, Sethi T.

Am J Respir Crit Care Med. 2012 Mar 1;185(5):537-46. doi: 10.1164/rccm.201106-0965OC. Epub 2011 Nov 17.


Inhibition mechanism of human galectin-7 by a novel galactose-benzylphosphate inhibitor.

Masuyer G, Jabeen T, Öberg CT, Leffler H, Nilsson UJ, Acharya KR.

FEBS J. 2012 Jan;279(2):193-202. doi: 10.1111/j.1742-4658.2011.08414.x. Epub 2011 Nov 30.


Identification of a novel streptococcal adhesin P (SadP) protein recognizing galactosyl-α1-4-galactose-containing glycoconjugates: convergent evolution of bacterial pathogens to binding of the same host receptor.

Kouki A, Haataja S, Loimaranta V, Pulliainen AT, Nilsson UJ, Finne J.

J Biol Chem. 2011 Nov 11;286(45):38854-64. doi: 10.1074/jbc.M111.260992. Epub 2011 Sep 9.


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

Öberg CT, Noresson AL, Leffler H, Nilsson UJ.

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


Inhibition of galectins with small molecules.

Oberg CT, Leffler H, Nilsson UJ.

Chimia (Aarau). 2011;65(1-2):18-23. Review.


The anti-angiogenic peptide anginex greatly enhances galectin-1 binding affinity for glycoproteins.

Salomonsson E, Thijssen VL, Griffioen AW, Nilsson UJ, Leffler H.

J Biol Chem. 2011 Apr 22;286(16):13801-4. doi: 10.1074/jbc.C111.229096. Epub 2011 Mar 3.


Probing the acceptor substrate binding site of Trypanosoma cruzi trans-sialidase with systematically modified substrates and glycoside libraries.

Harrison JA, Kartha KP, Fournier EJ, Lowary TL, Malet C, Nilsson UJ, Hindsgaul O, Schenkman S, Naismith JH, Field RA.

Org Biomol Chem. 2011 Mar 7;9(5):1653-60. doi: 10.1039/c0ob00826e. Epub 2011 Jan 21.


Protein flexibility and conformational entropy in ligand design targeting the carbohydrate recognition domain of galectin-3.

Diehl C, Engström O, Delaine T, Håkansson M, Genheden S, Modig K, Leffler H, Ryde U, Nilsson UJ, Akke M.

J Am Chem Soc. 2010 Oct 20;132(41):14577-89. doi: 10.1021/ja105852y.


Monovalent interactions of galectin-1.

Salomonsson E, Larumbe A, Tejler J, Tullberg E, Rydberg H, Sundin A, Khabut A, Frejd T, Lobsanov YD, Rini JM, Nilsson UJ, Leffler H.

Biochemistry. 2010 Nov 9;49(44):9518-32. doi: 10.1021/bi1009584.


Galectin inhibitory disaccharides promote tumour immunity in a breast cancer model.

Stannard KA, Collins PM, Ito K, Sullivan EM, Scott SA, Gabutero E, Darren Grice I, Low P, Nilsson UJ, Leffler H, Blanchard H, Ralph SJ.

Cancer Lett. 2010 Dec 28;299(2):95-110. doi: 10.1016/j.canlet.2010.08.005. Epub 2010 Sep 9.


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