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

Journal of Medicinal Chemistry

Volumn 56, Issue 3, 2013, Pages 1350-1354

  Van Hattum, Hilde ^a   Branderhorst, Hilbert M ^a   Moret, Ed E ^a   Nilsson, Ulf J ^b   Leffler, Hakon ^b   Pieters, Roland J ^a  

^a UTRECHT UNIVERSITY   (Netherlands)

^b LUND UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

GALACTOSAMINE; GALECTIN 1; GALECTIN 3; PROTEIN INHIBITOR; THIODIGALACTOSIDE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CYCLOADDITION; DEACETYLATION; DERIVATIZATION; SYNTHESIS;

AMINO SUGARS; GALECTIN 1; GALECTIN 3; LIGANDS; MASS SPECTROMETRY; MOLECULAR STRUCTURE; THIOGALACTOSIDES;

EID: 84873903645     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm301677r     Document Type: Article

References (34)

1. Di Lella, S.; Sundblad, V.; Cerliani, J. P.; Guardia, C. M.; Estrin, D. A.; Vasta, G. R.; Rabinovich, G. A. When galectins recognize glycans: from biochemistry to physiology and back again Biochemistry 2011, 50, 7842-7857
2. Levy, R.; Biran, A.; Poirier, F.; Raz, A.; Kloog, Y. Galectin-3 mediates cross-talk between K-Ras and Let-7c tumor suppressor microRNA PLoS One 2011, 11, e27490
3. Elola, M. T.; Wolfenstein-Todel, C.; Troncoso, M. F.; Vasta, G. R.; Rabinovich, G. A. Galectins: matricellular glycan-binding proteins linking cell adhesion, migration, and survival Cell. Mol. Life Sci. 2007, 13, 1679-1700
4. Carlsson, M. C.; Cederfur, C.; Schaar, V.; Balog, C. I.; Lepur, A.; Touret, F.; Salomonsson, E.; Deelder, A. M.; Fernö, M.; Olsson, H.; Wuhrer, M.; Leffler, H. Galectin-1-binding glycoforms of haptoglobin with altered intracellular trafficking, and increase in metastatic breast cancer patients PLoS One 2011, 6, e26560
5. Liu, F. T.; Rabinovich, G. A. Galectins as modulators of tumour progression Nat. Rev. Cancer 2005, 5, 29-41
6. Nakahara, S.; Oka, N.; Raz, A. On the role of galectin-3 in cancer apoptosis Apoptosis 2005, 10, 267-275
7. Rabinovich, G. A.; Liu, F. T.; Hirashima, M.; Anderson, A. An emerging role for galectins in tuning the immune response: lessons from experimental models of inflammatory disease, autoimmunity and cancer Scand. J. Immunol. 2007, 66, 143-158
8. Pieters, R. J. Inhibition and detection of galectins ChemBioChem 2006, 7, 721-728
9. Ingrassia, L.; Camby, I.; Lefranc, F.; Mathieu, V.; Nshimyumukiza, P.; Darro, F.; Kiss, R. Anti-galectin compounds as potential anti-cancer drugs Curr. Med. Chem. 2006, 13, 3513-3527
10. Giguère, D.; Sato, S.; St-Pierre, C.; Sirois, S.; Roy, R. Aryl O-and S -galactosides and lactosides as specific inhibitors of human galectins-1 and -3: role of electrostatic potential at O-3 Bioorg. Med. Chem. Lett. 2006, 16, 1668-1672
11. André, S.; Jarikote, D. V.; Yan, D.; Vincenz, L.; Wang, G. N.; Kaltner, H.; Murphy, P. V.; Gabius, H. J. Synthesis of bivalent lactosides and their activity as sensors for differences between lectins in inter- and intrafamily comparisons Bioorg. Med. Chem. Lett. 2012, 22, 313-318
12. André, S.; Maljaars, C. E.; Halkes, K. M.; Gabius, H. J.; Kamerling, J. P. Discovery of galectin ligands in fully randomized combinatorial one-bead-one-compound (glyco)peptide libraries Bioorg. Med. Chem. Lett. 2007, 17, 793-798
13. Arnusch, C. J.; André, S.; Valentinia, P.; Lensch, M.; Russwurmb, R.; Siebert, H.-C.; Fischer, M. J. E.; Gabius, H.-J.; Pieters, R. J. Interference of the galactose-dependent binding of lectins by novel pentapeptide ligands Bioorg. Med. Chem. Lett. 2004, 14, 1437-1440
14. Thijssen, V. L.; Postel, R.; Brandwijk, R. J.; Dings, R. P.; Nesmelova, I.; Satijn, S.; Verhofstad, N.; Nakabeppu, Y.; Baum, L. G.; Bakkers, J.; Mayo, K. H.; Poirier, F.; Griffioen, A. W. Galectin-1 is essential in tumor angiogenesis and is a target for antiangiogenesis therapy Proc. Natl. Acad. Sci. U.S.A. 2006, 43, 15975-15980
15. Salomonsson, E.; Thijssen, V. L.; Griffioen, A. W.; Nilsson, U. J.; Leffler, H. The anti-angiogenic peptide anginex greatly enhances galectin-1 binding affinity for glycoproteins J. Biol. Chem. 2011, 286, 13801-13804
16. André, S.; Pieters, R. J.; Vrasidas, I.; Kaltner, H.; Kuwabara, I.; Liu, F. T.; Liskamp, R. M. J.; Gabius, H. J. Wedgelike glycodendrimers as inhibitors of binding of mammalian galectins to glycoproteins, lactose maxiclusters, and cell surface glycoconjugates ChemBioChem 2001, 2, 822-830
17. André, S.; Ortega, P. J.; Perez, M. A.; Roy, R.; Gabius, H. J. Lactose-containing starburst dendrimers: influence of dendrimer generation and binding-site orientation of receptors (plant/animal lectins and immunoglobulins) on binding properties Glycobiology 1999, 9, 1253-1261
18. Vrasidas, I.; André, S.; Valentini, P.; Böck, C.; Lensch, M.; Kaltner, H.; Liskamp, R. M.; Gabius, H. J.; Pieters, R. J. Rigidified multivalent lactose molecules and their interactions with mammalian galectins: a route to selective inhibitors Org. Biomol. Chem. 2003, 5, 803-810
19. Cumpstey, I.; Sundin, A.; Leffler, H.; Nilsson, U. J. C2-symmetrical thiodigalactoside bis-benzamido derivatives as high-affinity inhibitors of galectin-3: efficient lectin inhibition through double arginine-arene interactions Angew. Chem. 2005, 117, 5240-5242
20. Cumpstey, I.; Salomonsson, E.; Sundin, A.; Leffler, H.; Nilsson, U. J. Double affinity amplification of galectin-ligand interactions through arginine-arene interactions: synthetic, thermodynamic, and computational studies with aromatic diamido thiodigalactosides Chem.-Eur. J. 2008, 14, 4233-4245
21. Delaine, T.; Cumpstey, I.; Ingrassia, L.; Le Mercier, M.; Okechukwu, P.; Leffler, H.; Kiss, R.; Nilsson, U. J. Galectin-inhibitory thiodigalactoside ester derivatives have antimigratory effects in cultured lung and prostate cancer cells J. Med. Chem. 2008, 51, 8109-8114
22. Salameh, B. A.; Cumpstey, I.; Sundin, A.; Leffler, H.; Nilsson, U. J. 1 H -1,2,3-Triazol-1-yl thiodigalactoside derivatives as high affinity galectin-3 inhibitors Bioorg. Med. Chem. 2010, 18, 5367-5378
23. Mackinnon, A. C.; Gibbons, M. A.; Farnworth, S. L.; Leffler, H.; Nilsson, U. J.; Delaine, T.; Simpson, A. J.; Forbes, S. J.; Hirani, N.; Gauldie, J.; Sethi, T. Regulation of transforming growth factor-β1-driven lung fibrosis by galectin-3 Am. J. Respir. Crit. Care Med. 2012, 185, 537-546
24. Volarevic, V.; Milovanovic, M.; Ljujic, B.; Pejnovic, N.; Arsenijevic, N.; Nilsson, U.; Leffler, H.; Lukic, M. L. Galectin-3 deficiency prevents concanavalin A-induced hepatitis in mice Hepatology 2012, 55, 1954-1964
25. van Scherpenzeel, M.; Moret, E. E.; Ballell, L.; Liskamp, R. M. J.; Nilsson, U. J.; Leffler, H.; Pieters, R. J. Synthesis and evaluation of new thiodigalactoside-based chemical probes to label galectin-3 ChemBioChem. 2009, 10, 1724-1733
26. Tornøe, C. W.; Christensen, C.; Meldal, M. Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides J. Org. Chem. 2002, 67, 3057-3064
27. Sörme, P.; Arnoux, P.; Kahl-Knutsson, B.; Leffler, H.; Rini, J. M.; Nilsson, U. J. 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 J. Am. Chem. Soc. 2005, 127, 1737-1743
28. Bianchet, M. A.; Ahmed, H.; Vasta, G. R.; Amzel, L. M. Soluble beta-galactosyl-binding lectin (galectin) from toad ovary: crystallographic studies of two protein-sugar complexes Proteins 2000, 15, 378-388
29. Lowary, T. L.; Hindsgaul, O. Recognition of synthetic O -methyl, epimeric, and amino analogues of the acceptor α- l -Fucp-(1→2)- β- d -Galp-OR glycosyltransferases Carbohydr. Res. 1994, 251, 33-67
30. Koike, K.; Sugimoto, M.; Sato, S.; Ito, Y.; Nakahara, Y.; Ogawa, T. Total synthesis of globotriaosyl- E and Z -ceramides and isoglobotriaosyl- E -ceramide Carbohydr. Res. 1987, 163, 189-208
31. Ballell, L.; Joosten, J. A. F.; Ait el Maate, F.; Liskamp., R. M. J.; Pieters, R. J. Microwave-assisted, tin-mediated, regioselective 3-O-alkylation of galactosides Tetrahedron Lett. 2004, 45, 6685-6687
32. Zhang, G.; Guan, Z.; Zhang, L.; Min, J.; Zhang, L. Synthesis of 2-amino-2-deoxy-β-glycosyl-(1→5)-nucleosides and the interaction with RNA Bioorg. Med. Chem. 2003, 11, 3273-3278
33. Sörme, P.; Kahl-Knutsson, B.; Huflejt, M.; Nilsson, U. J.; Leffler, H. Fluorescence polarization as an analytical tool to evaluate galectin-ligand interactions Anal. Biochem. 2004, 334, 36-47
34. Collins, P. M.; Öberg, C. T.; Leffler, H.; Nilsson, U. J.; Blanchard, H. Taloside inhibitors of galectin-1 and galectin-3 Chem. Biol. Drug Des. 2012, 79, 339-346